In this episode, Dr. Dan sits down with Jason Connell, a licensed psychotherapist, meditation teacher, and author of When Success Isn’t Enough: Why High Achievers Feel Empty and What to Do About It. Jason built the career many people chase. He performed magic as a child, became a professional speaker, filled theaters, and flew first class to international stages. He was also miserable. Therapy, and later a graduate degree in clinical social work, helped him name the pattern behind his pain. He calls it the success wound: gift, sensitivity, difficult experiences, and relentless hard work combining to produce outward achievement while leaving deeper needs untouched.

Jason and Dr. Dan challenge the belief that self-criticism fuels ambition. Using the image of a log that saves you in a riptide but has to be released before you walk onto shore, Jason explains why the strategies behind our success deserve gratitude and, eventually, a second look. Together they explore self-compassion as a source of sustainable drive, reconnecting with the body, relationships where love doesn’t depend on performance, and Jason’s idea of inner wealth: a life where connection, play, rest, and purpose match what you say matters most. From Dr. Dan’s championship softball season to Jason’s final night with old friends in Mexico City, both return to one question worth asking yourself. Where does life live for you?