I can see where you're coming from. But at the same time I take some risks. So it is a self fulfilling prophecy to a degree. If I played it safe, I wouldn't be where I am today. So I make myself put myself out there so that I have no choice to work hard to maintain it. But it's easier said than done. I did all this while stable, and once I became depressed I had to force myself to continue working to keep it all since I don't really have a safety net. Then again, as you mentioned, age might play a role in this since I am 32.
I really hope you find the courage and strength to achieve your goals. It's scary, but worth it in the end. Please take care and good luck!