The Pathless Path with Paul Millerd
Self-Improvement
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.
Episodes
- Angie Finished Her Memoir! - Angie and Paul on the creative process, parenting, travel, writing, life challenges, and books
Paul Millerd interviews Angie about her experiences writing a memoir. They discuss the creative process, balancing motherhood and writing, family stories, life challenges such as miscarriage and homelessness, and reflections on work and pu…
- Michael Ashcroft on Getting Lost and The Joys of Dad Life
Michael Ashcroft discusses parenting, the concept of getting lost, the pathless path philosophy, hustle culture, and travel with host Paul Millerd. This marks Ashcroft's fourth appearance on the podcast.
- What's After BigLaw & Consulting? - Allie Canton & Paul Millerd On Reinvention, Parenting on The Pathless Path & as Parent
Paul Millerd and Allie Canton discuss transitioning from traditional career paths to more authentic ways of living. They cover Allie's experience as a former lawyer, balancing parenthood, part-time work, and her interests while exploring n…
- Commit A Career Ending Move - Steven Foster on Permissionless Paychecks, Communal Living & Battling Life's Challenges While Pathless
Steven Foster shares his journey from Silicon Valley, exploring the idea of careers as a form of religion and discussing how communal living and nature-focused lifestyles helped him overcome significant personal and health challenges.
- The Yoga Of Work - Andrew Taggart
This episode features Andrew Taggart discussing the evolution of work philosophy, the role of telos in modern life, personal realizations, and writing as a practice. Topics also include rethinking Karma Yoga and the spiritual journey of wo…
- 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) - Curr…
- 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…
- 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 le…
- The Inner Game of Work: Pranab Sachi on Codependent Origination, Rob Burbea, Quake Books, Attentional Co-Piloting, Michael Taft, and "Non-Success"
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…
- How much money do you need to quit? I debate with Nick Maggiulli (and rabbit holes: wealth > income, why COAST FIRE rocks, and more...)
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,…
- Following Your Inner Compass - Lawrence Yeo on his creative journey, sharing ideas, self-publishing, and playing the long game
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 s…
- Hustle & Flow - Jack Moses on dropping out of school, hustle culture, spiritual paths, finding flow, and travel as transformation
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 cu…
- Paul Q&A Episode - Moving to Asia, Parenting, Preparing for Kids, Pathless Hardcover Art Edition
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 ab…
- Becoming A Writer - Nat Eliason on his upcoming fiction release, traditional publishing vs. self-publishing, AI tools, tinkering, readers, launch plans
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 rewa…
- "Dirtbag Rich" - Blake Boles & I Talk About Extracting More Freedom From Life
Links: Podcast Blake Boles Dirtbag Rich Site : https://www.blakeboles.com/dbr/ 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.…
- Matt Yao Interviews Me
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…
- Building A Life Around Good Work (Paul Interviewed by Abel James)
You can follow Abel's podcast here: Abel James Show 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 Commu…
- Good Work is Live! (Audiobook preview)
Check out and purchase Good Work here: https://pmillerd.com/goodwork Or from Amazon directly: https://amzn.to/4gwRSCN
- #175 20 Families as a "Traveling Village - Nikolaj Astrup on his experiment living in Thailand, Vietnam, and Japan with 20 families from around the world
- #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
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. Sh…
- 1 Year Dad Reflections - Conversation with Sky King & Nat Eliason
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 NEW: The Pathless Pa…
- #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
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. 🎥🍿…
- #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
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: Pers…
- #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
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 Mont…
- #170 Apprenticeships, Sabbaticals & "Good Work" — Steve Schlafman & Matt Yao on slowing down, deprogramming, unlearning, learning from others, deciding to quit, going on a sabbatical, not being jealous anymore, competitiveness and enoughness, finding good work, ambition, the apprenticeship, Downshift, decelerator, marriage, family and reframing money
Steve is a professional coach and the founder of Downshift — the world's first decelerator. He has left a career in venture, but he remains ambitious, it's just that his ambition is now to have a good, multidimentional life, where he can b…
- #169 "2M Subscribers, I love what I do, should I take a break?" — David Pakman on finding good work early, , how money and motivation changed over time, finding a balance in content creation, life after YouTube, his doubts about taking a sabbatical, having a daughter, dealing with public recognition and hateful comments, the lack of role models
David Pakman is a political commentator and the host of The David Pakman Show. He joins the podcast to explore a possible paradigm shift in the way he approaches his work and life after the birth of his daughter. 🎥🍿 YOUTUBE : WATCH HERE…
- #168 Building With "margin for life" — Justin Jackson on lessons from running a skate shop, optimizing for profit, running a "calm company," co-founding Transistor, having kids early, designing margins and how money actually does make him happy
Justin is the co-founder of Transistor, a podcast hosting platform on which The Pathless Path podcast is hosted. Justin is passionate about designing his company so that all the team benefits. He achieves that by making sure that there is…
- #167 Wandering in the Wilderness — Dom Francks on confronting fragility, his love of nature, the disconnect from nature, working as a software engineer, viewing yourself as a piece of poetry, how we're always embedded in nature and being guided by intuition
Dom is the lead guide at the VIVIFY Regerative Leadership Program. He helps leaders develop by taking them on an 8-day backpacking expedition in the Sierra mountains. Dom is passionate about preserving the natural world, staying connected…
- #166 Breaking Free of the Rules — Rick Lewis on being a child actor, dropping out of college, being a professional juggler, street performing and a clowning, the corporate world as an outsider, breaking rules, parenting and how to reinvent yourself
Rick Lewis could be succinctly described as "a speaker, author & professional consultant", but such technical labelling wouldn't paint a fair picture of who he really is. He describes what he's doing as "intelligent misbehavior". He's publ…
- #165 Gardening in the Digital Ecosystem — Kevin Espiritu on his fascination with the early Internet, how Poker broke his brain on money, starting his YouTube channel, Epic Gardening, taking a long term perspective, how to structure a video, transforming his YouTube channel, introducing new people to his audience, the probabilistic mindset and what he learnt from poker that helps him in his life
Kevin is the man behind the Epic Gardening channel. Although he had not read the Pathless Path at the time of the recording of this episode, he seems to be living it with every breath he takes. The only constant thing in his life seems to…
- [Repost] My Nervous System Guru & Friend - Jonny Miller on His Own Pathless Path, Grief, Friendship, David Whyte & More
Enroll In The 5th Cohort of Nervous System Mastery: You can get $250 OFF using the code PATHLESS => nsmastery.com Jonny Miller is a dear friend and I've had the privilege to get to know him closely over the past four years on our own journ…
- #164 Transformation For High Achievers — Joe Hudson on growing up with an alcoholic father, living around the world, transformation and self-discovery, becoming comfortable with yourself, emotional fluidity, expressing emotions, and the art of parenting
Joe is an executive coach and the founder of the Art of Accomplishment. Having worked as a venture capitalist, a consultant and an international banker, Joe discovered meditation on a trip to Asia and has practiced it since for over 25 yea…
- [Replay] Reinventing After Quitting A Top Job At Amazon - Christine Bader
Christine Bader is currently living in Bali, Indonesia, where she is spending time focused on her family and self. She is the author of The Evolution of a Corporate Idealist: When Girl Meets Oil and the former head of CSR for Amazon before…
- [Replay] Taking a "structured sabbatical" & Calm Companies - Jacqueline Jensen
Jacqueline Jensen has been a digital nomad for 3.5 years, living and working globally. It might surprise you to find out then, that she's written a book called " Travel Isn't The Answer. " While counter-intuitive, she argues for a return t…
- [Replay] Starting a "tribe" and living on an island with three kids - Ben Keene
After attending a few corporate recruiting sessions, he didn't take for granted that his path was to enter the corporate world. Twenty years later, he is still carving his own path and has recently returned from Koh Lanta, where he lived w…
- [Replay] How "total work" took over the world - Andrew Taggart
Andrew is a Practical Philosopher who believes that "there may be no greater vexation in our time than the question of how to make a living in a manner that accords with leading a good life." We dive deep into the questions of "what is the…
- [Replay] We Adopted a 4-Day Workweek - Tash Walker
Tash Walker is the founder of a firm and spends her Fridays making marmalade. Before instituting a four-day workweek at her firm, The Mix, she barely had time for her relationships. She decided to start doing research about different ways…
- [Replay] Living On A Boat for 1.5 Years - John Zeratsky
John Zeratsky was a designer in the tech industry has worked with hundreds of startups in his time at Google Ventures. He’s also obsessed with redesigning time and thinking about what matters in life. Earlier this year he just got back fro…
- [Replay] Packy McCormick on Injecting Fun To Newsletters
Packy says that his differentiation "is that I’m going to be having more fun than most people” I've been a big fan of the energy he's brought to his writing over the past couple of years. But he didn't set out to have a popular newsletter…
- #163 Luck Maximization — Jovian Gautama on being Indonesian in Taiwan, learning English from MTV and Reddit, graduating from a tourism high school, selling steel, podcasting, learning "tech" online, becoming the CEO of Castro
Jovian is an Indonesian living in Taiwan, who is deeply immersed in the American pop culture through the power of the internet. His background in tourism helps him with problem solving and talking too people, he has learnt English from wat…
- #162 Money, Work, Parenting & 1 Month In Taiwan - Angie & Paul on money scripts, cultural differences, being Taiwanese in the US, being American in Taiwan, perceptions of work in their families, life with a newborn, impostor syndrome, remote work and travel
After a month spent in Taiwan and 6 months into parenthood Angie & Paul share their thoughts and take some deep dives into various other topics. 🎥🍿 YOUTUBE : WATCH HERE ⌛TIMESTAMPS (00:00) - Podcast intro (03:15) - How Angie & Paul think…
- #161 9 Year Identity Crisis?! - Tom Critchlow on being stuck, indecisiveness, going to wander, taking every 7th week off, strategically dropping the ball, hiring an editor, and fear of finishing his book
Tom and Paul talk through Tom's challenges at this inflection point in his indie career, a book he's planning on shipping and how to think through indie consultant identity crises 🎥🍿 YOUTUBE : WATCH HERE Links: Tom's Site: https://tomcri…
- #160 - Why Manifesting Works — Erin Doppelt on how living in Israel and India changed her life, "snapshot manifestation", why women should work aligned with their menstrual cycle, entrepreneurship as freedom for women, pregnancy, and her new book
Erin is a spiritual psychology and meditation teacher, with a background in clinical psychology. She believes in experiencing rather than explaining and because of that she has been drawn to travel to places like India and Israel, which ha…
- #159 Living Intentionally After "Enough" - Bilal Zaidi on leaving Google, emigrating to the US, video games, the intensity of New York, writing poetry and spoken word, travel vs vacations, and money and creativity
Bilal was born in London to a family of Pakistani descent. A curious kid, with an interest in computers, he developed a successful website with over 500 000 readers in his teens. He ended up working at Google in the US. After a while Bilal…
- #158 From Rugby to TikTok Influencer — Ben Mercer on navigating the transitional periods in his life, being a professional athlete with an English literature degree, the diversity of the rugby world, various motivations in sports, his passion for rugby, his love of reading and writing, self-publishing and becoming a Tik Tok creator
Ben was a professional rugby player with an English literature degree — something not unheard of in the diverse rugby world, but also certainly not usual. After retiring from the sport, he was confronted with the task of redesigning his li…
- #157 Parenting & Our Future - Paul & Angie Check-In on Five Months of Parenting, Unexpected Happiness, Parenting Scripts, and The Time Bucket Exercise from Die With Zero
I'm trying to convince Angie to do more episodes, so if you like it please let us know by e-mailing both of us here. (00:16) - - Introduction and agenda for the podcast (04:14) - - Balancing work, fitness, health, and parenthood (14:14) -…
- #156 Saying "no" to something good — Jenny Blake on the inner CFO, spending every penny just to try, working at Google, running towards something vs. running away, creating assets for yourself, making yourself discoverable, and seeking advice from "friendtors"
Jenny is an author, international speaker, career and business strategist and executive coach. She has worked in a start up during her college years and then she worked at Google. At some point she decided to follow her passions and left h…
- #155 Homeschooling = Future of Education? - Hannah Frankman (Repost)
Hannah is awesome and you should listen to this podcast. She grew up homeschooled, is an endlessly curious person, has a deep sense of agency, and is a pro at carving her own path. She's done a ton of things including writing, coaching, an…
- #154 Learning to "Lean Out" - Dr. Dawn Baker's Journey from Medicine to 'Leaning Out', Embracing Unconventional Paths, Living Off-Grid, and Homeschooling
Dawn has a medical degree but she didn't pursue a traditional career as a doctor. She lives off grid with her husband and her homeschooled daughter. Dawn is passionate about finding a work-life balance and she wrote a book for professional…
- #153 Beyond Mimetic Desires - Luke Burgis on the temptations of conformity, contemplating life in Starbucks, thick desires and thin desires, letting go of control, the importance of play, learning from different work cultures, his stay in Rome and becoming a father
Luke has a background on Wall Street and has founded 3 companies in Silicon Valley. He describes his adult life as a constant state of uncertainty. At some point, he took a classics course, which he completed in a 24-hour Starbucks in a co…