March Madness Is the Easy Part

There’s a certain kind of madness that shows up every March.

Not the buzzer-beater, office-bracket, group-chat-chaos kind of madness. Not the “I swear this 12 seed is going all the way” delusion we collectively agree to participate in.

I’m talking about a quieter, more persistent version.
The kind that doesn’t end when the tournament does.

For the past week, people have been filling out brackets. 

Note: writing this on Thursday, brackets are locked. The tournament has officially begun.

Predicting outcomes. Assigning winners. Convincing themselves that if they just think hard enough, research enough, and think a little more… they can get it right. Maybe even win the $1M prize Warren Buffett has floating out there for the flawless bracket.

It’s control disguised as entertainment.

And I get it. I love a system. A clean path. A way to make sense of chaos.

But as I looked at my bracket, at the wins and losses I so confidently picked, I couldn’t help but wonder…

When did life start to feel like one giant bracket?

Career.
Money.
Parenting.
Where we live.
What we prioritize.
Who we’re becoming.

Round by round, decision by decision, trying to advance the right version of ourselves.

Because here’s what March reminds us, every single year.

You can be the number one seed and still have an off day.

One bad game. One injury. One distraction. One moment where things just don’t click. And suddenly, you’re out. Not because you weren’t good enough. Just because… it wasn’t your day.

And as I’m finding…  life works like that too.

The job you thought was a lock? Upset.
The plan you were sure about? Busted.
The version of life you imagined? Still loading.

But I think I’ve realized that losing in March doesn’t mean the story is over.

Some of those players still get drafted.
Some come back next year better.
Some weren’t supposed to win the tournament… they were just getting started.

And then there’s the Cinderella story.

Every year, a team no one saw coming makes a run. The right momentum. The right timing. The right belief.

I’ve had seasons like that in my own life. Periods where everything clicked. Right place, right time. Shots falling. Momentum building. It felt inevitable.

And I’ve had seasons where it didn’t.

Where it wasn’t my year to be the upset.

Where the only move was to go home, regroup, and get ready for the next run.

Here’s what the marketers behind ‘March Madness’ conveniently left out:

The madness doesn’t end in April.

It just evolves.

The stakes get higher. The decisions feel heavier. The outcomes are less predictable. And somehow, despite all our effort to map it out, life refuses to follow the bracket we built in our heads.

And still, we keep trying to predict the next round.

Is this it?

Treating every decision like there’s a perfect bracket we’re supposed to solve?

Or is the real work learning how to live inside the uncertainty… without needing to win every match-up?

Because if March teaches us anything, it’s this:

The most interesting outcomes are rarely the ones anyone saw coming.

And sometimes, the goal isn’t to win it all.

It’s to stay in the game long enough to see what kind of run you’re capable of.

March Madness has a way of pulling all of us in. Even a gay man who couldn’t tell you a single college basketball stat two weeks ago, suddenly acting like a bracketologist with strong opinions.

So if this one hit, send it to three people in your bracket of life. The ones you’d bet on, no matter the odds.

Until next Friday!

Chris