

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

Apr 10, 2019 • 56min
Beyond Average: Co-Creating A Life & Company (Tanya Zhang & Wesley Kang, NimbleMade.com)
Wesley Kang and Tanya Zhang are the co-founders of Nimble Made, an e-commerce clothing brand that makes “actually slim” dress shirts.
Before taking the leap to work full-time on their business, they worked in the corporate world in New York City. As first generation Asian-Americans, they had achieved “success” - good jobs, good salary. They were on their way. However, deep down both wanted something a little more. Some of Tanya’s challenges working as a freelance graphic designer on the side convinced them they should try to think a little deeper about building a brand and a business, instead of just helping other people.
As they found themselves thinking about the business all day at their full-time jobs and coming home ready to work on it, they realized they finally had to go all-in. Over the past year they have worked on the business and are starting to find some traction. As they’ve dealt with the challenges of running a business, they have also had to constantly reflect on how to manage a relationship both as committed partners and co-founders.
Check Out Nimble Made (unsponsored):
Interested in their shirts? Check out more at Nimble Made.
For their past reflections check out Wesley's guest post on entrepreneurship and Tanya's post on how her father inspired her to start the company.
Boundless / Reimagine Work:
Support the podcast on Patreon
Subscribe to the free weekly newsletter on our modern conception of work
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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (26k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Apr 3, 2019 • 53min
Lessons from 13 years of entrepreneurship & living nomadically (Chris Kirkland)
Chris Kirkland is a bootstrapped entrepreneur who has been living nomadically since 2006 and is the founder of several web businesses including artweb.com and tokyocheapo.com.
We talk about how he has experimented with money, creativity, health and his lifestyle over the past 13 years. His nomadic journey started when he took a trip to Japan and after two days decided "fuck it," I'm going to stay a bit longer.
We talk about his journey, entrepreneurship and his life experiments
Why entrepreneurs are really risk averse
His learnings from living nomadically and stoic exercises of living minimally
Prioritizing time over money as a bootstrapper
How running an online business was different in 2006 and why he "felt like he was cheating"
His experiments with becoming a "breatharian" and trying polyphasic sleep (do not try these at home)
How he thinks about running an online media business in 2019
His recommendations for cheap eats in Tokyo
More about Chris:
TokyoCheapo
Chris' Personal Site & Writings
Headstands Across The World
Boundless / Reimagine Work:
Support the podcast on Patreon
Subscribe to the free weekly newsletter on our modern conception of work
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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (26k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Mar 27, 2019 • 30min
Creating Art Filled With Magic (Martha Balaile)
Martha Balaile is a fantasy illustrator living in Cape Town, South Africa originally from Tanzania. Her mission is to figure out how magic, mythology and fantasy can have an impact on real life. She’s also the wonderful creator of the new cover art for this podcast.
Martha aspired to create “art that is filled with subtle lessons on living a magical and adventurous life.” Two of the lessons she has found:
Go with the flow
Be aware of fear
We explore these a bit and she shares some examples from fantasy that have inspired her. Check out the show!
We talk about:
What drove her to pursue an art career after growing up in Tanzania
What she wishes she learned in art school
What she looked from working with clients
How she switched from magic “standard” art to art she cared about
How she decided to take the leap to freelancing “early” in her career.
How she structures her day around her work
Her Top 3 Magic Podcasts:
Magic Lessons, Elizabeth Gilbert
Natalia Benson Podcast
Hippie Witch Magick For A new Age
Mythology Studios: Work With Martha
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Boundless / Reimagine Work:
Support the podcast on Patreon
Subscribe to the free weekly newsletter on our modern conception of work
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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (26k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Mar 20, 2019 • 21min
Reimagine Work & A Short Update From Paul
A quick little update from Taipei.
A couple links from the podcast:
Revisiting Keynes Prediction for a Post-Work 2030 in “Economic Possibilities for Our Grandchildren”
Luke Kanies Podcast Interview
Curiosity Conversation With Paul
Would love any feedback - e-mail Paul.
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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (26k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Mar 13, 2019 • 48min
From the basketball court to the yoga mat via the corporate world (Gabi Macra)
Gabi Macra was a top Canadian basketball player that never really thought about the "life after basketball" before dealing with a major injury towards the end of her college career.
Instead of following any sort of traditional path, she headed East to Japan where she came to teach English. She loved her experience there and now reflects on the immense value of learning how to teach and coach others helped her in the following years.
Instead of heading back to Canada, she headed to London where she had a successful career and journey as an actuary. She was a leader in her company but reached a point where she was dealing with health challenges and finding that her career was no longer giving her the fulfillment that it once was.
She ended up deciding to take some time off and told her boss that she was leaving. However, she ended up staying another 18 months as she helped the team transition with some other internal changes. Just knowing she was leaving enabled her to approach everything completely different and think about how she could best serve her team while also taking care of her own health.
She finally took the leap in 2018 and after several months of sabbatical, including some time in Bali, she realized that becoming a Yoga Therapist was something she was ready to commit to over the next few years. While preparing for that program, she also created a learning internship for herself in London (stealing this from Lydia Lee's podcast episode!) by taking 8 people interested in Yoga and creating a customized program for them. Her only goals: to learn a ton about how she can serve people and learn what to do next.
What we covered:
Her drive and motivation as a basketball player
Her experience living and working in Japan after university
Starting her actuarial career and what she enjoyed about work
Becoming successful but questioning her role as a successful worker as the center of her life
Her decision to take a sabbatical and leave the company (and how she ended up staying for 18 months but doing so with a completely different mindset)
Her recent creative projects, "learning experiments" and decision to start a long-term Yoga therapist training program
Links
Instagram: Gabi Macra and Real People Do Yoga
Website: Real People Do Yoga
For More Boundless:
Consider supporting the podcast on Patreon
Join The Reimagine Work Course Starting March 24th
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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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (26k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Mar 6, 2019 • 46min
Learning To Quit & Life Reinvention (Christine Bader)
Christine Bader is currently living in Bali, Indonesia, where she is spending time focused on her family and self. She is the author of The Evolution of a Corporate Idealist: When Girl Meets Oil and the former head of CSR for Amazon before leaving in 2017, a journey she details in an amazing essay titled “The year I learned to quit.”
She talks about leaving the corporate world and shifting her focus from building a career to building a life.
Topics Discussed:
Corporate social responsibility
Taking a sabbatical in Bali
Building a life
The greek concept of Kairos
Working in Asia
Working at Amazon
Recommended Reading
Can a business of any size be good?
The Year I Learned To Quit (New York Times)
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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (26k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Feb 13, 2019 • 1h 1min
Building & Investing In Calm Companies (Tyler Tringas)
Tyler Tringas is an entrepreneur and traveler. He's started two companies (one worked!) and now is founding Earnest Capital where he wants to help companies avoid going into $50,000 of credit card debt (like he did) to start technology companies. We talk about how this type of investing vehicle can help transcend some of the pressures to "scale at all costs" in ways that may not be suitable for most companies.
Topics
Digital nomads
Starting a company
Bootstrapping
How to sell a company
The four-hour workweek
Calm companies
Flaws with the VC model
Taking leaps
Transitions
Meaningful work while traveling
Related Links:
Earnest Capital
Tyler Tringas
His Journey Selling StoreMapper
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For More With Boundless:
Consider supporting the podcast on Patreon
Join 125+ People Carving Their Own Paths In The Slack Community
Set Up A Curiosity Conversation With Paul
Join The Free 3-Week Self-Employment Challenge
Sign up For The Strategy Toolkit - Learn The Secrets Of Strategy Consulting
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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (26k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Feb 8, 2019 • 46min
Paul on success, storytelling, learning & experiments (UX Gorilla Interview)
I joined the amazing Jagriti Pande for a fun conversation around a number of different topics. You can subscribe to her master series on UX designers and other creatives here.
Her amazing editing, way-too-kind-intro and fun clip at the beginning were such an amazing gift.
Let me know what you think!
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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (26k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Jan 30, 2019 • 33min
Launching Uncommonly: One Year Later (Chris Donohoe)
"I didn't think I'd be turning down work and choosing not to grow"I spoke with Chris Donohoe one year ago about his just-announced launch of his consulting firm, Uncommonly. He's more committed to carving his own path than ever and we walk through some of the lessons learned, pivots and his long-term strategy. Chris breaks down what he's learned over the past year, how he has started coaching people one-on-one and how he is thinking about structuring his time and day.Topics Discussed:Selling time versus projectsWorking a max 40-hour workweekTaking a coaching programThings he didn't expect 1 year into building his own firmWorking with an amazing co-founderHis reflections on leadership and his goalsUncommonly: Website-------For More With Boundless:Consider supporting the podcast on PatreonJoin 125+ People Carving Their Own Paths In The Slack CommunitySet Up A Curiosity Conversation With PaulJoin The Free 3-Week Self-Employment ChallengeSign up For The Strategy Toolkit - Learn The Secrets Of Strategy Consulting
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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (26k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Jan 23, 2019 • 1h 9min
Guest Episode: Joe Dumars x Adam Grant x Cody Royle
This episode is a special treat from friends of Boundless, Cody Royle, who came on the podcast last year to talk about what the business world can learn from sports.I wanted to share a special episode from his podcast that was just launched featuring the NBA great Joe Dumars and workforce research great Adam Grant. I thought the three of them had a special conversation. If you want to subscribe to Where Others Won't do so here:ItunesOvercastWebsite
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 PaulX: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (26k+ 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 HereI use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial


