Also, I've just turned fifty. This wouldn't be a problem if I didn't have a long hiatus from live performance. But it looms large when you're "not in training" so to speak. I'm starting to think that I might just be a bit old for this. After all, comedy is a pretty intense experience. You need to be a bit reckless. And I'm not sure if I've got enough of that spirit left in the tank. Well, I'll see how things pan out ...
Contradictory qualities required
In any case this desire to recapture the thrill of making people laugh has got me thinking about what kind of a person is actually attracted to doing standup. The medium demands an odd combination of psychological qualities, that's for sure.
It requires equal parts maturity, and immaturity. You have to know enough about human nature to be able to psychologically manipulate people en masse in order to make them laugh. Yet at the same time you have to be brazen, silly, and basically immature enough to actually want to do this. (And even just wanting to is not even enough. You have to need to do it!)
A big dollop of cynicism doesn't go astray either. I think that even if a standup is not overtly cynical, comedy routines almost always contain mockery of people and/or institutions. I know some comics do try to be overwhelmingly positive, joyous and life affirming. But they're usually the least funny ones!
It's a fine line
That said, you can't only be disdainful and derisive. You have to emanate some love of humanity. This will make the audience warm to you. And you can't be too much of a loner, either. Live comedy is a communal experience if ever there was one. So you have to convey the sense that you identify with your audience; that "we're all in this together".
The medium of standup is quite a tightrope act when you think about it -- even more so if you are literally walking a tightrope at the same time, which I'm sure some comics have tried ...