#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
#0353  –  Educational Entrepreneurship with Bob Luddy [not-audio_url] [/not-audio_url]

Duration: 44:27
Today, our guest is Bob Luddy, and we're discussing Educational Entrepreneurship. Bob is the founder of CaptiveAire, St. Thomas More Academy, Franklin Academy, Thales Academy, and Thales College, defines and discusses th…
#0352  –  Why Leadership Requires Lifelong Learning with Damon Lembi [not-audio_url] [/not-audio_url]

Duration: 41:54
Today, I’m joined by Damon Lembi, and we are discussing Why Leadership Requires Lifelong Learning. Damon is a 2x bestselling author and host of The Learn-It-All Podcast. He is also CEO of Learnit – a live learning platfo…
#0351  –  A Leader Worth Following with Shay Brickhouse [not-audio_url] [/not-audio_url]

Duration: 45:04
Today, I’m joined by Shay Brickhouse, and we're talking about becoming a Leader Worth Following. Shay heads up Landscaping Unlimited, a complete landscaping and hardscaping company based in Eastern NC. He took over this…
#0350  –  Scaling a $10 Million Business with Jeremy Jenson [not-audio_url] [/not-audio_url]

Duration: 40:50
Today, I’m joined by Jeremy Jenson, and we're talking about Scaling a $10 Million Business. Jeremy is the Founder & CEO of Encore Search Partners. He is an expert on The Entrepreneurial Operating System and prides himsel…
#0348  –  Becoming an Excellent Leader with Markus van Alphen [not-audio_url] [/not-audio_url]

Duration: 42:06
Today, I’m joined by Markus van Alphen, and we're talking about Becoming an Excellent Leader. Markus is a renowned leadership psychologist and author of more than 15 books in Dutch and English. His most recent books incl…
#0347  –  Personal Branding for Business Leaders with Tyler Mount [not-audio_url] [/not-audio_url]

Duration: 41:33
Today, I’m joined by Tyler Mount, and we're discussing Personal Branding for Business Leaders. Tyler is the founder and CEO of Henry Street Collective, an industry-leading branding and digital strategy agency. He is a ce…
#0346  –  Leadership Lessons from Combat Sports with Aslak de Silva [not-audio_url] [/not-audio_url]

Duration: 44:27
Today, I’m joined by Aslak de Silva, and we're talking about Leadership Lessons from Combat Sports. Aslak has nearly 20 years of experience as a practitioner and instructor of Han Moo Do martial arts, competing in 100 fu…
#0345  –  Human-Centric Leadership with Brent Kedzierski [not-audio_url] [/not-audio_url]

Duration: 41:17
Today, I’m joined by Brent Kedzierski, and we're talking about Human-Centric Leadership. Brent is a leading voice in the evolution of work, focusing on improving the human condition. His role at Hexagon, a global leader…
#0344  –  Career Conversations with Julie Winkle Giulioni [not-audio_url] [/not-audio_url]

Duration: 43:22
Today, I’m joined by Julie Winkle Giulioni, and we're discussing employee career conversations. Julie is a champion for workplace growth and development and helps executives and leaders optimize talent and potential with…