FAILING IS A PART OF LEARNING.
Starting at the bottom is not about humiliation. It's about humility—a realistic assessment of where you are in the learning curve.
Listen: You can't short-circuit the learning process. It takes time to get to the top, and that's good-because by the time you get there, you'll have learned what you need to know in order to stay there.
Comparing how you feel on the inside (bad) to the way someone else looks on the outside (great) is a losing proposition. It's an impossible standard.
In this day and age it's really stupid to be stupid about financial matters. It doesn't do you any good to make money if you don't know what to do with it other than spend it.