Starting Something

Questions and model answers

1. How do you keep track of ideas for things you might build?

   Badly, is the honest answer. I've got a note on my phone called ideas with about sixty things in it and I haven't opened it in a year. Half of them are two words long and I've no idea what they meant. What actually happens is the ones that matter keep coming back on their own. I'll have the same thought in the shower three months apart, and that's the signal, not the list. What I've started doing instead is telling someone. If I say it out loud to my brother and he asks a question I can't answer, I find out in about four minutes whether there's anything there. Writing it down never told me that. It just let me feel busy.

2. If you had a year and enough money, would you start something of your own?

   Probably not, and the reason isn't the risk. I've watched enough people do it to know the year isn't the constraint. The constraint is whether you can stand being the person who decides everything, including the parts you don't care about, like which invoicing software to use, which I promise you is not interesting. I'd love the building part, and I'd be bad at the eleven months of not-building that surround it. What would change my answer is a partner who actively wanted the other half of the job. On my own I'd do the interesting twenty percent well and everything else badly, and the rest is what kills things. So with the right person, yes, tomorrow. Alone, I'd rather keep the job I have.

3. Tell me about something you started that didn't work.

   A friend and I built a booking tool for barbershops. We spent five months on it and got eleven customers, which sounds like failure and was, but not for the reason we assumed. The product was fine. What we'd never done was ask a barber how they currently booked people. The answer was a paper diary and a phone, and they liked it — the thing we'd solved wasn't a problem anyone had. We found that out after building, from a shop owner who was very polite about it, which somehow made it worse. I still think about how many months that one conversation would have saved us. We could have had it in week one for the price of a coffee.

4. Do you think most people would be happier working for themselves?

   No, and I think the question mostly gets asked by people who already have the temperament for it. Working for yourself removes a boss and adds about nine other things: irregular income, no colleagues, and every decision arriving as yours. Some people find that liberating and most find it exhausting, and which one you are is not a matter of ambition or courage. It is closer to how you handle uncertainty when nobody is coming to resolve it. The version of the argument I'd accept is that more people should get to try, because most never find out either way. My father ran a shop for thirty years and told me once he would have been happier with a payslip and a Friday.

The Korean translation, the expression breakdowns, the reusable frames and the common-mistake notes for these four questions are in the book. The recording and this transcript are free, here and on YouTube.