"I can be penniless or I can be bitter." Why not both? If I try something risky and fail and end up penniless, I'll be penniless and bitter.
I have a friend who is a musician. He obsessed over individual songs that he produces for months, and doesn't release very much. I think he has this idea that he's going to be hugely successful someday, but I keep telling him, I think you would build more of a following if you released more of your work. The worst that could happen is that people don't like it that much, but there's something about getting used to putting yourself out.
There are also people who dream of a better work environment and never apply for other jobs. It can be risky to just quit your job when you have a family to care for, but it's often possible to interview in other places without leaving your current job.