

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

Jun 24, 2021 • 1h 4min
Money Fears, Self-Employment & Living Abroad With Kids - Jenni & Lisa Dazols
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 the way.
They run a business called Modern Family Finance and help people think about finances in a way that lets them live the life they want to live. They also run a charity bike ride in Taiwan supporting LGBTQ rights called Rainbow Ride.
Links:
Rushed and Tired (Portrait of a Modern Family)
Money Script Quiz
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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

13 snips
Jun 17, 2021 • 46min
A Sabbatical Every Seven Weeks - Sean McCabe
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 better but his business has continued to grow and they have figured out how to build mandatory (not like "unlimited vacation...) sabbaticals into the operating rhythm of the company. His mission is to help every company globally (yes, really) embrace this model by 2047. I'm on board.
Learn more about Sean
Sean's Sabbatical Blog
My Essay On Sabbaticals
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Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.
I'm launching a Freelance Consulting Skills Course that launches July 1. You can sign up here.
Podia - 14-day free trial
Teachable - 14-day free trial
Wealthfront - $5k managed for free
ConvertKit - First 1k subscribers for free
📘 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

29 snips
May 3, 2021 • 1h 2min
Ali Abdaal on Identity, Prestige, Creativity & Meaning and Deciding To Leave Medicine
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
📘 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

9 snips
Apr 13, 2021 • 53min
What happens six months (and three months) before you quit? - Michael Ashcroft
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
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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

Jan 26, 2021 • 59min
The Self-Employment Meta-Game (Dan Vassallo)
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-employed.
You can learn more about Dan at his site => Dan Vassallo
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To follow along with Paul subscribe to his newsletter => Boundless
Paul is also working on a book to launch later this year titled The Pathless Path
📘 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

Jan 19, 2021 • 1h 4min
Who are digital nomads? (Professors Rob Litchfield & Rachael Woldoff)
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 both moved to Bali for three months with their kids and immersed themselves in this world. I share some of my perspectives and they share what they learned, how it impacted how they lived their life and how they see these trends impacting modern work and institutions.
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If you want to support the podcast you can do so by using my affiliate link for one of the products I use and endorse.
📘 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

Jan 11, 2021 • 58min
Quitting To Teach History to 500k+ on TikTok (Michael McBride, Creator of Idea Soup)
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 from things like TikTok and other online platforms.
On his foundational belief: “If I had a thesis it's that education really does work and education really does matter”
His motivation and secret to his success: He said, “I find history so crazy and weird and fascinating that I think that;s contagious. If I had a mission it’s not to make them more educated, it’s to make them go. “How did roman's wipe their ass, that’s crazy,”
Listen to the episode to find the answer to this!
📘 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

Dec 24, 2020 • 42min
Curating Goodreads Remotely (Uri Bram, CEO of The Browser)
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, how he thinks about running a remote company and some of his favorite reads worth checking out.
Articles/Books mentioned
In Praise of Idleness and Other Essays, Bertrand Russell
Derek Parfit, Reasons and Persons
Leadership & Solitude, William Deresiewicz
Disadvantages of an Elite Education, William Deresiewicz
Seeing Like a State, James Scott
How Ghost Is Structured for the Long-Term
The Great Works of Your Life, Cope
Ada Palmer, Ex Urbe
Susan Bryson, Aftermath
Salary Negotiation: Make More Money, Be More Valued, Patrick McKenzie
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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

Dec 4, 2020 • 44min
Packy McCormick - Bringing Fun To Newsletters Since 2019
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 about his solopreneur journey,
The reason I asked him on the podcast is to talk about his recent newsletter on the future of work. He argues that “Employees will ultimately make the decision” about what work looks like post-pandemic. I think he is mostly right and we talk about what that might mean for people's lives.
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You can find ways to support Paul through affiliate links, newsletter sponsorship or direct gifts here
If you want to subscribe to Paul's weekly newsletter on the modern state of work, the solopreneur journey and creating online, you can subscribe here.
📘 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

Nov 3, 2020 • 23min
Podcast Update Nov 2020 - The Pathless Path
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
📘 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