We all dream about it. Cashing out, getting The Big Check™ and going on a shopping spree with “Bentleys and Benjamins”. But, once the fanfare wears off — What actually happens to all of us?

Do we walk away with a perma-smile until the day we die? Or do we just trade one set of problems for another? Are we actually happier?

As a Founder with a few exits of my own, I’ve had this conversation with dozens of Founders post-exit who have had anything from a $1 million exit to a multi billion dollar exit. What’s fascinating is that all of our outcomes tend to tell roughly the same story — and it’s rarely what anyone thinks it is.

Everyone has their own version of their outcome, but if I were to generalize my observations after some very deep ...