You Look Like Your Decisions

What a decade of invisible choices actually looks like

They say when you’re born, you look like your parents. And when you die, you look like your decisions.

About a year ago, I heard through a friend that someone close to me had said our relationship changed. That the reason it changed was money.

My first instinct was to be hurt. But I sat with it. And I started asking myself questions. Because that’s what I do when something bothers me more than it should. If it stings, there’s something underneath worth looking at.

So I asked: is it true? Did the money change me?

I had to be honest with myself. My lifestyle looks different now. The trips, the clothes, the dinners. From the outside, the before and after is obvious. So I can understand why someone would draw that line. Money arrived, Derek changed. Simple.

But is that what actually happened?

I went back further. What came before the money? A decade. Trying, failing, trying again. Businesses that didn’t work. Ideas that went nowhere. Years where I had nothing to show for the path I chose except the fact that I was still on it. The money didn’t arrive and turn me into someone new. The money arrived because of who I’d already become through a thousand small decisions nobody ever saw.

So the real question isn’t “did the money change me?” The real question is: what do people see when they look at your life, and are they seeing the cause or the output?

They were seeing the output. And calling it the cause.

That realization led me somewhere deeper. I asked: why did this bother me so much? If I’m confident in my decisions, why does one person’s misread sting?

Because it revealed a gap. Not between me and this friend. Between what I know to be true about my own path and someone else’s ability to see it. That gap is lonely. And no amount of being right about your own life makes that less true.

I’ve never shared this before. But for all of my twenties, I never kept more than $5,000 in my bank account. Not because I didn’t earn more. Because I chose not to hold it.

Every dollar above that line went back into the life I was building. Photography workshops. Flights to LA to shoot and take meetings. Better gear. Dinners with people passing through Toronto who I wanted to learn from, build with, stay connected to. I decided early that I would run lean and not tie my confidence or my identity to a bank balance. That I would over-index on growth and under-index on security.

It was nerve-wracking. There were months where income I was counting on arrived late and expenses lived on my credit card. But I knew my life was a startup. And I felt confident, from the amount of work I was putting in, that eventually it would pay off.

Nobody saw that decision. Not the friend who said money changed me. Not anyone. They saw what came after. They never saw the years I deliberately kept myself at zero so I could invest in becoming someone worth betting on.

So what does that mean about everyone else? If my life reflects my decisions, what does anyone’s life reflect?

I had to ask it honestly. If someone’s life looks like the default, like what you’d end up with if you never actively chose anything at all, does that mean they didn’t choose? That they followed? That they took what was handed to them and called it theirs?

I’m not asking that as a judgment. I’m asking because the same logic has to apply to everyone, including me. If my decisions built my life, then the absence of decisions built someone else’s. That’s not good or bad. It’s just the clearest way I know how to see it.

When you’re young, this is invisible. You and your friends can be completely different people, but your lives look the same. Same routines, same starting line. The differences are happening underneath, in what you choose to do with your time, what you give up, what you say no to when nobody’s watching.

I felt this early. Up until graduation, I had one friend group. Close friends from high school who grew super tight throughout university. But when I graduated and decided not to use my degree, I was suddenly exposed to the full world. I started building friendships in photography, in the music industry, downtown Toronto, different cities entirely.

And I remember noticing something. Whenever we’d go out as a group downtown Toronto, to Montreal, LA, wherever, I knew people in those cities. I had connections, conversations, rooms I could walk into. Not because I was special. Because I had been making a decision, over and over, to keep growing my world while it would have been easier to keep it the same size.

I couldn’t name it at the time. But I could feel a gap forming. Not in status. Not in money. In range. In the breadth of experiences, conversations, and knowledge that comes from choosing to keep expanding when nothing is forcing you to.

Then I asked myself the hardest question: what do I actually want this friend to understand?

Not that I’m right. Not that they’re wrong. Just that the money was never the thing. The decisions were always the thing. They were the thing when nobody could see them, they were the thing when everything was failing, and they’re still the thing now. The money is just what it looks like from the outside when a decade of decisions finally compounds.

And if I’m being fully honest, the question I keep coming back to isn’t about this friend at all.

It’s: am I still making decisions? Or am I starting to coast on the ones I already made?

Because the same principle that got me here can work against me if I stop. The moment I stop actively choosing is the moment my life starts drifting toward the default. Doesn’t matter what’s in the bank account. Doesn’t matter what the last decade looked like.

Your life looks like your decisions. It always has. The only question worth asking is: are you still making them?