Optimism, but with receipts

In September 2023 my wife and I put close to half a million dollars on a piece of land in Queenstown. We didn’t know if we could afford to build on it.

The title was eighteen months away. The deposit was ten percent. And the numbers on actually getting a mortgage to build the house we wanted didn’t work. Not yet.

We signed anyway.

I know how that sounds. It wasn’t reckless, and it’s more or less the reason I’ve gone quiet here. I haven’t properly published since before the twins were born, and they’re four and a half months old now. Three kids under two. Life got loud and I let the writing go. I’m not going to dress that up as a comeback. It’s just where the last stretch went.

But the way we made that land call is the same thing that carried us through the loudest year of our lives, and I’ve wanted to write it down for a while. We call it rational optimism. I’ve come to think it’s rarer than it should be.

Most people I meet land in one of two places.

One is hope with its fingers crossed. It feels good and plans for nothing, so when the downside turns up, and it always turns up, it has no answer except surprise. The other is the bracing crouch: scanning for what could go wrong, treating pessimism as a kind of intelligence. Safer, sure. It also spends its whole life defending a position and never builds anything on it.

Rational optimism is both of those at once, on purpose. You expect the good outcome and you actually believe it’s coming. Then you look the worst case straight on, price it honestly, and get ready for it. Once. Not so you can carry the fear around, but so you can set it down and get back to work. Heavy on hope, heavy on preparation, not much in the soft middle.

That’s what the land was. We didn’t cross our fingers on the numbers, we built them backwards. What would the bank actually lend us. What would we have to find ourselves. What would our income need to be to get approved for the build that wouldn’t leave the site half-finished. Then we worked out what it would take to get from where we were standing to that number.

We’d tried to buy a section maybe seven times that year and failed every time. Each failure should have thinned the belief. Instead it thickened it. By the time we signed, the hope wasn’t a feeling anymore, it was a list of things we’d already survived.

Then the downside landed. That ten-percent deposit was more money than either of us had ever seen in one place, and every dollar of it was already spoken for. So when the car started leaking oil, litres a week, we didn’t fix it. Two grand for a service was two grand we didn’t have. We just kept topping it up and kept driving, month after month, because every spare dollar had one job and that job was the land. We’d braced for tight. This was what tight actually looked like. And because we’d seen it coming, it stayed a hard season instead of a crisis. The worst case is rarely what breaks you. Getting ambushed by it is.

Now, this can start to sound like anxious over-preparation, and the gap between the two is the part I actually care about.

Anxious prep doesn’t trust anything. It’s so fixed on everything that could go wrong that it quietly shuts the door on the good things you couldn’t have planned: the luck, the timing, the person who says yes for no reason. It’s the same narrow cone I wrote about before, just built from fear of the downside instead of fear of not being certain enough. It white-knuckles through a life and files that under responsible.

Rational optimism does the work and then lets go. The letting go is the whole point. It’s what gets you through the hard parts and makes the good parts land bigger.

And then it pays you back. We’d designed the build to carry itself where it could: a small two-bedroom rental on the same site, leased out from the day it was finished. It covers enough of the mortgage that what we pay to live here now is less than it would cost us to rent the place. The house was worth more the day we finished it than everything we’d poured in. None of that was luck. We’d worked it out backwards, three years earlier, sitting on a deposit and pouring oil into a dying car.

And the rational half is earned. My optimism isn’t naive because there’s evidence under it. Seven failed sections. A build we somehow kept paying for. A wedding and a baby inside the same eighteen months. I can trust it’ll work out because I’ve watched it work out before, in worse conditions than I’m in now.

Which brings me to now. Three kids under two. A house that fits us today and won’t the day they’re all at school wanting to bring friends home. We can see the next thing coming from here: more room, more cost. So I’m working harder than I ever have. This year, becoming a dad of three, I’m on track to earn more than I ever have, from more sources than I ever have, while being a hands-on dad who works from the kitchen table more often than I’d like to. It is genuinely brutal. It’s also the best stretch of my life so far, and those two things sit together without any tension at all. Loaded heavy on both ends.

If I had to hand it over as something you could use, it’s four things.

Hope hard. Actually expect the good outcome. Optimism isn’t the reward for a safe plan, it’s the engine that makes the ambitious one worth attempting.

Reverse-engineer it. Start at the outcome and walk backwards to today. You can’t execute a vague hope. You can execute a path.

Price the downside once. Look the worst case in the eye, prepare for it, then put it down. Don’t carry it around for years as a personality.

Keep the receipts. Every hard thing you come through is evidence you can trust yourself with the next one. That’s the whole difference between optimism that’s naive and optimism that’s earned.

I’m not fully back yet. Three under two doesn’t leave much room for writing and I won’t pretend otherwise. But this is the thing I most wanted to say when I sat back down at the page, and there’s a second half to it. I’ve spent this year building something out of exactly this mindset: a setup that lets one person hold far more than one person should be able to. That’s the next piece.

Optimism on its own is a wish. With the receipts behind it, it’s a plan.