If I could sit across from you in your early twenties — the version of you who was trying so hard to be the right kind of man — I’d start with something simple:
You’re allowed to not know who you are yet.
You don’t believe that now. You think adulthood comes with a script. You think your small-town upbringing handed you the rules for loyalty, responsibility, settling down, staying put. You think “good men” don’t change their minds. Don’t walk away. Don’t deviate.
But your twenties won’t be about following the script.
They’ll be about unlearning it.
Let’s start with the part of your life everyone saw, but no one really understood: you drink every night.
And somehow, you keep everything together.
You’re composed.
You’re reliable.
You’re the one people count on — even when you don’t remember half the nights they say you handled so well.
That’s just who you were then: full control on the outside, blurry on the inside.
It wasn’t self-destruction.
It wasn’t spiraling.
It wasn’t hidden.
It was how you existed in a world that suddenly opened wide — loud nights, new friends, the first sense of belonging you’d ever really felt. Alcohol gave you a shortcut into connection before you knew how to access that openness on your own.
You’ll eventually unwind in calmer ways, but don’t turn this chapter into a cautionary tale.
You were young.
You were social.
You were figuring life out the same way everyone does in their twenties — by trying things, pushing limits, and sometimes forgetting the details.
You weren’t broken.
You were becoming.
And yes, there are moments from that era you’ll treasure.
Like the birthday you planned — hibachi dinner where everyone smelled like they’d worked the grill, followed by bottle service you secured through your industry connections.
At one point the birthday boy looked around and said,
“Only we would pay extra to cook our own dinner and then serve ourselves at bottle service — on my birthday.”
Everyone cracked up, because it was true.
Birthdays are supposed to be effortless, and you accidentally built the most hands-on one imaginable. But they loved it anyway.
And here’s what you didn’t see then:
Even when you over-engineered things, people still had a good time because you made them feel included.
You weren’t performing.
You were creating connection — long before you understood that was your strength.
There’s also the decade-long relationship.
You loved him. He loved you. And together you built an era that will always matter.
You’ll share a home, routines, comfort, holidays. You’ll feel proud of the stability you built — because stability was the closest thing you knew to connection at the time.
But looking back, you’ll realize something you couldn’t have understood then:
You confused duty with love.
You stayed because that’s what small-town values taught you:
stay loyal, stay steady, stay even when you’re quietly starving for something more honest.
You stayed because you thought good men don’t leave.
You stayed because leaving felt like failure.
You stayed because you didn’t yet know that people can grow at different speeds and in different directions — and that doesn’t make either person wrong.
That relationship wasn’t wasted.
It wasn’t a mistake.
It wasn’t lost time.
It was your first real education in partnership — what closeness feels like, what connection requires, and the point where staying is no longer the same thing as loving.
And when he someday reads what you write, you’ll hope he understands:
he mattered. That decade mattered. You grew because of it, not away from it.
Then, in 2012, the lake enters your life.
It begins the way most things do for you then: enthusiastic, a bit chaotic, and very performative.
You toss a power cable onto the fiberglass swim platform like someone who doesn’t yet grasp the cost of a boat. Chris — the captain who becomes a defining presence in your life — winces, then decides you’re worth teaching.
And he teaches you everything:
- how to coil a line
- how to tie off a cleat
- how to read wind, wakes, and weather
- how to dock without panic
- how to take the helm with real confidence
You go from eager chaos to dependable first mate faster than anyone expected.
But even then, you’re performing more than you’re connecting.
Being competent is still your armor.
That changes slowly — and then all at once.
Boating becomes less about tie-ups and loud weekends (though those still have their place), and more about the pieces that last:
- long, calm lake runs
- marina weekends that feel like summer camp
- morning coffee tucked into the cockpit while the lake is still calm
- nights full of storytelling and familiar faces
- camping in the harbor with people who’ve become chosen family
It becomes the first place in your life where you stop trying to earn belonging.
You simply… belong.
The water teaches you what your twenties never did:
Connection is better than competence.
Belonging is better than performance.
And community is something you build by showing up as yourself.
Boating becomes one of the great constants of your adult life — not because you mastered it, but because you finally let it matter.
And then there’s money — the topic you keep pushing into the “later” bucket.
Someone will tell you about compounding.
Listen to them.
You won’t want to.
You’ll assume you don’t make enough.
You’ll think investing is something you do after you “figure out adulthood.”
But the truth is simple:
you need time more than you need money.
Open the Roth.
Start small.
Let your future self thank you for choices you didn’t yet understand were generous.
This won’t feel like financial advice one day.
It’ll feel like self-respect.
And here’s what ties all of this together.
Moments matter more than results.
The path matters as much as any arrival.
Curiosity keeps you alive.
Comfort slows you down.
Community holds you together.
And people will remember how you made them feel — not how perfect you tried to be.
Younger you thinks adulthood is about “getting it right.”
Older you knows it’s about letting yourself change — without apology.
So here’s what I’d leave you with:
You weren’t lost.
You weren’t failing.
You were learning in real time with the tools you had.
And for where you were —
you were doing just fine.