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.

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Episodes

#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 (03:54) - - Balancing work, fitness, health, and parenthood (13:54) - - Growth of their child and the emotional journey of parenthood (15:54) - - Financial situation and the concept of abundance (26:54) - - Sharing a parenting mistake they made and how they learned from it (37:56) - - Learning new skills and therapies (48:55) - -...

Jul 28, 2023•1 hr 6 min•Ep. 157

#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 her job. She has already written three books, she runs a business on intuition and she continues discovering her own path. 🎥🍿 YOUTUBE : WATCH HERE Links: itsfreetime.com pivotmethod.com book royalty calculator Jenny's Books: Life After College Pivot Free Time ...

Jul 24, 2023•1 hr 3 min•Ep. 155

#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, and working at startups and has created jobs for herself, negotiated working remotely (before it was cool), and has done a ton of other things. She recently founded Rebel Educator which is a media brand that aims to share more about homeschooling and alternative ...

Jul 17, 2023•1 hr 20 min•Ep. 156

#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 women seeking to do so. 🎥🍿 YOUTUBE : WATCH HERE Links: Book: Lean Out Twitter: @DLBakerMD practicebalance.com Instagram: practicebalance ⌛TIMESTAMPS (00:00) - Intro (01:43) - The scripts Dawn grew up with (03:27) - Medicine, engineering and rock climbing (16...

Jul 11, 2023•1 hr 5 min•Ep. 154

#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 couple of months while living in Las Vegas. This led to him to contemplate deeper questions, leaving "entrepreneur Luke" behind and spending 3 years in Rome. Luke is now a Professor at the Ciocca Center for Principled Entrepreneurship and has written a book — "WA...

Jul 03, 2023•1 hr 20 min•Ep. 153

#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

Melvin has a PhD in psychology but to call him just "a psychologist" would be trying to fit him in too small of a box. He has left a successful clinical career to build his online "healthy business" – he is the person behind "Selling the Couch" podcast, he does sessions with entrepreneurs and he runs an online course where he helps therapists to move their business online. Everything he does is designed to allow him to be fully present as a father and a husband because, "What's the point of acco...

Jun 26, 2023•1 hr 11 min•Ep. 152

#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

Anna is the founder and CEO of Interintellect - a global community of thinkers. She grew up in Hungary and emigrated to London at the age of 30 and later to the US where she built her startup. She is passionate about staying curious as we age. While for some their late 20's are the end, she has chosen to treat it as the beginning. 🎥🍿 YOUTUBE : WATCH HERE Links: Interintellect Twitter: @TheAnnaGat Instagram: annagat_ Anna's Personal Website Writing ⌛TIMESTAMPS (00:00) - Intro (01:58) - The scri...

Jun 19, 2023•1 hr 14 min•Ep. 151

#150 - Why I Turned Down a $200k Book Deal (Solo Episode)

This is a solo episode of my podcast, inspired by Jenny Blake. I will do more of these if people like them. Let me know! For Video: YouTube 📘 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...

Jun 13, 2023•25 min•Ep. 150

#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

Danny Mirands is the host of The Danny Miranda Podcast. He's been hanging out on the internet since he was 14. We talk about his journey, almost getting sidetracked by the default path in college, and then betting on himself with his podcast. Danny is a friend, and he inspired me by how true he is to his own path, his ability to dream big in creative ways and spread love in the world. 🎥🍿 YOUTUBE : WATCH HERE Links: The Danny Miranda Podcast Twitter: @heydannymiranda Instagram: heydannymiranda ...

Jun 12, 2023•1 hr 25 min•Ep. 149

#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

Jessica is a producer and a podcaster. She is passionate about shadow work and is currently working on her documentary on post traumatic growth - "Dark Night of Our Soul". 🎥🍿 YOUTUBE : WATCH HERE Links: Link to Support The Movie - Dark Night of Our Soul Jessica on IMDb Instagram - jessicadepatie_ Hollywood Con Queen Podcast Bill Plotkin’s Journey of Soul Initiation @wordsarevibrations meme account ⌛TIMESTAMPS (00:00) - Intro (00:49) - Introduction (01:57) - The scripts Jessica grew up with (09...

Jun 05, 2023•1 hr 6 min•Ep. 148

#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"

Myles is a chef and a farmer's market enthusiast. He studied economics and was pursuing many other interests like filmmaking on the side. During his stay in Argentina, he realized that he wanted to follow his true passion - cooking. Although he hasn't gone to a fancy cooking school, he managed to get a position working under a former Michelin star chef in Tulum and now he's sharing his love for cooking on the Internet, making it approachable for other people. 🎥🍿 YOUTUBE : WATCH HERE If you're ...

May 29, 2023•1 hr 20 min•Ep. 147

#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

Simone Stolzoff has worn many hats. He's worked as a writer, designer, and now, Author. He grew up with "four parents", each having a unique influence on him, He grew up being told he could do whatever he wanted but realized there were assumptions behind that. Over the last couple of years, he's contemplated how we can design a life not centered around work (which obviously interests me as well) and has come to some interesting conclusions. 🎥🍿 YOUTUBE : WATCH HERE 📕Buy Simone's Book (Just Rel...

May 22, 2023•1 hr 7 min•Ep. 146

#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

Alex was crushing it early in his career, ending up on Wall Street after getting a combined JD/MBA. But after a few years, he went looking for his next mountain, aiming his ambition at the tech sector. He ended up co-founding LiveOak, a company he eventually sold in 2020. After that, he struggled to determine what was next and finally decided to walk away from more than a million dollars. Now he's embracing non-doing, reconnecting with his passions, and figuring out what's next. 🎥🍿 YOUTUBE : W...

May 15, 2023•2 hr 33 min•Ep. 145

#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

In 2015 Khe left a Wall Street carrier to pursue his own path of "uncomfortable introspection", reevaluating his life. This is a constant process - Khe is always being emergent to himself. Now he finds himself at a crossroads - after a great initial success in 2020, he recently had to scale down his cohort-based course. Although laying people off was tough, Khe welcomes the change as entering a new season of creativity. 🎥🍿 YOUTUBE : WATCH HERE Links: Twitter: @khemaridh radreads.co Download Kh...

May 08, 2023•1 hr 13 min•Ep. 144

#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

Kyle was a marketing executive who believed in the "hard work" ethic. After an existential crisis, he decided to carve his own path as a solopreneur and started Sloww - "a trusted resource of lifelong learning". Kyle describes his purpose as "synthesizing the art of living for students of life". 🎥🍿 YOUTUBE : WATCH HERE Links: Twitter: @KyKow Sloww: sloww.co Happiness Book Igikai 2.0 ⌛TIMESTAMPS (01:22) - The scripts that Kyle grew up with (13:59) - How to have an existential crisis (30:29) - D...

May 01, 2023•1 hr 13 min•Ep. 143

#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

Kevin is the founding executive editor of Wired magazine, a writer and a photographer. When he was young he dropped out of college and travelled to Taiwan, which he describes as a live changing experience. Kevin is passionate about owning his time, the importance of goofing off and staying optimistic about the development of technology. 🎥🍿 YOUTUBE : WATCH HERE Links: Kevin's website: kk.org Kevin's articles on Wired Excellent Advice on Living: Amazon ⌛TIMESTAMPS (01:01) - Taiwan and the import...

Apr 17, 2023•52 min•Ep. 142

#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

Billy used to be an avid skier, working odd jobs and traveling between the northern and southern hemispheres trying to catch the best skiing. In 2018 he e-mailed Ryan Holiday and pitched him on doing some work for him for free. In a couple of months, he was hired as Ryan's research assistant. Billy is one of the most curious people I know and we dive into his journey. 🎥🍿 YOUTUBE : WATCH HERE Links: Twitter: @bpoppenheimer Website: billyoppenheimer.com Billy's Newsletter ⌛TIMESTAMPS (00:56) - T...

Apr 10, 2023•1 hr 7 min•Ep. 141

#140 Tom Peters - Fired from McKinsey to Top Business Thought Leader

I'm sharing this conversation I had a couple of months ago with Tom Peters. Our convo got cut a bit short but it was a fun conversation reflecting on his trajectory, why he got kicked out of McKinsey To learn more about Tom: His Website 📘 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...

Apr 03, 2023•34 min•Ep. 140

#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

Trung is a writer at Workweek, cofounder of bearly.ai, and co-host of the Not Investment Advice podcast. He is passionate about playing the long game and unleashing the power of compounding. 🎥🍿 YOUTUBE : WATCH HERE Links: Twitter: @TrungTPhan Website: trungtphan.com Bearly.AI Podcast: Not Investment Advice Trung's writing at Bloomberg and Workweek Trung's Newsletter ⌛TIMESTAMPS (02:12) - College and getting up late (04:44) - Trung's great grandfather - Vietnamese hero (09:31) - Vietnam, import...

Mar 27, 2023•52 min•Ep. 139

#138 Money & The Creator Economy - Steph Smith on our lack of wisdom about money, reaching "ice cream freedom", The Hustle, balancing employment and side gigs, unconventional paths, opportunities in the creator economy and how not to get disappointed at your wedding

Steph Smith is the host of the a16z podcast and is an online creator, former consultant, former digital nomad and all-around badass. We talk about money, work, relationships, and weddings... 🎥🍿 YOUTUBE : WATCH HERE Links: Twitter: @stephsmithio Steph's book: doingcontentright.com a16z Podcast The Sh*t You Don't Learn in School Podcast Blog: stephsmith.io ⌛TIMESTAMPS (01:19) - The scripts that Steph grew up with (03:47) - Perceptions of money over time (29:15) - Working at The Hustle (33:57) - ...

Mar 20, 2023•1 hr 12 min•Ep. 138

#137 Life as Conversation - Russ Roberts on his relationship with his father, starting the EconTalk podcast in 2006, Adam Smith, why people want to be "lovely", aiming high, why it's hard to have fun, misunderstandings of the academic world, and moving to Israel in his 60's

Russ is an economist, a research fellow at Stanford University's Hoover Institution and president of Shalem College in Jerusalem. One of pioneers of podcasting, he's been hosting EconTalk since 2006. 🎥🍿 YOUTUBE : WATCH HERE Links: Twitter: @EconTalker EconTalk Website: www.econtalk.org EconTalk YouTube Channel ⌛TIMESTAMPS (03:25) - The influence of Russ' father (11:13) - What modern economics often fails to observe (16:15) - Adam Smith and human nature (27:05) - Starting EconTalk in 2006 (40:4...

Mar 13, 2023•1 hr 10 min•Ep. 137

#136 Complexity & Complicatedness - Sam Spurlin on playing hockey, why he quit teaching, studying at Claremont, leaving a PhD program, working pro bono too start his career, complicated vs complex systems, how to deal with ego in organizations, remote work failures, podcasting with his brother, and the importance of a retrospective meeting

Sam is a partner at The Ready - an organizational design consultancy operating fully remotely. He is also a prolific writer, passionate about personal development, self-managing organizations and adopting a more human, adaptive, and meaningful way of working. 🎥🍿 YOUTUBE : WATCH HERE Links: Twitter: @samspurlin Instagram: samspurlin LinkedIn: linkedin.com/in/samspurlin Sam's writing: samspurlin.com/writing Sam's writing on Medium: samspurlin.medium.com Newsletter: thedeliberate.substack.com/p/l...

Mar 06, 2023•1 hr 11 min•Ep. 136

#135 Beyond Comfort - Derek Sivers on why great musicians shake things up, ambition, and moving to a new country as a superpower, lessons from Singapore, and the scripts around having children

Derek Sivers has been a musician, producer, circus performer, successful entrepreneur, TED speaker, and book publisher. He has lived all around the world and has never let himself be too comfortable - constantly changing and following his inner ambition. 🎥🍿 YOUTUBE : WATCH HERE Links: Twitter: @sivers Website: sive.rs My Favorite Derek Book: Anything You Want ⌛TIMESTAMPS (00:54) - The scripts that Derek grew up with (05:45) - Comfort as a plateau that needs to be shattered (11:46) - Travel as ...

Feb 27, 2023•1 hr 9 min•Ep. 135

#134 The Office-Based Reality is Over - Dror Poleg on entrepreneurship in Israel, studying in Australia, working in China, Future of Remote Work and The Real Estate Business, How To Write A Top 5 Book in Almost Any Category, The Disappearance of The Middle-Skilled Job, Inequality and The End of The Offices

Dror worked as a real estate private equity exec, startup founder, front-end developer, parliamentary advisor, and soldier. Having lived all around the world he is now based in NYC, writing as an “Economic Historian”. Having predicted that remote work is going to become the new norm back in 2015, he has just published a survival guide titled "After Office". 🎥🍿 YOUTUBE : WATCH HERE Links: Twitter: @drorpoleg Website: drorpoleg.com After Office ⌛TIMESTAMPS (13:30) - Living in Australia and China...

Feb 20, 2023•1 hr 27 min•Ep. 134

#133 Creation Without The Ego - Isabel Unraveled on writing, "the chronic state of performing", detaching your sense of self from the work, finding the inner child, paying attention to your emotions, trusting your intuition and why people should stop pretending

Isabel is a writer who is very passionate about the creative process. She has some powerful original ideas about the relationship between the artist and their creation, trusting one's intuition, and why people should stop pretending. 🎥🍿 YOUTUBE : WATCH HERE Links: Twitter: @isabelunraveled Isabel's Writing: https://mindmine.substack.com ⌛TIMESTAMPS (0:11) Introduction (5:41) "The chronic state of performing" (12:00) Missing and rediscovering her passion for writing (34:38) Detaching your sense...

Feb 13, 2023•1 hr 8 min•Ep. 133

#132 Making Money Simple & Smart - Nick Maggiulli on blogging into a new career, writing for smart people, building relationships in the finance world, the lifestyle creep myth, dying with too much money, and money emotions

Nick Maggiulli is a finance data analyst and writer. He is the author of "Just Keep Buying" and has a blog titled "Of Dollars and Data". 🎥🍿 YOUTUBE : WATCH HERE Links: Twitter: @dollarsanddata Blog: Of Dollars and Data Nick's Book: Just Keep Buying ⌛TIMESTAMPS (0:47) The scripts nick grew up with (5:35) Writing books and blogging (32:44) Building relationships in the NYC finance scene (36:07) Why the writers shouldn't dumb down their books (37:33) Perceptions of money (1:07:26) Closing thought...

Feb 06, 2023•1 hr 11 min•Ep. 132

#131 The Art of Sabbaticals - Cécile and Michelle on finding "forgotten hobbies", writing online, improving their relationship with money, abundance mindset and rediscovering joy

Cécile has had a successful career in consulting, acquiring a senior position in a big company that has taken a leadership role in the energy transition in the UK. Although she was passionate about her job she decided to go on a yearlong sabbatical from work, traveling around the world and writing - creating space for her curiosity & creativity. Michelle has a background in sales but after a couple of years in the business she decided to go on a sabbatical that doesn't seem to have an end. W...

Jan 30, 2023•1 hr 29 min•Ep. 131

#130 You Have One Life - David Senra on finding his life's work, trial & error, the necessity of talking risks, mortality, balancing his entrepreneurial endeavours and family life and what can be learned from reading hundreds of biographies.

David Senra is the creator of Founders Podcast and is obsessed with bringing alive the knowledge of the most driven, curious, courageous, and interesting founders throughout history. He has spent almost all his time reading, re-reading, and recording one of the best podcasts on the planet right now. Links: Follow his podcast: @FoundersPodcast Listen: Founders Podcast or Itunes ⏳TIMESTAMPS 2:58 The scripts David grew up with 8:09 Working full time while in high school and during college 20:47 Tri...

Jan 23, 2023•2 hr 35 min•Ep. 130

#129 Friendly Ambitious Nerd World-Building - Visakan Veerasamy on Long-Orbit Friendships, Preemptive Defensiveness, "Hot Streaks," Writing A Book, Making $1000 for one copy & Negative Comments

Visakan Veerasamy is an internet creator and writer, he is passionate about the future of the internet, ideas, and how people can be bolder on their creative journeys. His mission is to build the greatest social graph of friendly, ambitious nerds that the world has ever seen. This is our second conversation and dives much more into his current work and how he thinks about the internet. 🎥🍿 YOUTUBE : WATCH HERE Links: Twitter: @visakanv Website: visakanv.com Buy Introspect: On Gumroad ⌛TIMESTAMP...

Jan 17, 2023•2 hr 38 min•Ep. 129

#128 Crafting A Life You Love - Amy Tangerine on working in fashion, carving her own path, starting a business, a third-life crisis, scrapbooking as contemplation and learning from and inspiring her children

Amy Tangerine is a long-time creator, entrepreneur, and mother. We talk about her path, starting a business that took off, her "third-life" crisis, learning to inject rest into her path, her relationship with her mother, having children, scrapbooking and building a business around work she loves. WATCH On YouTube FOLLOW AMY Her Website: amytangerine.com Twitter: @amytangerine Instagram: @amytangerine Facebook: @amytangerine TIMESTAMPS 0:00 Audio intro 0:12 Introduction 1:10 The scripts Amy grew ...

Jan 11, 2023•54 min•Ep. 128

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