Retired At 50 Freedom, Guilt… And What No One Tells You | Retirement Reality Ready For Retirement podcast

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Retired at 50 Freedom, Guilt… and What No One Tells You | Retirement Reality

2d ago 38:22

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Retiring at 50 sounds bold, almost unthinkable for most people, but for Kent, it was the only decision that made sense once life, loss, and perspective pushed everything into focus. In this conversation, he sits down with James Conole, CFP®, to share the honest story behind leaving work two decades earlier than expected.
Kent talks about saving from age 18, building a plan long before he knew what retirement would look like, and the complicated mix of discipline, luck, and family legacy that helped him reach this moment. He also opens up about the emotional side: the guilt of inheriting wealth after losing both his father and grandfather, the fear of telling coworkers and his mom, and the surprising relief when everyone responded with encouragement instead of judgment.
Nine months into retirement, Kent describes the freedom that comes from being fully present with his daughters, traveling on his family’s terms, rediscovering community through pickleball, and learning how to redefine productivity when your time finally becomes your own. And he doesn’t sugarcoat the harder parts — the identity shift, the loss of workplace validation, and the work it takes to build purpose outside of career.
This is what early retirement looks like when you stop planning only with your brain and start planning with your heart: more time, more presence, and a life shaped by intention instead of inertia.
Watch this episode of Retirement Reality — where real retirees share the highs, lows, and turning points that helped them choose a life they don’t want to postpone.
Want to be a guest on James’ show to help others by sharing your story? Complete this form: https://vwo3759x8i7.typeform.com/to/IwyScIeR

Kent is not a client of Root Financial Partners, LLC and received no compensation for participating in this video. His statements reflect his own opinions and experience and are not indicative of any specific client’s experience and are not a guarantee of results. No cash or non-cash compensation was provided, and no material conflicts are known.
Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.
The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.
Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements
Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

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Chapters

1. Opening Question: Shifting Identity (00:00:00)

2. Kent’s Early Retirement Setup (00:00:29)

3. Subscribe And New Content Plug (00:00:56)

4. Episode Overview And Teaser (00:01:02)

5. Kent Retires At 50: Why And How (00:01:09)

6. Savings, Tesla Wins, And Family Trust (00:02:27)

7. Guilt, Worthiness, And Identity (00:03:10)

8. Timeline Acceleration And Health Span (00:04:33)

9. From Accumulation To Vision: The Great Loop (00:05:29)

10. Presence On The Trip And With Family (00:06:51)

11. Hitting The Number And Job Changes (00:08:06)

12. Telling Work, Friends, And Mom (00:09:18)

13. Early Months: Freedom And Flexibility (00:11:18)

14. Travel, Camps, And Showing Up (00:12:33)

15. New Community And Pickleball (00:13:36)

16. What’s Been Hard: Structure And Motivation (00:14:30)

17. Homeschool Co‑Op And Being Present (00:15:55)

18. Fear Of Boredom And Future Plans (00:16:56)

19. The Heart Shift: Identity Beyond Work (00:17:38)

20. Practical Steps To Retire With Yourself (00:18:23)

21. Choosing Health Span Over Five Stars (00:19:17)

22. Closing Reflections And Thanks (00:20:07)

342 episodes

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