#0420  –  The Success Trap: Why High Achievers Feel Empty at the Top with Keren Eldad

#0420 – The Success Trap: Why High Achievers Feel Empty at the Top with Keren Eldad

Author: Jon S. Rennie March 14, 2026 Duration: 35:32
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

For anyone who’s ever felt that leadership advice can be too theoretical or disconnected from reality, Deep Leadership offers a grounded alternative. Host Jon S. Rennie operates from a simple, powerful belief: “Leadership is a People Business.” This isn’t about abstract concepts; it’s about the tangible, often messy work of guiding teams and organizations. Jon brings a unique perspective shaped by his time as a Cold War Submarine Officer and over two decades leading within Corporate America before founding his own manufacturing company. In each episode, he translates that extensive experience into practical, actionable insights you can apply immediately. The conversations here delve into the core of what makes leadership work-or fail-across business, culture, and society. You’ll hear from Jon and a variety of expert guests as they explore the philosophical and practical dimensions of guiding people, discussing everything from daily management challenges to broader cultural forces that shape how we work. This podcast is built on the conviction that leadership matters profoundly, and that getting it right requires depth, reflection, and a relentless focus on the human element. Tune in for thoughtful discussions that cut through the noise and get to the heart of leading well.
Author: Language: English Episodes: 424

Deep Leadership
Podcast Episodes
#0371  –  Scaling a Small Business with Randy Carr [not-audio_url] [/not-audio_url]

Duration: 37:14
Today, I’m joined by Randy Carr, and we're talking about Scaling a Small Business. Randy is the CEO of World Emblem, the largest Patch, Emblem, and Badge Producer in the world. World Emblem makes patches and emblems for…
#0370  –  Succeeding in a Dysfunctional Workplace with Eric Charran [not-audio_url] [/not-audio_url]

Duration: 39:54
Today, I’m joined by Eric Charran, and we're talking about Succeeding in a Dysfunctional Workplace. Eric is a visionary technology executive, author, and thought leader with over 25 years of experience in transforming gl…
#0369  –  Resilience at Work with Simon Bailey [not-audio_url] [/not-audio_url]

Duration: 38:36
Today, I’m joined by Simon Bailey, and we're discussing Resilience at Work. Simon is a researcher, advisor, speaker, and author. He is the world’s leading expert on the subject of brilliance. His groundbreaking research…
#0368  –  Leading a Team of Tough Rugged Bastards with John Dailey [not-audio_url] [/not-audio_url]

Duration: 45:47
Today, I’m joined by John Dailey, and we're talking about Leading a Team of Tough Rugged Bastards. John spent over 20 years in the Marines, mostly in special operations. When the Twin Towers went down, Dailey was in Aust…
#0367  –  Unlock the Potential of Your Employees with Pam August [not-audio_url] [/not-audio_url]

Duration: 51:59
Today, Pam August joined me to talk about how to unlock the potential of your employees. Pam is a sought-after speaker, facilitator, coach, and cocreator with a strong foundation of lifelong learning. She guides organiza…
#0366  –  High Performance Leadership with Dr. Carla Fowler [not-audio_url] [/not-audio_url]

Duration: 46:08
Today, I’m joined by Dr. Carla Fowler, and we're discussing High Performance Leadership. Carla is an MD, PhD, and elite executive coach. For the last decade, she has been a secret weapon for scores of CEOs, entrepreneurs…
#0365  –  Surviving to Thriving Leadership with Dr. Renee Moorefield [not-audio_url] [/not-audio_url]

Duration: 40:25
Today, I’m joined by Dr. Renee Moorefield, and we're talking about Thriving Leadership. Renee is a visionary leader and innovator in the field of human-centered leadership. She is CEO and co-founder of Wisdom Works Group…
#0364  –  Make Leadership Healthy Again with Dr. Philip Ovadia [not-audio_url] [/not-audio_url]

Duration: 39:57
Today, I’m joined by Dr. Philip Ovadia, and we're talking about how to Make Leadership Healthy Again. More than 3,000 heart surgeries taught Dr. Ovadia that good health comes from lifestyle and nutrition, not from surger…