

The Pathless Path with Paul Millerd
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.
Episodes
Mentioned books

Oct 17, 2019 • 23min
Geography & Culture Side Hustle Experiments w/ Rohith
I'm experimenting with some shorter episodes where I explore side hustles and creative experiments with people taking action on experiments they are excited about.
This one features Rohith Amruthur, creator of the Lost Geographer, which you can learn more about here. If you have any suggestions or want to come on the podcast, shoot me an e-mail.
If you'd like to support this podcast you can do so here.
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

9 snips
Sep 19, 2019 • 49min
The Phases & Emotional Journey Of Making A Work Shift (Stephen Warley)
I had a 2nd conversation with Stephen about the phases and emotional experiences of what a shift looks like. He's coached hundreds of people so has a good understanding of what people typically face.
I created this as part of my curious exploration of making sense of what it takes to reinvent in the modern world.
If you want to support the podcast, you can go here.
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Sep 4, 2019 • 1h 7min
Good Writing & Doing Work That Matters (Andy Sparks, CEO Holloway)
Andy Sparks founded a company called Holloway, which is trying to solve the problem of sharing knowledge online. He shared how his startup is trying to combine beauty, writing & deep knowledge to complex topics like Venture Capital and Hiring.
We talk about his journey, how he started writing, the professor that changed his life in college and how his father has influenced his approach to work & life. He also shares how he thinks about "a lake" as a metaphor for life and how he stays in touch with friends in a vulnerable way.
We talk about:
Andy's writing practice
Teaching & modern education system
A college professor that inspired him to think differently
Unlocking wisdom from books on the internet
Grappling with success & status in the modern world
How he stays in touch with the people that matter to hi
Learn more about Holloway here or subscribe to Good Work
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REINVENT: Learn more about the course here or lurk on my progress here
Patreon: Become a supporter here and get access to the curious rebel club for $1/month
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Aug 21, 2019 • 1h 4min
Coworking That Works & The 10k Independents Project - Alex Hillman, Indy Hall
" coworking at its best isn’t an occupancy based business at all. If the only time your members can get value from their membership is when they’re in the room, you’re limiting the potential of your community "
Alex Hillman runs one of the longest running co-working spaces in the world - Indy Hall - in Philadelphia. He thinks the word "coworking" has lost some of its meaning and that many companies are running "spreadsheet businesses" rather than cultivating community.
"That level of dependence on a single employer is brittle at best and dangerous at worst. And that single source of 50,000 jobs being Amazon, who is notoriously one of the most ruthless businesses in the world, is the WORST worst way to generate those jobs. "
We also dive into Alex's working model of a new project, the 10k independents project. Hear about why he thinks self-sufficient independents are better than Amazon (I tend to agree)
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Subscribe to the weekly Boundless newsletter - much more than a link drop - a deep dive into our modern relationship with work.
I'm launching Reinvent on October 1st and updating people on my content creation process here or purchase now for early bird access.
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Jun 19, 2019 • 1h 5min
Should Everyone Have A Coach? (Ben Brooks, Founder of Pilot)
Years ago, Ben wrote that his personal mission statement was “to help people reach their full potential” and our conversation touches on this theme in many different ways. Ben is a former car rental pro turned consultant turned HR executive. His work in HR landed him on the cover of Human Resource Executive but instead of staying on the path to CEO he decided to carve his own path.
Our conversation touches on a number of issues including coaching, entrepreneurship, how his relationship with work has evolves, management versus leadership and what he wants written on his tombstone. Some other topics we touch on:
Ben’s motivation to work at Enterprise Rent-a-Car after college and what he learned
His early entrepreneurial “ventures” starting at 12 years old
How his mindset about work shifted as he became successful in the corporate world
His experience hiring working with an executive coach in his late 20s
His experience coaching and favorite exercises
Why companies are scared of trusting their people
Why being a manager is actually an incredible opportunity for people
The learning and ownership upside of carving your own path
The value of having advisors, friends of confidants to celebrate “wins”
Balancing life & work and his personal sustainability
Deciding to give himself a raise as an entrepreneur
Links Mentioned:
What coaches can do for you (HBR)
Pilot: Executive Coaching For Organizations
Ben Brooks Coaching
Connect with Ben: LinkedIn, Instagram & Twitter
Boundless:
Want to support the podcast? Offer a one-time or recurring donation on Boundless.
Check out Boundless - The Site For Creative & Curious Rebels
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Jun 12, 2019 • 1h 6min
What living on a boat for 18 months can teach you about work & life (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 up in a small lake community
His love of sailing growing up
Why him and his wife change their mind on taking the trip in 2015
Rethinking convenience and comfort
What comforts are worth paying for
Belonging and community
How his relationship with money has changed
How him and his wife are structuring their life to work how they want
The one change that helps people be less addicted to their phones
Links Mentioned:
Designing Your Life
Sprint: How To Solve Big Problems and Test New Ideas In Just Five Days
Make Time: How To Focus On What Matters Every Day
Twitter: @jazer
Want to support the podcast? Offer a one-time or recurring donation on Boundless.
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Jun 5, 2019 • 49min
Hannah Wei on her nomadic life, Muay Thai fights, Tinder experiments & community
Hannah Wei has been living as a digital nomad for the last four years traveling across the US, Canada and Southeast Asia. When she is not working as a product consultant, she trains in Muay Thai, photographs people, and collaborates on local initiatives.
In our conversation we touch on many things, including:
Her upbringing in China and move to the US
Her creative inspirations as a child and how that evolved as she got older
Her experiment to code a bot to swipe on Tinder and tell people’s stories
What she has learned from Muay Thai
Her decision to compete in a professional Muay Thai fight in Thailand
What Muay Thai that has taught her about burnout, performance and success
How she defines success as a nomad depending on the region she is in
Follow Hannah
Hannah’s Website
Hannah on Twitter: @herlifeinpixels
Her personal review Notion group
How to pack up your life in eight steps
Tinder Photography Bot Experiment
Want to support the podcast? Offer a one-time or recurring donation on Boundless.
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

May 22, 2019 • 42min
Microadventures, Long-term Travel & Busking Through Europe (Alastair Humphreys
I talked to Alastair Humphreys after he had returned the previous night from a micro-adventure. It wasn't a four year biking trip or a challenging long walk across the desert (he's done that though!), but instead a short overnight camping trip with himself to re-connect with nature and his adventurous spirit. He helps others think about how they can design similar micro-adventures to find joy in the "5 to 9" rather than doing everything in service of the 9 to 5.
Links Mentioned:
Alastair Humphries
Subscribe to his newsletter "living adventurously"
His new book: My Midsummer Morning: Rediscovering How to Live Adventurously Hardcover – May 30, 2019
Want to support the podcast? Offer a one-time or recurring donation on Boundless.
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

May 15, 2019 • 1h
Dreaming, starting a tribe & 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 "no code" tools to start things like Rebel Book Club
How to think about a career in today's world
How finding a friend is one of the most important things to head in a new direction
Links Mentioned:
Ben Keene's site
Rebel Book Club
Tribe Wanted Fiji
Right to Dream
Escape The City
Moving to Koh Lanta with three kids
His experience after the six-months in Thailand
The 100 year life (book)
Curiosity Conversations with Paul
Want to support the podcast? Offer a one-time or recurring donation on Boundless.
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

May 8, 2019 • 50min
Heather McGowan on learning, adapting & identity in the future of work
Heather McGowan is the most thoughtful writer and speaker I follow on the future of work. She is able to connect the dots between work, culture, society and identity in a way that has captured the attention of many individuals, companies and universities around the world.
Heather’s career is also a perfect example of the type of path and work that was not possible in the past. Reflecting on her path she admits “this field just sort of emerged.” As her career has shifted more towards speaking, she has been able to design her life around learning. Through her talks, she is able to get feedback and combined with her own curiosity, it helps her focus on what to learn next.
In the working world, she focuses on how we can think about learning and work in a more holistic way and traces many challenges back to education. She cites research from Gallup showing that: “while 74% of surveyed fifth-graders are engaged with school, just 32% of surveyed 11th-graders are engaged.” Perhaps some of that disengagement is because people aren’t too excited about their job prospects. She worries that organizations in the short-term are still too focused on productivity, which depersonalizes the experience of work. As work increasingly becomes specialized - she calls it “atomization” - she fears that we will increasingly only focused on “explicit knowledge” instead of the deeper tacit knowledge that makes us special.
Find out more about Heather's work here or follow her on Linkedin.
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📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’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): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here