The Post-Deadline Drift

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.

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.

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.

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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.)