The other ninety-eight percent

Last night I got home after midnight. I'd been out with a few friends at the end of a really full week, and the plan, if I had one, was to go straight to bed. Instead, Colin was still up, and we ended up sitting together, just the two of us, catching up on a week that had been moving too fast for either of us to talk about while it was happening.

Somewhere in that conversation, he said something I haven't stopped thinking about since.

It wasn't a new idea. That's the part I want to be honest about up front. It was one of those ideas you've heard a million times, on posters and podcasts and the backs of books. That it's okay to make mistakes. That it's okay to fail. That failure is part of the journey, and things really do work out, and life can still be okay even when something doesn't happen the way you planned it, or the way you expected it to.

You've heard it. I've heard it. Colin has heard it a million times too.

But last night was different, because this time it wasn't a poster. It was a realization. A real one, deep down, the kind that changes how a person carries themselves. I could hear it in his voice. An idea he had always agreed with had become something he actually understood.

And the thing that carried it in, of all people, was Martin Short.

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Colin watched the Martin Short documentary this week. And what stayed with him wasn't the comedy. It was the math.

Martin Short has had, by any measure, an amazing life. And in the middle of telling that story, he offers this reckoning of his own track record: something like 98 percent of everything he ever did was, essentially, a failure. Flop after flop. Shows he was sure would make it big that didn't. Projects that came and went without a ripple. And over the years he came to understand that none of it was a detour from the amazing life. It was part of the process. Part of the journey. He just kept going, because the going is the work.

Looking back, the flops didn't cancel the life. The life was built out of them, and around them, and in spite of them, all at once.

That's what reached Colin. Not advice. A whole life, laid out end to end, with the failure rate left in.

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Here's why I think it took a documentary after midnight to land something Colin already knew, and why I suspect there's a version of this waiting for you too.

Lessons don't sink in on schedule. You can hear a true thing a hundred times and it stays outside you, agreed with but not absorbed, until the right situation or the right moment or the right messenger finally carries it in. That's not a flaw in you. That's just how the important ones seem to work. And it means the hundred times you heard it before weren't wasted. Each one nudged the switch a little closer, so that when the right moment finally touched it, the light didn't flicker on. It flooded the whole room.

For people like us, though, this particular lesson has an extra layer of hard.

Because when you're a real estate investor, failure doesn't feel like a show that closes on the weekend and gets forgotten. It's real money. It's a building you still drive past. Sometimes it's a partner's capital that came home slower or smaller than you projected, or a decision you'd take back in a heartbeat if you could. And you're the responsible one. You did the homework, you read the books, you ran the numbers more times than you can count. So when something goes sideways anyway, it doesn't feel like process. It feels personal. Proof, says the 3am voice, of the thing you're most afraid of: that underneath it all, maybe you don't know what you're doing.

So let me say the quiet math out loud instead. Every operator I respect carries a private list. The reno that blew past the budget. The tenant call they got wrong. The deal that stopped rewarding them long before it ended. We've told you about ours; we carried one for five years and wrote a whole issue about it. And the people whose portfolios look flawless from the outside are showing you their two percent. The other ninety-eight is off camera. Same as it was for Martin Short. Same as it is for us.

Failure doesn't have to be the end. It's just part of it. Part of the whole amazing journey.

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And then this morning happened, and I promise the timing is real, because it was too good to invent.

We had kids' music on, and one of my favourite songs from a Disney movie came on. "Try Everything." The one about how you're going to fall down, and fall down again, and the whole point is simply to get back up and try again. I love singing that song. I love that my kids hear it over and over and over. Because I don't think my generation heard that message much, and I know the generation before mine barely heard it at all. Somebody is finally teaching this to kids while they're still kids, and I get to be in the room where it plays on repeat.

Colin got there through a documentary and a quiet hour after midnight. My kids are getting it with their morning music, years before they'll need it. That's progress I'm proud to be part of.

But between the documentary and the Disney song, there's a practical question sitting there for people like you and me, and it's the one this newsletter exists for: what do you actually do with your own flops? Because most of us only ever do one of two things with them. We bury them, or we replay them at 3am. And neither one pays us back.

You've already paid for those mistakes. Paid in money, in months, in sleep. That's tuition. This week's Install is how you finally collect what it bought you.

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The Install

The Tuition Review. One small thing you can put into your business this week.

This one takes about twenty quiet minutes, once. There's nothing to set up and nothing to maintain. You just need a page and the willingness to look.

Step 1: Name your three. Write down the three things in your business that didn't go the way you planned. The ones that still have a little charge on them. One honest, ugly line each about what happened. Not the polished version you'd tell at a meetup. The real one. "Approved a tenant against my gut because the unit had sat empty six weeks. Eight months of grief." "Took the contractor's timeline at his word. Reno ran four months long."

Step 2: Add the friend line. Under each one, write the single sentence you'd say to a good friend who was about to make the same mistake. That sentence is the lesson trying to get out.

Step 3: Let AI turn tuition into rules. Open any free AI tool, ChatGPT, Claude, Gemini, whichever you've already got, and paste this above your three:

I'm a Canadian real estate investor with a full-time job and a small, self-managed portfolio. Below are three things in my business that did not go the way I planned. For each one I've written what happened and what I'd tell a friend about to make the same mistake. Do three things: (1) turn each one into a short, plain-language operating rule I can actually follow under pressure, written as "Rule:" plus one sentence on exactly when it applies, (2) tell me plainly if you see one pattern connecting all three, and (3) finish with two or three sentences that treat these as tuition I've already paid, not as a verdict on me. No pep talk, no generic advice. Use only what I gave you.

The three: [paste]

What comes back is a small, strange gift: your worst stories, rewritten as your sharpest rules. One of our JV partners said it perfectly after a deal of ours that ended without fireworks: this deal taught me many lessons and helped me redefine my buy box for the next one. That's the whole move, in one sentence. The failure already happened. The only question left is whether it gets to teach.

I'll be straight with you about where this stops, because that's the deal I want with you. The Tuition Review is a real brick. Do it this week and you'll walk into your next decision with rules where the flinch used to be. But rules on a page still depend on you remembering them in the moment, tired, at the kitchen table, with the clock running. The thing we've actually been building is the layer underneath, where the lessons don't live in your memory at all. They live in the business itself, and the same mistake quietly gets harder to make twice. That's not a brick you install from a newsletter. That's the house. And it's what we're building a place to share, with people exactly like you. It's getting closer.

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So that's the story this week, and it started with a late night at the end of a long one.

Ninety-eight percent. That's the number I keep turning over. Because if a man can flop that often and still look back on an amazing life, then the goal was never a spotless record. Not for him, not for us, not for you. The goal is to keep going, collect the lesson, and let the next attempt be a little smarter than the last.

Or, as the song my kids will hear on repeat again soon keeps telling them: falling down is in the plan. Getting back up is the plan.

Next Sunday, I'll be back.

I'm glad you're here.

— Nicole