The Pathless Path with Paul Millerd 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
Aug 25, 2025
Dennis Owen, a former airline professional, retired to Chiang Mai, Thailand, where he transformed his life through volunteering and community projects. He discusses the importance of 'retiring to' a fulfilling routine instead of merely leaving work behind. Dennis shares valuable insights into adapting to new cultures and the mental shift required for spending rather than saving in retirement. He highlights the significance of continuous learning, staying engaged with technology, and fostering connections to maintain purpose and well-being in this exciting new chapter.
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Moving To Chiang Mai With Purpose
- Dennis moved to Chiang Mai to work with an NGO he already knew and to be near an Asian community he respected.
- He found a co-living/co-working space that rebuilt his daily routine and social network after full-time work.
Retirement As Rethink And Reset
- Think of retirement as a rethink and reset, not a cliff jump into nothingness.
- Framing retirement this way makes the transition a continuation of career shifts, not an abrupt stop.
Build A Daily Routine And Community
- Create a daily routine after leaving full-time work because routine doesn't happen by itself.
- Find community spaces to meet diverse people and avoid isolating into same-age groups.
