"They all seem to be extremely (in some cases obsessively) curious about why they, in particular, have been successful. It seems almost as though they feel undeserving, as if the rest of their lives have been an attempt to prove their first success had a reason or formula."
You find the same thing if you talk to successful people in any field, once they get to talking shop. E.g. a successful playwright will be very curious about what drove his first big success. Not (necessarily) because he feels unworthy, but because he wants to write more successful plays.
The curiosity of the successful about success at whatever they've been working on is practically universal. It's partly cause and partly effect.
That's interesting. The reason I wrote a post about it, though, is because it seems somewhat disturbing/alarming to me. I think many first time startup founders have a very visceral, almost animal-like feeling that if they make it big and become a multimillionaire, their problems will be solved and they will have won the game.
It doesn't appear this is the case though. In fact, some of the people I have met have told me they felt worse after succeeding the first time. To quote one of them, who said he got bored:
"I actually learned this lesson even before I had any disposable income by playing the Sims. I cheated and had loads of cash. Made my house amazing, etc. But everybody was still unhappy and there was nothing left to do in the game."
It's good to see the post below by lionhearted, but I get the feeling that isn't a common occurrence.
It's an inside/outside effect. From the outside, business success / influential job / speaking at conferences / being a published author / whatever looks glamorous and amazing, if not a little touched by destiny.
Then you get in there and realize it's full of regular people who are petty, short-sighted, don't work very hard, make mistakes, have personal issues, got where they were with lots of luck, and so on. Just like you. And it doesn't really change your life that much. From the inside, it's not nearly so amazing as it seemed to the outsider you were.
But while disillusioned you is no longer an outsider, there are tons of other outsiders remaining, gazing at you the way you once gazed at your now-equals -- and because you now know that this jealousy/esteem/worship/whatever is unfounded, you feel unworthy of these emotions directed at you and seek to justify or earn them.
It's kinda like finding out that the hero you idolize is in fact an alcoholic and kicks his cat, only that hero is you.
Taken to extremes, this totally normal phenomenon becomes a psychological condition called "imposter syndrome."
This is true even on the micro level of HN karma points. I find myself wondering why certain comments or submissions get voted way up more than others. I think a lot of it has to do with the fact that our brains evolved to discover relationships so we have this innate drive to explain and prove what we experience so that we can replicate it as we feel our survival depends on our ability to do so.
I agree the curiosity of the successful about success is fairly universal, perhaps however there is more of an 'introspection' industry due to the democratisation of success - in other words, more people want to know why/how you were successful, and this in-turn can create a vicious cycle in which the creator/artist/achiever spends too much effort on the act of recreating something achieved before, and in turn producing a parody of their former work (I see Joseph Heller's post Catch-22 work as an example of this).
The issue of 'writers block' wasn't so pressing in early modern society - Shakespeare had to write more successful plays to make a living, to that extent I think playwrights envisioned their careers as the art of learning a craft: Shakespeare could not be considered a creative 'genius' until a long time after, once the concept of an individual genius had taken root.
Have you ever heard people like Marty Scorsese or Quentin Tarantino talk about what makes a good movie? I'm sure you've watched any number of shows on VH1, where bands talk about what makes a good rock or pop song great. It's why Annie Dillard wrote The Writing Life. Hang around novelists or genre fiction writers, and you'll start to hear about what makes a novel great, story arcs,etc...
You find the same thing if you talk to successful people in any field, once they get to talking shop. E.g. a successful playwright will be very curious about what drove his first big success. Not (necessarily) because he feels unworthy, but because he wants to write more successful plays.
The curiosity of the successful about success at whatever they've been working on is practically universal. It's partly cause and partly effect.