This week, Joe is still struggling. It's a constant struggle with this guy! But at least Joe isn't so much of a Debbie Downer today. Or a Negative Nancy for that matter. The big questions for this episode are: How much money is too much money to invest in his career? Should Joe hire a personal assistant? Is there a place Joe can hire a nerd squad to take his career to that next level? Would this make family life more enjoyable? Is this blog Socratic or what?

Joe's guest for episode five are psychologist Dr. Matt Bellace and Comedian Lee Camp.