The Time Freedom Podcast

Les Sherry Built Time Freedom Inside a Corporate Career

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Top 5 Takeaways:

  1. A job is just a job, not a career. When you're good at what you do, leaving a role is far less risky than most people think.
  2. You don't have to be an entrepreneur to live with time freedom. Les achieved it through a traditional career by making intentional choices over time.
  3. Post-adventure depression is real. Finishing a big, consuming goal can leave a hole that catches you off guard.
  4. Retire into something, not away from something. The four phases of transition (vacation, loss of purpose, exploration, new purpose) explain why so many retirees go back to work.
  5. There are things you can only do at certain times in life. Waiting for the “right time” can mean the window closes entirely.

    6. Chapters:

    0:00 – Introduction and Les Sherry’s Background

    2:19 – The Desire for Time Freedom

    5:02 – Planning a Year-Long Family Adventure

    7:36 – What It’s Really Like Traveling as a Family

    10:07 – Coming Home and Reintegrating

    12:30 – Transitioning Away from Traditional Work

    14:57 – Finding Purpose After the Journey

    17:15 – Key Lessons from a Year Abroad

    37:30 – The Four Phases of Transition Explained

    49:36 – Coaching, Independence, and What’s Next

    LES SHERRY 

    Les Sherry is an ICF certified executive coach with over 30 years of leadership experience across consulting, healthcare, and technology. He spent 11 years at Accenture before joining Kaiser Permanente, where he worked for nearly two decades. In 2012, smack in the middle of his Kaiser career, Les and his family packed their backpacks (100 pounds total) and spent a year traveling to 23 countries across six continents. Since retiring, he's picked up fly fishing, fly tying, piano, Muay Thai kickboxing, and is training to teach yoga. You can connect with Les on LinkedIn.

     

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    The Time Freedom PodcastBy Brian Herriot, Kirby Denison