What a 12-year-old taught me about success

A few weeks ago I sat in a meeting looking at a product spec I'd helped write. It was thorough. Properly scoped. Technically ambitious in the ways product specs are supposed to be. Everyone around the table was nodding. And I had this nagging feeling the entire thing was wrong, without being able to say why.

That weekend I rewatched Big. The 1988 film with Tom Hanks playing a 12-year-old trapped in an adult body. I'd seen it as a kid and loved it. This time I noticed I wasn't rooting for Josh anymore. I was watching the executives.

The scene I'd forgotten

There's a scene early in the film where the toy company pitches a new product. A skyscraper that transforms into a robot. The art is slick. The engineering is clever. The VP running the meeting walks through the market research, the positioning, the projected margins. Everyone is nodding.

Josh, who has been accidentally hired as a marketing executive because nobody knows he's 12, raises his hand.

'I don't get it'.

The room goes quiet. The CEO asks what he means. Josh shrugs and asks the only question nobody in that room had thought to ask.

'What's fun about it?'

The product dies in that sentence. Not because Josh was clever, but because he was the only person in the building still allowed to ask obvious questions out loud.

That was the feeling I'd had in my meeting. Every answer was correct. Nobody had asked if any of it was any good.

Why adults stop asking

I've written before about perfectionism and how it quietly wrecked me as an agency owner. I used to think the opposite of perfectionism was laziness. It isn't. The opposite of perfectionism is play.

Perfectionism is armor. You iterate on a design for the 40th time because somewhere along the way you stopped asking whether the thing is any good and started asking whether it's defensible. Defensible to a client, a board, a reviewer, a Twitter quote-tweet. The logic is: if nobody can criticize it, I'm safe. The cost is: nobody loves it either.

Kids don't have that armor yet. They ask if fish drink water. They tell you your haircut looks weird. They suggest putting the treehouse on the roof because why not. Most of their ideas are bad, and they genuinely don't care. The ones that aren't bad are often the ones the adults in the room would never have said out loud.

Somewhere between your first job and your tenth year of doing it, you trade that for sounding smart. You learn to hedge. To qualify. To sound smart instead of being curious. It feels like maturity. It's mostly fear in a suit.

The version that ships is usually the fun one

The thing that finally clicked for me, watching that scene again, is that 'what's fun about it?' isn't a soft question. It's the sharpest product test I know. It cuts through whatever politics or ego or sunk cost is propping up a bad idea, and it does it in four words.

I've been testing it against my own work for the last month, and it's embarrassing how well it sorts things.

The simplified Ralph loop post I wrote has outperformed things I'd spent ten times as long on. I almost didn't publish it. It was three files and a shell script. It felt too small. The reason it worked is that it was fun to copy and run. People could feel the idea in under a minute. That's the whole game.

Laravel TOON started as a side experiment because I wanted to see how much token budget I could claw back from JSON. It wasn't on any roadmap. I wrote the first version on a plane. It's now one of the projects I'm most proud of, and it exists because nobody was there to tell me it wasn't a real product.

With Onoma, the features users actually talk about are almost never the ones we argued hardest over internally. They're the ones where someone said 'wait, could it also do this?' and we built it in an afternoon because it sounded fun. Those are the ones that end up in screenshots.

Every time I can trace a good outcome back to a decision, the decision looks a lot more like Josh raising his hand than like a well-run meeting.

Using it as a shipping test

I've started asking the question out loud now. In spec reviews, in product meetings, in my own head when I'm staring at a draft I can't decide whether to ship. Not in a cute way. I just ask: 'what's fun about this?'

Three things happen.

Sometimes the answer is obvious and everyone brightens up. That's the version that's going to ship well, and usually we were already close to it before the meeting started overcomplicating things.

Sometimes nobody has an answer, and the room goes quiet the way it goes quiet in Big. That quiet is the important part. It means the thing we've been defending is probably not worth defending. We cut scope, or we cut the feature, or we admit the whole direction is wrong and start again. It's the cheapest way I've found to kill a bad idea before it becomes a shipped bad idea.

And sometimes someone gets defensive. That's usually the most telling answer of all. If the only way to justify a decision is to explain why the fun question doesn't apply, the decision was already broken.

The real lesson of the film

At the end of Big, Josh gets his wish reversed and goes back to being 12. He walks away from the corner office, the adult relationship, the success, the apartment full of toys. Most viewers read that as him giving something up.

I don't think he was. He was choosing play over performance. He'd figured out, earlier than most of us do, that the adult world isn't actually better. It's just more complicated. And complication isn't the same thing as meaning.

You don't need a magic wish to get back to that. You just need to stop performing adulthood quite so hard, and start asking the question everyone in the room is already thinking.

The obvious question is usually the important one. Ask it anyway. Most of the best things I've shipped started with someone in the room being willing to sound like a kid for ten seconds.