Classic workaholic. You probably think your utopia is to have so much money that you don't feel the need to work so hard and don't feel so guilty about spending some cash, but even if you make a million you'll find another way to challenge yourself and leave yourself wanting more. Maybe your next challenge will be to make a billion. And if you achieve it like so many have these days, then so what? You'll decide you want to become famous or make a difference in the world or write a book or help the starving or all of the above. It's what driven, competitive, workaholics do.

One of my favourite examples is Will Smith. This guy went from working class family in Phillie to an A-lister as a breakthrough "rapper". Then he got offered his own TV show and decided to try being a television actor. Once he had a hit TV show, he wanted to become a blockbuster movie star. Once he became one of the most bankable leading males in Hollywood, he decided he wanted an Oscar. So he started doing "serious" performances like Ali, I Am Legend and Pursuit of Happiness. And you can see the pain in his face when he talks about how he missed out for The Pursuit of Happiness and Ali. This despite the fame, the wife and kids and the millions and millions (and millions) of dollars. He will not stop until he gets that Oscar and it will be a major regret for him if he never does. Or if he does get it? Simple, he'll do what other actors do and become a politician or a director and start all over again.

Another favourite example of mine is Donald Trump. As a billionaire in the 80s who pretty much had it all, Donald decided he wanted his own NFL team. The problem was that the people who run the NFL decided this tabloid star wasn't the guy they wanted associated with their league. Did that stop Donald? No. He wanted his NFL team so badly that he created a franchise in a league which made a point of not competing head to head with the NFL - the USFL. Once he was in the door he then moved the USFL schedule to go head to head with the NFL and then tried to slap an antitrust suit on them when that move failed big time. His goal was to get the NFL to agree to merge with the USFL and thus he would finally have his own team. This of course failed and the USFL ceased to exist and now he will NEVER own an NFL franchise and he's still bitter about the whole thing to this day, as evidenced by the recent ESPN documentary about the whole thing.

The point I'm trying to make is, you are not alone. It's not a programmer thing. It's not something restricted to people at the bottom of the ladder or only a few rungs up. It's something every ultra-competitive person has and you need to recognise it and channel it in the right ways. You seem to have realised that you're reaching the point to which hard work alone can take you. Your depression probably stems with the likelihood that any attempts to progress come with big risk. As others have mentioned, now you need to take those risks and be willing to fail. This is probably the hardest part for aggressive competitors to accept. But the real successful guys like Donald Trump don't dwell on repeated bankruptcy or lack of NFL teams or other failures. They go out and start the next challenge, like creating a successful TV show and dating a former Miss World or whatever the hell Trump's doing these days.

Long term, embrace your ambition and drive and try to achieve all that you can - maybe try and learn how to be patient. Short term, get your act together! No offense, but right now you sound like one of those guys who gets to 21 and starts reminiscing about high school, or gets to 25 and starts getting nostalgic about college. Channel your competitiveness in healthier ways so that your career is not the only outlet. Join a gym or play some sports or something, anything that you can get some wins in and feel satisfied again. Your mojo will be back in no time.