Episode 51: From Sneaking Out at Night to Selling Her Brokerage: Kendra Cooke on Addiction to Achievement, Coaching, and Living With No Regrets

Episode 51: From Sneaking Out at Night to Selling Her Brokerage: Kendra Cooke on Addiction to Achievement, Coaching, and Living With No Regrets

July 8, 2026 · 1h 2m · Season 1 · Episode 51

About this episode

Kendra Cooke shares her journey from a high-achieving real estate career to coaching, discussing the fine line between success and addiction.

She was selling 220 homes a year, had her name on billboards, and was collecting plastic plaques for being #1, and she was one bad month away from bankruptcy. In this episode, Kristy Kuhl sits down with Kendra Cooke , a TEDx speaker, business coach, real estate leader, and author with more than 30 years of experience, for a raw, honest conversation about what nobody tells you about success: it can quietly become an addiction. Kendra shares the story of sneaking out of bed at night to go back to her office, the ultimatum from her husband that finally made her stop, and the moment a coach looked at her books and said, "You don't have a time management issue. You have a money issue." From leaving college two weeks in to pursue real estate, to opening her own brokerage as one of the few female owner-brokers in her market, to walking away from it all to coach full-time, Kendra's story is a masterclass in what happens when you stop chasing accolades and start building a life you actually want to live. Things You Will Learn: Why success and addiction often look the same and how to recognize the pattern What it actually means to run your business like a business (and why most people…

More episodes of Keep Rising with Kristy Kuhl

Explore listener stats, chart rankings, contacts and more on the Keep Rising with Kristy Kuhl podcast page.