I deal with this concern myself, and the answer I've been mulling over recently is related to the Big Fish In A Small Pond analogy. (In fact, I think of it in the same terms as your friend: winning my freedom)<p>In the Bay Area, things are very expensive and its hard to put money away, and its also hard to feel like "you've won" because other folks are so dramatically more successful than you. However, after visiting home for Christmas I realized that I'm actually quite successful. So the problem is that I'm a small or medium fish in a very large pond. So I don't ever feel like I'm free because I'm not a big fish. Whats unfair is that a lot of the big fish in SF owe their size to luck. Its not that they are necessarily objectively better than the smaller fish, they just got lucky. (Granted, sometimes they are better: Elon Musk).<p>So, my advice to your friend would be to seek a high paying job which allows telecommuting, for both him and his wife. Then, move to somewhere livable but dirt cheap. Then, sock money away like a madman. Then, once you've got a pile of cash...stop working. Stop working for 3 years or so, enjoy that 3 years of freedom. Build something, maybe it will take off.<p>Thats where my thoughts are right now, it'd be great to hear an update on what he thinks about it.<p>EDIT: I wanted to add this follow up. One of the interesting things about this conundrum is, for me, not being as successful/free as I want creates a significant amount of stress. I worry about it far more than I should. I worry about it to the point where it has a negative impact on my ability to think clearly because my mood is so depressed...and its like being stuck in a trap because I worry I'm not successful enough, but the worry depresses me enough that I can't pursue means of being successful. Its now a question of: Can I overcome that stress in my current situation, or, are things going to have to change?