August 25, 2025

How To Retire Well: Dennis Owen on Moving Abroad, Building Community, Volunteering, Adapting to New Cultures, Creating Routine, Consulting After Retirement, Managing Money Mindset Shifts, Staying Current with Technology, Health Habits, Navigating Expat Li

1 hour 2 minutes

In this episode, I talk with Dennis Owen about his journey from a long career in the airline industry to building a purposeful and active retirement in Chiang Mai, Thailand. Dennis shares how he intentionally “retired to” a new life filled with volunteering, consulting, and community involvement, rather than just leaving work behind. We discuss the challenges of adapting to a new culture, the importance of routine, staying curious, and the mental shift from saving to spending in retirement. Dennis emphasizes the value of purpose, continuous learning, and building a diverse community, while also sharing practical tips and book recommendations for anyone to continue to reinvent their path after work.

Click here to watch a video of this episode.

Topics Covered:

Transitioning from a long career to retirement
Moving abroad and adapting to a new culture
The importance of “retiring to” something, not just leaving work
Building routine and community in retirement
Volunteering and giving back
Consulting, ghostwriting, and staying mentally active
The mental shift from saving to spending
Staying current with technology and learning new things
Health, wellness, and daily habits
Navigating practical challenges of living abroad
Book and resource recommendations for retirement and reinvention
Advice for finding purpose and meaning after work

LINKS:

Dennis Owen on LinkedIn
The Pathless Path by Paul Millerd
The New Retirementality by Mitch Anthony
Outlive by Peter Attia
Die With Zero by Bill Perkins
Just Keep Buying by Nick Maggiulli

Chapters

(00:00) - Introduction and Guest Background

(01:56) - Early Career in the Airline Industry

(05:31) - Transition to Asia and Cultural Experiences

(08:07) - Volunteer Work and Personal Life

(15:51) - Retirement Philosophy and Activities

(22:15) - Creating Opportunities and Continuous Learning

(32:52) - The Reality of Retirement

(33:09) - Finding Meaning Beyond Money

(35:25) - Adapting to Technological Changes

(38:19) - Retiring in Chiang Mai

(42:34) - Balancing Health and Wellness

(44:17) - Embracing Lifelong Learning

(50:44) - Navigating Financial Decisions in Retirement

(59:02) - The Importance of Purpose and Learning

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By Paul Millerd

4.8

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