I see a lot of entrepreneurs get stuck in the "I have to go all in on this thing I'm not certain will work" vs. "I can do freelance/contract gigs on the side to fund my work and still have a decent standard of living until I prove out my idea(s)."

You're right that it comes down to goals and personality, but if you're in a position where you think a union is going to help save you, you may be better off working on your own thing.