The Time Freedom Podcast

Les Sherry Built Time Freedom Inside a Corporate Career

Episode Summary

Today on the podcast, Brian and Kirby welcome Les Sherry. Les, 62 and married 26 years to his wife Suzanne, lives in Danville, California. He spent his career in traditional corporate roles before retiring on his 60th birthday in 2023. Today he's an executive coach who helps leaders and teams unlock their potential. In this episode, Les shares how he and his wife dreamed up a year-long family trip around the world during their honeymoon in Thailand, then spent the next 12 years methodically planning and making lifestyle choices to make it happen. He talks about what it actually looks like to apply time freedom principles inside a traditional corporate career, what it takes to convince coworkers that you’re actually going through with a one-year sabbatical, and what the post-trip depression taught him about retirement.

Episode Notes

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.

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.