It’s 1 AM at Chicago O’Hare, and I’m having the kind of existential crisis that only happens in airports at ungodly hours.
My flight’s delayed. Again. I’m pretending to check emails while actually contemplating every life choice that led me here.
That’s when I see him.
He’s maybe 20 years old, wearing a bright hoodie and carrying a trophy so absurdly large it should have its own boarding pass.
This thing is taller than most toddlers.
And he looks happy—genuinely, inexplicably happy at 1 AM in Terminal 3.
I’m nosy, so I ask:
“Big win?”
He grins. “Yeah, just wrapped up a tournament. I’m a professional disc golfer.”
I do that polite thing where you smile supportively while internally thinking, “That’s adorable, kid.”
We chat for five minutes. Nice kid. Passionate about throwing Frisbees for a living.
We shake hands and part ways.
Then I do what any human with a smartphone would do at 1 AM.
I Google him.
Two Minutes Later
I’m staring at my phone like it just disproved everything I believe about how the world works.
This kid—this twenty-year-old with a Frisbee—has career earnings of over $850,000.
Eight. Hundred. Fifty. Thousand. Dollars.
He’s ranked top 10 in the country. Major sponsorships. Traveling the world doing what he loves.
And I’m sitting here with a doctorate and 25 years of experience, trying to figure out if I can expense a $15 airport salad.
The irony hits hard.
But here’s what really broke me at 1 AM:
It wasn’t the money.
It was the look on his face when he talked about disc golf. Pure alignment. No Sunday night dread. No “work self” versus “real self.”
No pretending to care about things that don’t matter.
Just complete integration between who he is and what he does.
And I realized something I’d been avoiding for years:
I gave up my version of disc golf a long time ago.
And I bet you did too.
The Conversation We All Had
You were probably 22. You were good at something—maybe even really good.
Something that made you lose track of time. Something you’d do for free. Something that felt like the most authentic version of yourself.
Then someone asked:
“But how are you going to make money doing that?”
So you looked at your options:
Option A: Follow your passion, risk looking stupid, possibly fail.
Option B: Pick something practical, build stability, make everyone proud.
Most of us picked Option B.
Not because we were cowards. But because Option B came with a guarantee Option A didn’t: Respectability.
And when you’re 22, respectability feels like oxygen.
The Trade
Here’s what nobody tells you about the safe path:
Security has a price.
We traded possibility for stability. Alignment for approval. Autonomy for a 401(k).
And for years—maybe five, maybe fifteen—that trade felt smart. Mature. Responsible.
Until it didn’t.
Until you’re 35 or 42 or 48, lying awake at 2 AM, realizing:
You built exactly the life you were supposed to build.
And it doesn’t fit.
What He Understood That We Didn’t
At some point, someone definitely told this disc golf kid to get a real job. To be realistic. To have a backup plan.
He didn’t listen.
Not because he was naive, but because he understood something we didn’t:
The “safe” path is only safe if you value the wrong things.
While everyone else his age was keeping their options open, sampling majors, building well-rounded resumes…
He was getting one percent better at one thing.
Every weekend. For years.
That’s not naive. That’s strategic.
Because here’s what 25 years taught me:
Diversification protects you from catastrophic loss.
But it also protects you from extraordinary gain.
And more importantly:
It protects you from ever discovering who you actually are.
How He Got There
This kid didn’t wake up at 20 making $850,000.
Early on, he made nothing. Maybe $100 here, a few hundred there. Sleeping on couches. Gas station food. Side jobs.
His friends were graduating, getting real jobs, posting LinkedIn updates about promotions.
And he was throwing a Frisbee.
The first 100 hours? Almost no results.
The next 1,000 hours? Small improvements, nothing life-changing.
Somewhere around 10,000 hours? Everything shifted.
He crossed a threshold. Went from “pretty good” to “one of the best in the country.”
And that’s when everything changed.
Most people quit at hour 200.
Not because they lack talent, but because they’re not seeing results fast enough and everyone’s asking when they’ll get serious.
This kid didn’t quit.
The Script We Were Given
Go to college
Get a good job
Work hard for 40 years
Climb the ladder
Retire at 65
Then—and only then—do what you actually want
That script is broken.
It asks you to postpone being yourself for 40 years.
It asks you to trade your twenties, thirties, forties, and fifties for a promise that when you’re 65—if you’re healthy, if you’re lucky—then you’ll finally get to live.
That’s not a career path.
That’s a hostage negotiation.
What I Traded
I have a doctorate. Publications. Leadership roles at major universities. A resume that looks impressive.
And at 1 AM, a kid with a Frisbee made me question all of it.
Not because my career is wrong—I’m proud of what I’ve built.
But because I realized what I traded to get here:
- Time for credentials
- Autonomy for approval
- The possibility of extraordinary for the guarantee of acceptable
And here’s the thing about acceptable:
It’s comfortable. It’s respectable. It pays the bills.
But it’s killing you slowly.
In the quiet 2 AM way where you realize you’ve spent 20 years becoming someone you don’t recognize.
Someone who cares about expensing airport salads instead of carrying giant trophies.
The Question
What’s your disc golf?
What’s the thing you were naturally good at that you shelved because someone asked how you’d make money doing it?
Everyone has one.
That thing you’d do for free. That made you lose track of time. Where you felt like the most authentic version of yourself.
And then you got practical.
You told yourself you’d come back to it later. When you had more time. More money. When you’d proven yourself.
Except later never came.
Because later you had a mortgage. Kids. Car payments. Aging parents. A reputation to protect.
And the distance between who you are and who you could have been just kept growing.
I’m Not Telling You to Quit Your Job
You have real responsibilities. Real bills. Real people depending on you.
But here’s what I am saying:
The opposite of “quit everything and chase your dream” isn’t “do nothing.”
What’s the smallest version of your disc golf that you could start right now?
Not the all-or-nothing bet. Not the dramatic life overhaul.
The 5 AM version. The side door. The thing you could start this weekend.
The thing that, in five years, might compound into something extraordinary.
Or at minimum, might make you feel like yourself again.
The Real Risk
We think the risky path is pursuing your passion.
We think the safe path is the stable job.
We’ve got it backwards.
The risky path is spending 40 years building a life that doesn’t fit.
The risky path is waking up at 50 and realizing you don’t know who you are because you spent three decades being who everyone else needed you to be.
That’s the real risk.
Pursuing disc golf?
At worst, you fail at something you love and get a regular job like everyone else.
At best, you build a life so aligned with who you are that work stops feeling like work.
And everyone else spends their lives wondering what if.
What I Wish I’d Known at 22
The people telling you to be realistic? They’re not trying to hurt you.
They’re projecting.
They picked the safe path. And now they need you to pick it too, because if you don’t, it means they had a choice.
And if they had a choice, that means they chose wrong.
So they need you to believe the safe path was the only path.
But it’s not. It never was.
The script is optional.
You can follow it. Millions do. Some are even happy.
But you can also build something so strange and specific and authentically yours that people don’t even have a category for it.
And that’s where all the interesting lives are built.
Not in the middle of the bell curve, doing what everyone else is doing.
But at the edges, where you’re willing to look stupid long enough to get good.
The Truth No One Says
Time is running out.
Not in a morbid way. Just mathematically.
If you’re 35, you’ve got maybe 30 productive years left.
If you’re 45, you’ve got 20.
Every year you spend building someone else’s dream is a year you’re not spending building your own.
What Happened Next
I made my flight. Got home around 3 AM. Went to work the next day like nothing happened.
But something did happen.
I can’t stop thinking about that kid at Gate B12.
Not because I want to become a professional disc golfer.
But because he reminded me:
The script is optional.
“Get a real job” is terrible advice.
And the courage to take yourself seriously before anyone gives you permission?
That’s not recklessness.
That’s the smartest competitive advantage that exists.
So What’s Your Disc Golf?
And more importantly: what are you going to do about it?
The 20-year-old at Gate B12 isn’t waiting for permission.
Why are you?
If this hit you at 2 AM while you’re questioning everything, you’re not alone.
We’re all just trying to figure out if it’s too late.
Spoiler: it’s not.
But the clock is ticking louder than it was yesterday.
Follow along
I write about non-linear careers, unconventional paths, and the courage it takes to bet on yourself.
Because the world has enough people following the script.
What it needs is more people willing to write their own.