Paul Millerd

The Pathless Path with Paul Millerd

Business EN ↓ 202 episodes

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,...

Author

Paul Millerd

Category

Business

Podcast website

pathlesspath.com

Latest episode

Feb 25, 2026

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Episodes

The Arc of The Practical Creator - Lawrence Yeo 07.06.2022

Being an undeclared major till his senior year of college, Lawrence didn’t really know what he wanted to do. After looking up which jobs make the most money, he decided to declare as an economics major, leading him to explore Investment Banking. While he didn’t end up working in investment banking, he was still pulled by the power of prestige, something he says “is a drug, and is most potent” when...

Podcast Update! Re-branded as The Pathless Path & LIVE Q&A From Youtube 01.06.2022

I offer a short little update on the next steps for the podcast and include a live Q&A I did on youtube last week. Video link: https://youtu.be/CGbw7Q8hoys 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 Community: Pathless Path Community 📲Connect + Follow Paul...

The Money Path or The Life Path? - Tim Malnick 28.03.2022

Tim Malnick has always lived between the two worlds of business and creative/activist circles.  In his twenties, he stumbled into a creative group of young people, of which “none of them following the obvious path.”  This gave him a lot of confidence that different kinds of paths were possible and enabled him to offer a diversity of perspectives that he was able to bring to many different environm...

Music, Entrepreneurship & Embracing Non-Work - Paul Canetti 21.03.2022

Paul Canetti is a professor at Columbia Business School and sits on the Strategic Advisory Board of Riverside Acceleration Capital. We explore his initial passion for music growing up, how he became an accidental founder, and how he's exploring his relationship with work after exiting his startup.   He was named one of Inc.'s “30 Under 30” and has founded multiple software businesses including MAZ...

The Magic of Writing with Sasha Chapin 12.02.2022

I talked with writer and writing coach Sasha Chapin about the role of writing in our lives, how we think about writing, and how he specifically helped with my process in the book. Check out Sasha here: Sasha Chapin (imsashachapin.com) & Buy Paul's Book https://think-boundless.com/the-pathless-path/ NEW: The Pathless Path Hardcover Premium Edition 📘 My 2nd Book Good Work: Learn More 📕 Buy My...

Khe Hy - Tales From The Pathless Path 09.02.2022

Join Khe's Supercharge Your Productivity course: https://10k.radreads.co/join-syp11/yzrsv (affiliate) Get access to Khe's $10k training which will help you wander towards the pathless path: https://radreads.co/millerd From a live event where Paul & Khe talk about their shared journeys of self-employment, creating online & more NEW: The Pathless Path Hardcover Premium Edition 📘 My 2nd Book...

The Pathless Path Launched! (reading of the introduction) 27.01.2022

Just launched my book, The Pathless Path!  Purchase the book here. This is the introduction of the book. I'll be releasing some clips of me reading the book and will eventually publish an audio book. 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 Community: Pathles...

Valuing Options & Possibilities On The Solo Creator Path with Kris Abdelmessih 10.11.2021

Kris Abdelmessih has one of the most unique perspectives on life and works I've stumbled across in the past few years.  He uses his experience as a trader to look at decision-making and work investments through the lens of options, pricing, and other financial models.  I enjoy his perspective because unlike other financial types, he seems to have a proper appreciation of non-work / non-productive...

The Formless Path - Money, Fatherhood & Creativity (Howard Gray) 27.09.2021

Howard Gray is the founder of Wavetable, a studio that helps brands and companies come together to develop fan-based experiences to help teams teach and share ideas. The two things that drive him are to "create space for people to do the work they want to do" and to help people "make sense of the world and overcome the tension of putting things out in the world" We dive into his idea of the formle...

The Shadow Side of Solopreneurship - Darren Joe 19.09.2021

“You can’t study or learn your way into a new identity” - I love this quote from Darren Joe.  He’s been thinking about carving a different path from 2003 to 2004.  He said that he was driven by a natural drive to be independent and do his own thing.  I found this pretty impressive because in those years not many people were doing what he was doing. He recently published a book titled The Fail-Safe...

Six Months In The Creator Economy - Michael Ashcroft (Part 3) 19.08.2021

In parts 1 and 2, I interviewed Michael about his plan to quit his comfortable consulting job and start a new path creating and selling courses online. Let's see how he reacts to his own quotes from a year earlier! ------------------------ The best way you can support me is to join in the conversation. Share thoughts on Twitter, send me an e-mail, and tell me what resonated or what you’d add or re...

Accidental Freelancer To Brand Consultant, Founder & Freelance Coach (Austin Church) 04.08.2021

Austin Church thought he was going to be a poet.  When that didn't go as planned, he joined the business world.  Six months later he was laid off in the 2008 recession.  Luckily, his firm hired him back as a freelancer and that completely changed his perspective on work.  Ever since he's been hacking a living, shifting roles as a freelancer, founder, entrepreneur, and coach.  We chat about his jou...

Burnout & "Living At Work" In 2020 - Natalie Rachel 22.07.2021

Natalie Rachel went through her own experience with burnout before turning to help others.  She found that "with burnout, rest doesn't touch it," you need a deeper strategy.  We compare notes on our own journeys where we were surprised by burnout.  We thought it was something that resulted from working long hours.  Natalie says a better way to think about it is as "self-neglect of reflection." Res...

Narratives, Work & What Matters - Ben Hunt 06.07.2021

Ben Hunt is a father, husband, former academic, author turned blogger, former hedge fund analyst, investment advisor, and farmer. And he’s also my podcast guest in this episode. His writing has been an inspiration to me as I try to carve my own path after leaving what he calls “Team Elite.” His philosophy of make, protect, teach focuses on local and bottom-up change in the world.  In addition, we...

Money Fears, Self-Employment & Living Abroad With Kids - Jenni & Lisa Dazols 24.06.2021

Jenni and Lisa Dazols read an essay six years ago which made them question their frantic & busy lifestyle.  They could barely take care of their dog.  They decided to take a break from a work.  We dove into their story of deciding to move abroad, taking a sabbatical, having kids, moving to Taiwan, launching a passion project, coaching people on their money fears, and what they've learned along...

A Sabbatical Every Seven Weeks - Sean McCabe 17.06.2021

Sean McCabe runs seanwes and in 2014 he was working seven days per week.   Yup, no breaks.  He knew he needed to make a chance but the problem? All of his friends and even his wife worked at the company.  He decided he would take every seven weeks off.  He quickly realized it was a bit unfair to his team and extended it to everyone in the company.   He's found that not only has his life gotten bet...

Ali Abdaal on Identity, Prestige, Creativity & Meaning and Deciding To Leave Medicine 03.05.2021

I had a conversation with Ali Abdaal about his year away from medicine, how he grapples with his identity, the challenges of veering off the course of traditional metrics of success, enjoying the journey, and the challenges he faces. More from Ali here: https://aliabdaal.com/ --------- Subscribe to Paul's Weekly Newsletter: http://boundless.substack.com NEW: The Pathless Path Hardcover Premium Edi...

What happens six months (and three months) before you quit? - Michael Ashcroft 13.04.2021

I talked with Michael Ashcroft six months before he was planning to quit his job.  We talked about his plan to quit his job, what was going through his mind, his fears and what he expected might happen. We then chatted again three months later after he submitted his notice and checked in on how he felt Fear Setting Exercise Michael's Website ---------- The best way you can support me is to join in...

The Self-Employment Meta-Game (Dan Vassallo) 26.01.2021

I had a delightful conversation with Daniel Vassallo a self-employed creator for the last three years who seems to have gone through many of the same "a-has" as I have.  He walked away from Amazon despite making an absurd salary of $500,000 a year.  We talk about why he made that leap, why he would never go back and some of the unexpected lessons and insights he's learned from becoming self-employ...

Who are digital nomads? (Professors Rob Litchfield & Rachael Woldoff) 19.01.2021

Robert Litchfield & Rachael Woldoff have recently written a book titled "Digital Nomads: In search of Freedom, Community, and Meaningful Work in the new economy" A married couple and both professors, they bring an interesting combination of perspectives.  Rachel is a sociologist specializing in urban communities and Rob is a management professor specializing in creativity and motivation. They...

Quitting To Teach History to 500k+ on TikTok (Michael McBride, Creator of Idea Soup) 11.01.2021

Michael Mcbride left his job almost a year ago to work on building out Idea Soup, an instagram and TikTok channel focused on helping re-inspire people’s passion for history and knowledge. We talk about his creations over the years, how he has felt since leaving his job over the last year, what he’s learned from engaging with young people on TikTok and how he sees the future of education emerging f...

Curating Goodreads Remotely (Uri Bram, CEO of The Browser) 24.12.2020

Uri Bram is the CEO of The Browser which runs regular newsletters to help people find good articles, podcasts, and videos to read.  He has been living as a digital nomad for over seven years and also runs The Browser as a remote company. We chat about Uri’s own journey, what it's like working with Robert Cottrell (who reads 10-12 hours a day), his early experiences becoming a kindle best-selling,...

Packy McCormick - Bringing Fun To Newsletters Since 2019 04.12.2020

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 a...

Podcast Update Nov 2020 - The Pathless Path 03.11.2020

I decided to record a short little update with my friend Travis.  What have I been up to, where have I been living throughout the pandemic and what is in store next for Reimagine Work. If you'd like to watch on YouTube, you can do that here: https://www.youtube.com/watch?v=7Xlqe6D-HfM NEW: The Pathless Path Hardcover Premium Edition 📘 My 2nd Book Good Work: Learn More 📕 Buy My First Book, The Pa...

Angie Wang - My Partner On This Crazy Journey 19.10.2020

I interviewed my wife, Angie, who has gone through a major career change and has launched a number of creative experiments and projects over the past couple of years.  She reflected on what its been like going along this journey alongside me and grappling with success, identity, being a woman in Taiwan and creating in public. Video Version Of The Interview: Watch The Interview on Youtube If you li...

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