◆ To My Future Kids Phillip An

WHEN YOU'RE HURTING

22. No Permanent Records

"Ever tried. Ever failed. No matter. Try again. Fail again. Fail better." —Samuel Beckett

Dear Kids,

So much of what makes the hard parts hard is the fear that they'll mark you forever — that one failure becomes a permanent stain. I want to take that fear away.

Let me tell you a secret: everything adults warned you about "permanent records" is a complete lie.

When I was your age, I believed in a mythical file folder that would follow me through life, stuffed with every detention slip, bad grade, and questionable decision. I was so terrified of making mistakes that I tried to be perfect. I studied hard, avoided risks, and followed every rule, thinking that's how you build a successful life.

But here's the thing: I didn't learn much from trying to be perfect — except how to be anxious. The real lessons, the ones that shaped me, came from the stumbles, screw-ups, and spectacular failures I couldn't avoid.

Recently, I listened to a podcast with Chris Sacca, the investor who bet early on companies like Twitter and Uber. He talked about his teenage years — running poker rings, hustling Blow Pops, and even trading live hog futures on a pager — and how the messiness of those experiences taught him resilience, creativity, and grit.

Something he said stuck with me:

"The last bastion of humanity is in the messiness. The things that feel like errors and bugs are actually the self-preservation aspects of who we are."

He's right. The grit that makes us stronger isn't forged in the comfort of perfection. It's born in the chaos of trying, failing, and trying again — it's the same reason I once told you that life truly begins at the edge of your comfort zone. And looking back, I wish someone had told me sooner that life isn't about avoiding messes — it's about figuring out which ones are worth making.

Life's real lessons come from the mess

Growing up, I thought life was a test with clear right answers. But now I see life isn't a test at all — it's more like an improv show. You try things, you fail, you learn, and sometimes you end up in a ridiculous situation you couldn't have scripted if you tried.

But here's what I observe now: we live in a world where kids are often shielded from failure. Parents, schools, and even society at large seem obsessed with coddling children, ensuring they never fall, never fail, never face discomfort. And I get it — failure is painful. Watching someone you love struggle is hard.

But the truth is, if you never fall, you never learn how to pick yourself back up. Resilience doesn't come from a bubble — it comes from bumps, bruises, and the occasional catastrophic screw-up.

A love letter to future screw-ups

Here's what I hope for you: not perfection, but glorious, beautiful messes. I hope you make mistakes big enough to leave a mark — but not a permanent one. And I hope you laugh your way through them.

May you skip school for an adventure of a lifetime. I hope one day, you get so swept up by the urge for adventure that you skip school, book a one-way flight to a country where you don't speak the language, and set off on your own. Maybe you'll find yourself riding a crowded bus through the mountains with a goat as your seatmate, wondering why you didn't pack snacks. And maybe, when you finally make it back home sunburned, broke, and jet-lagged, you'll realize you learned more in that week than in an entire semester of school.

May you experience a "city magic" disaster. I hope you find yourself in Berlin, dancing the night away in a warehouse-turned-statue-club, surrounded by strangers who look like they fell out of an art exhibit. And when you wake up the next morning, hungover in someone's flat, staring at a suspiciously large taxidermied owl and regretting your life choices, you'll learn that spontaneity makes the best stories — and that dread is just part of the ride.

May you get fired from a job that deserved it. I hope you work a job so soul-sucking that when you finally get fired for taking a two-hour lunch break to cry in a parking lot, you feel nothing but relief. And I hope you learn two things: first, that some paychecks aren't worth it, and second, that dignity is overrated — but health insurance is not.

May you fail so spectacularly, it becomes legendary. I hope you pour your heart into a band, a mural, or a podcast that no one listens to — and then watch it flop in the most public way possible. When your "avant-garde synth-folk" duo gets booed offstage at a bowling alley, I hope you laugh so hard you forget to be embarrassed. Bonus points if your failure becomes a meme.

Why these mistakes matter

These aren't just funny stories. They're soul-deep lessons that will shape who you are.

Skipping school teaches you to chase what matters (and to pack snacks). City disasters prove the best memories are unplanned and slightly mortifying. Terrible jobs teach you to value yourself more than a paycheck. Spectacular failures kill your fear of judgment — and make for legendary anecdotes at every dinner party you'll attend for the rest of your life.

I want to push back on something the world will quietly try to teach you. The pristine résumé, the unbroken streak of wins, the no-failed-classes transcript — it doesn't impress me, and you shouldn't let it impress you either. When I look back at the people in my life who turned out to be the most interesting, most generous, most fully alive, almost every one of them has a season of their twenties that looks, on paper, like a mess. A fired-from. A dropped-out-of. A broke-up-with. A moved-back-home-with. The messiness wasn't the obstacle to who they became. It was the curriculum.

In the age of AI, do the old rules still matter?

At the end of the day, I really believe this: in a world dominated by AI and automation, compliance training and standardized education aren't what's going to set you apart. Do we really think kids today need more worksheets or test prep? Probably not — but that's a rant I've saved for the education letter.

What I do believe is this: learning how to mess up, get back up, and laugh in the face of failure is more important than ever. Resilience, creativity, and adaptability can't be taught in a classroom. They're forged in the wild, beautiful chaos of real life.

The real "permanent record"

Forget the mythical file folder. The only record that matters is the one you'll write yourself — full of stories so wild, your future kids (and therapist) will need a minute to stop laughing.

So go on, kids:

Life isn't about avoiding messes. It's about deciding which ones are worth making.

P.S. If you do wake up in a Berlin police station, please don't call me for bail money. And maybe wear a helmet next time.

Love,

Dad.