On the back of my office door there is a poster that I made myself. It says something like this: "anxiety, boredom and self-doubt - these are your bedfellows. If you don't feel them, you might not be learning".
I think I made the poster because I often feel like shit about one thing or another. A customer that didn't call back; a fight with a partner; a proof of concept that didn't prove anything. You shouldn't feel shit about these things; when you are building a business you are creating something from nothing and as I just wrote, time wasted, dented reputation and money down the drain are what happens when it goes wrong. But you do feel shit, though, at least for a while, because these things do feel rotten.
Months later you look back though and you are 1. proud you gave it a shot and 2. happy with all your creative projects that didn't got awry. (But know this, if a few didn't go awry then you have not tried hard enough. This is something you should really feel shitty about but of course none of us ever do.) What I am trying to do now is accelerate this process so that as soon as something goes wrong I can 'chuck it in the fuck-it bucket' and move on. This is easier said than done.
Anyway, I reckon that my team and I are pretty brave because we've taken gigantic personal risks and we are still giving it a crack. What is true is that we are learning to be less timid because this bootstrapping the business business is really not for the faint hearted. Maybe we can draw our strength from knowing that not only does creativity often go awry but it is destined to go awry. We make take further strength from knowing that when it does go wrong we are bound to learn... no matter how painful that is.