I had done a fair bit of traveling during the holidays in my school days with my guitar and discovered that I could live on it. Admittedly, I traveled with a sleeping bag but I could always find somewhere to lay my head.
No, only disappointment in myself on those occasions I didn't manage to rise to the occasion as I felt I should've done. I can always see how to do it, and then the challenge is, Can I manage that each and every day?
If you stand still in any city long enough, you see everyone pass you by. So you're in Chicago. If you stand on the corner of Belmont and Clark, and you do that for three years, you'll pretty much have seen everybody in Chicago pass that junction.