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.
Hey, far be it from me to criticize someone who's trying to make a mark in the world. I myself am just past 40, a former child prodigy, not very successful in Silicon Valley, and still feel I have some creative works in me which are yet to be realized.
Where I have sincere worries for Dave is that he doesn't seem to have a specific idea of what would count as success -- other than, maybe, it would be big enough and impress enough people that it would silence his demons. I don't know Dave, but I have a strong suspicion that this is also what led him to slack off at university -- rebelling against this idea that if he isn't the smartest and most successful, he's nothing. Because it makes every minor setback a bitter failure, and even success turns to ashes in your mouth.
His mission statement shouldn't be that he wants a better epitaph. Other people get to write his epitaph, and by that time he'll be fucking dead. It's out of his control. What is in his control: whether his life was meaningful to himself. Did it express his unique talents, did it give him and others joy, did it help others? Did he make his own rules about how to evaluate his life or was he a slave to the caprices of fame and fortune? And this is about so much more than just a career.
I think I'll just leave this here. A clip from The Wire.
"The job will not save you."
> 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.
> something as big as, say, a Twitter knockoff for the enterprise.
It's been done! http://www.salesforce.com/chatter/overview/
I think he was referring to Yammer, and their recent acquisition.
DMC explicitly mentioned Yammer as one of the things that some of his former co-workers had done. (He neglects to consider all the things his other colleagues have done which failed, classic survivorship bias, but that's not my point.)
My point is, from a certain perspective, everything looks stupid, and everything has a limited impact, and everything could have been better. Maybe some people who work at Yammer feel they're doing something important, like democratizing information flows within big companies. But it's also a knockoff of various social networking tools for the enterprise. It's a matter of which perspective you choose.
DMC looks at Yammer wistfully because it seems like a big score that was within his grasp. But I bet that if DMC had worked at Yammer he'd be picking a narrative closer to this: I worked for a lame knockoff of innovative companies like Twitter and Facebook, and we failed to thrive independently, and in the end we had to be sold to a dying and clueless organization like Microsoft. And I made a little money, but I never achieved a higher executive rank - any idiot could have made the money I did, and it was barely enough to cover a small house in a not-so-great part of Palo Alto. But the real players made serious bank! People that I worked with who didn't seem much smarter than me! I wonder if I will ever do something worthy of the promise I had when I was a child....