Back by popular demand, here’s another list of lessons I would convey to my 20 year-old self:

1 – Travel more in your twenties

Work will eventually take you around the world, but not until your thirties. Looking back, you’ll wish you had started traveling much earlier. You’ll wish you had spent far less money buying “things” and getting drunk and spent more on experiences. You’ll wish you’d gotten lost more in unfamiliar places and eaten food you could barely pronounce. Eventually you’ll learn that the world is far bigger and more interesting than any small corner you call home. The older you get, the harder it becomes to disappear for a month with a backpack and no real plan. Responsibilities have a way of multiplying, so while you have the freedom, use it. The memories will outlast anything you could have bought, and nobody lies on their deathbed wishing they had spent more time drinking at their local bar.

2 – You don’t need hundreds of friends, just a handful of good ones

For years, you’ll spend far too much time trying to maintain friendships that exist mostly out of habit, proximity, or some vague sense of obligation. You’ll try to impress people that don’t matter. As you get older, something interesting happens: your circle gets smaller and your life gets better. The people who matter stick around. Everyone else is just background noise. Stop worrying about collecting friends like hockey cards, and focus on the people who are real. Focus on your family, on your passions, on building a life that feels authentic rather than popular. In the end, a few genuine friends are worth more than a thousand acquaintances who only know your highlight reel.

3 – Never wear a duck costume to a Halloween party

At the time, it seemed harmless, funny even. But within hours , nobody remembered your actual name. You were simply “Duckie” and not for the night or the weekend. More than a decade later, people were still yelling “Hey Duckie!” whenever you entered a room. When you and Lu first started dating, she too called you Duckie, because that’s how you were introduced. She kept it up for nearly a year until the realization finally hit that introducing her husband “Duckie” to normal adults might be strange. Nicknames are like ridiculous tattoos, they stick around forever. So wear a ghost costume instead. Nobody spends fifteen years calling a grown man “Ghostie.”

Hard to imagine that wearing a duck costume would set the course for your life for 15 years, but it did

4 – Don’t sell your vinyl collection at a garage sale

When CDs arrived, you became absolutely convinced that vinyl was dead. The future was digital. So you sold the collection you’d spent years building for nothing at a garage sale and proudly declared you’d never listen to another album again. Many moons later after the kids were born, you decided vinyl was actually the greatest thing ever created and began rebuilding your collection from scratch. The only problem was that many of the albums you sold for a dollar now cost fifty. Over the years, you’ve managed to buy back a surprising number of the same records you once owned. So basically, you paid someone to take them away, then paid significantly more to get them back. This is not investing or collecting, just being an idiot with extra steps.

5 – Buy more concert tickets

Music is, and always has been, one of the greatest joys in your life, and while you will go to a fair number of shows in your twenties, you don’t truly embrace live music until your thirties. From that point on, you start attending an industrial number of concerts. Some of your best memories will come from standing in crowded theatres and clubs listening to great live music. The regret isn’t the concerts you attended, it’s the ones you skipped, and over the years you’ll find yourself telling your kids “I had a chance to see them in a small club” or “I almost bought tickets for that tour.” Just buy the ticket.

6 – Fanny packs are not a fashion statement

For reasons that remain unclear, you spent a significant portion of your younger years wearing a fanny pack as though it was a perfectly reasonable fashion choice. It wasn’t. At the time, you convinced yourself it was practical. It held your wallet, your keys, your camera, and whatever other essential items you believed were necessary for an outing. What it actually held was any remaining chance of looking cool. Years later, you’ll be looking through a photo album and be mortified to notice the same thing in many shots. Not the scenery, or your hair, or the people standing beside you. But the fucking fanny pack. It sits there in so many photos like a polyester monument. Thankfully, AI can remove fanny packs from photographs with astonishing accuracy. Historians refer to this as correcting the mistakes of the past. Unfortunately, AI cannot remove the memory of you willingly wearing one.

A few selected fanny-pack photos from an almost endless repertoire 

7 – Get used to losing

You grew up hopelessly spoiled. From the day you were born until the year you turned eighteen, the Montreal Canadiens won nine Stanley Cups. You naturally assumed that every second year spring involved parades and banners. And then adulthood arrived. The Canadiens will win one more Cup when you’re twenty-five, and then apparently decide that that was enough winning for the rest of your lifetime. The three decades that will follow will become an advanced course in disappointment. Every October brings modest hope, every April suffering. You’ll invest thousands of emotional hours and convince yourself that this year will be different, but it won’t be. This lesson isn’t about hockey, though. It’s that not everything in life follows the script you grew up expecting. Sometimes the glory years end. Sometimes success becomes much harder to find. Sometimes all you can do is stay loyal, lower your expectations, and laugh at the absurdity of caring this much. Fortunately, years of cheering for the Habs as an adult will prepare you perfectly for running ultramarathons, aging, and owning businesses. All three involve a shocking amount of suffering combined with an irrational belief that next year will be better.

8 – Release the joystick, Duckie

You were spectacularly lazy in your twenties. You once spent three months playing an entire season of Ken Griffey Jr.’s baseball on your Nintendo. Three months. For those keeping score at home, that’s 162 regular-season games, playoffs, and a World Series. You effectively became the general manager, manager, hitting coach, pitching coach, broadcaster, and chief emotional support officer for the Montreal Expos, which were many more roles than you occupied in your own sad life at that time. The real Expos lost their shot at glory during the 1994 lock-out, but you heroically stepped forward in 1995 to finish the job yourself from the comfort of a couch. You also read approximately zero books during that same period. The lesson here isn’t that video games are bad, but rather that time has a funny way of disappearing when it’s attached to a controller. One day you’ll look back and realize that the skills that changed your life came from conversations, travel, running, taking chances, starting businesses, and occasionally doing things that made you uncomfortable. None of them came from winning a simulated World Series with a team that no longer exists. By all means, play the occasional game. Just don’t spend an entire season managing a baseball franchise when you could be building your own life instead.