Life's Plot Twist = Most people in C-level positions are "making it up as they go along". Don't worry too much if you are not doing a "perfect" job as a CTO. I consult for a various companies and it amazes me that you can do everything wrong (sometimes illegal) and still make millions. I try to convince these companies that if they did everything right, they can make so much more money. I too wish I could go back to being a developer. Being a consultant feels like you are getting paid lunch money to do everyone else's high-school homework.