The Pathless Path with Paul Millerd
The Pathless Path with Paul Millerd

The Pathless Path with Paul Millerd

Paul Millerd

Overview
Episodes

Details

The Pathless Path is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Russ Roberts, Kevin Kelly, Khe Hy, David Senra, Derek Sivers, Joe Hudson, Luke Burgis, Ben Hunt, Dan Vassallo, Steph Smith, Alex Pang, Visakan Veerasamy, Michael Ashcroft, Kyla Scalon, Trung Phan, Justin Welch, and more.

Recent Episodes

What's After BigLaw & Consulting? - Allie Canton & Paul Millerd On Reinvention, Parenting on The Pathless Path &  as Parent
NOV 20, 2025
What's After BigLaw & Consulting? - Allie Canton & Paul Millerd On Reinvention, Parenting on The Pathless Path & as Parent
Allie and I discuss our shared experiences of leaving traditional career paths to explore more authentic lives. Allie, a former lawyer, talks about navigating parenthood, part-time work, and her numerous interests while stepping off the default path. We chat about how Allie was inspired by 'The Pathless Path,' the ship, quit, and learn framework, and our upcoming experiments with nomadic living. Allie also talks about burnout, and alternative ways to live meaningfully.Follow Allie's writing and podcast on Substack: Practically On Purpose(00:00) - Introduction and Guest Overview (01:41) - Ali's Journey and Paul's Influence (02:48) - Defining the Pathless Path (04:41) - Living the Pathless Path (07:19) - Daily Life and Nomadic Living (20:38) - Traveling Village and Family Life (24:05) - Education and Raising Kids (28:03) - Ship, Quit, and Learn Framework (32:19) - Balancing Priorities and Curiosity (33:03) - Living a Minimalist Lifestyle (33:50) - Creative Paths and Family Support (36:24) - Cultural Differences in Marriage (39:52) - Economic Growth and Middle-Class Ideals (43:04) - Questioning the Traditional Career Path (45:32) - The Inspiration Deficit and Meaningful Work (49:36) - Challenges of the Creator Journey (56:54) - The Pathless Path Community Click here to watch a video of this episode. YQ3PyMQVF4KeM21wWwwC NEW: The Pathless Path Hardcover Premium Edition📘 My 2nd Book Good Work: 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 (26k+ 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
play-circle icon
60 MIN
Commit A Career Ending Move - Steven Foster on Permissionless Paychecks, Communal Living & Battling Life's Challenges While Pathless
NOV 13, 2025
Commit A Career Ending Move - Steven Foster on Permissionless Paychecks, Communal Living & Battling Life's Challenges While Pathless
In this episode, I have a deep conversation with Steven Foster, who opens up about his career journey from Silicon Valley to embracing a pathless life. We dive into his essay 'Commit a Career Ending Move,' reflecting on how modernity has turned careers into a form of religion. Steven shares his personal challenges, including severe health issues and family crises, and how embracing a more communal and nature-focused lifestyle has helped him navigate these obstacles. This episode is an exploration of redefining work, faith, and finding a deeper purpose beyond traditional career paths.(00:00) - Introduction to Steven Foster and His Career Journey (01:41) - The Religion of Work (03:42) - Steven's Early Career and Family Background (07:18) - Navigating the Tech Industry (20:11) - Leaving Silicon Valley (24:33) - Life After the Career-Ending Move (33:25) - Financial Shifts and Creative Solutions (34:37) - Navigating Personal Crises (43:58) - The Role of Community and Religion (56:00) - The Power of Permissionless Income NEW: The Pathless Path Hardcover Premium Edition📘 My 2nd Book Good Work: 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 (26k+ 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
play-circle icon
67 MIN
The Yoga Of Work - Andrew Taggart
SEP 8, 2025
The Yoga Of Work - Andrew Taggart
Click here to watch a video of this episode. Mentioned in the episodeAndrew Taggart’s websitePathways to the Dao (Andrew’s Substack)Leisure: The Basis of Culture by Josef PieperSecular Monks (article by Andrew Taggart)Why Buddhism is True by Robert WrightPierre Hadot (Philosophy as a Way of Life)The Pathless Path by Paul Millerd(00:00) - Introduction (04:02) - The Evolution of Work Philosophy (08:05) - The Role of Telos in Modern Life (14:59) - Personal Journeys and Realizations (37:34) - Writing as a practice and medium for understanding (48:54) - Rethinking Karma Yoga in Modernity (51:32) - The Mundane Nature of Daily Tasks (57:56) - The Spiritual Journey of Work (59:38) - Introspection and the Reality of Work (01:11:26) - Balancing Objective Conditions and Inner Peace (01:28:27) - The Concept of Inner Purification (01:35:49) - Final Thoughts and Future Projects NEW: The Pathless Path Hardcover Premium Edition📘 My 2nd Book Good Work: 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 (26k+ 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
play-circle icon
97 MIN
AMA Episode 200 - I answer questions on parenting, courage, being a prophet, taking risks, and money
SEP 4, 2025
AMA Episode 200 - I answer questions on parenting, courage, being a prophet, taking risks, and money
I took questions from people for episode 200.  Enjoy!Click here to watch a video of this episode. (00:00) - Introduction and Podcast Background (03:28) - Future of Education and Teaching (05:49) - Thoughts on Being a Prophet (06:29) - Current Pulling Forces and Changes (08:50) - Special Hardcover Edition Plans (10:25) - Managing Financial Anxiety (12:11) - Business Lessons from Corporate Life (15:04) - Evolving Perspectives on Parenting (17:35) - Self-Love versus Self-Improvement (21:10) - Building Community and Future Plans (23:13) - Courage and Sustainability on the Pathless Path (27:20) - Practical Advice for Going Off the Beaten Path NEW: The Pathless Path Hardcover Premium Edition📘 My 2nd Book Good Work: 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 (26k+ 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
play-circle icon
30 MIN
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
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 workLINKS: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 MaggiulliChapters(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 NEW: The Pathless Path Hardcover Premium Edition📘 My 2nd Book Good Work: 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 (26k+ 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
play-circle icon
62 MIN