Optimistic delusion

A few summers ago I said yes to a boat trip the day before it happened. I’d been promised a superyacht. Turned up to a river boat. The kind of boat that’s meant for a calm afternoon on the Thames, not for taking the length of the Mediterranean in open water.

The sea was rough. Properly rough. We were getting flung around for hours, the boat was groaning in ways a boat shouldn’t groan, water coming over the sides, and at no point in that day did the maths look good. Every rational person on board was running their numbers, working out exactly how this ended.

I wasn’t. I was already at the pub telling my mates about it.

We made it back. Course we did. And that’s the article.

The Switch

For most of my life I was the guy overthinking the worst case. Big social situations, sports games, walking up to people in bars, sending the message, putting my hand up in meetings. Every one of those moments I’d run the same broken calculation — what if this goes wrong, what if I look stupid, what if they laugh, what if it doesn’t work — and most of the time I’d talk myself out of doing the thing before I’d even started.

I called that being sensible. It wasn’t. It was just fear with a respectable accent.

Then at some point I flipped it. Not consciously, not because I read a book. I just got bored of being the bloke who didn’t do things. The man who watched other people’s lives happen and told himself he was being measured. So I started running the opposite calculation. Instead of asking what’s the worst that could happen, I started asking what’s the best that could happen — and then deciding, in my head, that the best was what was about to happen.

Delusional? Course it is. That’s the whole point.

Within months everything I’d been waiting for started showing up. The conversations got better. The girl I wouldn’t have approached started laughing at things I said. The job I shouldn’t have got, I got. The trips I shouldn’t have said yes to became the stories I now tell at the pub. Not because the universe rewards positive thinkers — let’s not get carried away — but because I’d been the bottleneck the entire time.

The thing standing between me and the life I wanted was a man running pessimistic models in his own head and calling it being realistic. Get him out of the way, and the world opens up. That’s not a metaphor. That’s actually what happens.

What Optimistic Delusion Actually Is

Let me be clear about this, because there’s a version of this idea that’s just manifest your dreams bro and that’s not what we’re talking about. I’m not telling you to write affirmations on your bathroom mirror. I’m not telling you to vision-board your way to a Ferrari. This isn’t The Secret with British spelling.

Here’s the actual thing.

Say there’s a 95 percent chance something goes averagely and a 5 percent chance it goes incredibly. The realist looks at that and says well, 95 to 5, I know what’s happening here. He plans for the 95. He prepares for the average. He turns up expecting the average. And then he gets the average, because that’s what he planned for. He calls it wisdom. It’s actually just a self-fulfilling prophecy in a nice suit.

The optimistic delusionist looks at the same numbers and goes — you’re telling me there’s a chance? Fuck it. Let’s go all in.

That’s not naivety. That’s not pretending the 95 doesn’t exist. He knows the odds. He’s not stupid. He’s just decided which number he’s going to live inside. And once you live inside the 5, you start behaving like the 5 is going to happen — the way you walk into the room, the way you speak, the questions you ask, the risks you take. Which is the only way the 5 ever lands.

This is the bit nobody tells you about probability. The numbers aren’t fixed. They move based on who’s playing the game. The 5 percent for the man who believes it’s 50 is genuinely closer to 50, because he’s become the kind of man the 50 happens to. The 5 percent for the man who believes it’s 1 is genuinely closer to 1, because he’s playing pre-defeated.

The realist isn’t seeing the situation more clearly than you. He’s just seeing it more safely. Those are different things and we’ve been confusing them our whole lives.

The Enemy

Every idea has one and this one’s obvious. It’s the lad who takes the safe option. Every time. The one who’s quietly chosen comfort and stability over anything that might actually cost him something. Picks the job he knows he’ll get. Dates the girl who’s a three out of ten on interest because she’s a sure thing. Stays in the city he grew up in because moving sounds like a lot of admin. Never approaches. Never asks. Never goes.

He’ll tell you he’s being smart. He’ll tell you he’s being responsible. He’ll tell you he’s playing the long game, looking after his future self, being a grown-up about it.

He isn’t. He’s just scared, and he’s dressed it up in language that lets him sleep at night.

The truth is he’s already lost and he doesn’t know it yet. Every safe choice he makes is a tiny vote against the man he could’ve been. And he’s made so many of them by now that the man he could’ve been has gone quiet. Doesn’t even show up in his thoughts anymore. He stopped imagining a different life a long time ago, and now he’s just running out the clock on the one he settled for.

I’d rather be in the grave than be that guy. I mean that. Genuinely. The thing he’s terrified of — looking stupid, getting it wrong, the punt not landing — is a worse fate to him than spending sixty years in a life he didn’t choose. He’s running away from embarrassment and straight into a long, quiet, beige existence and calling it wisdom.

Fuck that. The risk of looking stupid is the toll. You pay it once at the door and then you get to live the rest of your life inside the room. He’s standing outside in the rain because he doesn’t want to pay. That’s not caution. That’s a man losing a game he’s convinced himself he’s winning.

How It Actually Plays Out

A few years back I went for a job I had no business getting. On paper I wasn’t the candidate. They were looking for someone with a different background, more experience, more of the right boxes ticked. The realistic move was to apply, expect nothing, and use it as practice for the next one.

So I didn’t take it seriously. Didn’t agonise over it. Didn’t rehearse answers in the mirror or stress about the questions. I just decided I was getting it. Walked in already past the interview, mentally, already in the role. The version of me sitting across from them wasn’t auditioning. He was confirming.

I got it.

And the lesson isn’t manifestation works — the lesson is that the bloke who’d run the proper calculation, who’d accepted he probably wouldn’t get it, would have shown up as a man who probably wouldn’t get it. He’d have hedged. He’d have over-explained. He’d have asked safe questions. He’d have been deferential in all the small ways people don’t consciously notice but absolutely register. He’d have been exactly the candidate his calculation predicted he was.

I showed up as the man who had it. They hired the man who had it. That’s how this works.

It’s the same with the boat. We made it back because at no point did anyone running the optimistic model start panicking. The realists were doing the maths and turning grey. We were taking photos. One of those groups was useful in a crisis and one of those groups was a liability and I’ll let you guess which. Panic is contagious. So is calm. The man who’s already decided it’s going to be alright is the man steering the boat, not screaming at the waves.

Same with every approach I ever made. Every move at work. Every relationship I started. Every time I bet on myself with no evidence I should. The pattern is identical — the man who showed up already past it got it. The man who showed up hoping for it didn’t. And I’m not special. There’s no version of this where it’s a personality trait some people have and some don’t. It’s a decision. Made early. Made privately. And then carried into the room.

The Cost of Not Doing This

Here’s the part most people don’t want to look at.

The realist thinks he’s avoiding the cost. He thinks by staying in the 95 he’s the one playing it safe, hedging properly, protecting himself from the downside. He looks at the optimistic delusionist and goes well, he’s going to crash and burn eventually. He’s going to learn the hard way. I’ll be the one standing when it all goes wrong.

Except he won’t be standing. He’ll be sat exactly where he’s always been, in exactly the same job, in exactly the same flat, with exactly the same Friday night plans, watching other people’s lives happen on a phone. The cost he thinks he’s avoiding is actually the one he’s been paying his whole life, in monthly instalments, and he hasn’t once stopped to add up the total.

The thing nobody tells you about the safe option is that it’s not actually safe. It’s just a slow version of the same loss. You don’t avoid the pain by avoiding the risk — you just spread it out so thin you stop noticing it. Twenty years of mild regret feels different to one moment of acute embarrassment, but it adds up to a lot more weight. And by the time you feel it properly, you’re too far in to do anything about it.

Meanwhile the bloke running the 5 is failing constantly. He’s eating it on a regular basis. The job he didn’t get, the girl who said no, the trip that was a disaster, the business that went under. He’s collecting Ls the realist has spent his entire life avoiding. And the realist watches and feels vindicated.

But here’s what the realist doesn’t see. Every L the delusionist takes, he’s also collecting something the realist never will — the actual evidence that the world doesn’t end when the 5 doesn’t land. That he survived it. That he’s still here, still going. So the next punt is easier. And the one after that, easier still. The fear shrinks every time it gets tested and doesn’t kill you. The realist’s fear has never been tested. It’s grown to fill the entire room.

By the time the delusionist has lived ten years like this, the gap between them isn’t a gap anymore. It’s a chasm. And the realist still can’t see it, because he’s still telling himself he’s the smart one.