The Success Trap: Why High Achievers Feel Empty at the Top Success is supposed to make you happy… so why do so many high achievers feel trapped? In this episode of the Deep Leadership podcast, I talk with executive coach and author Keren Eldad about the hidden emotional cost of ambition. We explore why success and happiness often move in opposite directions, how leaders unknowingly build a “gilded cage,” and why perfectionism, hustle culture, and chasing the wrong goals can leave even the most accomplished people feeling empty. Keren shares practical insights on breaking free from the relentless pursuit of more, rethinking success, and leading from purpose instead of pressure. If you’re a leader, entrepreneur, or high performer who feels like your ladder might be leaning against the wrong wall, this conversation will challenge how you think about success.