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

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 retirementMoving abroad and adapting to a new cultureThe importance of “retiring to” something, not just leaving workBuilding routine and community in retirementVolunteering and giving backConsulting, ghostwriting, and staying mentally activeThe mental shift from saving to spendingStaying current with technology and learning new thingsHealth, wellness, and daily habitsNavigating practical challenges of living abroadBook and resource recommendations for retirement and reinventionAdvice for finding purpose and meaning after work LINKS:Dennis Owen on LinkedInThe Pathless Path by Paul MillerdThe New Retirementality by Mitch AnthonyOutlive by Peter AttiaDie With Zero by Bill PerkinsJust Keep Buying by Nick Maggiulli Chapters (00:00) - Introduction and Guest Background (01:36) - Early Career in the Airline Industry (05:11) - Transition to Asia and Cultural Experiences (07:47) - Volunteer Work and Personal Life (15:31) - Retirement Philosophy and Activities (21:55) - Creating Opportunities and Continuous Learning (32:32) - The Reality of Retirement (32:49) - Finding Meaning Beyond Money (35:05) - Adapting to Technological Changes (37:59) - Retiring in Chiang Mai (42:14) - Balancing Health and Wellness (43:57) - Embracing Lifelong Learning (50:24) - Navigating Financial Decisions in Retirement (58:42) - The Importance of Purpose and Learning 📘 My 2nd Book Good Work: LIVE! => Learn More 📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path 😁 Join 500+ In My Cozy Community: Pathless Path Community 📲Connect + Follow PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (25k+ People)Paul’s YouTube: Subscribe 🙏Further Ways To Support The Podcast:Accounting, Taxes, and Payroll for Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial