I think it depends on the kind of creative you are. I practice graphic design professionally and have noticed that some interns and some of my college peers prefer more rigid settings -- corporate, higher education, etc. While I don't think these places are ideal for creative growth -- unless you're working for Target, Nike, Coca-Cola -- the benefits and pay may be better -- we've still got to eat and pay bills.
Even at a small firm, I consider my job pretty stable. While I am working my way towards a more fluid career / following my heart, I still have the day-to-day living -- bills -- and myself -- fear, uncertainty, doubt -- to tackle before making the big scary leap. Even a creative's imagination has a limit.
As for encouragement, I think those go-getter creatives could do more to expose their personal stories. That could be meeting with creative groups in schools, posting stories on personal blogs, etc.