"Roughly speaking, you should identify what type of outcome you want and then work backwards to identify what skills you might need to get there."<p>I've tried this logical approach. It tends to make me miserable, since I lack the intrinsic motivation to follow through with my plan and then end up angry at myself for not having enough perseverance, or discipline, or whatever. Or even better: half way through my plan I realize that I don't even like the path I'm headed down, and that I only chose it based on a surface understanding of the field (like a child who thinks they want to be a doctor, but has no idea what that actually entails).<p>Something I've found that works for me is to just work on whatever I find interesting at the time. If you're a curious person, then what you find interesting will change from year to year. And since interests are generally not completely random, and tend to branch off from current interests, then over a period of a few years you'll find that you've automatically developed a set of complementary skills. And the best part is: you didn't have to plan anything, and you enjoyed what you were doing the whole time.
Marc Andreesen wrote about this same idea on his blog in back in 2007.<p>It was written just as well as this piece and given his success pioneering web browsers and building 3 separate billion dollar businesses in tech, it should be a good fit for HN: <a href="https://pmarchive.com/guide_to_career_planning_part2.html" rel="nofollow">https://pmarchive.com/guide_to_career_planning_part2.html</a>
I think this is more applicable to being an entrepreneur or manager rather than individual contributor. In my experience, most companies reward hyper-specialization.
Being a better illustrator than most is not really an easy task. And the guy from Dilbert is not really a better illustrator than most. I mean, he draws some very basic shit.