I think largely in bets. Starting Hopara is a bet – it's a bet that I'm going to be happier and more successful working at my own company rather than another company. There's nothing wrong with working for someone else; I just don't want to do it anymore.
Writing these posts, and then putting up this site with my doodles, is another bet. It kind of goes in the opposite direction of the working for myself one – it's more like, "What's the downside?" Well, that's kind of obvious, because it includes:
- People on the internet being mean to me (don't much care about that)
- Potential clients thinking I'm a nutjob because I draw cartoons every day (bit worried about that)
- Existing clients thinking that I don't spend enough time caring about them because I'm doodling (hasn't been a problem, yet)
- Me thinking that my doodles are crap, erasing them and starting over (happens maybe 3x / day).
- Spending so much time doodling that I'm not pitching potential clients enough (happened for about a week before I re-read my own advice about eating frogs).
I dwell on the bets I lost, and I'm constantly worried that I'm making a bad one, either because I know that I'm willfully ignoring some critical information or because I'm just not aware of it. This makes me a little better each time – I willfully ignore a little less – but it doesn't put me all the way into the 'good' category.
The nice thing about bets, though, is that I don't care too much about individual ones that fail, provided I didn't bet the farm on them. I've found that the trick is to break every really big bet down into tiny ones where the outcome doesn't matter. This start-up I'm running is a big, scary bet, but each individual pitch isn't, especially if I do the requisite 10-20 per day. Raising a kid is a big, scary bet that I'm not raising a total jerk, but that's dependent on the sum of thousands of interactions per week. And putting myself out there with silly cartoons everyday after having not drawn much of anything since the assistant to the art teacher in college made fun of my paintings (which were legit bad) is a scary thing emotionally, even if there's nothing financial tied to it, but the failure of any individual doodle to make more than me chuckle isn't that big of a deal.