Ha, thanks!
Some choices are hard because of uncertainty and fear of the unknonwn. People live through terrible relationships, suffer terrible commutes, work in soul-sucking places etc and are yet unable to quit because the alterntives are less defined.
While I have enough finances to be comfortable (and reduce uncertainty), I don't know of anyone personally who has made the choices I have, even though many are vastly richer than I. They continue to grumble about expenses and commutes and health issues. Middle class people vastly overestimate how much they really need, and peg their lifestyles to that bar, often at the cost of everything dear.
I have a very simple approach. I ask "What's the worst that can happen? Will this affect me next year?". I find that once I quantify it, most fears just melt away. Say my laptop gets stolen and everything in it is irretrievable. No backup, say. What's the worst? It would be a royal pain to get back my life, but by this time next year, I'd be just fine. Moving to a different country to do a PhD? What's the worst? I'll perform badly and get chucked out, and I will return and get another job. Five years from now it would be a fine story to regale my friends with.
Sorry. I'm getting wordier as I grow older!