The Pathless Path with Paul Millerd

Paul Millerd
  • 4.8 (66)
  • Entrepreneurship
  • Updated Weekly

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.

  1. Feb 25

    Angie Finished Her Memoir! - Angie and Paul on the creative process, parenting, travel, writing, life challenges, and books

    Check out Angie's book in Chinese: mit886.comMore about angie: Angiecreates.io Click here to watch a video of this episode. (00:00) - Welcome to the Pathless Path Podcast (00:11) - Life Updates and Creative Challenges (01:12) - The Journey of Writing a Memoir (05:14) - Revisiting Family Stories (08:25) - The Emotional Rollercoaster of Writing (10:29) - Balancing Motherhood and Creativity (13:09) - The Struggles of Working with Others (26:48) - The Impact of Miscarriage (34:08) - Rethinking Work and Parenting (42:17) - Struggles of Citizenship and Homelessness (42:43) - Emotional Turmoil and Support (43:07) - Guilt and Parenting Challenges (45:45) - A New Beginning in Thailand (46:40) - Balancing Work and Family (57:01) - Exploring Financial Literacy (01:12:23) - Publishing Journey and Cultural Differences (01:23:21) - Future Plans and Reflections

  2. 12/31/2025

    Michael Ashcroft on Getting Lost and The Joys of Dad Life

    I chat with Michael on parenting, getting lost, the pathless path, hustle culture, travel, and more. This is his 4th appearance on the show. Find more about Michael here: https://michaelashcroft.com/Or explore his writings on expanded awareness: https://expandingawareness.org/ (00:00) - Introduction / Teaser (01:39) - Introduction and Missing Guest (02:28) - Podcast Plans and Initial Banter (02:49) - Reflecting on Past Conversations (03:38) - The Journey of Self-Employment (12:12) - Life Updates and Health Challenges (16:05) - Parenting Reflections and Future Plans (19:38) - Balancing Work and Family Life (23:58) - Navigating Challenges and Personal Growth (30:02) - The Role of Fathers and Emotional Resilience (33:35) - The Impact of Miscarriages and Moving Forward (36:47) - Reflecting on a Challenging Project (38:17) - Book Sales and Audience Insights (39:57) - Future Plans and Creative Inspiration (40:51) - The State of Online Creation (50:21) - AI and Its Impact on Creativity (01:00:04) - Balancing Work, Family, and Creativity (01:05:26) - Fun and Games: Dictator or Hustle Bro? (01:08:26) - Concluding Thoughts and Future Outlook

    Michael Ashcroft on Getting Lost and The Joys of Dad Life

  3. 11/20/2025

    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 (00:43) - Ali's Journey and Paul's Influence (01:50) - Defining the Pathless Path (03:43) - Living the Pathless Path (06:21) - Daily Life and Nomadic Living (19:40) - Traveling Village and Family Life (23:07) - Education and Raising Kids (27:05) - Ship, Quit, and Learn Framework (31:21) - Balancing Priorities and Curiosity (32:05) - Living a Minimalist Lifestyle (32:52) - Creative Paths and Family Support (35:26) - Cultural Differences in Marriage (38:54) - Economic Growth and Middle-Class Ideals (42:06) - Questioning the Traditional Career Path (44:34) - The Inspiration Deficit and Meaningful Work (48:38) - Challenges of the Creator Journey (55:56) - The Pathless Path Community Click here to watch a video of this episode. YQ3PyMQVF4KeM21wWwwC

  4. 11/13/2025

    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 (00:43) - The Religion of Work (02:44) - Steven's Early Career and Family Background (06:20) - Navigating the Tech Industry (19:13) - Leaving Silicon Valley (23:35) - Life After the Career-Ending Move (32:27) - Financial Shifts and Creative Solutions (33:39) - Navigating Personal Crises (43:00) - The Role of Community and Religion (55:02) - The Power of Permissionless Income

    Commit A Career Ending Move - Steven Foster on Permissionless Paychecks, Communal Living & Battling Life's Challenges While Pathless

  5. 09/08/2025

    The Yoga Of Work - Andrew Taggart

    Click here to watch a video of this episode. Mentioned in the episode Andrew 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 (03:04) - The Evolution of Work Philosophy (07:07) - The Role of Telos in Modern Life (14:01) - Personal Journeys and Realizations (36:36) - Writing as a practice and medium for understanding (47:56) - Rethinking Karma Yoga in Modernity (50:34) - The Mundane Nature of Daily Tasks (56:58) - The Spiritual Journey of Work (58:40) - Introspection and the Reality of Work (01:10:28) - Balancing Objective Conditions and Inner Peace (01:27:29) - The Concept of Inner Purification (01:34:51) - Final Thoughts and Future Projects

    The Yoga Of Work - Andrew Taggart

  6. 09/04/2025

    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 (02:30) - Future of Education and Teaching (04:51) - Thoughts on Being a Prophet (05:31) - Current Pulling Forces and Changes (07:52) - Special Hardcover Edition Plans (09:27) - Managing Financial Anxiety (11:13) - Business Lessons from Corporate Life (14:06) - Evolving Perspectives on Parenting (16:37) - Self-Love versus Self-Improvement (20:12) - Building Community and Future Plans (22:15) - Courage and Sustainability on the Pathless Path (26:22) - Practical Advice for Going Off the Beaten Path

  7. 08/25/2025

    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

    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 (00:58) - Early Career in the Airline Industry (04:33) - Transition to Asia and Cultural Experiences (07:09) - Volunteer Work and Personal Life (14:53) - Retirement Philosophy and Activities (21:17) - Creating Opportunities and Continuous Learning (31:54) - The Reality of Retirement (32:11) - Finding Meaning Beyond Money (34:27) - Adapting to Technological Changes (37:21) - Retiring in Chiang Mai (41:36) - Balancing Health and Wellness (43:19) - Embracing Lifelong Learning (49:46) - Navigating Financial Decisions in Retirement (58:04) - The Importance of Purpose and Learning

    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

  8. 08/05/2025

    Worldschooling 2.0: Rekha Magon on Location-Independent Schooling, co-founding Boundless Life, Lessons during bed rest, rethinking family in a digital age, travel, freedom, and raising global citizens

    In this video, I talk with Rekha about Boundless Life and the idea of location-independent education. We cover her background, what led her to start Boundless Life, and how the program works for families who want a different approach to learning and community. For more: Boundless LifeBoundless EducationRekha on LinkedInRekha on Instagram (00:00) - Introduction to the topic of location-independent education (01:36) - Rekha's background and early influences (03:55) - Career beginnings and feeling unfulfilled (08:23) - Transformative experience during pregnancy (17:29) - Origins of Boundless Life (24:57) - Breaking traditional education assumptions (41:00) - Building community and relationships in Boundless (48:30) - Funding model and future growth (01:00:15) - Future plans and expansion

    Worldschooling 2.0: Rekha Magon on Location-Independent Schooling, co-founding Boundless Life, Lessons during bed rest, rethinking family in a digital age, travel, freedom, and raising global citizens
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4.8
out of 5
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About

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.

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