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Just get jobs doing shit you would like to learn and stop caring about money and success at anything but doing shit you would like to learn.
I think having goals is necessary though.
ie:
>if i had my own barn and workshop and land I'd...
>build gliders for displaced Palestinian refugees
>idea.jpg
Look into welding and machining, apprentice/school into work as a mechanic. Live Spartan (you probably do this anyway), and put it all towards building your barnyard glider ship and land and keep working as a mechanic/welder. Start a glider tourism company.
Even if it "fails" (doesn't result in millionaire status, Stacy's undivided devotion, and your own personal army of angry antisemite semites) it would still be funny as fuck.
And if that's not winning, what even is "winning"?