Answer by Hillary Rettig on Quora.
As a longtime career coach, my experience has been that people who can’t decide or commit to a career are almost always self-censoring. There is something they really want to do only they think they can’t or shouldn’t do it. They often come up with “Plan B’s” that are overintellectualized and a bit weird, whereas their true goal usually turns out to be simple and straightforward, as in:
“I want to own a restaurant.”
“I want to work with dogs.”
“I want to save the world.”
But the person may not have enough money to start a restaurant, may not understand that there are jobs and businesses where you can spend all day with dogs, or may think he/she needs to earn more money than in the typical activist job (or, equally likely, they think jobs are so scarce that applying to one is useless.)
All three of the scenarios are largely solvable, so despair and self-censorship are not indicated. A highly useful question one of my mentors taught me to ask is, “Am I trying to talk myself into doing something I really don’t want to do?” If you’re doing that, it’s probably not a viable long-term strategy. Look instead at what you really want to do and figure out ways to make it doable. (Obviously do research and consult mentors.)
Another reason for career indecision is perfectionism — you have an idealized, romanticized, exaggerated version of what a career should look like, so nothing in the real world matches up. Perfectionism is fundamentally delusional and can poison all your endeavors so best to work to overcome it. More on perfectionism and its solutions here: Perfectionism Defined
Finally, your “grass is always greener elsewhere” “wrong challenges” scenario strongly suggests another possibility–that you are self-sabotaging out of fear. Maybe there was a point in your jobs where you start to feel afraid — of failure, success, public speaking, writing, etc. — and that fear caused you to disengage or flee, with the rationalization that you’re bored or “this job’s not for me.” Perfectionism is the root cause here, too,
I hope this was helpful – good luck!