What is money really for?

What I didn’t know until I learned later is that squirrels forget. They buried a lot more than they ever dug back up, and many of those acorns are never found. Some of them quietly become trees that will one day feed the unborn squirrel. The diligence I admired was real, but so was forgetfulness, and the two seemed inseparable.

I’ve thought about that little act of forgetting more than I’d like to admit, because there’s something uncomfortable about it. We spend so much of our lives preparing for the future that we sometimes lose sight of what we were preparing for in the first place. We save, we invest, we delay gratification, and we make responsible decisions over and over again until, at some point, responsibility becomes a goal in itself. We become a squirrel, we are busy saving acorns until we forget to eat.

When memory is worth more than money

Last week, I wrote about my $1.92 daily Tim Hortons decaf and argued that sometimes the spreadsheet is wrong. That little habit was never about the coffee, but about buying myself those 20 uninterrupted minutes, squirrel and all. While I was writing it, I got to talking with my colleague and friend Jessica about a bigger version of the same question—the once-in-a-lifetime purchases that conventional financial wisdom warns us against. For him, it was flying to Europe on Taylor Swift’s Eras Tour. I laughed when he told me, because I had just done something remarkably similar.

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The way Jessica explained the decision is the part I keep coming back to. He had missed tickets at home, couldn’t justify the North American prices, and found himself one night scrolling through videos of other fans, in his words, dying inside to not be there. The tickets to Europe turned out to be half the cost, so he pulled the plane and stayed with him for about 10 minutes. Then, he asked himself one question: did he often regret spending money, or did he regret missing the concert? He booked a flight, then agreed, and cried for half an hour from pure joy.

Mine was Oasis. Not one night, but two, back to back, in the most expensive seats I could ever buy, more sales than I’ve ever bought for anything else in my life. I dragged my wife on the first night despite the fact that she’s not really a fan, I made my dear friend Katy wait by my side for two hours at the Oasis pop-up shop in London last summer, then I lined up for another two hours in the Toronto sun a few days before the show-just because of the sale.

If you had met me 20 years ago, you would not have believed that sentence.

The cost of being responsible all the time

In my early twenties, a series of poorly timed investments forced me to start over financially. Then came the life of the endless entrepreneur, who aspires to achieve something big while living a much smaller life than most people imagine. Those years taught me discipline, perseverance, and common sense, and left me with a financial relationship built almost entirely on surveillance. Money came in, bills were paid off quickly, savings and investments were prioritized, and whatever was left over—if there was anything left over—was what I allowed myself to indulge in from time to time.

Many people would call that a responsibility, and they are probably right. But responsibility has a dignity side that we don’t talk about often enough. When it comes to your financial identity, it can quietly convince you that spending money on you is something that always needs to be protected.

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When everyone around me was making upgrades, new cars and updated porches, I felt like a squirrel riding some tough season that I was sure was always just around the corner. For many years, I lived exactly that way, always saving, always preparing, until finally I could no longer remember what I was preparing for.

Then, Oasis announced their reunion.

Not a purchase, a milestone

I first saw Oasis in 2005, while studying in Cardiff, Wales. A few years later, they broke up, and like millions of fans I thought that chapter was closed forever. Between that night and this one, almost everything about my life changed. I moved countries several times, got married, became a father, and built successful and struggling businesses. I lived through financial crises that changed the way I thought about money, and many professional successes that seemed impossible. Twenty years have passed.

So, those tickets weren’t just entry to the show; it was a way of acknowledging the distance between the person I was and the person I was.

Did I buy cheap seats? That’s right. Went for one night instead of two, skipping the sale entirely? Without question. The optimizer in me suggested all of those methods, and got lost once. Not because I abandoned the financial principles I believe in, but because I finally understood that I wasn’t buying a product. I was marking a milestone, and that distinction is more important than the motivator wants to admit.

When we talk about investing, we almost always mean investing in assets that produce financial returns, be it stocks, real estate, business, or education. All of that is valid, but somewhere, many of us start to believe that money is the only thing that counts. What if that’s not true?

What if some of the most important things we ever spend money on are the very things that don’t produce a measurable spreadsheet?

Some things don’t need to be earned to keep

Jessica told me she still thinks about that weekend almost every day. He talks about the show the way people talk about the few nights that rearrange something for them: tens of thousands of fans inside the Munich stadium and tens of thousands more in the hills around it, all singing the same words at the same time. If certain songs come out now, you are transported back.