

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

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.
📘 My 2nd Book Good Work: LIVE! => 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 (25k+ 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

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.
📘 My 2nd Book Good Work: LIVE! => 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 (25k+ 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

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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📘 My 2nd Book Good Work: LIVE! => 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 (25k+ 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

May 1, 2019 • 1h 7min
Building A Company And Life Filled With Joy (Rich Sheridan, CEO)
Rich fell in love with coding as a child but lost that passion when coding just turned into a job in the late 1990s. As he looked around and saw everyone overwhelmed in his industry, he decided to take a different path. He co-founded of Menlo Innovations in 2001 with a personal mission to end human suffering in the workplace. He is also the author of two books Joy, Inc. and Chief Joy Officer.
Hear about his company has achieved gender diversity in the workforce, introduced pay transparency, embraces pair-working methods across all functions and other transformative principles.
Links/Books Mentioned
Menlo Innovations
Extreme Programming, Beck
The Fifth Discipline, Senge
Chief Joy Officer, Sheridan
Joy, Inc. Sheridan
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Support
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📘 My 2nd Book Good Work: LIVE! => 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 (25k+ 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 24, 2019 • 47min
A Mission-Driven Life & Career (Jerel Bonner)
Jerel calls himself one of the original "job-hoppers." While he never found a great fit in the corporate world, in the 1980s, he was inspired by Steven Covey to develop a "personal mission statement." He used this to shape his decisions in life.
In the early 2000's he decided to shake it up and headed to China for what turned into a 14 year journey of learning and adventure.
To learn more about Jerel click here.
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Boundless => Reimagine Work
📘 My 2nd Book Good Work: LIVE! => 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 (25k+ 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 17, 2019 • 55min
How To Fill Your Morning With Purpose & Joy (Craig Kulyk)
I met Craig at a conference called The World Domination Summit and when he introduced himself he gave me a pack of tea with his business card on it. Everything he does is like this - packed with thoughtfulness and humor.
Craig is also the creator of the Morning effect, something he ended up being passionate about after going from someone that hated mornings to a morning advocate over the past 7 years. He defines the morning effect as:
"the principle that what you choose to do in the morning can have an amazing impact on other parts of your life. It leads you to get up and be productive, do more of the things you wish you were doing, and embark on your days already feeling accomplished. All of that is a HUGE win, but honestly, it’s just the tip of the iceberg…"
He’s experimented with 100 morning rituals over that time and now works with people to help them take back their mornings and find “another 20 hours” a week as he did.
His story is more than another “hustle” hack - its grounded on bringing more presence, joy and creativity to ones life and is why I hope you check out the podcast this week!
For More => The Morning Effect Boundless Page
Books/Articles Mentioned:
When by Daniel Pink
The Power of Habit by Charles Duhigg
127 Morning Rituals
How to Schedule Your Workday
9 Lessons from a 9 Day Silent Meditation Retreat
Boundless / Reimagine Work:
Support the podcast on Patreon
Subscribe to the free weekly newsletter on our modern conception of work
📘 My 2nd Book Good Work: LIVE! => 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 (25k+ 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 10, 2019 • 55min
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
📘 My 2nd Book Good Work: LIVE! => 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 (25k+ 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 • 52min
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
📘 My 2nd Book Good Work: LIVE! => 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 (25k+ 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
📘 My 2nd Book Good Work: LIVE! => 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 (25k+ 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.
📘 My 2nd Book Good Work: LIVE! => 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 (25k+ 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