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, Khe Hy, Ben Hunt, Wade Foster, Dan Vassallo, Kris Abdelmessih, Steph ...
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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 ...
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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 website LinkedIn X (Twitter): @thejustinwelsh The Creator MBA The Saturday S…
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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 ...
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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 website Substack: The Common Reader X (Twitter): @HenryEOliver Second Act ⌛TIMESTAMPS (00:00) - Intro (00:11)…
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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 ...
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Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort 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 ste…
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#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 ...
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Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort 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 be a good dad for his kids. Matt has lef…
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#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 ...
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Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort 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 Links: The David Pakman Show X (Twitter): …
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#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 ...
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Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort 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 always a financial margin as well as a …
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#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 ...
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Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort 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 to it and practicing aliveness. 🎥🍿 YOUT…
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#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 ...
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Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort 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 public appearances have a much deeper goal …
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#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 ...
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Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort 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 be that is constatly reinventing himsel…
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[Repost] My Nervous System Guru & Friend - Jonny Miller on His Own Pathless Path, Grief, Friendship, David Whyte & More
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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 journeys. We've lived in Japan, Indonesia, and Mexico together. When we met we were both single but now are both mar…
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#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 ...
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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 years since then. Meditating as well as a deep study of various spiritual, psychological and neurological traditio…
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[Replay] Reinventing After Quitting A Top Job At Amazon - Christine Bader
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Join CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here Christine Bader is currently liv…
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[Replay] Taking a "structured sabbatical" & Calm Companies - Jacqueline Jensen
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Join CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here Jacqueline Jensen has been a dig…
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[Replay] Starting a "tribe" and living on an island with three kids - Ben Keene
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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 with his three children in Thailand for the last six months. We Talked About Ben starting a "tribe" in Fiji Earl…
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[Replay] How "total work" took over the world - Andrew Taggart
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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 good life?" and what he means by "sustaining life." He also shares his perspective on the concept of "Total Wo…
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[Replay] We Adopted a 4-Day Workweek - Tash Walker
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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 of working. There had to be a better way than the default options of "Summer Fridays" and "flexible work," that…
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[Replay] Living On A Boat for 1.5 Years - John Zeratsky
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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 from 18 months living on his boat "Pineapple" with his wife sailing around Central America, which he wrote about i…
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[Replay] Packy McCormick on Injecting Fun To Newsletters
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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. His real plan was to launch an in-person community. We chat about how the pandemic helped him figure out why t…
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#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 ...
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Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort 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 watching MTV, got one of his first jobs be…
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#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 ...
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Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort 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 (02:17) - How Angie & Paul think about work & money? (10:12) - Cultural di…
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#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 ...
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🥳 Join Find The Others: Learn More Here 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://tomcritchlow.com/ Strategic Independent: Book Draft ⌛TIMESTAMPS (00:00) - Intro …
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#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 ...
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Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort 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 have helped her connect to her roots and …
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#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 ...
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Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort 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 has left the company to carve his own …
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#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 ...
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Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort 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 life. Although it was initially tough, he…
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#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
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Want To Become A Better Writer? Join Write of Passage's Upcoming Cohort 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 (03:16) - - Balancing work, fitness, health, and parenthood (13:16) - - Growth of their child and the emotion…
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