The older I get, the more I realize how much stuff I got wrong over the years. If I could sit down with my 20-year old self, here is a brief list of lessons I would convey:

1 – It’s fine to make mistakes, just don’t keep repeating the same ones

To err is human, and you will screw up so often it will become part of your personal brand. Try to keep the repeat mistakes to a bare minimum, as you are pre-disposed to being a real dummy in your 20s. The goal here isn’t perfection, it’s variation. At very least make new mistakes so it feels like you’re evolving and not just stuck in a flat spin. You’ll do a lot of spinning.

2 – Your kids don’t give a shit about your résumé

Your kids, as adults, can barely articulate what you do for a living if asked, and they definitely don’t care what you’ve accomplished. They don’t read your blog or even know you have a website. What’s important to them is that the fridge is always full to the brim so that they can eat six times a day, and that you’re present and invested in their lives as a parent, and that you do fun things with them. Even though you’ve done plenty of that, you’ll wish you’d done even more and less of everything else you thought was important.

Fun family trip: Getting photobombed by a cow in the caldera on Corvo in the Azores (2014)

3 – Start early to invest in your future

Money, relationships, work ethic, and positive habits take time to grow. The earlier you start, the less heroic you’ll have to be when you suddenly wake up from your hangover one morning in your 30s and go “oh fuck!”.

4 – Beware of things that are permanent

You’re young and a bit reckless, so tattoos feel like personality. In 2026, your tattoos look more like a scattered collection of bad decisions made without adult supervision, basically permanent versions of old social media posts you wish you could delete. Maybe dial back the spontaneity a little. Start with something reversible, like streaks in your hair, before committing ink to your skin for eternity.

Naively getting a random tattoo inked on my shoulder (1999). I still struggle to describe what it is.

5 – You can’t easily drown with flotation devices on

The weight of the world will feel overwhelming at times – work, money, expectations, responsibilities, relationships, kids, your own stupidity. It sneaks up on you. One minute you’re fine, the next you’re convinced everything is collapsing and you’re somehow responsible for all of it. The trick is realizing you’re not meant to carry it all alone. Figure out early on who and what actually keeps your head above water, the people who answer your calls, the routines that stabilize you, the habits that don’t make things worse, and use those as your flotation devices. Keep them close. Wear them often. Because when things go sideways, you’ll already be wearing a life jacket, and not frantically looking for it while treading alone in cold, choppy waters.

6 – Smart people don’t buy used Fieros

At some point, you’ll convince yourself that the Pontiac Fiero is a misunderstood classic. A hidden gem. “It’s underrated and has a bad rap,” you’ll say, like you’ve uncovered something the rest of the world just wasn’t smart enough to appreciate. You’ll ignore the warnings, the reputation, the very loud and consistent feedback from literally everyone who has ever owned one. What you will actually buy is a slow, dangerous, and highly flammable lesson in regret. In hindsight, the bad press wasn’t unfair, it was generous. The Fiero didn’t have a branding problem, but it did have pretty much every other problem. And you, for reasons that will never fully make sense, decided you needed one. Thankfully you didn’t get a Fiero tattoo at the same time.

Proudly posing near my Fiero (1990). The engine caught fire a week after this photo.

7 – Don’t be such a fucking dickhead

This shouldn’t need explaining, but here we are. You have a knack for turning simple situations into unnecessarily complicated ones, usually by being impatient, overly blunt, or convinced you’re right when it doesn’t actually matter to anyone. You’re not solving problems, you’re manufacturing them and then acting surprised when they show up. Try being nicer. More compassionate. More humble and human. Maybe shut your mouth once in a while and listen longer, react slower, and accept that not everything on this planet requires your input. Most things in life are simple; you just have a habit of making them harder than they need to be.

8 – Some decisions change everything

You should take more early chances. Instead, you waited until your late 20s to finally get off your ass and earn your pilot’s wings, and that decision changed everything. Your world got bigger overnight, your perspective shifted, and suddenly life had more direction and focus. That’s the part you miss when you’re young, you think there’s time to figure it out later. There is, but later tends to come with more hesitation, more responsibility, and a lot more reasons not to try. Take your chances early on. If earning your wings could quietly rewrite the trajectory of your life once, imagine what a few more of these decisions could do.

Going for a flight in a C152 shortly after getting my pilot’s license (1997)

9 – Time isn’t as abundant as you think

You waste time like it’s renewable, like there’s always another stretch coming where you’ll finally get serious. There isn’t. Time just slowly disappears while you’re “busy” doing meaningless shit. It’s only when you start billing your time as a consultant that it really clicks: every hour suddenly has a price tag. As it turns out, time isn’t just money, it’s everything. You can make more money, fix most mistakes, even recover from a few disasters, but you can’t get a single minute back. Treat time like it matters earlier on, because eventually you’ll realize it’s the only thing that ever did.

10 – When the kids plead you for a dog, say no

The kids will promise to take the lead on everything: walks, feeding, training, play time, emotional support. Then the puppy shows up, spends the first 24 hours biting everyone’s toes like a tiny land shark, and every responsibility quietly transfers to you as if outlined in an exit clause buried deep in a consulting agreement you clearly didn’t write or sign. Jack arrived as the “family dog” and immediately became your dog. You didn’t need another responsibility, yet here you are with a full-time furry shadow who’s claimed your bed as his own. You won’t complain, because he’s your best friend and sidekick, but let’s not pretend this was a group decision. You got completely played.

Jack’s cute, but a real pain in the ass and he’s your dog