I’m 35 and if I could sit down with my twenty-year-old self for ten minutes, here’s what I’d tell him.

Lately I’ve been doing that thing people in their thirties tend to do.

Reflecting.

Not in a dramatic, mid-life crisis kind of way, but in those quiet moments on a long walk. I find myself thinking back to who I was at 20. The version of me who thought he had it all figured out, who was full of plans, opinions, and a fair amount of misplaced confidence.

If I could sit down with that guy for ten minutes, there’s a few things I’d want to tell him. Not because I have it all figured out now, but because I think I’ve made enough mistakes and learned enough lessons that some of it might have spared him a bit of grief.

This isn’t a sob story and I certainly don’t want it to sound like it. I’m genuinely grateful for the path I’ve taken. But if any of what I share gives someone else a bit of food for thought, that would be a nice bonus.

Here’s what I’d say.

You can’t connect the dots looking forward

This one isn’t mine. It’s from Steve Jobs’ 2005 commencement speech at Stanford, and it’s stuck with me ever since I first heard it.

His point was simple. You can only connect the dots of your life looking backward. In the moment, things often feel random, pointless, or like a detour. But years later, you realize how every experience, even the boring ones, were quietly preparing you for something.

Let me explain.

In my early twenties, I spent a few years working in an office in finance. I learned things like Excel, and a bunch of administrative skills that, at the time, felt completely unrelated to anything I actually wanted to do with my life.

Fast forward several years, and I found myself helping run a language school. We had a scheduling problem that no one could quite crack. So I sat down, opened up Google sheets, and built a custom scheduling system that ended up saving the school hours every week. It was in use until I left that position years later. 

Who knew that those tedious office years would come back and pay off in such a specific, useful way?

So if I could tell my younger self anything, it would be to stop trying so hard to make every decision part of some grand plan. Just do good work, learn what you can, and trust that it will all start to make sense eventually.

Take care of your body

Now, a small disclaimer before this one. This is just my experience, and it might not apply to everyone. But it’s a lesson I personally wish I’d taken more seriously.

Growing up, I was always active. I played multiple sports, was outside constantly, and never had to think twice about exercise. It was just part of life.

Then I hit my twenties.

University, work, travel, late nights, and the general chaos of that decade  pushed sport and exercise to the back burner. I wasn’t overweight or particularly unhealthy, but I lost the consistency I’d had as a teenager.

It wasn’t until my thirties that I really committed to being active again. These days, I’m at the golf range, working out or out walking most days, and I feel a lot better for it.

The thing is, I would have felt this good for a whole extra decade if I’d just kept going.

The body you have at 25 isn’t free. You’re borrowing against the body you’ll have at 45.

I’d tell my 20-year-old self to keep moving. Even when life gets busy. Especially when life gets busy, actually.

Stability should not be underrated

This one probably goes against a lot of the advice you’ll see online these days, where everyone seems to be telling you to quit your job, start a business, and escape the rat race.

But here’s the truth. I spend some of my twenties as a solo entrepreneur, jumping from one venture to the next. Some of those businesses failed outright. Others limped along just enough to keep me hopeful but never quite enough to feel secure.

One that still sticks with me was an online English school I quit my day job to build. The idea was to take all the lessons I’d normally give in a classroom and offer them online, either for free or for a small course fee, around 12 dollars. I genuinely believed in it. I was passionate about it. I spent months on it. 

It didn’t fail in the dramatic sense. It just never reached the point where I could make any meaningful money from it, and I didn’t have the resources to keep pouring time into something that wasn’t paying the bills. Eventually, I had to walk away from it. I simply couldn’t afford to keep going.

That’s the part nobody talks about when they tell you to chase the dream. Ideas need time, and time costs money.

I also learned that it’s incredibly difficult to build something meaningful when you’re constantly stressed about money. My creativity, patience, and good decision-making all suffered when I was operating from a place of financial uncertainty. Maybe some people can do, I could not. 

A bit of stability, whether that’s a steady job for a few years, a savings cushion, or just a clear plan for how you’re going to pay rent for the next few months, makes all the difference. It gives you the breathing room to take smarter risks, not just desperate ones.

This might just be my personality, and I know plenty of people thrive on chaos and uncertainty. But I’d tell my younger self to think a little less about the dream and a little more about the foundation that dream needs to stand on.

The romantic version of entrepreneurship rarely matches the reality. Build the safety net first. The leap is much easier when you know there’s something to catch you.

Make time for the people you love

The older I get, the more this one hits home.

In my early twenties, I was off traveling, chasing experiences, and convinced that the world was waiting for me. Friendships felt easy back then, almost endless. I assumed everyone would always be around when I got back.

But life has a way of pulling people in different directions. Friends move to new countries, get married, have kids, and start carving out their own little worlds. If you’re not intentional about staying in touch, years can pass before you realize you’ve drifted.

These days, I make a much bigger effort to call my family more often. I’ve reconnected with friends I’d lost touch with for years, and every conversation is a reminder of why those relationships mattered in the first place.

Research from the Harvard Study of Adult Development, one of the longest-running studies on happiness, has found that the quality of our relationships is one of the strongest predictors of long-term well-being. Not money, not career, not status. Relationships.

If only I read that in my twenties. 

I’d tell my younger self to pick up the phone, and call his mother. To text the friends he loves. To take that trip to visit them, even when it’s inconvenient.

The years go by faster than you think, and the people you take for granted today might not be around tomorrow.

The bottom line

I’m not writing any of this from a place of regret. The mistakes, the failures, and the wandering all shaped me into the person I am today, and I genuinely wouldn’t trade it.

But if my 20-year-old self happened to be reading this, I’d want him to know that some of the things he thought were important probably weren’t, and some of the things he overlooked are the ones that matter most in the long run.

If even one part of this gives you something to think about, then it was worth writing.

As always, I hope you found some value in this post. Until next time.