single-player plan, multi-player reality / #21
on over-planning and adaptive confidence
My seven-year-old nephew shuffles through his starting Uno cards, tilting them enough that everyone can see them — though I still can’t figure if he’s doing that on purpose.
He's got that look; the uncontained smirk that says he’s figured out the perfect strategy.
“I'm going to win,” he announces, before gleefully running to his mom to tell her all about it. “I will put this, then this, then this…”
I watch him point at each card, his moves played in a perfect sequence.
What he doesn’t account for is the stack of Draw 2s and Draw 4s sitting in my hands, waiting to blow up his beautifully choreographed plans.
Three rounds later, and he's holding basically half the deck in his hands. Uh oh.
To be fair, I’m pretty good at Uno. Thanks to a hyperfixation after downloading the app last year, I got super into the weeds of tactics and strategy, and genuinely think I can go pretty far into a tournament bracket.
But anyway, this isn’t about Uno strategy. It’s about best laid plans, and how both of us — me, and this small, confident child — have fallen into the same trap.
My nephew's mistake wasn’t in the cards he picked, or the sequence he played them in. It’s the assumption that everyone else would play passively; that no one else had their own agenda.
It’s single-player planning in a multiplayer game.
The real game lives in the spaces between players, and not in your hand.
I’ve done the same thing: years-long career roadmaps, financial projections with rigid parameters, and personal CRMs masquerading as relationships.
I discovered FIRE in 2019 and immediately set a 10-year plan: retire by 40, take no detours, all mapped out and obsessively recalibrated every month.
I treated it like a single-player game — input the savings rate, follow the graph, arrive on time.
But somewhere along the way, life reminded me I wasn’t playing solitaire. A leadership opportunity changed my career trajectory. The waves of layoffs and disillusionment with work rewired my priorities and redefined what “safety” meant.
I started asking new questions, and a year ago, I realized I was steps away from walking off the map — and curious what might happen if I did.
By the time I decided to quit half a year ago, I’d made the concession that my plan needed rethinking.
And yet, I’d somehow crossed my number. I didn’t even realize it until half a year later, a few weeks ago — but that’s another essay for another time.
It didn’t feel like I’d won. It just showed that the game was more complex — and more generous — than I gave it credit for. My plan was airtight, and life gave me Draw Fours for it.
There’s some part of my brain that would really like it if planning harder makes life more predictable, but alas.
So now I plan for margin, not for outcomes.
Instead of mapping out the exact sequence, I wonder about:
What info do I need to make the next decision?
What doors do I want to keep open?
Where can I build in flexibility?
What happens if someone (or life) plays a Draw 4 right now?
Take skiing, and now diving. Old me would've calculated: lift tickets + gear rental + certification costs + travel = months delaying my financial goals.
New me asked: What will I learn about myself, when I'm completely out of my element?
The expensive hobbies aren’t luxury spending; they are the price of admission to data I couldn't get any other way.
The goal isn't to win with the perfect sequence. It's to get comfortable playing whatever hand you end up having, despite your best planning (like how this specific Uno set has a Wild Forced Swap Card, which is about as annoying as it sounds).
My nephew will figure it out eventually — that confidence doesn’t come from scripting every move, but from learning to replan mid-hand, especially when someone slaps down a wildcard and grins.
Other things
Guess who’s now a diver (up to 18 meters) and already looking to buy my own mask and a dive computer to hyperfixate on this new hobby!
A new friend I met while diving thought that me having a physio meant that I’m an athlete, because only athletes have physios. Oh, if only, but I’ll happily take the assumption 😂
Until next time,
Jalyn