I found a hardware bug in my brain, and I need help, please.

Dan Savage once advised an anxious 15-year-old boy to stop worrying about getting his 15-year-old self laid and go do interesting, social, skill-improving things so that it would be easy to get his 21-year-old self laid. IMHO, this is good advice, and can be applied to any number of goals besides sex: love, friendship, career, fame, wealth, whatever floats your boat.

My problem is that whenever I try to follow advice like that, I find myself irrationally convinced that one or two days of skill-building are enough, and that I should start investing significant resources in putting myself on the market immediately, even though I know from experience that this is likely to (a) not be useful, (b) not be fun, and (c) probably even be a little depressing.

Usually I am good at learning from my mistakes, but I am surprised to find that I am consistently failing to learn from my experience here. Although this is not literally what I am doing, a crude caricature of my schedule goes something like this: Day 1, I go to the gym; day 2, I go to craigslist and strike out; day 3, I go to the gym; day 4, I go to craigslist and strike out, and so on for weeks.

No tips on how to use Craig's List, please; the problem is not domain-specific knowledge about marketing. I know this beause when I have the relevant skills, I'm pretty successful at finding love/sex/friendship/career/fame/money.

I'm looking for advice on how to really convince myself that I need to build skills for a long time before marketing myself.