Special thanks to Matt Metras, EA, for bringing this to my attention.

A hardware review channel on YouTube spent roughly 500 hours and about $70,000 taking apart televisions, and the result should probably change how you think about every appliance in your house that has a power cord and an opinion.

On September 6, Gamers Nexus published a 135-minute investigation into LG smart TVs, conducted with Wendell Wilson of Level1Techs and independent security researchers MrBruh and uturn. They bought retail sets, including the flagship G5 OLED. They watched the network traffic with Wireshark. They decrypted and decompiled firmware, rooted the televisions, and read the logs.

What they found is not a story about one bad company. It is a story about a bargain most of us accepted without ever being asked.

Let’s dig into what they actually found, because the headlines are compressing three very different problems into one scary sentence.

The television was mapping the house

The researchers found the tested LG sets repeatedly sweeping the local network and identifying other hardware on it. In one test, a single television inventoried at least 38 other devices, including smartphones belonging to staff who had no idea the test was running, plus smartwatches, printers, a 3D printer, thermostats, and HVAC equipment.

Firmware analysis also showed the sets picking up nearby Wi-Fi networks, including names, signal strength, and channel.

None of those devices were ever connected to the television. They were simply nearby.

Now, before anyone with a security background objects: device discovery on a local network is ordinary. Protocols like UPnP exist precisely so your phone can find your printer. Discovery by itself is not an incident.

What is unusual is the scope, the persistence, and the apparent purpose. This is not a television looking for a speaker to pair with.

I bought a display. Apparently I also bought something that keeps a running census of my house.

Automatic Content Recognition does not care which input you use

Automatic Content Recognition, or ACR, is the advertising technology at the center of this. It samples what is on the screen, turns it into a fingerprint, and matches that fingerprint against a reference database to identify the content.

The important part, the part most people get wrong: ACR keeps working when the television is being used as a plain HDMI monitor. Switching inputs does not switch it off. Gamers Nexus estimated one test set exchanged roughly 4GB of ACR-related data per month.

So if you run a laptop into an LG panel, the fingerprinting engine is still sampling. One physician who reviewed the findings reportedly asked the researchers the obvious follow-up question: what does that mean for a hospital display carrying a telemedicine session?

Hold onto that question. We are coming back to it.

The microphone finding, stated carefully

This is where accuracy matters more than outrage.

Researchers demonstrated intelligible microphone audio being captured while the television’s display appeared to be off in standby. They also found that disconnecting the set from the internet did not necessarily stop it. The television kept writing data locally and transmitted it once connectivity returned. Voice interactions were converted to plain text and stored in logs on the device itself.

Separately, they reported security vulnerabilities that would let a compromised television be used as a listening device. Those specifics are being withheld under responsible disclosure, which is exactly how it should be handled.

Here is the nuance that makes this a better story than “your TV is spying on you.” Gamers Nexus did not claim LG ships always-on eavesdropping. Cybernews noted that the findings relate to voice command handling rather than ambient background conversation, and that the researchers’ recommendation was practical rather than apocalyptic: disconnect the television and use an external streaming box.

Note the distinction, because it matters in the next section. “The television is off” and “the display is off” are not the same statement.

Texas had already challenged this

Here is the part I did not expect: Texas had already been litigating this.

On December 15, 2025, Texas Attorney General Ken Paxton sued five television manufacturers (Samsung, LG, Sony, Hisense, and TCL), alleging they used ACR to collect viewing data without consumers’ knowledge or meaningful consent. The complaints sought penalties under the Texas Deceptive Trade Practices Act of up to $10,000 per violation, and potentially up to $250,000 per violation for qualifying violations involving consumers age 65 or older.

Samsung reached an agreement on February 26, 2026. LG’s agreement was announced on May 11, 2026.

Under the LG agreement, the company will not use ACR to collect viewing data without informed consent, must display a pop-up disclosure explaining how viewing data may be collected and used, and must give consumers a clear way to opt out. The Attorney General’s announcement describes behavioral requirements rather than a monetary penalty, and LG admitted no liability. Cases against Sony, Hisense, and TCL remained pending.

Four months after that announcement, Gamers Nexus reported that in its testing, the “Do Not Sell My Personal Information” setting was still off by default, before a buyer had connected to the internet or agreed to anything.

A settlement changed what the company must disclose. It did not change what the device is capable of doing.

That gap, between a legal remedy and an engineering reality, is the whole ballgame.

LG’s denial answers a narrower question

Now put LG’s public statement against that backdrop.

In July, responding to earlier controversy, LG said its televisions do not collect, record, or store “ambient conversations,” and described voice recognition as an optional, user-initiated feature.

Read that sentence again and notice what it does not say.

It does not say the microphone is inactive in standby. It does not say the listening window closes the instant a request ends. It does not address local storage, or network scanning, or ACR sampling of an HDMI input. The denial is doing a lot of work, but mostly by answering a narrower question than the one being asked.

That is not a lie. It is a carefully bounded true statement, which is a different thing, and anyone who has read a privacy policy for a living recognizes the technique immediately.

Meanwhile, the same investigation surfaced footage of LG Ad Solutions president Serge Matta telling an audience, “We own the glass. We own the TV.”

Whatever he meant by it, it is a clarifying sentence. LG Ad Solutions puts its footprint at roughly 216 million smart TVs worldwide. At that scale, advertising is not an incidental feature bolted onto the television business. It is part of the business model, and the hardware is how you reach the audience.

Why this is a professional problem, not just a consumer one

Now back to that physician’s question, translated into our wonderful world of tax.

If you are a tax professional, you are a “financial institution” under the Gramm-Leach-Bliley Act, and the FTC Safeguards Rule requires you to maintain a written information security program. IRS Publication 4557 walks through the same expectations for practitioners.

The rule focuses on identifying and assessing risks to client information. A competent risk assessment has to account for the devices and information systems on your network: what is connected, what it can access, and what it can transmit.

Pull up your WISP and look at what you listed. Is the television on it? I know it isn’t. I know you’re rolling your eyes at me.

I am fairly confident yours covers workstations, laptops, phones, the network printer, maybe the router. I am equally confident it does not mention the television in the room where you take client calls.

That television, per this investigation, may be enumerating devices on the same network your practice management system lives on. It has a microphone. Its content-recognition system can keep sampling the display even when the display is being fed by an external computer.

To be clear about where the evidence stops: the investigation did not establish that LG was reading the contents of documents on screen. ACR fingerprints content to match it against a reference database, and your client’s Form 1040 is not in that database. But from a security standpoint, the fact that a content-recognition system tied to advertising can analyze an HDMI-fed screen at all is worth considering in your risk assessment.

And the operating system underneath it is a Linux derivative whose long-term security depends entirely on the manufacturer continuing to support it. LG’s webOS Re:New program promises four webOS upgrades over five years on covered models, with eligibility varying by model and year. That is a real commitment, and it is more than some competitors offer. It is also quite possibly less time than the panel will remain hanging on your wall.

We spend real money on endpoint protection and multi-factor authentication, and then we put an unmanaged, ad-funded, internet-connected computer with a microphone in the room where we discuss collection alternatives with people in the worst month of their financial lives.

What to actually do

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None of this requires paranoia. It requires about twenty minutes.

Turn off ACR. On LG sets, the ACR feature runs under Live Plus: Settings > General > System > Advanced Settings > Live Plus. Turn it off. While you are there, decline personalized advertising and turn off voice features you do not use.

Install firmware updates. Vulnerability findings are only useful if the patch reaches the device.

Take the television off your main network. The cleanest version: do not connect the panel itself to Wi-Fi or Ethernet at all. Use an external streaming box instead. I like Apple TV. That does not eliminate tracking or data collection, but it removes the television’s operating system from your trusted network and lets the panel be a panel.

If you will not disconnect it, segment it. Most modern routers support a guest network or a separate VLAN. Put every IoT device on it. The television can talk to the internet without talking to the machine holding your client files.

Some will argue that you should have an entirely separate internet connection for work and home. That is cleaner, but most people working from home are not going to pay for a second broadband connection. If you’ve ever been in my cybersecurity or WISP class, you know I will say that security is a spectrum.

Then put it in your risk assessment. Not because a regulator will ask about your television. Because the exercise of writing down every device that can hear, see, or enumerate your office is the entire point of having a plan.

The bigger question nobody asked

We have spent twenty years making appliances “smart” without ever stopping to ask whether they needed to be computers.

The refrigerator. The doorbell. The thermostat. The light bulbs. The vacuum. Every one of them arrives with an operating system, network access, cloud services, telemetry, an authentication scheme, and sometimes a microphone or a camera. Which means every one of them also arrives with software vulnerabilities, a privacy policy, an eventual end-of-support date, an advertising incentive, and a company whose economic interests are not identical to yours.

Nobody sat us down and offered that trade. It arrived as a default, and defaults are the most powerful thing in technology precisely because we so rarely examine them. We tolerate an astonishing amount of accumulated complexity, not because we evaluated it and decided it was worth it, but because reconsidering the default never made it to the top of the list.

This one is worth moving up the list. An LG OLED is a genuinely spectacular piece of glass. Let it be glass.

Sometimes the smartest thing you can do with a smart appliance is make it stupid again.

Later this month, I will be teaching a cybersecurity workshop for NATP.

Leave a comment

Sources

• Gamers Nexus, investigation into LG smart TVs, September 6, 2026 (with Level1Techs, MrBruh, and uturn)

• Cybernews, “Are 200 million LG TVs listening in, even when switched off?”

• CyberInsider, “LG Smart TVs found scanning home networks for nearby devices”

• Malwarebytes Labs, “LG TV flaws could let attackers listen in, even in standby mode”

• The Verge, “LG TVs caught spying even when offline or on standby”

• All About Cookies, “LG Smart TVs Caught Listening With the Screen Off”

• TechRadar, LG statement on ambient conversations, July 2026

• Office of the Texas Attorney General, LG settlement announcement, May 2026

• Secure Privacy, “Samsung and LG’s Texas ACR Settlements”

• Fordham Center on Law and Information Policy, “Your Smart TV May Be Watching You Back”

• LG, webOS Re: New Program

• FTC Safeguards Rule, 16 C.F.R. Part 314

• IRS Publication 4557, Safeguarding Taxpayer Data

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I have a habit I am not especially proud of, but not entirely ashamed of either. I buy technology to make my life better, and then I use roughly 5% of it.

Not because the tool is bad. Because configuring it fully requires a block of attention I never schedule, and the half-configured version works well enough that I stop noticing. The device gets used the way a smartwatch gets used as a watch. Technically functional. Almost entirely wasted.

Back in March, when I wrote about switching to voice dictation, I made a passing comment I keep coming back to: anytime I feel friction while working, I stop and ask whether there is a better way to operate.

That is an easy sentence to write. It is a harder thing to do at 2 p.m. on a Tuesday when the friction is small, and the deadline is not.

So here is the more useful version of the idea:

Most of the annoyances in your day are not twenty-minute problems waiting to be solved. They are twenty-minute problems you have been solving manually, five seconds at a time, for two years.

This week I finally sat down with two of mine.

I have two high-end Macs, and neither has ever stopped macOS from behaving in ways I didn't ask for. Let’s dig into both fixes, including the parts that did not go smoothly, because the messy version is more useful than the tidy one.

Fix one: the pedal in the drawer

Somebody recommended an Elgato Stream Deck Pedal to me a while back. Three pedals, heavy metal base, swappable springs, $89.99.

I bought it, plugged it in once, and put it in a drawer upstairs.

I do not even remember what I was going to use it for, but I am sure I had some grand vision.

Then I saw someone mention using a foot pedal to trigger Wispr Flow, the dictation tool I now use for most of my writing.

That clicked immediately.

I dictate dozens of times a day, and every one of those starts with a keyboard shortcut, which means my hands leave whatever they are doing so I can talk instead of type. A small, constant tax.

Meanwhile my foot has nothing to do at all.

What I wanted was true push-to-talk:

Pedal down, start listening. Pedal held, keep listening. Pedal up, stop and insert the text.

Three things stood between me and that.

The default shortcut was never going to be the easiest option. Flow’s push-to-talk shortcut on a Mac defaults to the Fn key, and Fn is a special case on the Mac, which is why Flow ships Control + Option as its fallback.

So I rebound push-to-talk to Control + Option. That worked perfectly from the physical keyboard, and it had another advantage: it is modifier-only, so I am not accidentally typing characters into whatever happens to be open. It also leaves Command + Control + Option available for Flow’s Command Mode.

A hotkey is not a hold. Stream Deck’s standard Hotkey action sends a shortcut. Push-to-talk needs a genuine key-down when the pedal goes down and a genuine key-up when it comes back up.

The Key Hold plugin from the Elgato Marketplace does exactly that, so its Hold Key action went on the left pedal.

And then it simply did not work.

Everything looked right on screen. Control + Option started and stopped dictation perfectly from the physical keyboard, which told me the problem lived somewhere on the Stream Deck side.

The temptation at that moment is to rip the plugin out and try another one.

Instead, I opened the plugin’s log.

The actual answer was sitting there:

helper failed to start: .../bin/keyholder EACCES

The plugin ships a small native helper called keyholder that does the real work of holding the keys down. The helper was there, but macOS was refusing to execute it because the executable permission was missing.

One chmod restored the executable bit, I restarted Stream Deck, and it worked exactly as intended.

Holding the pedal while I talk feels nothing like pressing a shortcut. It feels like using a transcription pedal, which is to say it feels like it should have worked this way from the start.

One caution worth writing down: a plugin update could replace that helper and strip the permission again. If the pedal quietly dies after an update, the log and that EACCES line are the first places I will look.

There is probably an attention-span lesson buried in this too.

My first instinct when the plugin failed was not to diagnose it. It was to replace it. I do not think that instinct is unusual. We have gotten very good at trying something once, deciding it does not work, and moving on. I am certainly not immune to that.

In this case, thirty seconds spent reading a log saved me from starting the entire search over again.

Fix two: half a second, over and over

The second fix cost nothing at all.

I run multiple Spaces (Apple’s name for virtual desktops) all day, and I keep Reduce Motion turned on because sweeping animations genuinely make me motion sick.

The same thing happens when I am a passenger in a car, particularly when Luis is driving, although that may be an entirely separate issue.

Think real-life Mario Kart.

With Reduce Motion enabled, switching Spaces produced an ugly side effect for me: a brief black screen before the next desktop appeared.

Call it half a second.

Half a second is nothing.

Half a second every time you switch, all day long, each one punctuated by a black flash, is not nothing.

Nothing I tried suggested this was a hardware bottleneck. It happened on a specced-out MacBook Pro, which is not a machine anyone can reasonably accuse of being slow. Restarting the Dock did not touch it. The pause appeared to be part of macOS’s Space-switching transition rather than a performance problem.

Years ago, a utility called TotalSpaces made desktop switching instantaneous, but its old approach no longer works cleanly on current versions of macOS.

What replaced it in my setup is a small, free, open-source project on GitHub called InstantSpaceSwitcher, installed through its Homebrew tap:

brew install --cask jurplel/tap/instant-space-switcher

Two notes for anyone following along, because this is where people tend to make a bad decision.

The app is not signed through Apple’s developer program, so macOS may block it on first launch. The correct fix is the normal per-app exception under System Settings → Privacy & Security → Open Anyway. (Always make sure you actually trust the software or plugin, or script before you run it, and if you have suspicions, make sure you have verified it is safe.)

There is never a reason to disable Gatekeeper or System Integrity Protection for something like this, and any utility that demands you do is a utility that does not go on a machine holding client data.

InstantSpaceSwitcher also needs Accessibility access because it intercepts the gesture and substitutes a synthetic, extremely fast one that effectively skips the normal transition.

The result is about as simple as software gets:

Swipe, desktop.

No animation. No black pause. The next Space is just there.

My reaction the first time I tried it is not printable in a newsletter.

Total cost: zero dollars and one sitting.

One honest note

It would be fair to say that this was more difficult than it needed to be.

Some of this kind of customization is less fussy on Windows. macOS is particularly protective about software that wants to press keys, control the interface, or intercept gestures on your behalf.

In this case, that is exactly what I was asking two third-party utilities to do.

Much of what I described above is Apple’s protective layer doing exactly what it is designed to do: making it harder for software to simulate input or control parts of the system without permission.

I would still rather have those protections than not, given what sits on these machines. But there is no version of this where I pretend the finagling was necessary. It is part of the price of the platform, and it is worth knowing that going in.

The part where AI actually earned its keep

This is worth naming, since this newsletter spends a lot of time on AI and most of that time is spent on the flashy uses.

I did not solve either of these from scratch.

I opened a conversation with ChatGPT and described what I wanted to accomplish in plain language, as an outcome.

Not: “What is the API for macOS Spaces?”

Just: here is the annoyance, here is what I want instead, what are my options?

Then I worked through the answers, checked the settings myself, and read the log when something failed.

That may be the most useful thing AI changed in this whole exercise.

It did not magically fix either problem.

It changed the economics of whether the problems were worth fixing at all.

Before, a five-second annoyance might have had a twenty-minute solution, but finding that solution could mean an evening of Google results, old forum posts, Reddit threads, abandoned GitHub issues, and experiments that went nowhere.

The uncertainty was enough to make ignoring the problem rational.

Now I can describe the outcome I want in plain language and get to the useful part much faster. I still decide what gets installed, what permissions it gets, and whether the answer makes sense.

It does the digging.

I stay the one deciding what actually changes. But it can take the solution and implement it. You can grant access to another application, and it can change the settings. That is the magical part.

The unglamorous, genuinely useful version of AI: compressing the research phase of a small annoying problem enough that the twenty-minute fix stays a twenty-minute fix instead of quietly becoming a Saturday.

The distinction that matters

Not every annoyance deserves twenty minutes.

This is where advice like this usually goes wrong. It becomes “optimize everything,” which is really just permission to spend Saturday installing apps you will abandon by Thursday.

The line I try to hold is between the twenty minutes that retires a problem and the twenty minutes that adds one more thing to maintain.

Three questions before you spend it:

How often do I actually hit this? A few times a month, let it go. Dozens of times a day, and you have been paying that toll for years without ever counting it.

Does the fix use something I already own? Not always possible, but this is where some of the highest returns hide. The unopened box. The feature never enabled. The setting you did not know existed. You already paid for it. The only remaining cost is attention.

If it breaks in six months, what happens? A good fix degrades back to how you work today, which is exactly what both of mine do. A bad fix becomes a dependency, and then you have a new problem wearing a solution’s clothes.

What to do with this

Here is the assignment, and it is deliberately small.

Between now and next week, notice one thing that irritates you more than once a day. Not the big broken process. The small one. The click you always make twice. The file you always go hunting for. The shortcut your hands leave the keyboard to press.

Write it down the moment it happens, because you will not remember it later. That is exactly why these things survive for years: too small to remember, too frequent to matter.

Then give it twenty minutes and whatever you already own.

And if you would rather not troubleshoot it alone, this is something I would like to try for paid subscribers.

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Send me one tech pain point to start.

The click you make twice. The app that will not behave. The thing you bought and never set up.

I will write back with what I would try, and when it is the kind of problem that is easier to show than describe, I will send a short screen recording instead.

I will also periodically write about some of the more interesting pain points readers send in or leave in the comments, along with the fixes that worked.

That is the part worth sitting with.

Neither fix required new hardware, a new subscription, or a rebuilt workflow. One was equipment already sitting in my house. One was a free utility somebody published on GitHub for no reason other than the same thing annoyed them.

The technology was already here.

What was missing was twenty minutes and the willingness to stop treating the annoyance as too small to fix.

Which brings me to what is next on the list.

I own an expensive digital camera that spends most of its life being an expensive object.

It can be used as a webcam.

Twenty minutes, a cable, and the right software would put it on every Zoom call I take, and I have quietly been hoping that looking slightly more cinematic on Zoom might take fifteen years off me.

I will report back.

But I suspect this is where we find the limits of what technology can actually fix.

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Gloria Steinem died Wednesday at her home in New York City. She was 92. The announcement came from her own Instagram account and her foundation’s, and it said she kept working for equality until the very end. Secretary Hillary Clinton, paying tribute, put it better than I could: “She pushed open doors not just for herself, but for literally millions of women behind her…..”

What I want to write about is narrower, and it is one thing I know how to do, which is read the law. Because here is what I have come to believe after a few years of representing people in front of the IRS: statutes are a confession. They’re where a society writes down what it assumes and then charges money on that assumption. And the assumptions about women (and others) are still sitting in the Internal Revenue Code, some of them in the past tense, some of them very much not.

First, the personal part

I would not have a tax practice without women.

My Family

My great-grandmother, who always thought I was capable of anything and always wanted me to succeed in business. Sadly, she didn’t live long enough to see that happen.

My grandmother, a retired enrolled agent. That’s how I even knew what an EA was. As a child, I witnessed her tirelessly advocate for her clients and represent them before the IRS. She worked extremely long hours in an era that lacked technology and most certainly didn’t see women as equal.

My mother, who has always been my biggest supporter. From good to bad, she is always there to listen or go to war on behalf of her children if needed.

My sister Hollie, who works alongside me. EA, MBA, amazing mother, and the person who catches the things I may not think about. No version of The Youngblood Group functions without her.

My friends

I wouldn’t stay sane (okay, fine, semi-sane) without the women in my life.

Meg (who is not in tax) and I text a lot, at strange hours, about a wide range of topics. She also does a lot of my editing for writing for publications. It is nice to have a friend outside of the industry so you can get a different perspective.

Natalie taught me so much about real estate but has also, over the years, given me unique perspectives on various world issues I wouldn’t have considered.

Shannon and I host a podcast together, an idea that arose over good vegan food and talking about the troubles of the industry. We also went through the USTCP process together (we’re still waiting on admission). Shared trauma, perhaps?

I met Sherrill a few years ago at a dinner. She convinced me I could do something very hard and always gives her honest opinion. Honest, straightforward feedback is rare these days, and I treasure it.

Amber was perhaps the first tax professional I became friends with. I will never forget my first tax conference, and being the very introverted person that I am, she made sure I talked to people. She has also given advice and referrals, and has been known to vigorously defend her friends in social media “discussions.”

Now, therapists aren’t our friends; they are our therapists. However, I think we should all have one, and Candy has certainly contributed to my success.

“Not that long ago” is doing a lot of work

Here is the thing most people, including most tax professionals, have no feel for: the legal architecture that made women financially dependent was not dismantled in some long-forgotten era. It came down in the lifetime of people who are currently working.

Let’s look at the actual dates.

The Equal Credit Opportunity Act was signed on October 28, 1974, and took effect one year later. It did not give anyone a right to credit; nobody has that. It made it unlawful to discriminate in a credit transaction on the basis of sex or marital status. (Race, color, religion, national origin, age, and additional protections came in the 1976 amendments.) Before that, federal law did not prohibit a lender from denying a woman credit or pricing it higher because she was a woman or because she was unmarried. Banks routinely required a male cosigner, a husband or a father or a brother, on applications for credit cards, loans, and mortgages. Regulation B, which gave it teeth, took effect alongside the statute in 1975.

The federal Fair Housing Act did not prohibit sex discrimination in housing until August 22, 1974, when a provision of the Housing and Community Development Act of 1974 added “sex” to its protected classes. The original 1968 Act covered race, color, religion, and national origin. For six years, a landlord could turn a woman away, or charge her more, on the basis of sex, and the Fair Housing Act had nothing to say about it.

Billie Jean King won Wimbledon six times in singles and holds a record twenty titles there overall. In 1971 she became the first woman athlete to earn more than $100,000 in a single season. And in the early 1970s, by her own account, she still could not get a credit card in her own name. Credit ran through her husband’s income, and her husband was a law student she was supporting.

You will often hear that women could not open a bank account before 1974. That is not entirely accurate. There was not a federal law that barred women from holding a bank account, but the states and bank policy varied significantly.

What was true is arguably worse, because it was structural rather than statutory. Credit was rationed by marital status as an ordinary, lawful business practice. A married woman’s card was issued as “Mrs. Husband’s Name,” and here is the part that matters: the credit history accrued to him. She could pay every bill on time for twenty years and have no file of her own. So when he died, or when the marriage ended, she was not a person with damaged credit. She was a person with no credit, starting from zero at fifty.

Translation: the law did not have to forbid her from participating. It just had to permit a system in which, when she did participate, the record belonged to somebody else.

Now, let’s talk about some tax implications.

Moritz v. Commissioner: Caregiving, Gender, and the Tax Code

Before the innocent spouse cases, one detour, because it may be the oddest feminist tax case in American law, and it is strange because the taxpayer was a bachelor from Denver.

Charles E. Moritz was a never-married man who worked and cared for his elderly invalid mother, who lived with him and whom he supported. He was an editor for a Philadelphia publishing house, running its western division out of his home in Denver and traveling eleven states to visit authors. In 1968, he paid for nursing help so that he could continue going to work, and he claimed a dependent-care deduction under what was then IRC § 214.

At the time, former § 214 did not make the deduction available to every taxpayer who paid dependent-care expenses in order to remain employed. It drew categories. In substance, the deduction was available to a taxpayer who was a woman, a widower, a divorced man, or a husband whose wife was incapacitated or institutionalized, but only where the care was for the purpose of enabling the taxpayer to be gainfully employed.

That meant the statute could reach a working woman. It could reach a widower. It could reach a divorced man. It could reach a married man whose wife was incapacitated or institutionalized. But it did not reach Moritz: a man who had never married and who was paying for care for his dependent mother so he could keep working.

The Code did not expressly ask who was actually doing the caregiving. It sorted taxpayers by assumptions about who needed relief from caregiving duties to work. The premise was gendered: caregiving was treated as women’s work, and the tax benefit was structured around that assumption.

The IRS disallowed Moritz’s deduction. He took the case to the Tax Court himself, without a lawyer, and lost. On appeal, Ruth Bader Ginsburg and Martin Ginsburg took the case and argued it together, she as a constitutional lawyer building a sex-discrimination strategy, he as a tax lawyer who understood the Code’s mechanics.

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On November 22, 1972, the Tenth Circuit reversed. In Moritz v. Commissioner, 469 F.2d 466 (10th Cir. 1972), the court held that former § 214’s classification violated the equal-protection component of the Fifth Amendment’s Due Process Clause. The Supreme Court declined review, leaving the Tenth Circuit’s decision in place.

The strategy matters because it captures the Ginsburg method in miniature. The vehicle for a foundational sex-discrimination argument was not a woman excluded from the workplace, but a man denied a caregiving deduction. A legal regime built on assumptions about women also confined men. And a court that might not yet see the full injury when discrimination ran in one direction could be made to see it when the same stereotype injured someone on the other side of the line.

Here is a detail that makes the case stranger still. By the time the Tenth Circuit ruled, Congress had already rewritten the statute. The Revenue Act of 1971 removed the sex-based classification from § 214, but only for taxable years after 1971. Moritz’s case was about 1968. He was left to fight over the year when the old rule still applied.

The statutory story did not end there. Former § 214 did not survive the decade. The Tax Reform Act of 1976 repealed it and replaced the deduction with a credit, originally codified as IRC § 44A and now reflected in IRC § 21.

Today’s dependent-care credit under IRC § 21 is framed differently. It applies to employment-related expenses paid for qualifying individuals, including certain dependents who are physically or mentally incapable of self-care, where the expenses are incurred to enable the taxpayer to be gainfully employed. Under those rules, care for an elderly parent may qualify when the statutory requirements are met.

The deduction that assumed care was women’s work did not survive. But Moritz remains important because it exposed the deeper flaw: when law writes stereotypes into tax rules, it does not merely burden the group supposedly being “protected.” It organizes everyone’s life around the stereotype.

Innocent spouse, and who actually walks through the door

When two people file a joint return, § 6013(d)(3) makes them jointly and severally liable for the entire tax. Not half each. Each of them, for all of it. The IRS may collect the whole balance from either one, and it does not care which of them earned the income, wrote the checks, or understood the return.

I want to be fair about this before I go further. Innocent spouse relief cuts both ways. I have represented men on these claims. I have seen cases where the requesting spouse was the one running the scheme and the claim was opportunistic.

The statute is written in neutral terms, and it should be.

But you cannot look at the history of this provision, or at a caseload, and pretend the neutrality is the whole story. For most of the twentieth century, the household model the joint return was built on had one person earning, one person managing the money, and one person signing where she was told to sign. And as we just covered, federal law still permitted creditors to discriminate on sex and marital status, while ordinary credit reporting practices could leave a married woman without an independent financial history of her own.

Put the two dates next to each other. The modern joint return, with income splitting, arrived in 1948. Congress did not prohibit sex and marital-status discrimination in credit until 1974. That is twenty-six years in which a wife could be held personally liable for the entire tax on a joint return while a lender could lawfully turn her down because of her sex or her marriage, and while ordinary credit-reporting practice could leave her with no independent record of her own.

Congress noticed slowly. The first innocent spouse provision came in 1971, in Public Law 91-679. The modern framework, IRC § 6015, dates to the 1998 restructuring act, with three doors: traditional relief under 6015(b), allocation of the liability under 6015(c) for spouses who are divorced, legally separated, widowed, or who have not lived in the same household for the preceding twelve months, and equitable relief under 6015(f) when neither of the first two fits. For those of us in community property states, § 66(c) provides separate relief from the operation of community income rules, generally in non-joint-return cases.

A Name to Know

Cathy Lantz. Her husband was a dentist who went to prison for Medicare fraud. They had been married six years. He told her he would take care of the tax problem. He did not. He asked the IRS for the innocent spouse form, called her “the innocent spouse” in his own correspondence with the Service, and died before he filed it.

By the time she sought innocent spouse relief, she was unemployed and broke. In 2006 the IRS took her $3,239 refund and applied it to a joint 1999 liability that had grown past $1.3 million. That is what finally sent her to file. The IRS did not reject her because the equities were weak. It conceded she would have qualified. It rejected her because she missed a deadline, a two-year deadline the Service wrote into its regulations for equitable relief under § 6015(f).

The Tax Court held that deadline invalid, in a divided opinion, with a law school clinic at Valparaiso University handling her case. Congress had put two-year limits directly into §§ 6015(b) and 6015(c), but not into § 6015(f), the catch-all equitable-relief provision. That omission mattered. If Congress had wanted the same deadline there, the Tax Court reasoned, it knew how to say so. Lantz v. Commissioner, 132 T.C. 131 (2009).

The Seventh Circuit reversed. In Judge Posner’s opinion, the agency could impose a filing deadline even where Congress had not written one into the subsection itself. So Lantz lost, not because the case against relief was compelling, but because the court upheld the regulatory time bar. Lantz v. Commissioner, 607 F.3d 479 (7th Cir. 2010).

And the detail I cannot get out of my head is this: in the same opinion that enforced the deadline against her, the court walked through the hardship tools the Service already had. Release of a levy that creates economic hardship under § 6343(a)(1)(D). Currently-not-collectible status. And then the court noted the irony that the Service had already declared the taxes owed by her husband, the crooked dentist, currently not collectible, and that she was entitled to the same relief a fortiori, with no deadline for seeking it. In other words, the system had tools for mercy. It had used one on him.

She lost. But the IRS later abandoned the two-year deadline for equitable relief anyway. In Notice 2011-70, the Service announced that § 6015(f) requests would no longer be barred merely because they were filed more than two years after the first collection activity. Rev. Proc. 2013-34 carried that approach forward. Then in 2019 Congress wrote it into the statute itself. The Taxpayer First Act added § 6015(f)(2): for unpaid liabilities, a request is timely if made within the § 6502 collection period; for amounts already paid, within the refund-claim period. The rule that beat Cathy Lantz no longer controls.

Strangely, its two-year language is still sitting in the 2002 regulations, even though the IRS stopped applying it to § 6015(f) claims in 2011 and Congress superseded it in 2019. (Treasury and the IRS withdrew the long-pending proposed § 6015 regulations in December 2025 rather than finalize them. The core framework today is the statute, the 2002 regulations apart from that obsolete deadline, and Rev. Proc. 2013-34.)

She lost the case and helped win the rule. Which is a very specific kind of unfair.

The arc, laid out:

• 2009: The Tax Court strikes the regulatory deadline.

• 2010: The Seventh Circuit reverses. Lantz loses.

• 2011: Notice 2011-70. The Service abandons the two-year rule on its own.

• 2013: Rev. Proc. 2013-34 rebuilds the equitable framework around abuse and financial control.

• 2019: Congress writes the timing rule into § 6015(f)(2) and generally confines the evidentiary record in Tax Court review through § 6015(e)(7).

• 2025: Treasury and the IRS withdraw the proposed regulations rather than finish them.

Sixteen years. And the woman who started it had $3,239 taken from her.

Rev. Proc. 2013-34. This one is quieter, and I think it is the most important administrative development in this area in twenty years. It changed how the IRS accounts for abuse and financial control by the non-requesting spouse. Under the older framework, knowledge of the item giving rise to the understatement could be a serious obstacle to relief. Under Rev. Proc. 2013-34, actual knowledge is not weighed more heavily than other factors. And if the non-requesting spouse abused the requesting spouse, or controlled the household finances by restricting access to financial information, and that abuse or control kept her from challenging the return for fear of retaliation, the knowledge factor can weigh in her favor even if she knew, or had reason to know, of the item.

Read that against the credit history point above.

In 2013, the IRS formally acknowledged that financial control and restricted access to information can fundamentally change how a spouse’s knowledge should be judged.

Thirty-nine years after ECOA. The tax system catches up eventually. It just does it at the speed of a revenue procedure.

What this means at my desk

• Consider the implications of every joint balance for § 6015, and in community property states for § 66(c). Not just the ones someone asks about.

• Before you ask who knew, ask whether there was a valid joint return at all. Signature, tacit consent, and duress can decide the matter before § 6015 is ever reached.

• Ask who signed and who knew, separately. They are different questions, and clients answer them differently.

• Develop the financial control facts, not just the abuse facts. Rev. Proc. 2013-34 gives you room here, and practitioners underuse it because control is harder to document than a police report. Who had online banking credentials. Who saw the mail. Who needed permission to spend.

• Build the administrative record like you expect to litigate it. Since the Taxpayer First Act added § 6015(e)(7), Tax Court review generally rests on the administrative record plus newly discovered or previously unavailable evidence. Treat the administrative record as the case, not as a warm-up.

• Explain joint and several liability during the engagement, not after the notice. It is the single most under-explained concept in a divorce, and most people learn it from a levy.

• Be mindful of conflicts of interest, and do not assume a waiver cures one. Under Circular 230 § 10.29, you can represent both spouses only if you reasonably believe you can competently and diligently represent each of them, the representation is not prohibited by law, and each affected client gives informed consent confirmed in writing (within thirty days, retained for thirty-six months). An innocent spouse claim can make the spouses’ interests directly adverse. Some of these conflicts cannot be waived, and the right answer is often that one spouse needs separate representation.

• Many clients assume that if they are married, then they must file together. I have seen this particularly in older clients who feel like there is something “weird” if they don’t file jointly.

The same fear, in a different room

I said Rev. Proc. 2013-34 was the most important administrative development in this area in twenty years. Here is the part of it that reaches past tax.

In 2013 the IRS conceded, in writing, that a person can know something is wrong and still not challenge it, because challenging it would cost her more than staying quiet. Fear of retaliation is now an accepted reason why an innocent spouse did not speak. It took the Service decades to say that out loud.

We should be able to recognize the same thing in our own profession. Circular 230 holds us to standards of competence and diligence. How we treat other professionals should be a standard we hold ourselves to whether or not anything requires it.

For too many years at conferences and various events, I have heard not only rumors but also direct accounts from women who have been sexually harassed or subjected to unwanted sexual advances in this industry. This has probably been allowed to happen far longer than many of us know. It must stop.

Many of the people it happens to do not speak up, for exactly the reason the IRS finally acknowledged: the cost of speaking out falls on the person who was wronged. Anyone who does choose to speak should be taken seriously and supported. But the burden of cleaning up a profession should not sit with the people it harms. Conference organizers, firms, professional associations, and the rest of us in the room have that obligation. This should never be chalked up to “boys being boys.” (I hate that statement.) This is misconduct we, as an industry, should never tolerate. I am always perplexed when women dismiss it, but I am equally perplexed when men dismiss it.

You should not need to imagine that she is your wife, your daughter, or your mother. A colleague deserves safety and professional respect because she is a colleague, and because she is a person. That is enough.

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Ninety-two

Steinem was 92. She lived to see § 214 repealed, ECOA signed, the Fair Housing Act amended, and a revenue procedure quietly acknowledge that financial control can change how a spouse’s knowledge should be judged.

Most people who spend their lives in this slow fight do not get to see the statutes change.

The changes she did not live to see are ours to make.

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Josh and Shannon get into what actually separates a business deduction from a personal one.

Shannon reports back from the Brass Tax EA Bootcamp and the first year of at-home EA exam proctoring (the metal detector stories are real). Then: why an unlicensed preparer cannot represent you before the IRS no matter what the Facebook group says, how to tell whether a CE speaker actually knows the material, and §162 versus §262 by way of an influencer who deducted the Grammys, a dancer who depreciated her chest, and two business partners who were very sure the Rolexes were ordinary and necessary.

Plus: why the adversarial posture toward the IRS is mostly bad strategy.

CASES

Sami v. Commissioner, T.C. Memo. 2026-69 (Aug. 18, 2026) — An IT manager/social media influencer deducted roughly $97,000 in celebrity meet-and-greets, Grammys and Emmys tickets, and signed Kobe Bryant shoes. The celebrity expenses went down, but the result wasn't a complete wipeout: the court allowed portions of several business expenses under Cohan and credit-card processing fees in full.

Hess v. Commissioner, T.C. Summary Opinion 1994-79 — Yes, that case. Cynthia Hess, stage name “Chesty Love,” successfully treated her surgical implants as depreciable business property. And much of what tax professionals repeat about this opinion is wrong.

WELL, ACTUALLY…

• Hess is not T.C. Memo. 1994-79. It's a nonprecedential small-tax-case summary opinion.
• “Not precedent” does not mean “not citable.”
• She was 56FF in the tax year before the court; the later 56N implants came afterward.
• Sami was a mixed result, not a complete denial.
• Calling Sami “the first influencer case” may be premature.
• The Dinah Shore gown deduction appears to be tax folklore, not a reported case.
• And Suleiman Sami is one person. Suleiman is his first name.

Code: IRC §§162, 262, 7463(b), 67(h)

MENTIONED

Brass Tax Presentations — brasstax.com
AskTomG — asktomg.ai (Disclosure: Josh has a financial interest.)
Tom Talks Taxes — tomtalkstaxes.com
U.S. Tax Court — ustaxcourt.gov

Full show notes, citations, source documents, links, and corrections: wellactually.tax

This podcast is general commentary on federal tax law and procedure, not tax, legal, or accounting advice. Tax outcomes depend on facts. Views expressed are the hosts’ own.

This started as a conversation about books.

Anytime I travel anywhere, there are two things I seek out: independent bookstores and coffee shops. If those two are in the same location, all the better. There is now a third: record stores, because I have fallen in love with vinyl, and the vibe is really cool . But primarily, bookstores and coffee shops.

Shannon Hall and I were in Cleveland, both speaking at NATP Taxposium, which was a really great event. When we weren’t speaking, instead of going to classes, we decided to find other things to do. Obviously, a bookstore and a coffee shop were on the list, and of course a ghost tour. There’s always a ghost tour with Shannon.

Cleveland deserves credit here. Shannon is vegan (which is something I aspire to), which turns every conference city into a small logistical research project, and Cleveland turned out to be genuinely good at it — one excellent meal after another. The Tofu wings were excellent. One exception: a restaurant that had apparently decided dill belonged in every single item on the menu. Not as an accent. As a governing principle. Dill is one of those things that I do not like. I have never liked it, and I probably never will, and I don’t have to.

Somewhere between a cappuccino, a chocolate chip cookie, and a conversation about books, we thought it would be really fun to have a podcast where we talk about books. Then it grew. Because it turns out you cannot get two Enrolled Agents talking about anything for very long before the conversation finds its way to a Tax Court opinion somebody misread, or a vendor claim that doesn’t survive contact with §7216, or the fact that an IRS publication has never once been primary authority. The books stayed. Everything else moved in around them.

So we recorded it.

Well, Actually… is now live on Apple Podcasts, Spotify, and YouTube, and it will be here on Substack too. Episode 1 is up. It’s called “We Passed, We Traveled, We Have Opinions,” which is an accurate summary and also the entire pitch.

What the show is

Shannon Hall is an Enrolled Agent in Long Beach, California, and the president of CSTC (California Society of Tax Consultants). Earlier this year, we both sat for — and passed — the U.S. Tax Court non-attorney exam. We are currently awaiting admission.

The premise of the show is friendly pedantry. Getting the detail right matters. The difference between a primary source and a persuasive one matters. And “I don’t know” is a perfectly good answer as long as it’s followed by “let’s find out.”

That means no hot takes. It means we cite things. And it means that when something we believed turns out not to survive a look at the source, a rule one of us misremembered, a claim the whole profession repeats because the whole profession repeats it, we say so out loud. That's the well, actually.

It also means the show isn’t only about tax. We both read constantly, both work in a profession being reshaped in real time by software that most of its vendors can’t accurately describe, and both have opinions about coffee, ghost tours, and whether hardbacks are still worth buying if you’re going to read the Kindle edition anyway. All of that is in scope.

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What’s in Episode 1

A debrief of a summer that ran through Reno, Cleveland, and New Orleans:

• The Tax Court exam — what it actually takes, what the pass rate looks like, and why you don’t need a master’s in taxation to sit for it

• The AI vendor hall — the gold rush currently happening in conference exhibit spaces, and the §7216 question that most vendors would prefer you not ask

• WISPs and MFA — the data security obligations that a lot of practitioners are still treating as optional

• A five-hour research spiral in a rented house in the desert, which produced the first official well, actually of the series: an IRS publication is not primary authority. It never has been. It can also, it turns out, simply be wrong.

Runtime is about thirty minutes.

Where this is going

A few things we’re planning, in rough order of how soon you’ll see them.

A regular release cadence. Episode 2 is already in motion. The failure mode for new podcasts is not the launch, it’s the six-week gap after the launch.

Guests. This is the part I’m most looking forward to. The profession is full of people who are extraordinarily good at a narrow, difficult thing and almost never get asked to explain it at length. We’re going to have them on and let them talk. We will also have people we respect and make a difference.

More tech and AI, treated seriously. I’ve spent thirty years in tech, and I’ve watched this industry adopt technology in a way that is by turns admirable and alarming. There’s a real conversation to be had about what these tools can do, what they cannot do, and what your professional obligations are when you point one at client data. We intend to have it, repeatedly, with people who know more than we do. But it will be done in a fun and easy-to-understand way. No complex dissertations.

Books. Fiction, nonfiction, the occasional detour into nuclear brinkmanship. This isn’t a bonus segment at the end of the tax talk. It’s the thing the show was originally going to be, and we’re not giving it up.

More snark. Episode 1 is, by design, mostly a debrief — two people catching up after a summer apart. If you came in expecting sharper elbows, fair. They’re coming. Well-intended snark is one of the load-bearing pleasures of this profession, and we were on our best behavior for the first take. That won’t hold. This industry has some toxicity in it, and we will go there. We will also stay firmly PG-13 (also known as 1 espresso martini instead of 2) while we do.

If there’s someone you want to hear from, or a topic you’d like us to explore, please reach out.

One last thing. I have said, out loud, more than once, that I would never do public speaking. I have also said I would never have a podcast. I now teach continuing education, and I am announcing a podcast in the same paragraph, which suggests my predictive accuracy about my own behavior is somewhere below that of a coin toss.

I started speaking because, as a child, I had a speech impediment, and as an adult I got the idea from a book that if you do hard things you don’t want to do, you’ll eventually enjoy it and be better off for it. Also, thankfully, as a child, I had speech therapy (Ms. Sloan). Thanks, Mom.

So if you get tired of hearing me, blame my mother. :)

How to listen

• Apple Podcasts

• Spotify —

• YouTube — https://www.youtube.com/@wellactuallytax

• RSS (for the Overcast, Pocket Casts, and Castro contingent) — https://api.riverside.com/hosting/lTiHAKvf.rss

• Substack — right here. New episodes will land in your inbox with show notes.

• The website — https://wellactually.tax

If you listen and it lands, the single most useful thing you can do is leave a rating on Apple or Spotify.

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Nothing in this podcast constitutes tax, legal, or accounting advice, and no client relationship is formed by listening or by reading. We discuss general principles. Your situation has facts in it. Facts matter.

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Josh and Shannon open the first episode of Well, Actually with the small talk (105 degrees in Texas, an angelic glow in Long Beach) and get to the substance quickly: what they'd change about every tax practice in the country if they had one wish, why "our lawyer says 7216 doesn't apply" is a red flag, how to actually vet an AI vendor, and what OPR's guidance on artificial intelligence does and doesn't say about billing.

Then a detour through ghost tours, continuation school, GEDs, acting degrees, and whether you need a master's in taxation to sit for the USTCP exam. (You don't.)

The episode ends on the first official well, actually of the series, courtesy of a five-hour research spiral in a rented house in the desert: an IRS publication is not primary authority. It has never been primary authority. It can also, it turns out, simply be wrong.

Interested in the USTCP Exam? Check out www.taxcourtexam.com

If you’re old enough to remember 2024 and 2025, you may recall the seemingly endless waiting for courts and FinCEN to decide the fate of beneficial ownership information reporting.

BOI reporting became something of an interest of mine. I still believe the underlying idea made sense. I also hoped the filing requirement might discourage people from forming unnecessary entities, or, at the very least, encourage them to obtain competent advice before doing so.

But for most businesses, BOI reporting is now officially over.

In an August 11 final rule, the Financial Crimes Enforcement Network formally exempted U.S. companies and U.S. persons from BOI reporting. The rule becomes effective upon publication in the Federal Register.

What Happens to Information Already Filed?

FinCEN says it will delete previously submitted information when it reasonably believes the information relates to a U.S. person. This includes information about:

• Beneficial owners;

• Company applicants; and

• Individuals who obtained FinCEN identifiers.

According to FinCEN’s new frequently asked questions, affected individuals do not need to request deletion. FinCEN will identify U.S.-person information using indicators such as a U.S. passport or driver’s license and remove it from the BOI database.

FinCEN ID holders who are U.S. persons also have no obligation to update or correct the information they originally submitted to obtain their identifiers.

Who Still Has to Report?

The Corporate Transparency Act has not disappeared entirely.

An entity may still be a “reporting company” if it:

1. Was formed under the laws of a foreign country;

2. Registered to do business in a U.S. state or Tribal jurisdiction; and

3. Does not qualify for another exemption.

Even then, the foreign reporting company is generally required to report only information about foreign beneficial owners. It does not report U.S. persons as beneficial owners, and U.S. persons are not required to provide their information for the report.

The final rule also eliminates the requirement for foreign reporting companies to identify U.S. persons who acted as company applicants—that is, individuals who assisted the foreign entity in registering to do business in the United States.

FinCEN’s FAQs explain that a foreign entity registered to do business in the United States generally must file its initial BOI report within 30 calendar days after receiving notice that its registration is effective. Foreign reporting companies must continue to evaluate whether another regulatory exemption applies.

What Should Firms Do Now?

For tax and accounting professionals, this ends the issue for domestic clients. They do not need to file.

Firms should consider:

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• Removing BOI filing reminders for domestic companies;

• Disabling automated BOI follow-up emails;

• Updating client organizers, engagement letters, checklists, and website guidance;

• Advising prior filers that they do not need to update or correct their reports; and

• Preserving a separate review process for foreign entities registered to do business in the United States.

Clients who previously filed do not need to submit another report to withdraw their information or claim the new exemption.

A Predictable Ending to a Very Loud Debate

None of this should be particularly surprising. The current administration had already made clear that BOI enforcement against U.S. companies and U.S. persons was not a priority.

Before that, however, BOI reporting became a hotly debated subject on social media. Some viewed it as government overreach. Others argued that helping clients prepare BOI reports constituted the unauthorized practice of law.

In the vast majority of cases, it did not. I thought I would say that again, because I know I said it 1,000 times in 2024 and 2025.

Helping a client gather information and submit a government filing does not automatically become the practice of law merely because the filing concerns a legal entity. As with many professional-services questions, the answer depended on what assistance was being provided, not simply on who clicked the submit button.

The Bottom Line

BOI reporting is over for U.S. companies and U.S. persons. Domestic entities have no filing obligation, prior filers have no continuing update obligation, and FinCEN says it will delete the U.S.-person information it previously collected.

The remaining reporting population consists primarily of certain foreign entities registered to do business in the United States, and even those entities generally report only their foreign beneficial owners.

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Lately I have become interested in a word that we do not use nearly enough.

Not kindness.

Not diplomacy.

Not competency. (Hello Circular 230 §10.35)

Sycophancy.

The trading of truth for approval.

I always thought sycophants were easy to identify. Caricatures in books, like the courtier who is all too eager to laugh at the king’s jokes or the employee who agrees with every idea from their boss.

I have begun to wonder if the modern version is far more subtle and is becoming more accepted, to the point of being rewarded.

Think about the incentives around us.

Social media rewards agreeing with your audience. The algorithm wants engagement above all. Influencers learn that certain opinions and ideas will gain followers, thereby increasing their popularity and putting more money in their pockets.

Professional organizations aren't immune either. Every organization eventually develops gravity. Certain personalities become indispensable. Certain speakers become untouchable. Certain donors become too valuable to challenge. Before long, people begin protecting reputations instead of principles. And once that happens, institutions stop correcting themselves.

The corporate world tends to reward those who tell leadership exactly what they want to hear rather than what they actually need to hear.

Politics? Need I really say much? I could write volumes about my thoughts, but then I might lose some subscribers. Perhaps I am proving my own point.

Friendships aren’t immune, because we often surround ourselves with people who reassure us and tell us what we want to hear rather than tell us the unvarnished truth.

None of this requires someone to lie.

It makes honesty more costly.

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This is how a culture of sycophancy takes hold.

It is not through one dramatic act of cowardice but through thousands of small calculations.

“Should I really say something?”

“This is wrong, but it isn’t my battle.”

“This will cost me access.”

“I’ll look the other way this time. Next time, though…”

I have seen this play out before. Someone reports serious misconduct, and somehow the institution’s attention shifts from the alleged conduct to the character, motives, or behavior of the person who reported it. The complainant becomes the problem.

Comedian Ricky Gervais has a quote that resonates with me:

“Just because you’re offended doesn’t mean you’re right.”

I like the quote because discomfort is not evidence that something is false. Nor is offense evidence that something is true. The question is whether we are willing to examine a claim honestly when doing so is uncomfortable.

Can we tell the truth when there is something to lose?

Perhaps the most fascinating example is artificial intelligence (AI).

One of the problems AI companies now openly discuss is “sycophancy.” Left unchecked, AI becomes too eager to agree with the user. It flatters. It validates. It mirrors beliefs instead of examining them.

Think about that for a moment.

We built machines using human conversations.

One of the first human habits these systems learned to reproduce was our desire to be liked.

Isn’t it ironic?

Perhaps AI is not showing us something foreign. Perhaps it is holding up a mirror.

It may tell you your reasoning is correct.

That your position is well supported.

That there is a case directly on point.

When there isn’t.

I’ve always admired impressive people.

The successful.

The wealthy.

The expert.

But as I slowly drag closer to being forty-five, I’ve had an epiphany.

I have become much more interested in intellectually independent people.

The person who can respectfully disagree with the CEO.

The board member willing to say, “This is wrong.”

The friend who says, “That wasn’t your best. Here’s what worked and what didn’t.”

The colleague who stands up for what is right even if it isn’t popular.

Lately, I have been reading Marcus Aurelius. He wrote something that feels increasingly rare today:

"If anyone can refute me, show me I'm making a mistake or looking at things from the wrong perspective. I'll gladly change. It's the truth I'm after."

Today, changing your mind is often seen as a weakness. Questioning your own side can be treated as betrayal or disloyalty. Certainty is rewarded. Humility rarely is.

Agreement is rewarded, but honest dissent often carries a cost.

Maybe this is why true independence has become so valuable.

I’m becoming less interested in people who are always right.

I’m much more interested in people who are willing to be wrong.

People who can say:

“I changed my mind.”

“I don’t know.”

Or perhaps the hardest sentence of all:

“I think you’re wrong.”

Said respectfully and honestly, without calculating what it might cost.

I don't believe I'm immune to this. Every one of us enjoys approval. Every one of us hesitates before saying something that could cost us professionally or socially. The question isn't whether we're tempted by sycophancy. The question is whether we recognize the temptation before it becomes our character.

Stoicism has reminded me that courage is not measured by how loudly we speak, but by what we are willing to risk in service of what is true.

Every generation has had its sycophants.

What has changed, I think, is what we reward.

Algorithms, organizations, politics, media, and yes, even AI increasingly reward the same instinct:

Tell people what they want to hear.

Avoid discomfort.

Protect the powerful.

Preserve access.

Perhaps history won’t remember us for the opinions we held.

Maybe it will remember whether we possessed the courage to tell the truth when agreement was easier.

Because, in the end, integrity is not measured by what we profess, but by what we are willing to risk for the truth.

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A few things:

1. If you haven’t checked it out yet, be sure to check out AskTomG.AI. This is one of those projects I wake up excited to work on. We have spent a ton of time and brainpower on this, and it will only get better. If you have questions, please reach out to me.

2. I am excited to be speaking at the annual NYSSEA conference in October. It is one of my favorite conferences.

3. Well, actually - a podcast venture with Shannon Hall, EA, is launching later this month. Check out the website for more details!

4. I will be at the IRS Forums in San Diego, CA, in September.

5. I have several webinars and workshops coming up for NATP. You can check those out here.

Tom Gorczynski and I already covered the rules. We wrote about the Section 7216 disclosure and use framework, and we covered OPR’s guidance on AI in federal tax practice over on Tom Talks Taxes. If you have not read those, start there. I am not going to repeat them.

Tom Talks Taxes

OPR Issues Guidance on Practitioner Use of AI

The IRS Office of Professional Responsibility quietly sent an email to practitioners about the ethical issues of using artificial intelligence (AI) tools in tax practice…

Read more

3 months ago · 13 likes · 5 comments · Thomas A. Gorczynski and Josh Youngblood, EA, CRETS

This article is the other half of the conversation. You know the rules apply. Now what do you actually do? Here is what I do, with examples you can use or adapt as needed.

1. Sanitize Before You Type

The single highest-value habit. Before anything goes into an AI tool, strip it of identifying information. Not just the name and Social Security number. Anything that could reasonably identify the client when combined.

Here is what that looks like in practice. Say you are researching a potential filing requirement.

Do not type this:

“My client Kirby Rockefeller, who lives in La Jolla, California, SSN ending 4821, received an inheritance of $700,000 from his uncle in Portgual. His uncle was not a US citizen, Kirby is. Does he have filing requirments? He also has $450,000 of real estate investment income.”

Type this instead:

“Client received an inheritance from a foreign relative. Are there any filing requirments?”

Same useful output. Zero client data disclosed. Notice what got removed: name, SSN, exact dollar amount, city, and occupation. For example, A dental hygienist in Dallas married to a TI employee who sold RSUs in 2023 is not anonymous. It is a person with a name that takes one LinkedIn search to find.

My rule: if the prompt could survive being read aloud at a conference without anyone identifying the client, it is clean. If you hesitate, it is not.

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2. Build a Verification Step You Cannot Skip

Every citation gets verified before it leaves your office. Not spot-checked. Verified. Here is my actual workflow for anything AI-assisted that contains authority:

Pull the cited case, code section, or revenue procedure from the actual source. Tax Notes, the Tax Court’s DAWSON system, uscode.house.gov, or eCFR. Confirm it exists. Confirm it says what the output claims it says. Confirm it supports the argument I am making, not just the topic I am discussing.

That third check is the one practitioners skip. A real case cited for the wrong proposition is as bad as a fake case.

Make this physical if you have to. I know practitioners who print AI-assisted drafts and initial next to each citation as they verify it. That sounds tedious. It takes ten minutes.

You could also use an AI tool that gives you that information. Not to self-promote, but AskTomG.AI does exactly. You get the citations, the links to the citations, and you can build your research memo. You make the judgment call. It also now has a research library if you’re looking for a specific code cite, or just want a more traditional search.

3. Interrogate Your Vendors Like They Work for You

Because they do. Before any AI tool touches practice work, I want written answers to five questions:

Is my input used to train the model, and can I turn that off? Where is the data stored and for how long? Who at the vendor can see my prompts? Is there a business tier with a data processing agreement?

Here is the example that makes this concrete. The consumer version of most AI chatbots uses your conversations for model training by default or buries the opt-out in settings. The business and enterprise tiers typically exclude your data from training contractually. Same model. Same interface. Completely different risk profile. The price difference is usually the cost of one client lunch per month.

If you cannot get answers, that is an answer. Under the FTC Safeguards Rule (16 C.F.R. Part 314), you are required to assess your service providers, and an AI vendor holding your prompts is a service provider. Document what you asked, what they answered, and when. Put it in your files. A reasonableness standard rewards people who can show their work.

4. Write the AI Section of Your WISP

I know, you are probably sick of the word WISP. But, your Written Information Security Plan should answer four questions about AI: which tools are approved, who may use them, what data may be entered, and what happens when someone breaks the rule. Here is sample language you can adapt:

“The firm has approved the following AI tools for practice use: [tool, tier, and account type]. All other AI tools are prohibited for any work involving client information. No client-identifying information may be entered into any AI tool without a documented exception approved by [name]. Identifying information includes names, taxpayer identification numbers, addresses, exact dollar amounts, employer names, and any combination of details that could reasonably identify a client. All AI-assisted work product containing citations or calculations must be independently verified before delivery to a client or submission to any taxing authority. Violations must be reported to [name] within 24 hours and will be treated as a potential security incident.”

Five sentences. That is genuinely most of it. The firms that get hurt will not be the ones with imperfect policies. They will be the ones with no policy, because no policy means no training, no accountability, and no evidence of reasonable safeguards when someone asks.

5. Train Your People With Scenarios, Not Slides

A policy nobody understands is decoration. Skip the hour of slides and run fifteen minutes of scenarios at a staff meeting. Here are three I would use:

A staff member wants to paste a client’s bookkeeping export into a chatbot to categorize transactions. Allowed? (No. Bank data is loaded with identifying detail: payee names, locations, amounts. Sanitizing a full export is impractical, so this needs an approved tool with a data agreement, or it does not happen.)

A staff member uses AI to draft a penalty abatement letter with no client details, then adds the specifics in Word afterward. Allowed? (Yes. This is the pattern you want. Generic in, specific out, on your own machine.)

A staff member asks AI to summarize a Tax Court case and includes the summary in a client memo without reading the case. Allowed? (No. The drafting was fine. Skipping verification was not.)

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If your team can sort those three correctly, your training worked. Get a signed acknowledgment and calendar it annually.

6. Keep the Data You Feed AI Behind the Same Locks

An overlooked one. AI tools are accounts, and accounts get compromised. If your chatbot history contains months of practice prompts, that history is now sensitive data sitting behind a password. Treat the account accordingly: a unique password from your password manager, multi-factor authentication turned on, and a passkey if the vendor supports it. Review the connected devices and active sessions occasionally, the same way you should with email. And periodically delete conversation history you no longer need. Data you do not retain is data nobody can steal.

7. Let AI Inform. You Decide.

The habit that holds the rest together. AI is excellent at surfacing authority, organizing facts, drafting language, and pressure-testing an argument. It does not exercise professional judgment, and nothing about your obligations lets it. This is exactly how we built AskTomG.AI: the tool informs, and the practitioner retains every decision under Circular 230.

The practical example: when AI gives me an answer on a representation question, I do not ask “is this right?” I ask “where would this break?” Then I go verify the load-bearing authority myself. The tool sharpens my thinking. It does not replace it. The day you catch yourself forwarding an AI answer to a client without that step is the day to reread everything above.

Pick the two that close your biggest gaps. If I had to choose for you: sanitize your prompts starting with the very next one, and send your primary AI vendor the five questions from item three. Both cost nothing. Both are documentable. Both move you from “I use AI” to “I use AI responsibly,” and that distinction is the whole game.

The tools are worth it. I would not run my practice without them at this point. But the trust your clients place in you predates the technology, and it will outlast whatever tool you are using this year. Protect it accordingly.

Have questions? I know tech questions can sometimes be sensitive and you may not want to publicly post them, so send me a message.

I am going to try something this week that I have been meaning to do for a while.

For Paid Subscribers: (If you aren’t a paid subscriber, you can upgrade below)

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Drop your questions in the comments, and I will answer as many as possible.

Ask me about anything in these lanes:

• IRS representation. Keep it general, not specific to your client’s facts. I cannot give advice on a case I am not engaged in. But how a process works, how I would think about an approach, what I wish I had known earlier, all fair game.

• Practice management. Pricing, engagement letters, workflow, saying no, the stuff nobody teaches you.

• Technology and security. The tools I actually use, what is worth the money, how I think about the FTC Safeguards Rule, and keeping client data safe.

• Building a practice. How I got here, what I would do differently, what the first few years actually looked like.

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Where to find me this summer

Right now I’m at NATP Taxposium in Cleveland, Ohio. So far, Cleveland has been a fun city. Taxposium has been great. Yesterday I talked about what to do when you make mistakes in your practice. Today we will discuss digital asset crimes, and tomorrow we will discuss cybersecurity. Last night I went on a ghost tour and learned about the city's history.

Thursday, it is back home for a while. The next conference for me is NYSSEA in Saratoga Springs, NY. I will be discussing IRS penalty abatement and co-teaching a class on tech practice automation with Matt Metras, EA, which I am very excited about. The speaker lineup is really great!

You can watch this video below for more info:

NYSSEA Invite

I hope to see you there!

One more thing

If you have not seen it yet, Tom Gorczynski (Check out his Substack, Tom Talks Taxes) and I built AskTomG.AI. It gives tax professionals fast access to solid information without rendering judgment. It informs. You decide. That was the whole point. The practitioner keeps the call, which is exactly where Circular 230 says it belongs.

Take a look at AskTomG.AI. We love getting user feedback and are always improving the product.

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A plain-English guide for people who have never touched it

Two kinds of people are dominating the AI conversation right now, and they are both loud.

The first is the gatekeeper. The tech person, or the consultant, or your family member who works “in computers,” who has decided that AI is far too complicated for you to touch without supervision. Every question gets answered with three more warnings. Every use case comes with a framework, a caution, and a lecture. The subtext is always the same: this is complicated, you are not, call me.

The second is the person at the other end of the bar. The one pasting everything into a chatbot at 11 p.m. with the enthusiasm and judgment of someone six drinks in. Company financials. A customer list. Their kid’s medical records. Straight into a free tool whose terms of service they have never opened. When you ask about privacy, they shrug. Nothing bad has happened yet. They believe AI is their confidant.

I have spent around 30 years in IT and another career in tax, a profession where mishandling data is not embarrassing; it can be a federal crime. (Yes, I know, fear mongering, some say, but I do not write the laws, I just write about them.) So I am allowed to say this: both of these people are wrong. The gatekeeper is wrong because this technology is learnable by anyone who can read, and you do not need permission to learn it. The drunk uploader is wrong for reasons ranging from embarrassing to career-ending, depending on what was pasted.

Between them sits everyone else. The person who hears “AI” forty times a day and could not explain what it actually is if a friend asked. The person nodding along in meetings, hoping nobody calls on them. This piece is for that person. Whatever you do for a living, whatever your age, whatever your comfort with technology. No jargon without a definition. No hype. No doom. No invoice. Just what the technology is, what the big tools are, how the pieces fit together, and what to do with it in your first week.

A Quick Programming Note

Some of you opened this expecting a tax article. Fair. Here is the plan for the next couple of months: I am alternating. An AI topic one week, a tax topic the next. Somewhere along the way the two are going to intersect, because in this profession they already do, and those weeks should be interesting.

This is still Josh & Taxes. The taxes are not going anywhere. But this technology is changing how everyone works, not just tax professionals, and I have spent too many years straddling both worlds to pretend otherwise. If a given week is not for you, forward it to someone it is for. Today’s issue is built for exactly that. Send it to the person who keeps asking you about AI because you are “the tech one,” or to your parents, or to that one coworker. They do not need to know anything about taxes. They just need to be curious.

Now, the actual article.

What AI Actually Is

Start with what it is not. It is not a robot. It is not a search engine. It is not a digital person with opinions and feelings. And despite what half your feed implies, it is not magic.

The AI everyone is talking about right now is a specific technology called a large language model. Here is the plainest explanation I can give you.

Take an enormous amount of text. Books, articles, websites, documentation. Feed it into software that studies the patterns in that text until it becomes extraordinarily good at one task: predicting what words should come next. That is the core mechanism. Prediction.

Your phone already does a primitive version of this. Type “thank you for your” and it suggests “time” or “help.” A large language model is the same idea scaled up by a factor that is hard to comprehend. And at that scale, something surprising happens. A system built to predict the next word turns out to be able to draft a letter, summarize a contract, explain a concept at a fifth-grade level, plan a week of meals around what is already in your refrigerator, and critique your reasoning in a conversational way.

Nobody fully expected that. Capabilities emerged that few predicted, which is why the last few years have felt so sudden. Although maybe it should not have surprised anyone. Humans are very predictable.

So here is the working definition I want you to carry around: modern AI is software that has read more than any human ever could and can generate useful text on demand. It is a very well-read assistant with no judgment, no credentials, and no accountability. That framing is useful, because you already know how to work with a person like that. You give clear instructions. You review the work. You never let them sign anything.

The Big Three

There are dozens of AI tools. For a beginner, three matter. They are more alike than different, and everything in this article applies to all of them.

ChatGPT, made by OpenAI. The one that started the frenzy in late 2022 and the name most people use for the entire category, the way people say Kleenex when they mean tissue.

Gemini, made by Google. Woven into products you already use. If you have noticed AI summaries in Google search results or suggestions appearing in Gmail, you have already met Gemini, whether you wanted to or not.

Claude, made by Anthropic. It is all the rage right now. I use it because it handles nuance well, it writes like an adult, and Anthropic takes safety and data handling generally more seriously than most of the industry. (The bar is low.)

Here is the part that should lower your anxiety: you do not have to pick the right one. All three work the same way. You type, they respond. All three have a free tier. All three have an individual paid plan in the neighborhood of twenty dollars a month. The skills you build in one transfer directly to the others. Choosing between them is like choosing between cars. Real differences exist, people have loyalties, and a beginner should stop agonizing and just start driving one.

The Vocabulary

Eight terms. Learn these, and every AI conversation gets easier to follow. I am sure someone reading this is already typing “well, technically.” Here is the deal. I want people to learn something. I am not here to prove I am smart or that I have all the answers.

AI (artificial intelligence). The umbrella term for software performing tasks we normally associate with human intelligence. Broad enough to be nearly useless in conversation, which is why the next term exists.

Generative AI. AI that creates new content. Text, images, audio. ChatGPT, Gemini, and Claude are generative AI. The fraud-detection system at your bank is AI but not generative.

LLM (large language model). The prediction engine described above. The technology under the hood of all three tools.

Model. A specific version of that underlying brain. Each company makes several, and the version names change constantly. Ignore them. You will pick one from a dropdown menu and mostly never think about it again.

Prompt. Whatever you type into the box. The single most important skill in all of this is writing better prompts. Not coding. Not math. Writing clear instructions, which is a thing you already do every time you ask anyone for anything.

Context window. The tool’s working memory within a single conversation. Everything you have typed, everything it has answered, every file you have uploaded. It is large, but it is not infinite, and it does not automatically carry over when you start a new conversation.

Knowledge cutoff. The model was trained on text up to a certain date and does not inherently know what happened after. Most of these tools can now search the web to fill the gap, but you should always assume an AI’s built-in knowledge has an expiration date. Prices change. Laws change. People change jobs. The model may not know.

Hallucination. The industry’s polite term for the model confidently making things up. A fake statistic. A book that does not exist. A quote nobody ever said. Hallucinations are not rare glitches. They are a known behavior of the technology, built into how prediction works, and they are the single biggest reason the verification habit I describe later is not optional.

The Layers

People get confused about these tools because they conflate four different things: the brain, the meter, the doorway, and the furniture. Every one of the big three stacks the same way.

Layer one: the model. The brain itself. Each company offers a fast, capable default model and a heavier, more powerful one for complex work. As a beginner, use whatever is selected when you sign up. Model shopping is a hobby for later.

Layer two: the plan. The meter. How much you can use the tool, and which models you can reach. Free plans are real, working versions with daily usage limits, not crippled demos. The roughly twenty-dollar monthly plans buy far more usage and the stronger models. Start free. When you hit the usage wall and find yourself annoyed, that annoyance is your signal to consider paying. You will hit it. We all do.

Layer three: the app. The doorway. The same tool is reachable through a website, a desktop app, and mobile apps. There are also developer doorways, such as an API (application programming interface) that lets programmers build the AI into their own software. When any product tells you it is “powered by AI,” it usually means the company built on one of these doorways. You do not need that layer. Start with the website.

Layer four: the features. The furniture inside. Conversations, file uploads, and workspaces, covered next. Features vary by tool and plan and change monthly. Do not try to keep up. Learn three.

Keep the layers separate in your head and the landscape stops being confusing. When someone says “we built it on the API,” that is layer three. When they complain about hitting limits, that is layer two. When they rave about some new capability, that is usually layer four.

Three Features Worth Knowing in Week One

All three tools have some version of each of these.

Conversations. Every exchange happens in a chat, and the tool remembers everything within that chat. So you can refine as you go. “Make it shorter.” “Less formal.” “Now turn that into a checklist.” You do not have to get the prompt perfect on the first try. Treat it like a conversation, not a vending machine.

File uploads. Drag a PDF, a spreadsheet, or a photo into the chat and ask questions about it. Summarize this lease. Compare these two insurance quotes. What does this letter from the school actually want from me? This is where the tool stops being a toy.

Workspaces. Claude calls them Projects. ChatGPT and Gemini have their own versions of the same idea: a folder where you store reference material and standing instructions the AI uses in every conversation inside it. A teacher might load a curriculum. A small business owner might load their price list and brand voice. A family might load the details of an upcoming trip. Every conversation in that workspace starts with the context already in place. This is the feature most beginners find last and wish they had found first.

One housekeeping item before you upload anything: open the privacy settings and read them. Every one of these tools has controls governing what happens to your data, including whether your conversations can be used to improve the models. Understand them and set them deliberately. Two minutes now. Do not skip it.

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What to Actually Use It For

You do not need a fancy use case to justify these tools. Start with the unglamorous stuff.

The writing you dread. The email you have rewritten four times because the tone keeps coming out wrong. The complaint letter to the airline. The awkward message to a neighbor. Give the AI the situation, tell it the tone you want, and let it produce a draft. You will edit it. You will still save twenty minutes.

Making long things short. A 40-page contract. A rambling email thread. The 26-page benefits enrollment guide from HR. Upload it, ask for a one-page summary in plain English with the deadlines pulled out, and get on with your day.

Explaining things at your level. This might be the most underrated use of the entire technology. Paste in the confusing thing, the explanation-of-benefits form, the paragraph of legalese, the error message, and say “explain this to me like I have never seen one before.” Then ask follow-up questions. It will not sigh. It will not judge. It has infinite patience for questions you might feel silly asking a person. This is one of my favorite use cases.

Thinking out loud. Stuck on a decision. Unsure how to handle a difficult conversation. Weighing a job offer. Talk it through and ask the AI to argue the other side. It will not make the decision for you. It will make sure you have considered angles you missed at 11 p.m. Please do not mistake this for a therapist. AI can exhibit sycophantic behavior. (Meaning it often wants to agree with you and flatter you excessively.)

The everyday stuff. Meal plans built around what is actually in your pantry. A packing list for a trip with a toddler. A workout plan that accounts for your bad knee. (Not medical advice.) Interview practice before the big one. A birthday toast when you are staring at a blank page. None of this is glamorous. All of it is time back.

And if you have a profession, you have professional uses. I am a tax professional. I use these tools to draft client communications, turn messy processes into written procedures, and translate technical concepts into plain English. Whatever your version of that is, drafting lesson plans, writing listing descriptions, summarizing case notes, it exists, and it probably works better than you expect.

Three Real Examples

Categories are nice. Seeing the actual words is better. Here are three scenarios, with the exact prompt you would type. Notice that none of them require technical skill. They require the same thing good delegation requires: the situation, the audience, and what you want back.

Example one: the airline owes you. Your flight got canceled, the rebooking added a day to your trip, and the airline’s app offered you a coupon. You are angry, and angry first drafts get deleted by customer service. So you type:

“I need a complaint email to an airline. My flight was canceled four hours before departure, the rebooking got me home a full day late, and I paid $180 out of pocket for a hotel. I want a refund of the hotel cost and compensation for the delay. Tone: firm and factual, not angry. Keep it under 200 words. Include a specific request and a deadline for response.”

What comes back is a clean, businesslike letter with your facts organized and your ask stated plainly. You drop in your confirmation number, adjust one sentence, and send it. Ten minutes, start to finish, and the version that went out is the version that gets read instead of flagged. Now, if you have done much traveling, you know this is more about venting and less about getting an actual result.

Example two: the letter that reads like it was written to confuse you. Your health insurer sends an explanation of benefits. It says “this is not a bill” and then lists $2,300 in charges. You take a photo of it, upload it to the chat, and type:

“This is an explanation of benefits from my health insurance. Explain in plain English what happened, what the insurance paid, what I might actually owe, and what questions I should ask if I call them. Assume I know nothing about insurance.”

The tool walks through the document line by line. Allowed amount, what that means. Deductible applied, what that means. Then it gives you three questions to ask on the phone. You did not become an insurance expert. You became a person who can make that phone call without dreading it. Maybe it will help you enough so that you do not have to make that call.

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Example three: the blank page at 9 p.m. Your manager asked you to “say a few words” tomorrow at a lunch marking a coworker’s 20 years with the company. You have been staring at your phone for twenty minutes. You type:

“Help me write a short speech for a work lunch honoring a coworker’s 20th anniversary with the company. Two minutes max. Details: she started at the front desk and now runs the entire operations team, she trained half the people in the room, and she is famous for never missing a deadline and never taking credit. Tone: warm and a little funny, nothing sappy. Give me two versions.”

Two drafts come back. Neither is perfect. But the second one has a structure you like, so you reply “keep version two, but end on the people she trained, not the deadlines.” Thirty seconds later you have your speech. You will still deliver it in your own words. The blank page is gone, and the blank page was the whole problem.

That is the pattern in all three: situation, audience, what you want back. No magic words. No secret techniques. If you can brief a person, you can prompt a machine.

The Guardrails, Briefly

This is where I keep you from becoming the person at the end of the bar.

Do not put confidential information into an AI tool without understanding where it goes. Your company’s financials. Customer data. Other people’s medical or legal details. Anything you would not want forwarded outside the room. If your profession has confidentiality rules, and if you are a doctor, lawyer, therapist, financial professional, or tax professional, it absolutely does, then those rules apply to chatbots just as much as they apply to email. In my field, mishandling client data is a federal crime. Yours may be similar. “Nothing bad has happened yet” is not evidence that you are doing it right. It is evidence that you have not checked. I have said this in person to rooms full of people, and I will keep saying it. I am not trying to scare you. I am trying to keep you off the cautionary-tales slide in someone’s presentation.

And remember the vocabulary word from earlier. Hallucination. If a fact, a statistic, a citation, or a quote is going anywhere that matters, verify it against a real source first. Every time. No exceptions. Every tool in this article will eventually hand you something that does not exist, and it will do so with total confidence. The AI is the well-read assistant. You are still the one who signs.

Your First Week

Here is the assignment. Pick one of the three tools. It genuinely does not matter which. Create a free account. Then pick one piece of writing you have been dreading. Give the AI the situation, the audience, and the tone. See what comes back. Refine it twice. Send the version you edited.

That is it. Not a life overhaul. Not a course. One tool, one task.

The people who are getting real value from this did not start with a grand plan. They started with one small task, got a result, and got curious. Curiosity compounds. So does avoidance.

You do not need the gatekeeper. You do not want to be the drunk uploader. You also do not need to sign up for my AI masterclass. (There isn’t one…. yet?) The middle path is not exciting, which is why nobody is loud about it: learn the basics, keep private information out of it, verify everything, and put the tool to work.

You survived learning email. You survived the smartphone. You will survive this. And this one, unlike the others, might actually be fun.

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There is a sentence I hear more often than I would like. It makes me cringe, actually.

“I have done it this way for twenty-five years and nothing bad has ever happened.”

The person saying it is usually explaining a mistake. Not a small one. Something they have gotten wrong for a very long time, confidently, without interruption. And when I, a colleague, or a friend points it out, that sentence is the shield. Twenty-five years. Or thirty, or forty, or ten. No problems. Case closed.

Here is what that sentence actually means. It means they have done it wrong for however many years and have never been checked. That is not the same as being right. It is the same as being lucky. The two feel identical from the inside, which is exactly the problem.

I could fill this piece with examples of ridiculous tax positions people have held for decades, the erroneous Schedule C to ‘fix an issue’ that has never once been questioned because it has never once been examined. But the more I sit with it, the more I realize the tax part is incidental. The defect is not professional. It is human.

There is a comfortable story people tell about mistakes. That the careful ones do not make them, and the sloppy ones do, and you can tell which is which by the mistake itself.

It is a nice story. It is also wrong.

Everyone makes mistakes. The careful and the sloppy, the expert and the novice, the person with forty years in and the person on their first day. The mistake is not the thing that separates them. What separates them is what happens next.

Because there are two ways to be wrong.

The first way is to be wrong and never find out. To do a thing incorrectly for twenty-five years, protected by the fact that nobody with the standing to correct you ever looked. This is the preparer with the erroneous Schedule C. It is also, if we are honest, most of us about most things. We hold beliefs we have never tested, repeat facts we have never checked, run processes we inherited from someone who inherited them from someone else, and we call the absence of consequences proof that we were right all along. We were not right. We were unexamined. There is a difference, and the difference is luck.

The second way is to be wrong, find out, and own it completely. This one is rarer, and it is the entire point.

What owning it actually looks like

Yesterday, Nina Totenberg, a journalist I have admired for a long time (and still do), made a mistake.

I have followed her reporting for years, the way you follow someone whose work taught you how to understand a thing you care about. Her memoir about her decades-long friendship with the late Justice Ruth Bader Ginsburg, Dinners with Ruth, sits on my shelf. So when I say I felt for this reporter, I mean it.

She misheard a single word leaving the courtroom. Missed the “s” at the end of it. And on the strength of that one unheard consonant, she reported that a Supreme Court justice was retiring when he was not. A small, human, entirely ordinary error, of the kind anyone who has ever moved too fast will recognize.

Then she did the thing you are supposed to do. She owned it completely. In a message to Justice Alito, she called it the worst professional mistake of a fifty-year career, said it was entirely her fault and no one else’s, and personally apologized. She went on the air and said the same thing to the public. No hedging. No blaming the process. No “mistakes were made” in the passive voice that lets everyone off the hook.

That is the harder path, and almost nobody takes it cleanly. When we are caught out, the reflex is to minimize, to contextualize, to find the technicality that makes it not quite our fault. She did none of that. She questioned herself, out loud, and corrected the record. That is not a weakness. That is the strongest thing a person can do when they have gotten something wrong, and it is strong precisely because it is so rare.

And a certain kind of person could not wait to pile on. The mockery was instant. Her age became the weapon of choice, as if being in her eighties were the crime rather than mishearing a word. The people sharpening those knives were not doing the hard thing. They were doing the easy, pleasurable thing that hides its mediocrity behind a costume of rigor.

Here is what I want you to see. Owning a mistake and mocking one are opposites, and they come from opposite places. Owning it is aimed inward, and it costs you something. You have to admit you were the one who was wrong, and then you have to say so, in public, with your name on it. Mockery is aimed only outward. It costs nothing. It produces a small warm hit of superiority and requires no examination of anything, least of all yourself.

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The person dunking on someone else’s honest mistake is not the sharp one in the room. They are the twenty-five-year preparer pointed in a flattering direction, still refusing to ask a hard question about themselves. They have simply found a way to feel correct without ever having to be examined. It is the same failure as the first. It just looks like confidence instead of stubbornness.

People make mistakes. People fix them and move on. That is not the failure. That is the process working. The failure is the refusal to examine, whether it shows up as the person who never checks their own work or the crowd that would rather laugh than look.

I reached out to Ms. Totenberg to express my support and did not expect a reply. I got one.

The only thing I want you to take from this

There are two ways to be wrong, and you get to choose which way you are.

You can be the person who has done it this way for twenty-five years, protected by luck, calling the absence of a consequence a verdict of innocence. Or you can be the person who checks, catches it, and says so plainly when it is your turn to be wrong. Because it will be your turn. It is everyone’s turn eventually. The only question is what you do when you get there.

And extend that same standard to other people, because the day is coming when you will need it extended to you. The person who owns their own mistakes, who checks their own work first, is also the person best equipped to be gentle with someone else’s. They know how easy it is to miss the “s.” They have missed it themselves.

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So the next time you catch yourself reaching for the shield, the twenty-five years, the nothing-bad-has-happened, the it-is-not-really-my-fault, stop. Ask the harder question. Was I right, or was I just never checked?

And the next time you watch someone else own a mistake the way it is supposed to be owned, cleanly, completely, with their name on it, do not reach for the knife.

One day, the mistake is yours, and you will remember who did not reach for theirs.

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The highlight, though, was sitting on a panel with Tom Gorczynski, EA, USTCP, and Shannon Hall, EA, USTCP Elect (awaiting admission), talking about something most of us avoid thinking about until it’s too late: closing your practice, and what it takes to build a firm somebody would actually want to buy. In short, don’t die at your desk. That’s not a plan.

Your firm is probably not sellable. Yet.

Here’s the uncomfortable truth we kept circling back to on that panel: most tax practices aren’t businesses. They’re jobs with letterhead. The value walks out the door every night, drives home, and repeats it the next day. If the firm only works because you personally are in it, you don’t have an asset. You have a very demanding hobby that pays you.

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A sellable firm looks different. It has documented processes, so the work doesn’t live in one person’s head. It has recurring revenue that isn’t tied to a single personality. It has clean books, organized client files, engagement letters that actually exist, and a team (even a small one) that can function when the owner is at a conference in Reno. It has clients who are loyal to the firm, not just to you.

And here’s the part that matters even if you never plan to sell: every single one of those things makes your practice better to own right now. Less chaos. Fewer fires. The ability to actually take a vacation. Building a sellable firm and building a livable firm turn out to be the same project.

If you do nothing else this year, write down how you do the three things you do most often. That’s the start.

Tom and Shannon were, as always, sharp and had a wealth of information. Panels (with the right people) are one of my favorite things to do. It allows you to have a dialogue between everyone, including the audience.

Now for the thing I’m ecstatic about

For the past several months, Tom and I have been building something together, and on Monday, we’re finally announcing it.

AskTom (asktomg.ai) launches Monday, June 15. We’re doing a live launch event on Zoom, and you’re invited:

AskTom Launch Event Monday, June 15 at 1PM PDT. - Register here

AskTom is an AI tax research assistant built specifically for tax professionals. Not a chatbot with opinions. A research tool with receipts.

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Why this is different from asking ChatGPT or Claude a tax question

I know what some of you are thinking, because I’ve heard it in the hallway at every conference this year: “Can’t I just ask Claude or ChatGPT?”

You can. And sometimes it’ll be right. The problem is you won’t know when it isn’t, and “the AI told me so” is not a position you want to defend in an exam or in front of Appeals or worse yet, Tax Court.

Here’s what we built differently:

It only reads the real authority. AskTom works from a curated corpus of primary sources: the Code, Treasury regulations, court opinions, and IRS guidance. It isn’t trained on Reddit threads and SEO blog posts about “tax hacks.”

Every claim comes with a citation. Not a vague gesture toward “IRS rules.” An actual pinned citation you can click, read, and verify yourself. If you can’t trace it to authority, you shouldn’t be relying on it, and neither should your software.

It knows the hierarchy of authority. A Code section, a regulation, a Tax Court opinion, and an IRS FAQ do not carry equal weight, and AskTom is built to respect that. General AI tools treat them all as equally true sentences on the internet.

Your client data never enters the pipeline. Research questions, not client files.

The framing I keep coming back to is Circular 230. Our job as practitioners is to exercise due diligence and make informed judgments. AskTom doesn’t replace that judgment; it gets you to the relevant authority faster so you can apply it to your client’s facts. The research gets faster. The responsibility stays yours. That’s exactly how it should work. It will make you a better tax practitioner.

Trusted commentary kept in its lane.

And it is affordable

The big research platforms can be wonderful, and they’re also priced for firms with a partner track and a holiday party budget. Most of the practitioners I know are solo or small-firm, and they’re making do with Google/Claude/ChatGPT and a “prayer”.

AskTom is priced for actual working practitioners. For most of us, that’s less than one billable hour a month for a tool you’ll use often.

I hope to see you there!

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I am going to try something this week that I have been meaning to do for a while.

For Paid Subscribers: (If you aren’t a paid subscriber, you can upgrade below)

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Drop your questions in the comments, and I will answer as many as possible.

Ask me about anything in these lanes:

• IRS representation. Keep it general, not specific to your client’s facts. I cannot give advice on a case I am not engaged in. But how a process works, how I would think about an approach, what I wish I had known earlier, all fair game.

• Practice management. Pricing, engagement letters, workflow, saying no, the stuff nobody teaches you.

• Technology and security. The tools I actually use, what is worth the money, how I think about the FTC Safeguards Rule, and keeping client data safe.

• Building a practice. How I got here, what I would do differently, what the first few years actually looked like.

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Where to find me this summer

A few places.

Tax Retreat 2026, San Antonio, June 3rd to 6th. I am co-presenting Built This Way: Technology, Infrastructure, and Security Decisions with Aaron Dickerson, CPA, on Thursday from 11:45 AM to 12:45 PM Central.

CSTC Summer Tax Symposium, June 7th to 10th in Reno at the Silver Legacy. I am teaching three sessions this year. Two on Tuesday: one on responding to IRS notices, and one on innocent spouse relief. Then, on Wednesday, I am joining Tom Gorczynski and Shannon Hall for a panel on closing a practice, which is timely given the succession-planning language in the proposed Circular 230 changes. Details and registration

CSEA Super Seminar, June 16th to 18th, also in Reno, at the Peppermill. I am attending this one, not speaking, so if you want to grab coffee and chat, hit me up. Conveniently, it lands right after CSTC, so you can make one trip out of both.

NATP Taxposium 2026, Cleveland, July 13th to 15th. I am teaching three sessions this year, spread across all three days, so I will be there from start to finish. Monday, I am presenting Fixing Common Errors in a Tax Practice. Tuesday is Cryptocurrency and Other Digital Asset Crimes. On Wednesday, I close out with Cybersecurity Best Practices for Tax Professionals. Early registration runs through June 12th before rates go up on June 13th, so if you are thinking about it, now is the time. Use code 26ROCK for $100 off your registration.

Hope to see you at one of the events. Always great to put a face with a subscriber.

Last week, I was getting a facial when I heard how someone had lost access to everything.

My esthetician was telling a story while he worked. He had lost his phone number. Not lost it in the casual sense. Lost it in the sense that someone else now had it. He woke up to dead service one morning, and by the time he figured out what was happening, the attacker had used the number to reset his banking credentials, drain several thousand dollars, and lock him out of every account he owned.

I lay there with my eyes closed and thought about how many people I know would not survive that week.

The attack has a name. It is called port-out fraud, and it is a close cousin of SIM swapping. SIM stands for Subscriber Identity Module, the chip or digital profile that links your phone number to your carrier. The two attacks get used interchangeably, but they are not the same thing. A SIM swap moves your number to a new SIM inside your current carrier. A port-out moves your number to an entirely different carrier. Same outcome either way. The attacker now receives your text messages and phone calls. Your phone goes dead. Theirs comes alive with your life on it.

From there, the script is depressingly simple. Click “forgot password” on a bank login. Receive the verification text. Walk in. Too much consumer security in 2026 still rests on the quiet assumption that the person holding your phone number is you.

The Numbers

This is not a fringe attack.

The Federal Bureau of Investigation’s Internet Crime Complaint Center, known as the IC3, logged 971 SIM-swap complaints and $17.4 million in reported losses in 2025. That is down from the $72.6 million peak reported in 2022, but the decline should not make anyone comfortable. Victims often report the downstream fraud: bank theft, crypto theft, fraudulent credit-card charges, or identity theft. The phone-number takeover can disappear inside the larger police report.

A Princeton study tested SIM-swap authentication practices across five U.S. prepaid wireless carriers and found that all five used authentication challenges that could be subverted.

One of the largest publicly reported examples remains what was widely reported to be the FTX hack in November 2022. More than $400 million in cryptocurrency was allegedly drained after attackers used a SIM-swapping scheme to take control of a target’s phone number. In March 2025, a law firm announced a $33 million arbitration award against T-Mobile over a customer whose cryptocurrency was stolen after a SIM-swap attack that the claim alleged the carrier should have stopped.

You do not have to be a crypto whale to be a target. You just have to have a bank account.

What the Carriers Will Not Tell You

FCC rules adopted in 2023 now require wireless providers to use stronger authentication for SIM-change and port-out requests, notify customers when those requests are made, and take additional steps to protect customers from SIM-swap and port-out fraud. In practice, these protections are often opt-in. The burden is still on you to go find the toggle.

Here is the checklist. Do this today.

1. Turn on port-out and SIM locks at your carrier. (The location of these settings can change.)

• Verizon: Sign in to the My Verizon app. Open Account, then Security settings. Enable both Number Lock and SIM Protection. Number Lock helps block port-outs. SIM Protection helps block SIM and device changes. Do both.

• AT&T: Open the AT&T app. Tap the person icon, scroll to Wireless Account Lock, and swipe to lock. AT&T also describes Wireless Account Lock as a control that disables certain account transactions and account changes.

• T-Mobile: Enable Account Takeover Protection or Port Out Protection for each line, and turn on SIM Protection where available. T-Mobile describes Account Takeover Protection as free protection against unauthorized ports, and its fraud guidance describes SIM Protection as a feature that prevents bad actors from moving your number to a new SIM card or eSIM.

2. Get every account you can off SMS-based two-factor authentication.

SMS stands for Short Message Service, the original text messaging protocol. Two-factor authentication, also called multi-factor authentication or MFA, is the second step a system asks for after your password. SMS as a second factor is the entire reason this attack pays. Move everything that matters to an authenticator app (Duo is my preference), a hardware key, or biometric passkeys. Banks, email, brokerage, social media, tax software, anywhere money lives or identity is verified.

The National Institute of Standards and Technology, known as NIST, does not ban SMS outright, but it treats phone-network-based authentication as restricted. NIST specifically tells verifiers to consider risk indicators such as device swaps, SIM changes, and number porting before sending an authentication code.

3. Set a real account PIN with your carrier.

A PIN, or Personal Identification Number, is the short numeric code a carrier representative will ask for before making changes to your account. Not your birthday. Not the last four of your Social Security number. Not the same PIN you use for your debit card. A unique, random number that exists only to authenticate carrier requests.

4. Lock the SIM itself.

On iPhone and Android, you can require a PIN to use the SIM after a reboot. Turn it on. It is one more layer between an attacker and your number.

Each carrier ships a SIM with a default PIN. Common default include: Verizon and AT&T 1111, and T-Mobile using 1234. Confirm your own default with your carrier before you enter anything, because three wrong attempts lock the SIM and force you to call for a PUK (PIN Unblocking Key) to recover it. Exhausting the PUK attempts can disable the SIM for good. Once you are in, change the default to a number only you know. Left at 1111 or 1234, the lock protects nothing.

Keep in mind that it will require a PIN before connecting to the cellular network. If you lose your phone, that can be problematic because a service such as Find My on iPhones would not update your location until the device reconnects.

5. Stop using your phone number as a recovery identifier.

Wherever a service lets you use app-based recovery instead of a phone number, switch. Treat the phone number as a partially public identifier, not a credential. Because that is what it has become.

But What About...

Two reasonable questions land hard once the toggles are flipped, and they deserve straight answers.

“Could not someone just log into my carrier account and turn the lock off?”

In theory, yes. In practice, the lock raises the bar substantially.

To turn off Number Lock or SIM Protection, an attacker now needs your actual carrier portal credentials, not just enough scraped personal information to social engineer a customer service representative. That shifts the attack from “make a convincing phone call” to “break into a specific online account.” Changes to SIM or port settings may also generate notifications, which give you a chance to catch the attack before the next domino falls. The FCC order requires customer notification for SIM-change and port-out requests.

The catch is that your carrier login is now a high-value credential in its own right. Treat it that way.

• Use a long, unique password from a password manager. Not the one you also use for streaming.

• Turn on MFA for the carrier account itself, and use an authenticator app or a passkey. Do not use SMS to the line you are trying to protect. That creates a circular dependency the attacker can exploit.

• Watch every carrier security email and text. Treat them like fire alarms, not spam.

Is the lock perfect? No. It forces an attacker to clear two hurdles instead of zero. Many opportunistic attackers will move on to an easier target.

“Does any of this work if I do not have a physical SIM card? I am on eSIM.”

Yes. The principle is identical.

An eSIM, or embedded SIM, is just a digital version of the same credential. The attack does not care whether the SIM is a piece of plastic or a software profile on your device. The attack targets the carrier’s verification process, which decides whose device gets to receive your number. Carriers can and do issue new eSIM profiles to a different device just as readily as they used to ship physical SIM cards in the mail. eSIM provisioning fraud is a documented and growing attack pattern.

Verizon’s SIM Protection materials state that the control can block transactions requiring a new physical SIM or eSIM. T-Mobile also describes SIM Protection as applying before changing to a new SIM card or moving an eSIM to a new device. Flip the toggle regardless of which kind of SIM you carry.

In some ways, eSIM-only phones may raise the stakes slightly. There is no longer a physical card to ship to a fraudulent address, which means one small friction in the old attack chain is gone. The toggle is the new friction.

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The Practitioner Footnote

For tax professionals reading this, this is very important.

If your Written Information Security Plan, or WISP, relies on SMS-based MFA to satisfy your Federal Trade Commission Safeguards Rule obligations under 16 C.F.R. Part 314, you have a single point of failure that a port-out call can dismantle. The Gramm-Leach-Bliley Act framework the Safeguards Rule sits on top of does not name SMS. It does require reasonable safeguards.

In my view, “reasonable” in 2026 no longer means relying on a six-digit code texted to a number that can be hijacked at a strip-mall phone store. The FTC Safeguards Rule, built on the Gramm-Leach-Bliley Act definition of a financial institution at 16 C.F.R. 314.2, classifies tax and accounting professionals as covered financial institutions and requires them to develop, implement, and maintain an information security program. The IRS guidance for practitioners restates that obligation in plainer terms.

Your practice management software, your e-filing portal, your bank, your email, your client portal. If any of those still default to SMS for the second factor, you are one phone call away from a breach notification you will not want to write.

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In Closing

My esthetician finished my facial. I paid, walked out into the parking lot, and made sure Number Lock and SIM Protection were turned on in the Verizon app before I drove away.

Go turn yours on. Then send this to someone who would not survive losing their phone number for a week. Sometimes it is the simple quick things that have a huge impact. As always, if you have any questions, let me know.

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I have a friend who uses Microsoft Edge and Bing (I think that was once a search engine?), I routinely give her a hard time because, well, it is fun. My spouse uses Firefox, and every time I sit down at his computer, I’m like, " What is this, 2000? Well, maybe they are on to something. (We can’t tell them that, though.)

Google Chrome has been up to something. Open File Explorer or Finder. Navigate to your Chrome user profile directory. Look for a folder called OptGuideOnDeviceModel. That folder is likely 4 gigabytes in size. You did not download it deliberately. You did not see a prompt. If you delete it, Chrome will quietly put it back the next time the right conditions trigger.

That file is Gemini Nano, Google’s on-device large language model. It is being deployed silently to any device that meets Google’s hardware threshold and triggers any feature that uses it. There was no consent prompt. There was no settings toggle until February of this year, and even now, the toggle is rolling out unevenly across operating systems and Chrome versions. Delete the file, and Chrome will redownload it the next time a triggering condition fires, unless you have first disabled the underlying flags. Security researcher Alexander Hanff documented the behavior, and outlets including The Verge, Tom’s Hardware, Android Authority, Gizmodo, and Malwarebytes have since confirmed it on Windows, macOS, and Linux.

Set the privacy lawyers and the EU regulators aside. As a pure security matter, the behavior pattern is the part that should bother you.

Pattern recognition

Walk through what Chrome actually did on your machine.

It downloaded several gigabytes of new code and data without notifying you. It installed that payload into a directory in your user profile that you almost certainly did not know existed. It did not ask whether you wanted the feature. It did not tell you what the file does. If you find the file and delete it, it puts the file back. The opt-out is buried behind two experimental flags in a developer settings page that no normal user will ever open, plus a Settings menu toggle that may or may not be present depending on your version.

There is a worse detail. Researchers analyzing Chrome’s internal feature flags found that the browser enables the OnDeviceModelBackgroundDownload flag before the corresponding user-facing settings are exposed. Translation: Chrome can begin pulling the model to your machine before any control surface exists for you to see it on, much less object to it. The setting that would let you say no is published after the fact.

Read the previous two paragraphs again with the vendor name redacted. Pretend you do not know who shipped this. The security community has a phrase for software that installs itself without consent, hides in obscure folders, persists across user removal, and ships its control surface after the install begins. The phrase is not flattering.

The argument that Google is a trusted vendor and therefore the behavior is acceptable inverts the security model. Trust is what allows you to install software in the first place. It is not what software is supposed to use to justify behavior you would otherwise reject. A trusted vendor that ships malware-shaped behavior is in some ways the worse outcome, because the defenses you have in place are less likely to flag it.

What actually triggers the download

The trigger pattern deserves its own attention. The model does not necessarily install the moment you launch Chrome on qualifying hardware. It downloads when something activates a feature that uses it.

A user clicking Help Me Write triggers it. A website you visit calling the Summarizer API triggers it. An extension you have installed requesting an Origin Trial token triggers it. AI-assisted tab grouping, autofill, smart paste, page summarization, on-device scam detection, and writing suggestions can all trigger it.

The set of conditions that can cause Chrome to begin pulling several gigabytes of code and weights to your computer is broader than most users would guess, and it includes conditions that third parties decide for you. Loading the wrong page is enough.

What the install expands

The presence of the model itself adds attack surface to your machine.

Gemini Nano on Chrome powers a growing list of features. Help Me Write. On-device scam detection. Smart paste. Page summarization. AI-assisted tab grouping. Autofill. Writing suggestions. A Summarizer API that any website you visit can call. Each of those is a code path that takes input and produces output, all running on your machine, all sharing the same underlying model.

For anyone with a security background, the relevant questions are the ones you would ask about any new local service. What inputs can reach it? What outputs can it produce? What other components on the system can interact with it? What is the audit trail when the service runs? Where are the logs?

Chrome has not made those answers easy to find. The Summarizer API is callable by any origin without a meaningful consent mechanism. Help Me Write integrates with text fields, including those inside web applications you may use for sensitive work. The model itself updates through Chrome’s existing update channel, which means the integrity of what runs on your machine is downstream of whatever Google decides to ship next, on whatever schedule Google chooses, with no separate review or approval step.

For most users, none of that matters in any practical sense. For anyone whose endpoint touches data they care about, it matters the same way any unaudited local service running with user privileges has always mattered.

The bigger pattern

Hanff connected the Chrome behavior to a broader trend across desktop platforms. Microsoft is embedding Copilot into Windows and Office on a similar trajectory. Anthropic’s Claude Desktop reportedly installed browser integration bridges across Chromium browsers without a prompt. The default posture for major software vendors right now is to ship AI features and explain them later, if at all.

This is not a one-time incident. It is the new operating mode. Your endpoint is not a stable artifact you configured once. It is a continuously mutating surface that vendors are reshaping in the background, on their schedule, for their priorities.

A security model that assumes your machine looks today the way it looked last quarter no longer holds. Periodic baseline review used to be a hygiene practice you could let slip without immediate consequence. It is now a first-order control. You cannot reason about your defenses if you do not know what is running.

The alternatives are different

Worth being precise about something. This is Chrome’s behavior, not Chromium’s.

Gemini Nano rides on Google’s Optimization Guide component update infrastructure. That infrastructure is a Google service that lives on top of Chromium, not inside it. Other Chromium-based browsers fork from upstream Chromium and strip out Google’s service layer, replacing it with their own. None of them inherit Chrome’s silent model deployment pipeline.

Microsoft Edge keeps its AI cloud-routed. Copilot in Edge sends prompts to Microsoft’s servers, the same way Chrome’s omnibox AI Mode does. No silent multi-gigabyte local model installed by the browser. Edge has its own issues, and Microsoft is pushing on-device AI hard at the operating system level on Copilot+ PCs, but that is OS-level deployment tied to specific hardware classes you bought deliberately, not browser-level silent install.

Brave strips Google services from Chromium aggressively and replaces them with its own privacy-focused versions. Brave’s AI assistant, Leo, is opt-in, defaults to cloud routing through an anonymizing reverse proxy, and supports a Bring Your Own Model option for users who want to run local models through Ollama. Local models in Brave are user-installed, not browser-installed.

Vivaldi went the other direction entirely. The CEO put it in writing last year that Vivaldi will not ship AI features in the browser. If your concern is exactly the pattern Chrome is establishing, Vivaldi is the most aligned Chromium browser available.

Opera, Arc, Dia, Comet, and the rest of the AI-forward Chromium browsers each handle integration differently. None has been documented doing the Chrome-style silent local install.

Firefox is not Chromium-based at all. Mozilla uses the Gecko rendering engine and operates under different governance from Google, Microsoft, or Apple. Firefox does have AI features, and it has explicit, documented user controls for them. As of Firefox 148, released in February of this year, an AI Controls panel in Settings lets users disable every generative AI feature in the browser with a single “Block AI enhancements” toggle. Smaller features like language translation and PDF alt text use local specialist ML models, but they are listed in the panel and individually toggleable. The optional sidebar chatbot routes to third-party providers the user picks (ChatGPT, Claude, Gemini, Copilot, or Mistral), not one Mozilla assigns. Mozilla has publicly committed to a kill switch approach for future AI features. None of this is a silent multi-gigabyte LLM install.

Safari is the other major non-Chromium browser, and it ships only on Apple platforms. Its AI integration is Apple Intelligence, which is an operating system layer rather than a browser feature. Apple Intelligence requires explicit opt-in, requires specific hardware (Apple silicon Macs, recent iPhones and iPads), runs many tasks on-device using Apple’s own model infrastructure, and routes more complex tasks to Apple’s Private Cloud Compute. Settings includes an Apple Intelligence Report panel that logs what was processed off-device. Whatever your view of Apple’s broader posture, none of this is the Chrome silent install pattern. The model deployment ships through OS updates with explicit consent flows, not through browser background downloads.

The point is not that any of these browsers is perfect. The point is that silent multi-gigabyte local model deployment is a Chrome decision, not a Chromium constraint. If you switch off Chrome, you do not inherit this problem.

Check your own machine

Before you act, verify what is actually sitting on your disk.

On macOS, open Terminal and run:

du -sh ~/Library/Application\ Support/Google/Chrome/OptGuideOnDeviceModel/

That returns the total size of the folder including everything inside it. If you prefer Finder, press Cmd + Shift + G, paste in ~/Library/Application Support/Google/Chrome/OptGuideOnDeviceModel/, then right-click the version subfolder inside and choose Get Info to see the rolled-up size.

On Windows, press Win + R, paste in %LOCALAPPDATA%\Google\Chrome\User Data\OptGuideOnDeviceModel\, then hit Enter. In File Explorer, right-click the version subfolder, choose Properties, and read the size off the dialog.

A few things to know going in. The OptGuideOnDeviceModel folder contains a versioned subfolder with a name like 2025.8.8.1141, and the actual model lives one level deeper inside that. Alongside weights.bin you will find smaller sibling files including encoder_cache.bin, adapter_cache.bin, manifest.json, and _metadata. If you check the size of a single file rather than the whole folder, you may be looking at a sibling that is one or two hundred megabytes rather than the main weights. The file you want to verify, specifically, is weights.bin. Reports across the major coverage put it in the 2GB to 4GB range, with Google itself acknowledging that the exact size varies by Chrome version and hardware tier.

Mine was exactly 4.0 gigabytes. That number landed without notice on a network managed end-to-end with endpoint protection on every machine. If your number is similar, your defenses missed it, too.

That is the article in one sentence.

What to do this week

You have two paths. They are not mutually exclusive.

If you are staying with Chrome:

1. Open Chrome. Type chrome://flags in the address bar. Find optimization-guide-on-device-model and set it to Disabled. Find prompt-api-for-gemini-nano and set it to Disabled. Restart Chrome when prompted.

   1. Set to disabled

      

   2. Set both disabled

      

2. Go to Settings > System and look for an “On-device AI” or “Use AI features in Chrome” toggle. The rollout is uneven across versions and operating systems, so this option may or may not be present. If it is, switch it off.

   1. 

3. Navigate to the OptGuideOnDeviceModel folder using the paths mentioned above. Delete its contents. With the flags disabled, Chrome will not redownload the model.

4. Review your endpoint protection logs and network monitoring for the past several months. A 4GB download from Google’s servers should have left a trace. If your tools did not flag or even log the event, you have a visibility problem worth fixing on its own merits.

5. Put a recurring quarterly task on your calendar. Walk through what is actually installed on each of your machines, compared to what you assume is installed. If the comparison surprises you, you have just learned something useful.

If you are leaving Chrome, and you should consider it:

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The friction has dropped close to zero. Brave, Edge, Vivaldi, and Firefox all import bookmarks, passwords (You should be using a dedicated password manager), extensions, and history from Chrome in a couple of clicks. Most extensions you use will work in any Chromium browser unchanged. A small number of sites still test only against Chrome, and the workaround is to keep Chrome installed for those specific cases with AI features disabled per the steps above, and run something else as your daily driver.

Three reasonable paths:

• Brave is the easiest recommendation for practitioners who want a Chrome-equivalent experience with adversarial privacy defaults. Drop-in replacement for daily use.

• Vivaldi is the recommendation for practitioners who specifically want a browser whose vendor has publicly refused to ship AI features. Most aligned with the concern this article raises.

• Firefox or LibreWolf are the recommendations for practitioners who want out of the Chromium monoculture entirely. Firefox has added some local AI features but they are opt-in and not deployed Chrome-style. LibreWolf strips them. Different rendering engine, different governance.

• Safari is the natural recommendation for Mac, iPhone, and iPad users already in the Apple ecosystem. Apple Intelligence is hardware-gated, opt-in, and surfaces what it does. Different engine, different governance, opposite deployment posture from Chrome.

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None of them is perfect. All of them are better on the specific axis at issue here than Chrome is right now.

The takeaway

The takeaway is not that Google is uniquely guilty. When I was reading about this earlier, I remarked to a friend that “Big tech is so #$*&# corrupt,” and his response was “Especially a company that once had the motto don't be evil.” Major software vendors have collectively decided that pushing AI features as default-on, opt-out-buried features is acceptable. They are correct that most users will not push back. They are wrong about whether the behavior is fine.

You do not have to accept it on the machines you control. The simplest move this week is to stop using Chrome as your daily driver. The longer move is to apply the same scrutiny to everything else running on your endpoints with your privileges. Both are overdue.

What browser are you using?

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There is so much noise about AI right now. Half the feeds I open are people insisting it changes everything. The other half are people insisting it is hype that will pass. Both are partially right, and both are missing the part that actually matters: how you use it.

I get the same question, in different shapes, from people who have tried these tools and walked away frustrated.

“Why does mine come out generic?”

The answer is almost never the AI. It is almost always the prompt.

I have a line I keep coming back to, and it is the only one I want you to remember from this article: AI is a magnifier. Smart in, smarter out. Sloppy in, sloppier out. (That is a sharper version of my original line, which was: if you are smart, you will be smarter; if you are dumb, you will be dumber.) The model is not the bottleneck. The prompt is.

This is true whether you are using Claude, ChatGPT, Gemini, Copilot, or whatever new tool will be on the front page next week. The interface changes. The logos change. The pricing changes. The fundamental skill of asking the tool a question worth answering does not.

I have heard the same complaint from people in completely different fields. A doctor who tried it once and gave up because “it just told me obvious things.” A real estate agent who said it kept producing “generic listing copy that sounds like every other listing.” A small business owner who said it was “fine for grammar but useless for anything real.”

In all three cases, I asked to see the prompt. In all three cases, the prompt was one sentence long.

Learning a new tool requires an investment of time. A small one, but real. We are now conditioned for instant gratification, which in my opinion is far more damaging than what AI will do.

You cannot ask a one-sentence question and expect a thoughtful, specific, useful answer. You would not accept that from a junior team member. You would not accept it from a contractor. You should not accept it from yourself when you are the one writing the prompt.

The Simple Method

The framework I use and teach is four letters. RCTF.

That stands for Role, Context, Task, Format. Every great prompt has all four. Skip one and the output drifts. Hit all four and the output stops looking like AI and starts looking like a deliverable.

R, Role

Tell the AI who it is supposed to be.

Not “you are a helpful assistant.” That is the default, and the default is mediocre. Tell it the actual role you want it to inhabit.

“Act as a senior tax advisor with twenty years of experience explaining complex tax issues to a client who does not understand taxes.”

“Act as a real estate agent writing a listing for a buyer, not a window-shopper.”

“Act as a financial advisor preparing for a difficult conversation with a retiree who lost money in the market.”

The role does two things at once. It activates a body of knowledge. It also sets a tone. A “senior tax advisor” sounds different from a “tax accountant.” A “patient teacher” sounds different from a “subject-matter expert.” Pick the role that matches what you actually need on the other side of the prompt.

C, Context

This is the part most people skip, and it is the part that matters most.

Give the AI the background. The situation. The constraints. The audience. The thing that is true about your specific case is not true about a generic case. Remember, though, do not use any PII about the client.

“My client is a W-2 employee earning around $180,000. They had a major life event this year, the sale of a primary home. They also had capital gains of $50,000 from various stock sales. They had no estimated payments because last year they got a refund. They are confused about why they owe.”

You can already feel the difference between that and a one-sentence “client wants to know why they owe.”

Context is where these tools turn from a search engine into something actually useful for your specific situation.

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T, Task

State the verb. Be specific.

Draft. Summarize. Compare. Analyze. Outline. Calculate. Critique.

The reason this matters is that AI tools default to “explain.” Ask a question, get an explanation. But explanations are usually not what you actually need. You need a draft. You need a comparison. You need a checklist. You need an outline. Tell it which one.

Pair the verb with a quantity. “Draft a 200-word reply.” “Outline a 5-section memo.” “Compare three options in a table.” Word counts and section counts are the cheapest way to make the output usable on the first pass.

F, Format

Tell the AI what shape the output should take.

A memo. An email. A bulleted list. A table. A one-page handout. A client-friendly explanation that avoids jargon. A table with three columns.

Format is the part where the output stops looking like AI and starts looking like the thing you need to send. You can paste it. You can print it. You can drop it into your client portal. The format is not an afterthought. It is the difference between “this is interesting” and “I am sending this.”

A Real Before-and-After

Here is the prompt most people write:

> “Write me an email explaining why my client owes more this year.”

Here is the same prompt with RCTF:

> “Act as a senior tax advisor explaining a tax outcome to a client. [Role] My client is a W-2 employee with an approximate income of $150,000 to $200,000. They asked why they owe more this year than expected. They had a major life event, the sale of a primary home, and no prior-year refund. They also had capital gains of $50,000 from various stock sales. [Context] Draft a 200-word reply in plain English. [Task] No jargon. Include one real-world analogy a non-accountant would understand. Tone: warm, expert, never condescending. End with ‘happy to chat more if helpful. Please book a meeting using the link in my email signature.’ [Format]”

The first prompt gets you a generic email. The second one gets you something close to what you would have written yourself, in roughly the time it takes to make a cup of coffee.

The difference is not the tool. It is the prompt.

The Moment That Always Lands

When I walk people through this, the moment that always lands is when someone tries an old prompt, then rewrites it with RCTF, then watches the second output. Their face changes. They get quiet. Then they say something like, “I have been blaming the wrong thing.”

That happens almost every time. Without exception.

People assume that getting better output means picking a smarter model, or upgrading to a paid plan, or learning some advanced technique they read about on Reddit. None of that is wrong, exactly. But all of it is downstream of the prompt.

A great prompt on a free model beats a sloppy prompt on the most expensive model in the world. Every single time.

Why This Is

Remember the small business owner I mentioned at the top, the one who said AI was useless for anything real? A few weeks after that conversation, she sent me a one-line follow-up. “I tried RCTF on my social media posts. They sound like me again.”

Same tool. Same business. Different prompt.

RCTF works whether you are drafting a contract, a recipe, a newsletter, or a toast. It does not care what you do for a living. It cares whether you respect the tool enough to use it well.

The people who get the most out of these tools are not the most technical people. They are the ones who treat the prompt like a brief to a junior associate. That is not a technology skill. It is a thinking skill, and, like any thinking skill, it improves with practice.

It also explains why some of the loudest skeptics are people who tried these tools once, got a generic answer, and concluded the technology was overhyped. They are not wrong about what they got. They are wrong about why they got it.

The Boundaries

A reminder, because the boundaries matter as much as the prompt.

If you are a tax professional, anonymize before you paste. No real names. No SSNs or EINs. No real dollar amounts. IRC §7216 and §6713 do not care which AI plan you are on, nor whether you toggled training off. Plan tier does not override federal law.

If you are not a tax professional, the same logic applies in every other context. Do not put client data, patient data, financial data, or anything else you would not put on a public website into an AI tool unless your firm has explicitly approved it. The chat window feels private, but that does not make it private.

And in every case, verify before you send. These tools can hallucinate citations, dates, and authority. The output looks confident even when it is wrong. We all know that being confidently wrong is still wrong. If you need an example of what this looks like, I can point you to some Facebook groups. You sign off on what reaches the client or the reader. Not the AI.

The Loop Back

The line I keep coming back to.

AI is a magnifier. Smart in, smarter out. Sloppy in, sloppier out.

The prompt is the part that decides which of those two you get. Not the model. Not the plan. Not the company building the tool. The prompt.

If you have been frustrated with AI tools, try this. Take the worst prompt you wrote this week, the one where you got a garbage answer and gave up. Rewrite it with Role, Context, Task, and Format. See what comes back. I would bet a coffee (a good coffee) that the difference is bigger than you expected.

Reply, comment, or email me. I read everything and do my best to respond.

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Me? I rewrite my own prompts more than I would like to admit. Every time I do, the output gets better. Every time I do not, I have only myself to blame.

What is the first prompt you are going to rewrite this week?

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If you are a tax professional, the companion to this article is a 12-prompt library structured around RCTF and ready to copy, customize, anonymize, and use. It covers client communications, IRS notice response templates, year-end planning letters by income segment, newsletter explainers, web copy, two interactive calculator specs, and an SOP-via-interview prompt that gets the process out of your head and into a document.

Paid Josh & Taxes subscribers can grab the PDF below.

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I have seen the same question, or some version of it, posted in a Facebook group dozens of times. “How do I handle X situation with the IRS?”

No context. No details. No specifics about the client, the issue, or what the person has already tried.

The responses come in fast. Most of them are variations of “need more info” or “what kind of notice?” A few people take a guess and give an answer that turns out to be wrong because they are solving a different problem than the one the asker had. The thread sprawls. Twenty replies later, somebody finally pulls enough information out of the original poster to give a real answer. By that point, half the responders have moved on, and the asker has waited a full day for help that could have arrived in ten minutes.

I have watched this pattern play out in tax practitioner groups, subreddits, X/Twitter posts, and LinkedIn discussions. The platform changes. The dynamic does not. Somebody asks a question that nobody can answer without a follow-up interview, and a small disaster of wasted time unfolds.

It also makes me forgiving of the people who post questions that make the rest of us want to throw our phones across the room. Nobody is born knowing how to ask a good question in a professional forum. It is a skill, and like most skills, you get better by paying attention to what works and what does not. What follows is what I have learned by watching what actually works.

The Problem

Every active group has a version of the same patterns. Someone posts a question that has already been answered dozens of times in the group. Someone else posts the same question in twelve different groups simultaneously. Someone asks a question so vague that answering it requires guessing what they actually want to know. Someone posts a screenshot of an error message with no context and expects a diagnosis.

This is not a character flaw. Most people who post these questions are stressed and stuck, trying to get unstuck as quickly as possible. They are not trying to waste anyone’s time. They just have not been taught that how you ask shapes what you get back.

Here is the thing that took me too long to figure out: asking a better question is not about being polite or following etiquette. It is about getting the answer you actually need. The people who ask well get help faster, get more useful help, and build relationships with the experts in the room. The people who ask poorly get ignored, get wrong answers, or get told to search the archives.

There is also a downstream cost that nobody talks about. The experts in any group have a finite amount of patience and time. Every time they answer the same poorly-framed question for the hundredth time, that patience erodes. Eventually, they stop answering at all, or they leave the group, and the quality of the whole place degrades. The people who ask well are not just helping themselves. They are helping the community survive.

Before You Post

The best question is the one you do not have to ask because you found the answer yourself in two minutes.

Search first. Every major platform has a search function. Facebook groups have one. Reddit has one. LinkedIn has one. Use it. Search for two or three keywords related to your question. If the question has been asked before, you will often find the answer and the thread where people discussed the edge cases. That thread is usually more useful than posting fresh, because you get to see how the answer holds up under follow-up questions.

If the search fails, check the pinned posts, the group rules, and any FAQ document the moderators have put together. A surprising number of common questions have dedicated resources that nobody reads. The moderators put those resources together because they were tired of answering the same question. Reward that effort by reading them.

Then check the source. If your question is about a specific product, platform, law, or tool, the authoritative source probably has a documentation page or a help center. Ten minutes with the actual source beats ten hours of crowdsourced guessing. The source is also usually more accurate than whatever the group remembers because the source updates while group memory does not.

There is also a category of questions that do not belong in a group at all. If you need legal advice for your specific situation, you need a lawyer. If you need medical advice, you need a doctor. Groups can give you general information, point you to resources, and share experiences.

If you have done all of that and still do not have an answer, now you can post. You will be in a much better position to ask a useful question because you will know exactly what you already ruled out.

How to Write the Question

Lead with the actual question. Not “Hi everyone, hope you are all having a great day, I have a weird situation.” Just the question. People are scanning. Give them something to scan.

Provide context in the next sentence or two. What are you trying to accomplish? What have you already tried? What does not work? Specifics matter more than you think. “My client got a notice” is not enough. “My client got a CP2000 proposing additional tax of $4,200 based on unreported 1099-NEC income. Do I need to file an amended return?” is something people can actually work with.

Include the details that would let someone answer without asking follow-up questions. If you are asking about software, mention the version. If you are asking about a process, mention what step you are on. If you are asking about a document, mention what kind and from what year. The goal is to let the first person who sees your question give you a useful answer instead of forcing them to interview you first.

Tell people what you have already tried. This is the single most underused move in question-asking. If you say “I tried X and it did not work because Y,” you save the responder from suggesting X. You also signal that you have done some thinking on your own, which makes people much more willing to invest time in helping you. A question that shows effort gets effort in return. A question that shows none gets none.

Skip the story. Nobody needs to know the entire history of your relationship with the client, your feelings about the situation, or your theory about why the other side is incompetent. That belongs in a different post, or in a different venue entirely. The question post is for the question.

Be specific about what you want. Are you looking for a citation? A recommended next step? A confirmation that your plan is reasonable? A second opinion? Say so. People want to help, but they cannot read your mind, and vague questions get vague answers.

A useful exercise: before you post, read your draft and ask yourself whether a stranger could answer it without asking you a single follow-up question. If the answer is no, you have more work to do. Add the missing context, cut the irrelevant context, and try again. Five minutes of editing on the front end saves an hour of back-and-forth on the back end.

On Being Rude

There are two flavors of rudeness in online groups, and both of them poison the well.

The first is the entitled asker. This is the person who posts a question and then gets annoyed that nobody has answered within an hour. The person who demands help without offering context. The person who responds to a clarifying question with “just tell me the answer.” The person who follows up with “bump” every two hours. The people in the group are not obligated to help you. They are volunteering their time and expertise for free. If you are rude about it, they will remember, and next time they will scroll past.

The thing about entitlement is that it is often invisible to the person displaying it. They are stressed, they need help, and the urgency feels like enough justification on its own. It is not. Your urgency is not anyone else’s problem. The people who answer questions well do it because they want to, not because they owe you anything. Treating them like staff is the fastest way to lose access to the only resource that was actually going to help you.

The second flavor is the smug answerer. “You should know this.” “This is basic.” “I have been doing this for 25 years.” That last one is my favorite, because sometimes the honest response is that you have been doing it wrong for 25 years and never noticed. Experience is not the same thing as being right. Years in the chair do not substitute for a citation.

The smug answerer is doing real damage even when their answer is technically correct. They are training newer members to stay quiet. They are teaching everyone who is watching that asking a question carries a social risk. The next person who has the same question will not ask it. They will guess, or they will get the answer wrong, or they will give up. The community gets smaller and dumber every time someone gets publicly shamed for asking.

If you have been doing this long enough that beginner questions annoy you, you have two choices. You can answer the question kindly and move on, or you can scroll past. Those are the only two options that do not actively harm the place you are participating in.

The AI Copy-Paste Problem

There is a newer version of bad answering, and it is getting worse.

Someone posts a question. Within minutes, another member pastes a response that is clearly the unedited output of an AI tool. Confident. Comprehensive. Authoritative-sounding. Often completely wrong, or right in a way that does not match the actual facts of the question, or right in general but missing the specific exception that makes it wrong here.

The person who posted the AI answer did not read it carefully. They did not verify it. They did not check whether the citations the AI included were real, because half the time they are not. They wanted to be the person who answered first. They wanted the social credit for knowing the thing. The accuracy of the answer was secondary to the appearance of having one.

This is a different failure mode than ordinary smugness, and it is more dangerous. The smug answerer who has been doing it wrong for 25 years at least believes their own answer. The AI-paste answerer is not even an actor in their own response. They are a delivery mechanism for output they did not check. The asker, who came to the group looking for human expertise, gets back a hallucinated regulation citation and a confident summary of a rule that no longer exists.

I am not anti-AI. I use AI tools every day. AI is genuinely useful when you treat it as a research partner that needs supervision. It is corrosive when you treat it as a vending machine that produces correct answers, because most of the time, it does not.

If you are going to use AI to help you answer a question in a group, the rules are simple. Read the output carefully. Verify any citation it produces by pulling up the actual source. Test the answer against the specific facts the asker provided. If the AI hedged, keep the hedges. If the AI cited a rule, confirm the rule exists and says what the AI claims. Then, if you are confident the answer is right, post it in your own words and disclose that you cross-checked it.

What you do not do is paste the raw output, slap your name on it, and walk away. That is not answering. That is laundering AI output through your professional reputation, and it damages both you and the group. The next time you post a real answer, the people who watched you paste a wrong AI response last week will discount it. You spent your credibility, and you got nothing in return except the brief satisfaction of being first.

Citations Over Feelings

When a question turns into a disagreement, the only thing that matters is the source.

If you are answering a question and you have a definitive answer, point to it. The statute. The regulation. The documentation. The reported decision. Whatever the authoritative source is in your field. “I have always done it this way” is not an answer. It is a personal habit dressed up as expertise.

If you are asking the question and someone gives you an answer with a source, read the source before you argue with them. Pull it up. Read the relevant section. Then decide whether it actually applies to your situation. If it does, you have your answer. If it does not, you can now explain specifically why your facts are different, which is a completely different conversation than “I do not think you are right.”

If you are answering and someone challenges you, produce the source or revise your position. Those are the only two options. Doubling down with more conviction does not make you more correct. It just makes the next person less likely to take your answers seriously.

There is a particular kind of failure mode that shows up in every professional group. Someone posts a confident answer. Someone else points out that the confident answer is wrong and provides a citation. The first person, instead of acknowledging the error, pivots to attacking the second person’s tone, credentials, or motivation. This is how a group loses its credibility. Every time it happens and goes unchallenged, the signal-to-noise ratio gets worse. The people who actually know what they are talking about start to leave, because they do not want to spend their time fighting people who are wrong but loud.

The fix is simple but unglamorous. When you are wrong, say so. “Good catch, I had that backwards.” “You are right, the rule changed.” “Let me reread the statute.” Those sentences cost nothing, and they buy you credibility. The people who are willing to be corrected publicly are the people whose answers other people start to trust.

This is how professional groups are supposed to work. The goal is to find the correct answer, not to win the thread. Everyone in the room benefits when the conversation stays anchored to what the source actually says. Everyone loses when it devolves into who feels more strongly about their position.

What Not to Do

Do not cross-post the same question in multiple groups at the same time. It annoys the people who are in all of those groups, it fragments the answers across multiple threads, and it signals that you are prioritizing speed over quality. If you have been waiting a day and the question is genuinely urgent, it is fine to try a different venue. But do not carpet-bomb. The people who do this almost always get worse answers than the people who pick one venue and ask carefully.

Do not post the question and then disappear. If someone asks you a follow-up, answer it. If someone gives you an answer that does not fit your situation, say why. The thread is a conversation, not a vending machine. The people who answer questions remember who engages and who ghosts. Engagement is currency in any group, and you spend it down every time you take an answer and run.

Do not argue with people who are trying to help you. You can push back on an answer if you think it is wrong. That is fine. But “that is not what I asked” when the person is answering what you actually asked is a good way to make sure nobody helps you next time. If the answers do not address your question, the most likely explanation is that your question was not clear, not that everyone misread it.

Do not post a screenshot of a long document and ask people to read it for you. If you want someone to review something, be specific about what part you have a question about and what the question is. Pointing at a wall of text and saying “thoughts?” is not a question. It is a request for unpaid labor.

Do not ask questions that would require someone to do your job for you. “How do I handle this entire case?” is not a question. It is a request for free consulting. Narrow it down. Pick the specific decision point you are stuck on, and ask about that.

Do not delete your post after you get the answer. The next person who has the same question will find your thread through search, and the answer will be valuable to them. Deleting it because you got what you needed is selfish in a way that is hard to articulate but easy to feel. The group helped you. Leave the answer behind for the next person.

After You Get an Answer

Thank the people who helped you. Not with a gif. Just a sentence. People remember who is gracious and who is not, and it matters more than you think the next time you need help.

If the answer solved your problem, say so. This helps the next person who finds your thread through a search. There is nothing more frustrating than reading a thread that ends with “got it, thanks!” and never finding out which of the four answers actually worked.

If you figured it out yourself before anyone responded, post the answer in your own thread. This is one of the most valuable things you can do for a group, and almost nobody does it. Your future self will be grateful when you search for the same problem two years from now and find your own answer waiting.

If you got an answer that was wrong and you eventually figured out the right one, come back and post the correction. This is harder than it sounds, because it requires admitting that the original answer did not work. Do it anyway. The next person who finds the thread needs the correction more than you needed your ego protected.

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The Part That Is Hard to Say Nicely

Some of the people who ask bad questions are not going to read this article, and if they did, they would not see themselves in it. That is fine. This article is not really for them.

It is for the person who has been in a group for a while, notices the patterns, and wants to do better. It is for the person who has asked a question recently that did not get the response they hoped for, and is wondering why. It is for anyone who has ever felt the low-grade frustration of watching a thread devolve because the original poster did not give anyone enough to work with.

Asking good questions is a professional skill. It is worth developing. The people who do it well get better answers, build stronger networks, and spend less time stuck. That is a real competitive advantage in any field.

It is also a skill that quietly signals everything else about how you work. People who ask precise, well-scoped questions in public are usually the same people who write good emails, run good meetings, and produce good work. The reverse is also true.

The way you ask a question in a Facebook group is a tiny window into how you operate everywhere else. People notice. They form opinions about who they would refer work to, who they would hire, and who they would partner with. None of this is fair, but all of it is real.

And if you are on the answering side, remember that you were a beginner once, too. A short reply pointing someone to the search function is more useful than a long reply about how they should have searched. We are all trying to get better at this.

The groups that thrive are the ones where the people asking questions take the time to ask them well, and the people answering take the time to answer kindly. That is not complicated. It is just rare. Be the kind of participant that makes the place better for everyone else, and the place will be better for you when you need it.

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Examples

Let’s talk about a few examples. I am changing names to protect the guilty

Yes, in fact, we have seen this. Had you utilized a search, you would have seen that 7 other people had similar fact patterns this week. This one is popping up daily and is admittedly annoying me.

I won’t mention the lady who does this routinely in certain Facebook groups. But it isn’t helpful, and some of us may talk about you.

No, just no.

If you recognized yourself in any of those examples, you are not alone. Everyone has been at least one of those people at some point. I have probably been all three on different days. The point is not to feel bad about it. The point is to notice the pattern and choose differently next time.

Asking well is a small discipline. So is answering well. Neither is hard, but both require a moment's pause before you hit post. That pause is the whole game.

The next time you are about to ask a question, take a beat. Search first. Write the question. Read it back. Ask whether a stranger could answer it without interviewing you. Then post.

The next time you are about to answer one, take a beat. Read the question carefully. Check the source. Resist the pull to be first. Ask whether the answer you are about to post would help the asker, or just make you feel useful.

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There is something that happens after April 15.

Motivation seems to evaporate. I feel it right now, sitting at my desk with a list of things I wanted to tackle the moment the deadline passed. The list is still there. The tasks are still real. Some of them are things I was genuinely excited about three weeks ago. And yet when I look at the list this morning, I cannot seem to make myself start.

For three months, I was up at 4:30 or 5:30 every morning. Seven days a week. No exceptions. That was the rhythm, and the rhythm worked because I was not just doing returns. I was building an office I love walking into. I was saying yes to new projects. I was teaching. I was writing. I was taking on opportunities I have wanted for years, and when a new one appeared, I said yes to that too. Because why would I not? This is the game. This is the part I love.

And then the deadline passed, and I hit a wall.

The Word I Hate to Use

I am going to use a word, and I am going to hate using it.

Entrepreneur.

The word is overused. It has been worn smooth by a decade of influencer content, hustle-bro podcasts, and LinkedIn posts with stock photos of sunrises. Every person who has ever sold a course on how to sell a course calls themselves one. I cringe writing it. I’ve almost deleted it twice.

But underneath all the noise, the word is pointing at something real, and I do not have a better one.

Some of us are almost addicted to it. Let’s be real, who doesn’t love some dopamine? It is not a career choice. It is part of our identity. We wake up thinking about business ideas. We go to bed thinking about business ideas. The shower is a think tank. The drive home is a think tank. The moments when normal people are decompressing are the moments we are mentally drafting the next thing. A piece of writing. A new service. A better workflow. A conversation we want to have. A problem we cannot stop turning over.

The idea of a 9 to 5 feels like prison to people like us. Not because we are lazy. Not because we are unwilling to show up. The opposite. It feels like prison because the structure itself is built on the assumption that you do the work someone else designed, on the timeline someone else set, for reasons that belong to someone else. For people wired like us, that is not stability. That is suffocation. Plus, the idea of someone telling me what to do, yeah, that’s a hard pass.

People who have never done this for themselves do not get it. They cannot. They hear “I love my work” and translate it in their heads to “I like my job,” which is not even close to the same thing. Loving your work means the work is not separate from you. It is how you think, how you process, how you make sense of the world. It is the thing you cannot stop doing even when you are trying to stop doing it.

Which brings me to the problem.

The Cost of Saying Yes

The thing that got me here is not the volume of returns. It is the volume of yes. Every new project I took on was something I wanted. Every opportunity I chased was one I had been working toward. The office is not a burden. It is the thing I have been building in my head for years, finally real. The teaching, the writing, the new directions, none of it is work I resent. All of it is work I chose. Enthusiastically.

But it turns out that saying yes to everything you love has the same cost as saying yes to everything you hate. Your body does not distinguish. Twelve hours of work on something that lights you up still costs twelve hours. Sustained enthusiasm is still sustained output. And when you stack a dozen things you love on top of each other, what you end up with is the same exhaustion as the person doing a dozen things they resent. You just get to the exhaustion later and feel guiltier about admitting it.

This is the trap for people wired this way. The work is not separate from us. The work is an expression of us. Turning it down feels like turning down some version of who we are. So we do not turn it down. We say yes. We keep saying yes. And somewhere around mid-April the body we have been ignoring sends up a flare and the motivation we were running on just, stops.

The Part We Do Not Like to Say Out Loud

Here is the other thing driving all of this, and I do not think we talk about it enough.

We are not going to live forever.

All of us are going to die. That is not a morbid observation. It is the most basic fact of being alive. And the older I get, the more I notice how much of my drive comes from a quiet awareness that the clock is running.

I am going to be honest about something. Within the span of a month, my family lost two of our dogs. One of which was while I was out of town last week. Gaga (gorgeous and profoundly empathetic) and Pinky (always happy and full of love). They were my parents’ dogs. If you have never lost an animal you loved, you might not understand what I am about to say, and that is okay. If you have, you already know.

I have always believed that losing furry family members hurts in a way that losing humans does not. I know how that sounds. Some of you are already rolling your eyes. People are complicated. Relationships with people are complicated. Even the best human in your life is, by definition, a person, which means there are edges and misunderstandings and the low-grade friction of two flawed beings trying to exist in proximity to each other. That friction is part of what makes human love meaningful. It is also what dulls it, around the edges, in small ways you do not notice until they are gone.

Dogs do not do that. Cats do not do that. Whatever was in their bowl this morning, they forgave you for it by dinner. Whatever mood you came home in, they met you at the door anyway. There is no edge. There is no friction. There is just presence. Uncomplicated and unconditional.

Losing them is a specific kind of grief, and I will not pretend it is not sitting in the background of everything I am writing here. It is part of why the wall hit as hard as it did. It is part of why the motivation disappeared after the April 15 deadline instead of April 30. Grief does not check your calendar. It waits until the adrenaline drops, and then it shows up.

So when I talk about the clock running, I am not being abstract. I watched it run out, twice, inside of a month. That has a way of rearranging your priorities, whether you asked it to or not. It’s weird. It’s life.

There are articles I want to write. Courses I want to teach. Clients I want to help. Ideas I want to build. The list is longer than the time I have, and I know it. So I say yes. So I wake up at 4:30 to 5:30. So I stack the plates until they bend.

The world is not making this any easier to ignore. On any given day, the headlines read like a fever dream. Wars grinding on. Institutions wobbling. The occasional reminder that nuclear Armageddon is, apparently, still on the menu. I try not to doomscroll, but I also cannot pretend I do not see it. None of us can. The uncertainty is part of the air we breathe now.

That awareness is both fuel and poison. It is fuel because it reminds me not to waste the days. It is poison because it convinces me I cannot afford to stop, even for a week, because what if the week I take off is one of the ones that mattered.

But here is the math I keep forgetting. If the time is short, then the time I spend exhausted and unable to start is time I have already lost. Grinding through a wall is not a good use of time. It is just burning it with the lights on. A week of actual rest, taken on purpose, gives me back weeks of real work on the other side. A month of half-powered grinding gives me nothing.

If we are going to live like the days are precious, we have to actually live like the days are precious. That includes the ones where we stop. That includes the ones where we grieve. That includes the ones where we sit with something hard instead of working around it.

“Just Get a Hobby”

Here is the part I want to say carefully, because it is the part most people get wrong.

Our spouses, partners, and friends who do not work for themselves do not understand this. They see us working all the time and they say things like, “Why do you work so much?” and “You should get a hobby.” They mean well. They love us. And they are missing something important.

For those of us who work for ourselves, the work is not a burden we are trying to escape. The work is how we are built. Creating and doing is what fuels us. Being in control of what we make, when we make it, and how we make it is not something we tolerate. It is something we need.

I know how that sounds. It sounds like one of those motivational posters in the break room of a company none of us would ever work for. “Create your own destiny.” “Be your own boss.” I cringe typing it. But underneath the bumper-sticker language, it is true. The thing that makes us capable of doing this work in the first place is the same thing that makes it hard for us to stop. We are not grinding (another word that is overused by “influencers” and “hustle culture” types) because we are miserable. We are grinding because building something is the most alive we ever feel.

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So when someone tells you to “just get a hobby,” or — my personal favorite (sarcasm)— “you should touch grass,” they are not wrong exactly. They are using the wrong language for the wrong audience. I roll my eyes every time. “Touch grass” is for people whose problem is that they spend too much time scrolling on a couch. That is not my problem. That has never been my problem. Now, am I on the couch on my phone? Yeah, but I’m not mindlessly scrolling. I’m intentional about it (eye roll).

A hobby, for people like us, is not a substitute for work. It is a smaller, lower-stakes version of the same instinct. Making something. Getting better at something. Being in control of something. A few months ago I decided to take up crocheting again. I learned when I was a kid. It is very relaxing. I bought some really cool yarn and then, like many things, moved on. I plan to get back to it because it was very much like meditation. My next project is perfecting the cappuccino.

That distinction matters. If you try to “rest” by doing nothing at all, you will be miserable within a day. I know because I have tried. What works is redirecting the impulse to make toward something small and low-stakes until your system recovers enough to take on the big stuff again.

What “Unplug” Actually Means

I want to push back on the word “unplug” for a second, because it gets used like it means one thing, and it does not.

For some people, unplugging means getting off social media. And sure, there is a version of that worth doing. The latest Twitter controversy does not need my attention. I rarely care anymore. I have not started one in a long time, and I do not miss the reflex. That part of the internet is just noise dressed up as importance, and walking away from it is almost always a net positive.

But I am not deleting my accounts. Because social media is also where a small group of friends lives. People who get what I am doing. People who actually understand why a reply from IRS Chief Counsel is exciting, or why a client makes me want to put my head through a wall. It is unrestrained humor. It is shop talk with people who speak the language. It is the closest thing a solo practitioner has to coworkers, except the coworkers are self-selected and genuinely fun.

That is not something I am trying to unplug from. That is one of the things keeping me sane.

So when I talk about unplugging this week, I do not mean silence. I do not mean a digital detox. I mean, stepping out of the content treadmill. I mean, closing the client email tab. I mean, not checking the practice management software to see what came in overnight. I mean, letting the algorithm-driven parts of my attention rest while keeping the friendships that actually sustain me.

Unplug from the parts that drain you. Keep the parts that fill you up. That is the distinction nobody explains when they tell you to “get off your phone.”

The Case for a Real Week Off

Most of us do not take a real week off after a stretch like this. We take a weekend. Maybe a long weekend. Then we are back at the desk, feeling vaguely behind and unsure why we cannot focus.

A weekend is not enough. A weekend is what you take after a hard Friday. Three months of 4:30 wake-ups chasing a dozen projects you love needs more than forty-eight hours to metabolize.

A week is different. A week is long enough for your brain to actually stop scanning for the next thing to say yes to. The first two days, you will still feel like something is wrong. You will keep checking your email. You will jump when your phone buzzes. You will feel a pull to start something, anything, because starting is how you are wired. Somewhere around day three or four, something shifts. The background noise quiets down. You start sleeping differently. You find yourself thinking about things other than work for extended periods without catching yourself.

That is when the rest actually starts working. And it is the part most of us never get to because we cut the break short.

What to Do With the Week

Here is the trap. If you do not plan the week, you end up scrolling your phone on the couch for seven days, wondering why you still feel terrible. Worse, if you are wired like me, you will just fill the silence with a new project by Wednesday.

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So here is what I would suggest. Pick three things before the week starts. One of them is a hobby. One of them is a place. One of them is something you want to learn. These become the guardrails that keep you from either collapsing into the couch or quietly starting a new venture by Wednesday afternoon.

I can tell you mine.

The hobby is the cappuccino. I got an espresso machine a while back, and I have been fumbling through it between client meetings for months. My first attempt looked like a dishwater latte wearing a hat. My second was worse. Next week I am going to actually practice. Not in ten-minute stolen windows. Mornings. With intention. I will be bad at it for a while, and that is the point.

The place does not have to be far. See something unfamiliar. Some of the best ideas I have ever had about my practice came to me when I was nowhere near my practice. That is not a coincidence. Distance from the work is how you see the work clearly.

The learning is whatever has been nagging at the edge of your attention for months. The book you keep meaning to read. The documentary you saved and never watched. The topic has nothing to do with the Internal Revenue Code. Let yourself be a beginner at something again. Reading a new Revenue Procedure is work. Learning why certain chords sound sad, or how long it takes ICBMs to reach their target (I’m mostly kidding, but hey, nuclear war has been an interest since I was a kid), or how to identify the birds at your feeder, is something else entirely. That kind of learning reminds you that your brain is a general-purpose instrument, not a tax machine.

Three things. Small enough to actually do. Specific enough that you cannot fake them. The hard part for me is that I will reach for something technology-related, which is fun but also creeps back into work territory. Technology and tax are the two things I love, and they both end up being work if I am not careful

Let the 4:30 Go. For a Week.

One more thing to the practitioners who, like me, ran on 4:30 wake-ups for the last three months.

Let it go. For a week. This morning, I finally got out of bed at almost 7 AM.

You earned the early mornings because the work demanded them. The work is not demanding them right now, and the reality is it never did; we all just made the choice to do it. Sleep until you wake up on your own. Do it for seven days and see what happens. I suspect that around day four, your body will start sleeping the way it is supposed to, and around day six, you will wake up naturally at a reasonable hour, feeling like yourself again.

The Work Will Still Be There

I know what some of you are thinking. You have representation cases waiting. You have extensions to work through. You have planning meetings on the calendar. You have new projects you are excited about. You cannot just disappear for a week.

You can. The work will still be there on the other side. Your clients will survive (and if you don’t, they will replace you). The opportunities you are chasing will still be chaseable. The projects you cannot wait to start will still be waiting. Nothing meaningful gets worse because you took a week to be a person.

What does get worse is you, if you never stop.

The Summer Ahead

Summer is going to be busy with lots of travel to conferences. June, I am teaching at CSTC Summer Tax Symposium. If you’re in Reno or want to be, check it out. I will also be attending CSEA Super Seminar in Reno.

Then, in July, there is the NATP Taxposium in Cleveland, Ohio.

I’m looking forward to teaching about Innocent Spouse Relief (Is there such a thing as an innocent spouse??), Cybersecurity, and a few other things.

A few webinars will land in between. I will post details as they go live.

Your Turn

So tell me. Are you feeling it too?

Did you hit the wall this week? What did you say yes to this year that you would say yes to all over again, even knowing the cost? Has someone in your life told you to “just get a hobby” or “touch grass” and made you want to roll your eyes so hard they got stuck? And what would happen if you gave yourself a week before you tried to start the next thing?

I want to hear it. Drop it in the comments. Tell me what hobby you are picking up, where you are going, and what you are learning. And if any of you have actually mastered the cappuccino, I could use some tips. Mine still looks like it lost a fight.

I have lots of fun content planned, AI, how-tos, etc. (maybe an announcement or two). I haven’t done a giveaway in a while. I enjoy giving stuff away. So, one lucky commenter will get 3 months free of Claude Pro. (But please, for the love of God, do not put client data in it.)

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On Tax Day, this distinction matters more than you think.

A friend/colleague in the tax world said something to me a while back that I have given a lot of thought to. It was one of those offhand comments that lands like a pebble in your shoe. You keep walking, but you can’t stop thinking about it.

I’m paraphrasing, but it was basically:

I spent the next few weeks pulling on that thread until it unraveled something I needed to see.

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The Polite Lie vs. The Caring Truth

Being nice is comfortable. It’s the path of least resistance. It’s telling someone what they want to hear because it’s easier than watching their face fall. It’s smiling and nodding and saying “yeah, that should be fine” when you know it won’t be.

Being kind is harder. Being kind is telling someone the truth, even when it’s inconvenient. Even when it makes the conversation awkward. Even when they might not like you as much afterward.

Nice is pleasant. Kind is useful.

Nice protects the relationship in the moment. Kind protects the person in the long run.

What This Looks Like in Tax Practice

I think about this distinction constantly now, especially today, April 15th, when the weight of filing season sits on everyone’s shoulders.

Being nice is telling a client, “Sure, we will get that filed, no problem.” Being kind is saying, “I am sorry, but this is after our deadline. We will file an extension and work on this after April 15th.”

Being nice is letting a colleague’s questionable position slide because you don’t want to create friction. Being kind is pulling them aside and saying, “Hey, I think there’s some exposure here. Let’s talk through it.”

Being nice is agreeing to take on one more client, one more extension, one more “quick question” because you don’t want to disappoint anyone. Being kind (to yourself, in this case) is saying, “I can’t do that well right now, and you deserve someone who can.”

Nice avoids the hard conversation. Kind starts it.

The Rabbit Hole

Once this idea was planted, I started seeing the nice-versus-kind split everywhere. In friendships. In business. In the way we talk to ourselves.

How many times have I been “nice” to myself by not confronting a habit that wasn’t serving me? How many times have I been “nice” to a client by softening a message so much that the actual point got lost?

The uncomfortable truth is that niceness can be a form of avoidance. It can masquerade as warmth while actually being a way to dodge responsibility. You get to feel good about yourself (”I didn’t want to hurt their feelings”) without actually helping anyone.

Kindness requires something niceness doesn’t. It requires courage. It requires caring more about the person’s outcome than about how they perceive you in the next five minutes.

Kindness Has a Longer Time Horizon

Here’s what I keep coming back to. Nice operates on a short clock. It’s optimized for right now. For this conversation. For today’s comfort level.

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Kind operates on a longer timeline. It asks, “What does this person need to hear so that six months from now, they’re in a better position?” Sometimes that’s encouragement. Sometimes it’s a reality check. Sometimes it’s a boundary.

The best mentors I’ve had in this profession were kind, not nice. They told me things I didn’t want to hear. They challenged positions I was attached to. They pushed back. And every single time, I was better for it. I've always loved people who tell me exactly what they think.

A Tax Day Reflection

Today, as the filing deadline lands and the dust starts to settle on another season, I want to challenge all of us (myself included) to audit something that doesn’t show up on a return.

Where are you being nice when you should be kind?

Where are you smoothing things over instead of saying what actually needs to be said?

Where are you choosing comfort over clarity?

The colleague who dropped this idea into my world probably doesn’t know how far it traveled. That’s often how the most important lessons arrive. Not in a seminar or a textbook, but in a passing comment from someone who cared enough to say the true thing instead of the easy thing.

That’s kindness. And it’s worth more than all the niceness in the world.

What are you changing for next tax season?

Me? I’m saying no more often. No to things that waste time. No to clients that I do not want to work with. Life is short, remember that.

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