A Snow Day Isn’t a Life Plan
The Problem With Trying to Choose the Best Life
I’m finishing Designing Your Life by Burnett and Evans, and near the end they introduce something called the “life design choosing process.”
It goes like this:
Gather and create.
Narrow things down.
Choose.
And then, jokingly, they say the fourth step is “agonize.”
But the real fourth step is:
Let go and move on.
And that’s where I got stuck.
Because I realized something about the way I make decisions.
I don’t just want to choose.
I want to choose the best.
And the second I use that word, the whole thing collapses.
What does “best” even mean in a life?
At the end of my life, I’m not going to be able to look back and say:
“Yes, that was the optimal path.”
There were always going to be other versions:
Other jobs I could have taken
Other risks I could have tried
Other identities I could have grown into
Not just different outcomes, but different lives.
And there’s no world where I get to compare them side by side.
So “best” isn’t just hard to find.
It’s not a real category.
But my brain doesn’t care.
It keeps running the simulation anyway.
If I do this, I get these benefits.
If I do that, I lose these things.
But if I choose differently, maybe I gain something else entirely.
And suddenly the opportunity cost isn’t just financial.
It’s existential.
But I also need to be honest about something.
My instinct to look for the best is really an instinct to pursue excellence.
And that has served me really well.
It’s one of the reasons I’ve gotten opportunities I didn’t expect.
It’s one of the reasons people come to me and ask, “How would you do this?”
Because over time, I’ve trained myself to see pathways.
Not the future exactly, but a version of it.
If someone does this work, in this way, over time…
here’s where it likely leads.
That shows up most clearly in how I teach.
When I’m working with a group of students learning guitar, I’m not just watching them play notes.
I’m trying to see each individual.
What does this student need right now?
I can usually see the next step.
Not just where they are, but where they’re going.
I see them struggling through a few chords…
and I can already picture them performing on stage, confidently, identifying as a musician.
And I try to help them bridge that gap.
Because I’ve seen it before.
When students practice with some structure, some timing, some intention…
they improve.
And when they improve, something shifts.
They don’t just play better.
They start to see themselves differently.
Those scattered notes start to sound like something real.
Something worth hearing.
That instinct, that pull toward excellence, isn’t the problem.
It’s helped me build a life I care about.
But I’m starting to see where it breaks down.
Because that same instinct works beautifully inside a path…
…and completely falls apart when you try to use it to choose the path itself.
Excellence is a great compass once you’re moving.
It’s a terrible tool for deciding where to go.
This has been hitting me especially hard right now.
I’m finishing up my year as a teacher, and for the first time, I don’t have to work.
I reached financial independence.
I thought that would make this decision easy.
I imagined it would feel like a snow day.
You wake up, realize you don’t have to go in, and there’s this wave of relief.
That feeling is so good you wish you could bottle it and sell it.
(Honestly, it would outperform most index funds.)
You feel light. Free. Untethered.
Like you’ve escaped something.
But that’s the thing.
A snow day is an escape.
It’s not a direction.
And that feeling, as good as it is, doesn’t tell you what to do next.
The problem was that I kept trying to let go of the other options.
But focusing on letting go just made me think about them more.
You can’t think your way out of a thought by targeting it directly.
At one point, Burnett and Evans suggest something almost ridiculous:
List your options… and then randomly cut them in half.
And what often happens is immediate clarity.
Either:
The options you wanted are still there
Or the ones you wanted just disappeared
And your reaction tells you everything.
What I started to realize is that my problem wasn’t really about teaching.
It wasn’t about how many days per week I should work.
It wasn’t about optimizing the schedule.
It was that I was trying to answer the wrong question.
I was asking:
What is the best version of my life from here?
But that question has no answer.
There’s no external answer to which life is best.
Just like there’s no external answer to who the best guitarist is.
The question only resolves through living.
We don’t answer it with facts.
We answer it with our lives.
Not by finding the best path…
but by bringing our best to the one we choose.
So my brain just kept looping.
Like it was being paid per simulation.
The shift, for me, was smaller than I expected.
Instead of choosing a perfect plan, I started choosing a direction.
Not:
What should my work look like?
But:
What do I want my time to feel like?
And the answer wasn’t “nothing.”
As much as I love the idea of permanent snow days, I know that’s not actually me.
I like spending time writing. Reading. Building things slowly.
That feels like a long-term trajectory, not an escape hatch.
And I also need some structure, some friction, some community.
A place where people and ideas push back.
So the decision wasn’t really about teaching.
It was about choosing to spend some of my time in a place that gives me those things.
That’s it.
Not best. Not optimal.
Just… aligned enough to step into.
And I still don’t feel clear.
That part hasn’t changed.
There’s still a version of me that wonders:
What if the other option was better?
What if I’m missing something?
What if I look back and wish I chose differently?
(Which, to be fair, feels like something Future Me is contractually obligated to do at least once.)
But I think I’m starting to see that clarity was never going to come from answering the question I was asking.
Because I was asking for certainty in a situation that only allows movement.
In a previous post, I wrote about financial fingerprints.
No one asks which fingerprint is the best.
We just look at them for what they are:
A record of a life lived.
This feels similar.
I’m not choosing the best life.
I’m choosing the next set of marks.
And maybe that’s enough clarity.
Not knowing exactly where it leads.
But knowing I’m stepping forward instead of standing still.
Because the real risk isn’t making the wrong choice.
It’s staying stuck trying to prove that a right one exists.