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

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

From The Pathless Path with Paul Millerd by Paul Millerd

August 25, 2025 · 1h 3m · Episode 199

About this episode

Dennis Owen shares his journey of building a purposeful retirement in Thailand, emphasizing community, continuous learning, and adapting to new cultures.

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…

People in this episode

Hosts: Paul Millerd, Paul

Guest: Dennis Owen

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

Keywords

  • retirement
  • expat life
  • community building
  • volunteering
  • consulting
  • health habits
  • technology

Mentioned in this episode

Products: Riverside, Readwise

Books & works: The Pathless Path, The New Retirementality, Die With Zero, Good Work, Pathless

Places: Chiang Mai, Thailand, Asia, US

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