Hey Tim, I love the dreams you are holding. In fact, I loved them so much, ten years ago I decided to start living my own. At the time, it was just me that made the leap. The thing which made it OK was having a six month safety net (i.e. enough money to maintain our lifestyle which I wouldn’t touch unless I’m running out of money). Ten years later that safety net continues to sit there. Earlier last year, my wife joined me. In our case she supports me and our lives. She is one of the primary reasons I’ve had so much business this past year. Many of the items in your pros/cons list resonate with me. However, I think you will find many of the cons are just stories you’re telling yourself. Don’t get me wrong … being self-employed has plenty of challenges, but I no longer think of them as cons … they are a just a part of the choice I am making. The good news is … there is no con you cannot overcome given it’s just a story you make up. When it is right for you … you will know it.