@Andy ran an anonymous survey a while back, got a bunch of useful data, ran some numbers, and wrote up a wonderful post called ‘The psychology of successful bootstrappers’. It’s a great read. Take a look.
What I find interesting is I’ve become WAY less neurotic by being a bootstrapper.
Before if I shipped code I went into neurotic overdrive worrying about if people liked it or if I did a feature right. Almost paralyzed me sometimes and I just wouldn’t allow my work to be seen by the outside world.
Now I take great pleasure in shipping software as often as I can. I’ll deploy to 3 production systems this week from a combination of my product and the consulting thats funding it.
I think you (bootstrappers in general, not you in particular) need to develop a thick skin. The first time someone asked for a refund I took it personally. Now I don’t bat an eyelid.