
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

5 snips
Mar 28, 2022 • 1h 8min
The Money Path or The Life Path? - Tim Malnick
Tim Malnick has always lived between the two worlds of business and creative/activist circles. In his twenties, he stumbled into a creative group of young people, of which “none of them following the obvious path.” This gave him a lot of confidence that different kinds of paths were possible and enabled him to offer a diversity of perspectives that he was able to bring to many different environments.
One of the things he spends a lot of time on now is helping people transcend their relationship with money. He runs The Money Workshop with people helping them explore the scripts people have with money and realized that people have one of two orientations towards the world:
#1 The Money Path: “One day when I sorted this out I’ll get to do what I want”
#2 The Life Path: “Do what you love and the more you follow it you will have your needs met with and without money”
Which one are you?
Learn More About Tim’s work here 👉 Different Space - Transformational learning & development by Tim Malnick
New to Reimagine Work? Learn more about Paul here
JUST LAUNCHED: 📕The Pathless Path
📘 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

Mar 21, 2022 • 59min
Music, Entrepreneurship & Embracing Non-Work - Paul Canetti
Paul Canetti is a professor at Columbia Business School and sits on the Strategic Advisory Board of Riverside Acceleration Capital. We explore his initial passion for music growing up, how he became an accidental founder, and how he's exploring his relationship with work after exiting his startup.
He was named one of Inc.'s “30 Under 30” and has founded multiple software businesses including MAZ and ClickEasy (originally Bounce House), both of which were acquired in 2021. He is an angel investor, startup advisor, and the author of an upcoming book about the business implications of augmented reality.
He also hosts Tech News for MBAs
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New to Reimagine Work? Learn more about Paul here
JUST LAUNCHED: 📕The Pathless Path
📘 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

29 snips
Feb 12, 2022 • 47min
The Magic of Writing with Sasha Chapin
I talked with writer and writing coach Sasha Chapin about the role of writing in our lives, how we think about writing, and how he specifically helped with my process in the book.
Check out Sasha here: Sasha Chapin (imsashachapin.com)
& Buy Paul's Book https://think-boundless.com/the-pathless-path/
📘 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

13 snips
Feb 9, 2022 • 1h 2min
Khe Hy - Tales From The Pathless Path
Join Khe's Supercharge Your Productivity course: https://10k.radreads.co/join-syp11/yzrsv (affiliate)Get access to Khe's $10k training which will help you wander towards the pathless path: https://radreads.co/millerdFrom a live event where Paul & Khe talk about their shared journeys of self-employment, creating online & more
📘 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

Jan 27, 2022 • 8min
The Pathless Path Launched! (reading of the introduction)
Just launched my book, The Pathless Path!
Purchase the book here.
This is the introduction of the book.
I'll be releasing some clips of me reading the book and will eventually publish an audio book.
📘 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

Nov 10, 2021 • 1h 51min
Valuing Options & Possibilities On The Solo Creator Path with Kris Abdelmessih
Kris Abdelmessih has one of the most unique perspectives on life and works I've stumbled across in the past few years. He uses his experience as a trader to look at decision-making and work investments through the lens of options, pricing, and other financial models. I enjoy his perspective because unlike other financial types, he seems to have a proper appreciation of non-work / non-productive time.We explore his recent break from trading, his creative journey writing on the internet, and finding his people, and he challenges me to think differently about how I'm spending my time with my work.The conversation dramatically shifted how I'm thinking about the possibilities of my path. If you are on a self-employed path, this is a must-listen:For Kris' newsletter: Party at the Moontower - (moontowermeta.com)------------SUPPORT BOUNDLESSSubscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.🆕 I launched Freelance Consulting Skills Course. You can find out more and sign up here.If you'd like to support the podcast, consider using my affiliate linksPodia - 14-day free trialTeachable - 14-day free trialWealthfront - $5k managed for freeConvertKit - First 1k subscribers for freeCharles Schwaab No International ATM Fees
📘 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 27, 2021 • 1h 13min
The Formless Path - Money, Fatherhood & Creativity (Howard Gray)
Howard Gray is the founder of Wavetable, a studio that helps brands and companies come together to develop fan-based experiences to help teams teach and share ideas.
The two things that drive him are to "create space for people to do the work they want to do" and to help people "make sense of the world and overcome the tension of putting things out in the world"
We dive into his idea of the formless path, why the creator economy is in danger of being hijacked, how he sees himself as a guide rather than as a creator, and why fatherhood is helping him "sharpen" his focus.
Links Mentioned
Howard Homepage
Labels In, Labels Out
Jobs, Vocations, Careers
SUPPORT BOUNDLESS
Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.
🆕 I launched Freelance Consulting Skills Course. You can find out more and sign up here.
If you'd like to support the podcast, consider using my affiliate links
Podia - 14-day free trial
Teachable - 14-day free trial
Wealthfront - $5k managed for free
ConvertKit - First 1k subscribers for free
Charles Schwaab No International ATM Fees
📘 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 19, 2021 • 1h 4min
The Shadow Side of Solopreneurship - Darren Joe
“You can’t study or learn your way into a new identity” - I love this quote from Darren Joe. He’s been thinking about carving a different path from 2003 to 2004. He said that he was driven by a natural drive to be independent and do his own thing. I found this pretty impressive because in those years not many people were doing what he was doing.
He recently published a book titled The Fail-Safe Entrepreneur. In it he argues that almost all solopreneurs strive for three things: Freedom, Adventure, Meaning. I definitely agree. However, he says many fail to reach these aims because they ignore the shadow side of this path. He details four things - FAIL: Failure, anxiety, instability, loneliness.
We explore many things in this conversation including:
Grappling with the achiever identity
Longing for independence and freedom
Parental approval
Building Community
Experiments
Defining success
You can buy his book the Fail Safe Solopreneur on Amazon
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SUPPORT BOUNDLESS
Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.
🆕 I launched Freelance Consulting Skills Course. You can find out more and sign up here.
If you'd like to support the podcast, consider using my affiliate links
Podia - 14-day free trial
Teachable - 14-day free trial
Wealthfront - $5k managed for free
ConvertKit - First 1k subscribers for free
Charles Schwaab No International ATM Fees
📘 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 19, 2021 • 24min
Six Months In The Creator Economy - Michael Ashcroft (Part 3)
In parts 1 and 2, I interviewed Michael about his plan to quit his comfortable consulting job and start a new path creating and selling courses online.
Let's see how he reacts to his own quotes from a year earlier!
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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

Aug 4, 2021 • 58min
Accidental Freelancer To Brand Consultant, Founder & Freelance Coach (Austin Church)
Austin Church thought he was going to be a poet. When that didn't go as planned, he joined the business world. Six months later he was laid off in the 2008 recession. Luckily, his firm hired him back as a freelancer and that completely changed his perspective on work. Ever since he's been hacking a living, shifting roles as a freelancer, founder, entrepreneur, and coach. We chat about his journey and more.
Learn more about Austin and his great writing on freelancing here.
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SUPPORT BOUNDLESS
Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.
🆕 I launched Freelance Consulting Skills Course. You can find out more and sign up here.
If you'd like to support the podcast, consider using my affiliate links
Podia - 14-day free trial
Teachable - 14-day free trial
Wealthfront - $5k managed for free
ConvertKit - First 1k subscribers for free
Charles Schwaab No International ATM Fees
📘 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