
businessMar 14, 202635:32failed
#0420 – The Success Trap: Why High Achievers Feel Empty at the Top with Keren Eldad
About this episode
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.
Learn more about Keren Eldad and her book Gilded https://amzn.to/4bqmRPaSubscribe to Deep Leadership for more conversations that help build a world with better bosses
Sponsors:
Cadre of Men
Farrow Skin Care
Salty Sailor Coffee Company
Leader Connect
The Qualified Leadership Series
____
Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE
Learn more about your ad choices. Visit megaphone.fm/adchoices
Get every episode summarized
Each time Deep Leadership publishes, we email you a written briefing from the transcript — the topics, who appeared, and any specific claims, with the ad reads skipped.
Email me new episodesFree for 3 shows. No card needed.
Hosts & guests
No transcript yet
This episode has not been transcribed. Request it and it moves to the front of the queue.
More episodes
More from Deep Leadership

#0429 – Why Smart People Get the World Wrong with Peter Lamont
Deep Leadership
May 2, 202640:05pending

#0428 – Why Self-Awareness Is the Leadership Skill Most Leaders Lack with Marg...
Deep Leadership
Apr 30, 202635:57pending

#0427 – Leadership Decisions You Can’t Afford to Get Wrong with Dr. Linda Henm...
Deep Leadership
Apr 25, 202636:31pending

#0426 – Stop Being the Fixer & Start Leading People with Robert Heath, Sr.
Deep Leadership
Apr 22, 202639:10failed