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The Pathless Path with Paul Millerd

Business & Economics Podcasts

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.

Location:

United States

Description:

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.

Language:

English


Episodes
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The Yoga Of Work - Andrew Taggart

9/8/2025
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 📘 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 Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up HereJoin Here

Duration:01:37:38

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AMA Episode 200 - I answer questions on parenting, courage, being a prophet, taking risks, and money

9/4/2025
I took questions from people for episode 200. Enjoy! Click here to watch a video of this episode. 📘 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 Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up HereJoin Here

Duration:00:29:55

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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

8/25/2025
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. Topics Covered: 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 MaggiulliChapters 📘 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 Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up HereJoin Here

Duration:01:02:39

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

8/4/2025
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 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:01:05:54

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The Inner Game of Work: Pranab Sachi on Codependent Origination, Rob Burbea, Quake Books, Attentional Co-Piloting, Michael Taft, and "Non-Success"

7/28/2025
In this episode, I interview my friend Pranab Saachi, and we get specific about the ideas and influences that have shaped his thinking. We talk about codependent origination from Buddhist philosophy, the concept of “quake books” that have shifted his worldview, and his own approach to “attentional co-piloting” as a practical alternative to traditional coaching (which he then has me try out live on the call). Pranab references teachers like Michael Taft and Robert Burbea, and explains how Internal Family Systems and Joe Hudson’s Art of Accomplishment have factored into his work. We also discuss his abandoned “Non-Success Podcast” idea and why he’s more interested in experiments than achievements. Some topics we talked about include: 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:01:21:31

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How much money do you need to quit? I debate with Nick Maggiuli (and rabbit holes: wealth > income, why COAST FIRE rocks, and more...)

7/21/2025
In this episode, I'm pumped to welcome back Nick Maggiulli to the podcast (https://youtu.be/deMXbaI-Ir4). We dive into various topics about money and financial independence, with a focus on Nick's endorsement of the 'COAST Fire' strategy, something I accidentally embraced after quitting my job. Nick shares his personal stories of financial challenges growing up and how these experiences shaped his approach to saving and spending. We debate the right time to take financial leaps and discuss how data-driven trends are making more Americans wealthier today. Nick introduces his wealth ladder concept and explains how it can help you live life on your terms. His new book is here: https://www.amazon.com/Wealth-Ladder-Proven-Strategies-Financial/dp/0593854039 I loved his first book too: https://youtu.be/WWXPNK06r-k 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:01:19:11

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Following Your Inner Compass - Lawrence Yeo on his creative journey, sharing ideas, self-publishing, and playing the long game

7/8/2025
Lawrence is one of my favorite creators. He shares with passion, vulnerability and care. I chatted with Lawrence Yeo about his new book, 'The Inner Compass,' exploring themes of self-reflection, creativity, and the journey of writing and self-publishing. We discuss the importance of engaging with the world to gain a deeper understanding of oneself, the role of ambition in creative work, and the dynamics of traditional versus self-publishing. Click here to watch a video of this episode. To find his book and support his work: BOOK: https://compass.moretothat.com SITE: https://moretothat.com CHAPTERS 00:38 The Journey of Self-Reflection 01:12 Creativity and Connection 06:38 The Nature of Creativity 08:55 Success and Inner Fulfillment 16:51 The Risk of Authenticity 18:51 Self-Publishing Insights 36:51 The Power of Short Books 38:06 Self-Publishing vs. Traditional Publishing 39:58 Creative Intentions in Writing 42:07 Overcoming Fear in Publishing Choices 44:17 The Pathless Path: Choosing Your Journey 47:48 The Next Book: Exploring Money and Identity 52:05 Innovative Approaches to Book Launches 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:01:11:12

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Hustle & Flow - Jack Moses on dropping out of school, hustle culture, spiritual paths, finding flow, and travel as transformation

7/1/2025
In this episode, I have a conversation with my friend Jack Moses. Three years ago, Jack emailed me after reading my book, declaring he was dropping out of college. Over time, I've been amazed by his life's actions, from embracing hustle culture to diving deep into spirituality. Recently, Jack led a retreat in Thailand, inspiring me with his courage and optimistic outlook. Join us as we discuss spiritual journeys, trusting our paths, and taking bold steps early in life. You can check out his podcast too 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:01:15:22

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Paul Q&A Episode - Moving to Asia, Parenting, Preparing for Kids, Pathless Hardcover Art Edition

5/30/2025
Personal updates about life, including his recent move back to Asia, reflections on work and career paths, parenting experiences, and insights into education and self-publishing. I share the challenges and joys of parenting, how I think about decisions in regards to kids, and evolving thoughts on publishing and creative projects. Topics 00:00 Introduction and Life Updates 05:32 Reflections on Career Paths and Work Culture 08:43 Family Relocation and Adjustments 11:06 Traveling with Children: Tips and Experiences 14:40 Advice for New Parents 17:34 Approach to Education for Children 20:33 Self-Publishing Journey and Future Projects 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:00:28:04

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Becoming A Writer - Nat Eliason on his upcoming fiction release, traditional publishing vs. self-publishing, AI tools, tinkering, readers, launch plans

5/14/2025
Hello! I'm back! Expect a slow ramp, but there are new episodes coming! I talked with Nat Eliason about his journey as a writer, from early experiments with ideas to fully embracing writing as a career. We discussed the challenges and rewards of moving from nonfiction to fiction, the trade-offs between traditional and self-publishing, and the importance of audience engagement. We also explored how AI is impacting writing, strategies for gathering feedback, and fiction’s role in addressing societal issues. Nat closed by sharing his vision for the future of his writing and the opportunities ahead. Links & book info! Buy herehttps://shop.nateliason.com/products/huskBuy hereHis Websitenewsletter 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:01:16:19

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"Dirtbag Rich" - Blake Boles & I Talk About Extracting More Freedom From Life

3/17/2025
Links: PodcastBlake BolesDirtbag Rich Site Episode Desription Paul Millerd is a 39-year-old writer, ex-consultant, and advocate for ditching the default path in favor of what he calls “the pathless path.” (pmillerd.com / @p_millerd) Paul walked away from a promising corporate consulting career—think McKinsey, prestige, and six-figure salaries—to pursue a life of writing, experimenting, and global wandering. He describes how he initially struggled with unlearning his achievement-oriented mindset, why the idea of good work (work that energizes) became his guiding principle, and how his first self-published book, The Pathless Path, briefly and unexpectedly earned six figures. We discuss the philosophical basis of work and money, how to avoid the traps of both scarcity and overachievement, and how the value of exercising your freedom is limited by how others exercise their own freedom. (In other words: if you're free to hike on a sunny Wednesday afternoon, and no one's available to go with you, are you really free?) Paul and his wife have a young daughter, and they struggle to find and live near other, like-minded families. We talk about how online communities help Paul stay connected while living nomadically between Texas and Taiwan and how online self-education was invaluable to his success. We conclude with a discussion of navigating fear and uncertainty on the pathless path. Throughout the conversation, Paul stays refreshingly honest about the tensions between freedom and stability, the allure of easy money, and the ever-present temptation to fall back into old habits of achievement and validation. Energized by this conversation, I ended up talking more than usual about the tricky balance of factors that leads to a Dirtbag Rich existence. Full transcript: 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:01:05:25

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Matt Yao Interviews Me

12/5/2024
This was a fun episode. A friend, Matt Yao, reached out to see if he could interview me about my recent book, Good Work. We first connected when he called me in the summer of 2022. He was in the middle of my book and knew he needed to quit his job. Over the last few years, he's been on a transformational journey, experimenting with writing, coaching, and several other side quests. Hope you enjoy this conversation. You can learn more about Matt here: Matt Yao 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:00:51:38

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Building A Life Around Good Work (Paul Interviewed by Abel James)

11/5/2024
You can follow Abel's podcast here: Abel James Show 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:01:35:11

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Good Work is Live! (Audiobook preview)

10/11/2024
Check out and purchase Good Work here: https://pmillerd.com/goodwork Or from Amazon directly: https://amzn.to/4gwRSCN

Duration:00:05:47

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#174 Agency Is A Skill — Cate Hall on leaving law for poker, developing agency, deterministic vs probabilistic economy, risk, burnout, asking dumb questions, defining ambition, seeking real feedback, and the surface area of luck

5/29/2024
Cate seemed to be fully entrenched on the default path — she had graduated from Yale and became the Supreme Court advocate on her way to becoming a partner in her law firm. But she didn't want to live the lives of the people around her. She pivoted hard, you could almost hear car brakes squeaking as she made the turn, and over a year she became the number one female poker player in the world. She later started art and perfume companies and led operations at Avlea — a pandemic medicine company. One might think she's simply a superhuman, and what she did is beyond the grasp of mere mortals, but Cate claims that agency is learnable and joins the podcast to tell us how. 🎥🍿 YOUTUBE: WATCH HERE Links: X (Twitter): @catehallLinkedInCate's ArticleHow to be More Agentic⌛TIMESTAMPS 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:01:02:19

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1 Year Dad Reflections - Conversation with Sky King & Nat Eliason

5/13/2024
This is from Sky King's podcast: https://skmp.supercast.com/ Guest info: Nat: https://www.nateliason.com/ Nat also has an amazing book coming out which I highly recommend, "Crypto Confidential": https://amzn.to/44BJ74I 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:01:24:59

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#173 Solopreneurship After Burnout — Justin Welsh on burnout, taking ownership of his time, struggling with a results oriented mindset, non-monetary success, becoming a top LinkedIn influencer, income goals, The Creator MBA, dealing with fears around money

4/16/2024
Justin is a former startup executive who helped build two startups past valuations of $1B, teams of 150+ people, and raise over $300M in venture capital. Now he’s building his one-person knowledge business toward $5M in annual profit. 🎥🍿 YOUTUBE: WATCH HERE Links: Personal websiteLinkedInX (Twitter):@thejustinwelshThe Creator MBAThe Saturday Solopreneur⌛TIMESTAMPS 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:01:06:52

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#172 Success In The Second Half Of Life — Henry Oliver on John Stuart Mill, Samuel Johnson, Penelope Fitzgerald, why we shouldn't dismiss Gladwell, writing, late bloomers, the importance of finding the others, Tyler Cowen's help and the lessons from Audrey Sutherland

4/1/2024
Henry is a writer, speaker and brand consultant. He joins the podcast to discuss his upcoming book — Second Act — in which he analysises the phenomenon of late bloomers and what we can learn from them. 🎥🍿 YOUTUBE: WATCH HERE Links: Personal websiteSubstack:The Common ReaderX (Twitter):@HenryEOliverSecond Act⌛TIMESTAMPS 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:01:08:58

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#171 "All Work Is Noble," Montessori, and Kids & Work — Matt Bateman on starting growing up with the internet, digital and industrial literacy, studying philosophy and learning how to teach, starting the Guidepost school network, how to train teachers, how children learn and work, values in education, agency, and writing his new book

3/25/2024
Matt Bateman has a PhD in philosophy. He has abandoned the academic career, to pursue education in the Montessori system. A dad of three, he is passionate about educating children. Having worked a lot with training the teachers in the Montessori approach, he has now taken a step back to focus on writing his book. 🎥🍿 YOUTUBE: WATCH HERE Links: Matt's Twitter@mbatemanmontessorium.comguidepost⌛TIMESTAMPS 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul @p_millerd@pathlesspaulSubscribe to PathlessSubscribe🙏Further Ways To Support The Podcast: CollectiveCheck out CrowdhealthLaunch Yours HereSign Up Here

Duration:01:15:23