This week, Alex tackles the topic of why he dropped out of school - what it meant for him and his family, the reasons behind it and the things he missed out on because of his choices. Alex is joined by Leigh Abramson, who's another "dropout" of sorts - after a successful career as an attorney, things still didn't feel right - so she quit her job and became a writer. We cover all the big questions: when is it okay to quit something, especially when you've poured time, effort and money into it? When should you see a career or schooling path through? And how do you know if it's the right to completely reinvent your life?