Motivation for not settling for the 9-to-5

I am graduating this spring and I don't necessarily want to go back to the 9 to 5 grind. Of course I'm conflicted given my familial/financial obligations, but I think I'm headed toward one of those crossroad moments where if I decided to get a conventional job, then I don't know when I'll have another opportunity to get outside of the box. This guy provides me with some affirmation that I can go the unconventional route, but still be okay.