> Wow, I sure do hope he finally does that one thing that nobody, absolutely nobody can deny is important -- something as big as, say, a Twitter knockoff for the enterprise. Then he'll never have any nagging doubts about himself ever again.
In my experience, the degree to which you're successful has no effect on those doubts. I've put out a number of highly successful pieces of software, had a ton of attention in the press (technical and not), etc; I still feel like I'm largely failing to live up to my abilities, and that I peaked when I was 17. Maybe I need something hyper-successful that makes me a ton of money, but I doubt even that will kill the doubts.
At the end of the day, it just comes down to saying "this is what I've done, and who cares if I could've maybe, possibly done better?" but that's not so easy.
This is really quite germane: http://www.youtube.com/watch?v=86x-u-tz0MA. While she talks about writing, I think it applies to the kind of thing you are talking about here.
In my experience, the degree to which you're successful has no effect on those doubts. I've put out a number of highly successful pieces of software, had a ton of attention in the press (technical and not), etc; I still feel like I'm largely failing to live up to my abilities, and that I peaked when I was 17. Maybe I need something hyper-successful that makes me a ton of money, but I doubt even that will kill the doubts.
At the end of the day, it just comes down to saying "this is what I've done, and who cares if I could've maybe, possibly done better?" but that's not so easy.