The Pathless Path with Paul Millerd - podcast cover

The Pathless Path with Paul Millerd

Paul Millerdpathlesspath.com
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

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 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 ...

Dec 05, 202452 minEp. 190

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

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 Twitter: @p_millerd Instagram: @pathlesspaul Paul’s Newsletter: Subscribe to Pathless (23k+ People) Paul’s YouTube: Subscribe 🙏Further Ways To Support The Podcast: Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): Collective Looking for alternati...

Nov 06, 20242 hr 35 minEp. 189

#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. 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. O...

May 29, 20241 hr 2 minEp. 186

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 📘 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 Twitter: @p_millerd Instagram: @pathlesspaul Paul’s Newsletter: Subscribe to Pathless (23k+ People) Pau...

May 13, 20241 hr 25 minEp. 184

#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. 🎥🍿 YOUTUBE : WATCH HERE Links: Personal website LinkedIn X (Twitter): @thejustinwelsh The Creator MBA The Saturday Solopreneur ⌛TIMESTAMPS (00:00) - Intro (01:34) - The scripts that Justin grew up with (09:59) - Attention and social media (11:43) - Liking your jo...

Apr 16, 20241 hr 7 minEp. 183

#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: Personal website Substack: The Common Reader X (Twitter): @HenryEOliver Second Act ⌛TIMESTAMPS (00:00) - Intro (00:49) - Guest introduction (01:35) - The scripts that Henry grew up with (05:48) - John Stuart Mill (08:19) - Samuel Johnson (15:01) - "The common reade...

Apr 01, 20241 hr 9 minEp. 182

#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 Montessori approach, he has now taken a step back to focus on writing his book. 🎥🍿 YOUTUBE : WATCH HERE Links: Matt's Twitter — @mbateman montessorium.com guidepost ⌛TIMESTAMPS (00:00) - Intro (01:32) - The scripts that Matt grew up with (05:18) - Growing up with...

Mar 25, 20241 hr 15 minEp. 181

#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 be a good dad for his kids. Matt has left a traditional path early on to write, travel and discover his own path. When he met Steve, he offered him to become his apprentice and joined Downshift. 🎥🍿 YOUTUBE : WATCH HERE Links: Downshift Steve's website Steve's ...

Mar 18, 20241 hr 24 minEp. 180

#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 Links: The David Pakman Show X (Twitter): @dpakman YouTube: David Pakman Show Instagram: david.pakman ⌛TIMESTAMPS (00:00) - Intro (01:50) - The scripts that David grew up with (04:04) - David's first steps on the internet (06:51) - Finding an alternative path (...

Mar 12, 20241 hrEp. 179

#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 always a financial margin as well as a "margin for our emotional health, margin for our physical health, margin for life." 🎥🍿 YOUTUBE : WATCH HERE Links: Personal website X (Twitter): @mijustin Justin's podcast Transistor ⌛TIMESTAMPS (00:11) - Guest introduct...

Feb 27, 20241 hr 14 minEp. 178

#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 to it and practicing aliveness. 🎥🍿 YOUTUBE : WATCH HERE Links: Personal website VIVIFY (Get $500 off if you mention this podcast) Substack ⌛TIMESTAMPS (00:00) - Intro (01:56) - The scripts Dom grew up with (07:18) - Dom's grandfather, a WW2 vet (09:43) - Expe...

Feb 20, 20241 hr 10 minEp. 177

#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 public appearances have a much deeper goal than just pure entertainment. Rick is passionate about discovering and breaking the hidden rules that rule our behavior and stifle our growth as people. 🎥🍿 YOUTUBE : WATCH HERE Links: Personal website Pivot to the Po...

Feb 13, 20241 hr 20 minEp. 176

#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 be that is constatly reinventing himself. From professional poker, gaming, web design, indie consulting, blogging to running a huge YouTube channel about gardening with almost 3 mil. subscribers, we meet at his next crossroads, after he's decided to take a step...

Feb 05, 20241 hr 14 minEp. 175

[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 journeys. We've lived in Japan, Indonesia, and Mexico together. When we met we were both single but now are both married in cross-country relationships and have navigated finding work that matters, getting married, and living in foreign countries together. 🍿 Wat...

Jan 30, 20242 hr 58 minEp. 174

#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 years since then. Meditating as well as a deep study of various spiritual, psychological and neurological traditions allowed him develop his unique ability to help others with personal transformation. 🎥🍿 YOUTUBE : WATCH HERE Links: Art of Accomplishment Podcast ...

Dec 11, 20231 hr 14 minEp. 173

[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 leaving in 2017, a journey she details in an amazing essay titled “ The year I learned to quit. ” She talks about leaving the corporate world and shifting her focus from building a career to building a life. Topics Discussed: Corporate social responsibility Ta...

Nov 27, 202346 minEp. 165

[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 to awe and wonder with what is already around us. She talks about different moments of wonder she has experienced (including a breathtaking view in Montenegro) and different techniques for how people can "Live With a Sense of Curiosity, Passion, and Awe Anywhere...

Nov 20, 202345 minEp. 167

[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 with his three children in Thailand for the last six months. We Talked About Ben starting a "tribe" in Fiji Early internet adventures His experiences coaching people with career transition The decision to move to Thailand with his three kids for six months Using...

Nov 13, 20231 hrEp. 164

[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 good life?" and what he means by "sustaining life." He also shares his perspective on the concept of "Total Work," a phrase first put forth in 1947 by the German Philosopher Josef Pieper, and shares how that phrase became central to his current writing on the ...

Nov 06, 20231 hr 9 minEp. 169

[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 of working. There had to be a better way than the default options of "Summer Fridays" and "flexible work," that never seem to make less anxiety or stress-ridden. In her research, she discovered many examples of Swedish companies embracing 4-day workweeks and al...

Oct 30, 202346 minEp. 166

[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 from 18 months living on his boat "Pineapple" with his wife sailing around Central America, which he wrote about in an article titled “ What quitting my job to sail around central america taught me about fulfillment .” In this conversation we talk about: Growing u...

Oct 23, 20231 hr 6 minEp. 163

[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 . His real plan was to launch an in-person community. We chat about how the pandemic helped him figure out why that wasn't a good idea and how he's thinking about his solopreneur journey. The reason I asked him on the podcast is to talk about his recent newslet...

Oct 16, 202344 minEp. 162

#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 watching MTV, got one of his first jobs because he was browsing Reddit and he is now the CEO of Castro, the podcast app. Jovian is a magnet for opportunities, which apparently come to him simply because he just assumes that people are nice. 🎥🍿 YOUTUBE : WATCH HE...

Oct 12, 20231 hr 27 minEp. 171

#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 (02:55) - How Angie & Paul think about work & money? (10:50) - Cultural differences, ask vs guess (15:36) - Defining work, feedback from the family (23:00) - How are Angie & Paul thinking about having kids? (29:47) - Angie's relationship with writing (44:38) - Accepting compli...

Sep 18, 20231 hr 18 minEp. 170

#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://tomcritchlow.com/ Strategic Independent: Book Draft ⌛TIMESTAMPS (00:00) - Intro (00:49) - Guest introduction (03:13) - Tom's problem — indecisiveness (07:27) - What does Tom think he should be doing? (09:50) - Not working, go and wonder, owning time (14:07) - 7th wee...

Aug 23, 202349 minEp. 161

#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 have helped her connect to her roots and to what matters. Erin is passionate about discovering her true self, meditation, snapshot manifestation, and taking aligned action. She is finishing up a new book and is about to have her first child — a new chapter for wh...

Aug 14, 20231 hr 10 minEp. 160

#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 has left the company to carve his own path. He has founded Creator Lab and discovered a passion for spoken word poetry, which enables him to better connect with his family 🎥🍿 YOUTUBE : WATCH HERE Links: X (Twitter) — @bzaidi Creator Lab Website Creator Lab B...

Aug 10, 20231 hr 28 minEp. 159

#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 life. Although it was initially tough, he took the slow approach of focusing on the things he enjoys doing, which proved very beneficial in the long term. Ben has self-published 3 books so far, he is freelancing, running courses and he recently became a rising Ti...

Jul 31, 20231 hr 13 minEp. 158