The Pathless Path with Paul Millerd

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.

"Dirtbag Rich" - Blake Boles & I Talk About Extracting More Freedom From Life
Mar 17, 2025 – 01:05:25
Matt Yao Interviews Me
Dec 5, 2024 – 51:38
Building A Life Around Good Work (Paul Interviewed by Abel James)
Nov 5, 2024 – 01:35:11
Good Work is Live! (Audiobook preview)
Oct 11, 2024 – 05:47
#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
Jun 26, 2024 – 43:37
#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
May 29, 2024 – 01:02:19
1 Year Dad Reflections - Conversation with Sky King & Nat Eliason
May 13, 2024 – 01:24:59
#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
Apr 16, 2024 – 01:06:52
#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
Apr 1, 2024 – 01:08:58
#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
Mar 25, 2024 – 01:15:23
#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
Mar 18, 2024 – 01:24:16
#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
Mar 12, 2024 – 01:00:09
#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
Feb 27, 2024 – 01:13:34
#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
Feb 19, 2024 – 01:09:32
#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
Feb 12, 2024 – 01:19:30
#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
Feb 5, 2024 – 01:13:33
[Repost] My Nervous System Guru & Friend - Jonny Miller on His Own Pathless Path, Grief, Friendship, David Whyte & More
Jan 29, 2024 – 01:57:54
#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
Dec 11, 2023 – 01:13:36
[Replay] Reinventing After Quitting A Top Job At Amazon - Christine Bader
Nov 27, 2023 – 45:55
[Replay] Taking a "structured sabbatical" & Calm Companies - Jacqueline Jensen
Nov 20, 2023 – 44:35
[Replay] Starting a "tribe" and living on an island with three kids - Ben Keene
Nov 13, 2023 – 01:00:24
[Replay] How "total work" took over the world - Andrew Taggart
Nov 6, 2023 – 01:09:14
[Replay] We Adopted a 4-Day Workweek - Tash Walker
Oct 30, 2023 – 45:51
[Replay] Living On A Boat for 1.5 Years - John Zeratsky
Oct 23, 2023 – 01:06:08
[Replay] Packy McCormick on Injecting Fun To Newsletters
Oct 16, 2023 – 44:07
#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
Oct 12, 2023 – 01:27:14
#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
Sep 18, 2023 – 01:18:19
#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
Aug 23, 2023 – 49:13
#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
Aug 14, 2023 – 01:10:08
#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
Aug 10, 2023 – 01:28:24
#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
Jul 31, 2023 – 01:13:07
#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
Jul 28, 2023 – 01:06:03
#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"
Jul 24, 2023 – 01:02:43
#155 Homeschooling = Future of Education? - Hannah Frankman (Repost)
Jul 17, 2023 – 01:19:46
#154 Learning to "Lean Out" - Dr. Dawn Baker's Journey from Medicine to 'Leaning Out', Embracing Unconventional Paths, Living Off-Grid, and Homeschooling
Jul 10, 2023 – 01:05:10
#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
Jul 3, 2023 – 01:20:15
#152 The Creator Therapist - Melvin Varghese on Emigrating to Texas, his work as a clinical psychologist, starting a podcast, the birth of his daughter, re-evaluating life and money and detaching identity from work
Jun 26, 2023 – 01:10:33
#151 Culture Without Culture War - Anna Gát on growing up in Hungary, emigrating at the age of 30, staying curious as we age, Interintellect, building a startup, bad advice and trusting your gut, her article in 2018, culture without culture war, creating your own gatekeepers, and success in the UK vs US
Jun 19, 2023 – 01:13:35
#150 - Why I Turned Down a $200k Book Deal (Solo Episode)
Jun 13, 2023 – 24:42
#149 "I will sell out Madison Square Garden" - Danny Miranda on starting a blog at 14, following your intuition, discipline, meditation, his podcast, retreats, masculinity, compassion, "The True Path", thinking big, and trusting The Universe
Jun 12, 2023 – 01:24:54
#148 Embracing Post-Traumatic Growth - Jessica Depatie on her Korean background, shadow work, producing a documentary - "Dark Night of Our Soul", expanding your perspective through travel, what does it mean to rest, defining growth, the hero's journey, and memes
Jun 5, 2023 – 01:05:40
#147 You Can Love Cooking Too - Myles Snider on intuitive cooking, living in Argentina, working in Tulum, food industry scripts, health myths, the beauty of "slow cooking"
May 29, 2023 – 01:19:45
#146 Separating Work & Identity - Simone Stolzoff on the myth of a "Dream Job," last-minute around the world trip, journalism, work, identity, writing his book, knowing when to quit, and the dangers of turning passion into a livelihood
May 22, 2023 – 01:07:24
#145 Capitalist by Day, Spiritual by Night - Alex Hardy on achievement, Wall Street, tech startups, exiting his company, pride & suffering, his sabbatical, suppressing his curiosity and rediscovering his passions
May 15, 2023 – 01:33:26
#144 The Creator Pivot - Khe Hy on laying people off, collapsing course demand, seasons of creativity, having zero change in net worth in eight years, competitiveness, investing, coaching, and marriage on the pathless path
May 8, 2023 – 01:12:32
#143 The Art of Living - Kyle Kowalski on how to have an existential crisis, synthesizing the art of living, curiosity as fuel, his relationship with money, "killing himself to work" and "purpose washing" in big companies
May 1, 2023 – 01:12:46
#142 Goofing Off On Purpose - Kevin Kelly on why we should subsidize travel for young people, owning his time, a rest ethic, riding his bike across US, his love of YouTube, staying optimistic about the future, raising children and his new book
Apr 17, 2023 – 51:40
#141 Ryan Holiday's Secret Weapon - Billy Oppenheimer on growing in Philadelphia, almost going to law school, role models, working with Ryan Holiday, his research process, the notecard system, skiing, and the downsides to fame
Apr 10, 2023 – 01:07:22
#140 Tom Peters - Fired from McKinsey to Top Business Thought Leader
Apr 3, 2023 – 33:40
#139 Compounding Memes - Trung Phan on his great grandfather, living abroad, the expat community in Asia, writing, working at The Hustle, children and work, balancing his various activities, going solo, and playing the long game
Mar 27, 2023 – 52:00

Recent Reviews

iwitty96

Insightful and inspiring

I love this show. So many great interviews and speakers from different backgrounds who are so inspiring to me, someone whose planning her sabbatical. The episode with Michelle and Cecile made me realize I need to do it!! Thank you Paul.
Michelle the Change Architect

Love the challenge to live outside the box

Paul and his guest are well informed and create curiosity to help spark it in others. Interesting content and ideas as well as encouragement to do your own work; unique to you.
Njjjjjjttty

Good guests with unique stories and insights to share

I first learned about Paul from another writer and blogger I follow. I enjoy the way Paul brings a diverse set of people with interesting perspectives, it helps to decondition one from the standard scripts and ideas that often unknowingly govern our lives.
Yo Mama700!

Be prepared to lose all interest in your job

This podcast and “The Pathless Path” book have made it EXTREMELY hard to work my regular, boring job 😂 For better or for worse, though I think it’s a good thing. I feel like I’ve woken up after 2 years of sticking my head in the sand. I LOVED entrepreneurship when I was in college, but lost my passion as I got my first job, started a family, bought a house, etc. But now I’ve been slapped in the face and reminded that there is more to life than a paycheck. I’m now deeply contemplating my passions and gaps where I can add value to others lives, and hope to launch my own solopreneur journey in the next month or 2. Thank you for waking me up Paul. And thank you for colabing with others in this podcast doing similar things, their stories are inspiring.
K HH

Great podcast

"The Pathless Path with Paul Millerd" is a super cool podcast that totally shakes up the traditional career journey. I really appreciate how it pushes you to think outside the box and question the usual norms around work and success. Millerd's conversations are thought-provoking and inspire you to find your own unique path to happiness and fulfillment in your professional life.
mehrnaz mehrnazi

Highly recommended

Just listened to episode #151 and it was enlightening!
xsiamesedreamx

Stumbled onto The Pathless Path

Paul is such an authentic human being and his thinking and writing will challenge your commonly held beliefs and assumptions around work. He has been a huge source of inspiration to me and I highly recommend both his podcast and his book, The Pathless Path.
Chen wan tu

Big fan of Paul’s work, his book and this podcast!

It’s authentic and the guest list is top notch.
An Epic Year

Refreshing & Insightful

Paul’s podcast and book fill a gap in discussions about self-employment, building your own future, creating a fulfilling work life. I connect with Paul’s journey and many of his guests who spent years in corporate America because we were conditioned to believe that it would provide wealth, status, and security. Now, technology allows us to rewrite and reimagine our passions. I’ve spent the last 8 years self-employed and wouldn’t go back.
Batmanhhvhh

Highly recommend!

If you’re a writer, artist or creative person I highly recommend going down the Pathless Path rabbit hole. So many good convos on untraditional paths and how to navigate them. Paul asks great questions and has a knack for finding great guests.
Tori1233456741

Nerdy, Vulnerable, and Captivating

Paul’s conversations with his guests are top-notch. You can tell he’s interested in what his guests have to say, and he’s also not afraid to push them a bit or challenge some of their views. Always a treat to listen to!
obacker19

Insightful, entertaining and actionable 🙌

I feel completely at home with Paul during his interviews - bowled over by the brilliant advice and nourishing conversations he facilitates. He and his guests provide some incredibly actionable and compelling content, spotlighting how work is evolving in the 21st century and how you and your company can stay ahead of the curve - Highly recommend listening and subscribing to Reimagine Work!
Steeze.0

Great shows!

Stumbled upon the show randomly, but now gotta go back and listen to every episode.
tm5501987

Love the podcast

Great stories from people who have followed different paths Inspiring! The interviewer has a great style.
Aprilann4282

Worth your time

Awesome guy, not just out for your money. Although I didn't have a specific goal, he was able to give me general guidance without me feeling as though there were ulterior motives unlike so many other business "counselors/advisors" out there.
ervgotti24

Excellent! Extremely relevant to all

The guests are interesting, engaging, and very insightful. Paul does a great job building rapport and eliciting genuine responses. The conversation is fluid and the length is just right. Keep it up!
Larmoz

Great show

Very bold and great insight, hope he does well