It sounds like you’re anticipating happiness to come from external factors. Just so you know, it never will. It’s only inside yourself that you’ll find it. Then once you do, everything external becomes play - your business, the risks you take, the challenges you face. You become so stable internally, that no matter what storm is raging outside, inside you’re at ease.
Check out some books by Thich Nhat Hanh.
You’re already doing great. Good luck.
Timmy Karter, Bald and Bankrupt, Kurt Caz, Sabbatical, and Itchy Boots are my favorites