Everyone loves an underdog story. That's why you hear these stories so often. Someone tells you about when he was a teenager and was told he was a loser and worthless and would never amount to anything. Then as an adult, he is wildly successful and credits part of his success to being motivated by all the naysayers and people who told him he'd never make it. It's a classic story that inspires people.
A story you hear less often (if at all) is the one of someone starting out with all the advantages. Someone was successful in high school and graduated at the top of her class in college. Someone who could choose to do anything and be anybody with backing and support from family and friends. That person fails to achieve "greatness" by her own definition. That person selects an "ordinary" job and lives an "ordinary" life. Or worse yet that person may develop destructive behaviors. What a bummer. Who wants to hear that story?
Success can be a disadvantage. The reason is that when you are successful, you do not learn anything. When you have an easy path forward, you may become entitled and get derailed when things finally get hard. But if you struggle through challenges, failing along the way, you become stronger and more resilient.
My past success in school and in traditional jobs has made it much more difficult for me to be successful branching out on my own as an entrepreneur. I have a lot to unlearn as well as learn. Mine will not be the classic underdog story, but a new one that shows how the disadvantage of success can be overcome.