
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.
Latest episodes

Jan 2, 2020 • 31min
Longform Thoughts: Why Organizations Undermine Creativity & Potential
For the re-launch of the Boundless podcast, I'm releasing a previously Patreon-only audio discussion of a piece I wrote - Crisis at Work - which was published in the fall of 2017. *You can read the piece here*: Crisis At WorkI talk through six key reasons why organizational fail to unlock human potential:We're defaulting to the wrong goals (shareholder value)We're mistaking authority for performance (the Tom Brady principle)We aren't providing a connection to purposeWe don't understand how organizations operate (Chaos theory)We aren't giving people autonomyWe're choosing comfort over growthBoundless Links:Subscribe to the newsletterSupport On PatreonJoin The VIP Facebook Group (upcoming book club on Bullshit Jobs in September 2018)
📘 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

Dec 10, 2019 • 47min
A Remote Company With 40 Vacation Days?! (Amir Salihefendić, CEO Doist)
Amir Salihefendić is the Founder and CEO of Doist, a fully distributed, remote company that creates productivity tools (Todoist & Twist). We dive into his story of moving from Bosnia to Denmark as a child and how he started Doist while in college. He’s built a growing technology company in a fully remote setting, often experimenting with different ways of working and sharing the thinking behind the decisions as he goes on the doist blog as a major supporter of the remote work movement.
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Like the podcast? Show some love on twitter or become a patron
📘 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

Dec 2, 2019 • 53min
The Lazy Person's Guide To Freedom, Generosity & Creative Work (Moataz Ahmed)
Moataz Ahmed otherwise known as “motizzy” is a graphic designer, consultant and hand lettering artist. He recently published Part 1 of his book titled, “Lazy Person’s Guide to Freedom” and we talked about his journey and book in this conversation.
We also talk about:
How we naturally started freelancing by helping people
His embrace of the “gift mindset”
How he improved his will-power and motivation
How he thinks about freedom and justice
How freedom should also be about speaking out for other people’s freedom
Learning new languages and the benefit of cross-cultural insight for design work
You can learn more:
Motizzy.com
Lazy Person’s Guide To Freedom ($0+ Gift Pricing)
His great design work on instagram
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=> Ways to support Reimagine Work
📘 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

Oct 30, 2019 • 1h 16min
Twitter Friends & Threads, Self-Employment & Curiosity (Visakan Veerasamy)
I connected with Visa on twitter, where he’s made many friends over the past several years. I wanted to interview Visa to talk about his leap to self-employment over the past couple of years, but we talked about so much more. We talk about:
What the word “nourish” means to him
His evolution on procrastination and getting started
How to find like-hearted humans on twitter
The “asshole problem”
The curious humans of twitter
How he creates his own work
See the episode notes here
Follow Visa on twitter
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If you want to support the podcast, take our courses or support Boundless, check the link 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

15 snips
Oct 22, 2019 • 1h 3min
Rest, Leisure, Working Less & The 4-Day Workweek (Alex Pang)
Alex Pang is the author of Rest about how you can do more while working less and is author of the forthcoming Shorter, which shares stories of companies that have shifted to a four day workweek.
Hear about Alex's own sabbatical, how he changed his relationship to rest and what he's learning now.
Read more about Alex and get a copy of his book here
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Want to support the Boundless Podcast? Join as a Patron 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

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