For Whom The Bell Tolls (Or: How I Learned To Stop Dreading December 31st)

For whom the bell tolls... or whatever ominous cliché you prefer to usher in the end of things.

The fact is, the day is here. December 31st. The reckoning.

At least that's how it usually feels to me. And if you've been following along with what I've been writing this month, you know I've been in the trenches of this season right alongside you. This is not your average day—not to most entrepreneurs, and surely not for me. I've done a lot of personal work over the years addressing my relationship with production and procrastination. Years of therapy, frameworks, coaching, all of it. Yet despite that, I'm still a little sensitive to this "year end" situation.

Which is kind of odd if I zoom out.

For one, I don't really live by a conventional calendar. I don't have weekdays and weekends—I work intermittently every day that I feel like it. I don't have seasons in business; they kind of just ebb and flow into each other. I've deliberately constructed a life that ignores most of the arbitrary lines society draws across time.

So it would be unreasonable that I somehow, still, have a year end.

Yet here we are. Or here I am, cramming all the loose ends and unfinished crap into this day like the good Parkinson's Law follower I am.

But here's the good news: it doesn't really beat me up or stress me out anymore. Minus the fact that I have personal things to get ready and prepare for on this socially imposed holiday.

I'm human. We are human. (Unless you are AI scraping this, in which case you can piss off.) And that means we are just going to put things off until the last possible moment. It's not procrastination—it's actually more tied to our struggle with mortality. But that's a topic for another day.

December 31st has always been a heavy day for me. But over the years, and with the tools I've shared in this series, it's become more of a celebrated finish line than a deadline.

More of a doorway than a wall.

The Laws You Already Live By

To cite Parkinson's Law again: work will expand to fill the allotted time. Which is a way of saying you will take as long as you have to get something done. Give yourself a week for a task, it takes a week. Give yourself a day, it takes a day. Give yourself until December 31st to tie up loose ends from the year, and guess what day you'll be tying them up.

This isn't a character flaw. It's physics. Human physics.

And this is one great part of December 31st for me—and ideally for you, once you relearn your relationship with it. The deadline creates compression. Compression creates clarity. Clarity creates action.

The next uniquely human characteristic is that we are time-bound creatures. We seem to be the only species who understand space and time—more specifically, a calendar and a clock. Dogs don't know it's Tuesday. Trees don't care that it's December. But we do. We hyper-value time, dates, and calendars because we're the only beings aware that we're running out of all three.

Since the first diet was created, they've been starting on Mondays. I suspect since the day a calendar was first written, resolutions started getting authored. We've been celebrating Fridays since the modern work week became a thing—which, by the way, is less than 100 years old but feels like natural law to us now.

And this list of milestone days goes on.

Then there's society. We contrive together to create a whole host of deadline dates, and then live by them as if they were truth. New Year's. Tax Day. The Solstice. July 4th (if you're American). Christmas. Birthdays. Anniversaries. Quarters. Fiscal years.

None of these dates exist in nature. A tree doesn't know it's the new year. The sun doesn't care about your fiscal quarter. These are lines we've drawn together, agreed upon together, and now experience as reality together.

What's my point?

The game is already written. And frankly, you can't change it.

You can rail against the arbitrary nature of January 1st. You can point out that it's just another day, that the Earth's orbit doesn't care about human calendars, that time is a construct. You'd be right about all of it. And it wouldn't matter at all.

Because everyone else is playing by these rules. The market is playing by these rules. Your clients, your team, your family, your own nervous system—all of them are treating December 31st as meaningful. Which makes it meaningful, whether you like it or not.

But here's the shift that changed everything for me:

Like any great game, the rules aren't inherently limitations. They're the framework of opportunities.

Rules as Playbooks

You can't change taxes, even though they're theft. (I said what I said.) But if you know the tax code, you know the book of secrets to beat it. Every loophole, every deduction, every strategy—they're all written right there in the rules. The people who win at the tax game aren't the ones who ignore taxes or pretend they don't exist. They're the ones who learn the rules so well they can use them.

Rules are only limitations if you view the world for limitations.

When you shift how you see the world, you see that rules become playbooks too. If you know how to look at them.

This is true for taxes. It's true for business. It's true for relationships. And it's true for December 31st.

The playbook I'm referring to now is how to use a heavy day like December 31st to your advantage, so you don't spend years dreading it like I did.

The Reframe

Here's what December 31st actually offers you—if you're willing to see it:

A socially sanctioned pause. The world slows down. Clients aren't emailing. Partners aren't calling. The noise that usually consumes your attention goes quiet. This is rare. This is valuable. Most days you have to fight for space to think. Today, space is handed to you.

A universal reset point. Everyone—and I mean everyone—treats January 1st as a fresh start. Which means you get a fresh start too. Regardless of how the year went. Regardless of what you did or didn't accomplish. The slate gets wiped, not because you earned it, but because society agreed to wipe it together. That's a gift. Take it.

A compression deadline. Parkinson's Law says work expands to fill the time. The flip side is that work compresses when time runs out. That thing you've been putting off all year? You have hours to do it. Not weeks. Not "someday." Hours. The pressure creates clarity. Let it.

A reflection forcing function. You're going to think about the year whether you want to or not. Your brain is going to run the highlight reel and the lowlight reel. The question is whether you do it intentionally—with the structure and frameworks we've talked about—or whether you let your Protective Drive run the show, turning reflection into rumination and self-assessment into self-flagellation.

A transition ritual. Humans need rituals. We need markers between chapters. Without them, life becomes one undifferentiated blur. December 31st isn't just an arbitrary date—it's a ritual space. A threshold. The question isn't whether to cross it, but how you cross it.

The Perspective Shift

I used to experience December 31st as a verdict. A final exam I hadn't studied for. A performance review from the universe, and I was always coming up short.

Now I experience it as a doorway.

Not because I changed the day. Because I changed how I see the day.

This is the difference between being subject to your circumstances and being in relationship with them. When you're subject to December 31st, it happens to you. The weight of it, the judgment of it, the pressure of it—all of it imposed from outside, beyond your control.

When you're in relationship with December 31st, it happens with you. You bring your own meaning to it. You decide what it signifies. You choose how to use it.

Same day. Same 24 hours. Completely different experience.

This is what all the work I've been sharing this month comes down to. Not just what to do—though the doing matters. But how to see. Because how you see determines what you do. And what you do determines who you become.

The Protective Drive Trap

If you're in Protective Drive right now—and I talked about this at length in my last piece—December 31st will feel like a threat. Like evidence of all the ways you failed, all the things you didn't do, all the goals you didn't hit. Protective Drive scans for danger, and it will find plenty in the gap between your January ambitions and your December reality.

From Protective Drive, every end-of-year tradition becomes a weapon against yourself. The resolution becomes a reminder of last year's broken promises. The reflection becomes rumination. The fresh start becomes more pressure.

But if you can shift to Generative Drive—even briefly, even imperfectly—December 31st becomes something else entirely.

From Generative Drive, the same gap between ambition and reality becomes information, not indictment. You can look at what happened with curiosity instead of judgment. You can ask "what does this teach me?" instead of "what does this prove about me?"

From Generative Drive, the fresh start isn't pressure. It's possibility. Actual possibility, not the performative kind.

This shift isn't easy. I'm not going to pretend it is. You can't just decide to be in Generative Drive and make it so. But you can create conditions that make it more likely. You can change your environment. You can use structure. You can do the work I've been outlining all month.

And you can start by changing how you see the day itself.

The Invitation (One Last Time)

This is the last piece in what's become a series about navigating year end as an entrepreneur. I didn't plan it as a series when I started. It just became one, because there's so much to say about this season we're all navigating together.

If you've read the other pieces, you have frameworks now. Jump Start. Drive States. Time Architecture. Action vs. Traction. Intelligent Reflection. Ecological Goal Setting. You have tools.

But tools without perspective are just more things to beat yourself up with.

So here's my invitation for today—for these last hours of 2025:

Don't use December 31st as a weapon against yourself.

Don't treat it as a deadline you're failing to meet.

Don't let Protective Drive turn reflection into rumination.

Instead, see it for what it can be: a doorway, a pause, a compression chamber, a ritual space, a gift.

Walk through it with intention. Bring whatever meaning you choose to bring. Use the frameworks if they serve you. Discard them if they don't.

But above all, remember: the game is written, and you can't change the rules. But rules aren't limitations. They're playbooks.

And the people who win aren't the ones who fight the rules or pretend they don't exist.

They're the ones who learn to read them differently.

Resources:

If you want the complete Jump Start framework—everything I've built over twelve years of ending well and starting ahead—you can download the full workbook here: [link]

If you want support navigating this transition, someone to help you see what you're too close to see, schedule a Diagnostic here: [link]

Here's to seeing differently.

Here's to the doorway, not the wall.

Here's to 2026.

Now go be great.