I like a lot of what you said, but with all due respect I don't think I'm your intended audience for this pep talk. Remember, I just finished up two years running my own bootstrapped startup that was making no money -- most people wouldn't consider me particularly risk adverse. :) My life situation is now such that I can't afford another extended break from the workforce for a while at least.
Also, I think the "you should always be 100% confident in your success" (which I've heard from other people as well) line of thinking is kinda BS. We know most startups fail. Even most startups by smart, dedicated and hard-working people fail. For the two years I was doing my own thing, I didn't spend much time on backup plans, but I did keep my door open to recruiters and friends who approached me with other opportunities. Not doing so would not have made my startup any more likely to succeed, and by doing so I ended up with a soft landing at a prestigious and high-paying job, if nothing else. I think it's much wiser to expect the best, but still prepare for the worst.