I was just like this too. I would have preferred experiencing more failure when I was younger when the risks held less consequences. Now I feel like I never met the expectations of my former self but now my future aspirations are more achievable. Rather than running my own business like I always wanted to do or working for a big-name tech company, I'll be happy when I self-publish the book I'm working on with no expectation of it being successful. I am happy with progress since progress is better than failure and doesn't have the same negative consequences when I don't succeed.