Worthwhile goal indeed, but I think it's a terrible way to try to achieve it. I'd opiniate that one will make much more money from a medium-paying job he's fully passionate about than a high-paying one he doesn't like very much (in the general case).
At the very least, you'll be much more happy in the former scenario. I think a good strategy for making a lot of cash is pursuing strategies that are at least moderately sustainable, and that won't result in a total waste if you don't succeed to meet your expectations.
For example, I have a startup of my own, and I put long hours on it because I enjoy it and learn a lot! Even if I don't ultimately succeed commercially, I'll walk away from that experience with a net "profit"!
So, to answer your question, I think it's loser to pursue a career you don't really enjoy just to have a shot at winning the "lottery".
... Loser.