
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

Aug 24, 2022 • 1h 14min
#110 The Very Online Quasi-Wandering Monk - Tasshin Fogleman on Metta, Monasteries, Leisure, Work, Twitter and Finding Work That Matters
I spoke with Tasshin Fogelman about his life's work to bring more love into the world, how he navigates life as a modern online monk, what he learned from spending time at the monastic academy, and what he see's as work worth doing.You can learn more about his work here: https://tasshin.com/📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
📘 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

8 snips
Aug 2, 2022 • 1h 1min
#109 Autism at Work, Early Blogging & Unconventional Paths - Tara McMullin
Tara McMullin is a writer, host of the What Works Podcast, and also cofounder of a podcast production studio. She's been working with small business owners for more than 13 years and has a deep understanding of what makes them tick. She’s recently written about realizing she was autistic and how that has impacted her role in the workplace.🍿 Watch On Youtube🔗 Links:Tara's Site: Explore What WorksTwitter: @taragentileHow learning I’m autistic changed the way I work Finding A Way to Take Up Space A Conceptual Analysis of Autistic Masking: Understanding the Narrative of Stigma and the Illusion of Choice 📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessVideo Episodes & Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
📘 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

7 snips
Jul 27, 2022 • 1h 32min
The Nonlinear Life Path: College at 16, Med School in Cuba & Starting Over After Kids - Aida Alston
Aida Alston is no stranger to alternatives to the default path. From testing out of high school at 15, to finishing college with no debt, then going to medical school for free in Cuba, Aida has been walking her version of a pathless path for a long time. But she's at a transition point now. She decided not to pursue clinical practice as a physician—again turning away from the default path right in front of her. She's been a full-time stay-at-home mother since then to her two children, raising them bilingually after becoming bilingual in Spanish herself during her time in Cuba. She's a self-described early AND late bloomer, having sped through milestones early on but now slowly figuring out what's next for her work and family. She understands many of the challenges of going off the default path—like the paradox of choice—and how decision-making and prototyping are skills to be learned and practiced while building a pathless path.She is from San Francisco originally but now lives in New York with her husband and kids.👉 Follow Aida on Twitter and Read Her Writing Links Mentioned:Life Is in The TransitionsLate BloomersLost ConnectionsThe Hilarious World of Depression📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
📘 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

Jul 19, 2022 • 52min
Fixing The Healthcare System For Indies x Web3 - John Paller
John Paller is a Denver-based entrepreneur and the Founder of Opolis, a Digital Employment Cooperative for independent workers. He is also the founder of ETH Denver, the world’s largest Web3 and Ethereum festival. Prior to discovering Ethereum in 2015, John spent more than 15 years in talent acquisition, HR Technology, and employment systems, building multiple successful enterprises. John brings a breadth of experience in fundraising, investor relations, community outreach and crypto economies, guiding his vision of democratizing employment and growing decentralized communities. In 2014, John was awarded “40 Under 40” by the Denver Business Journal for his contribution to shaping the future of business. CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Become a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
📘 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

10 snips
Jul 12, 2022 • 1h 38min
How To Set Goals & Do Things That Matter - Malcolm Ocean
Malcolm ocean is a fellow wanderer of the pathless path and as is such - is hard to describe. He runs a software company, Complice which helps people turn big goals into day-to-day actions. More broadly from my vantage point, Malcolm appears to be one of the most deeply curious humans alive about how we make things happen at the individual and group levels.Follow Malcolm:WebsiteTwitter @Malcolm_OceanSign Up For Complice and get one bonus weekCrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Become a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
📘 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

17 snips
Jun 28, 2022 • 1h 20min
Lessons From Homeschooling, Skipping College & Carving Her Own Path - Hannah Frankman
Hannah is awesome and you should listen to this podcast. She grew up homeschooled, is an endlessly curious person, has a deep sense of agency, and is a pro at carving her own path. She's done a ton of things including writing, coaching, and working at startups and has created jobs for herself, negotiated working remotely (before it was cool), and has done a ton of other things. She recently founded Rebel Educator which is a media brand that aims to share more about homeschooling and alternative education with a broader audience online.Follow Hannah:@HannahFrankman / Twitter@rebelEducator / TwitterLinks Mentioned:3 Reasons Homeschoolers Often Become Entrepreneurs - Foundation for Economic Education (fee.org)No, You Don’t Need to be “Qualified” to Homeschool Your Children - Foundation for Economic Education (fee.org)📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Become a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
📘 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 22, 2022 • 1h 10min
What Do Digital Nomads Tell Us About The Future? - Lauren Razavi (Executive Director, Plumia)
Lauren and I first talked when I was locked down in Taiwan in 2021. It was amazing to connect with another nomad and writer after weeks of not seeing people. I was also a bit stuck in my book writing process and she gave me a ton of helpful hints to take my book to the next level.
I was excited to interview Lauren because she just finished her own book, Global Natives about her own experience as a nomad (since 2013!) and also the past, present, and future of the movement. I think she is one of the most thoughtful perspectives on the future of work and global mobility.
Currently, Lauren is Executive Director of Plumia, the mission to build an internet country for digital nomads at SafetyWing, a Y Combinator company that raised a $35 million Series B in 2022. She is also author of the book Global Natives and writes the Counterflows newsletter) about borderless living. She tweets @LaurenRazavi.
SPONSOR: CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here
Links Mentioned
Path Role Model: Pia Mancini
Minimum viable state
Book Recommendation: Slouching Towards Bethlehem by Joan Didion
Timestamps
2:01 Introduction
3:22 Lauren's Influences Growing Up
6:30 Lauren's Idea of Home
9:00 Paul on International Couples
10:24 Lauren on how she sees "place" & digital citizenship
12:44 Becoming a Digital Nomad
17:26 Paul's experience in Bali
19:34 Digital Nomads being self-reflective
23:51 The fear of asking questions about life
30:10 How everything changed in 2020
31:52 Why the remote work is here to stay
34:21 Asking better questions - Nomads and Settlers
43:52 Lauren's approach to writing - working with an editor
51:21 The most interesting experiments with countries/policies
58:23 The problem with the real estate
1:02:28 Rapid fire questions with Lauren
📕Buy Paul’s Book (Published Jan 2020): The Pathless Path
📲Connect + Follow Paul
Twitter: @p_millerd
Paul’s Newsletter: Subscribe to Boundless
Paul’s YouTube: Subscribe
🙏Further Ways To Support The Podcast:
Become a sponsor of the Podcast / Newsletter
Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course
Want to launch a course? Podia or Teachable are both great
Web Hosting: Skystra Fast WordPress Hosting
Host your own community" Circle 14-day free trial
📘 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 14, 2022 • 1h 8min
Growing up in Hawaii, Corporate Detours & The Future of Audio - Sky King
This episode is with Sky King, the founder of Modern Stoa, a podcast advertising company for podcasters. His path is fascinating - he grew up in Hawaii, rarely wore shoes, was heavily influenced by Asian culture, had a father who was retired, and somehow ended up in a massive corporation right after college. In 2016. he became fascinated by how the media was shaping the 2016 US election and decided it was time to act. From a cold email to Ryan Holiday to helping build Aubrey Marcus' podcast, Sky was on his way. His long-term vision is to build an alternative to traditional advertising in audio.We talk about this and a lot more including:Why he quit a good job to work at a smoothie barHow a cold email to Ryan Holiday changed his lifeGrowing up in HawaiiSerendipitous events that lend to him moving to AustinThe future of AudioLinks MentionsModern StoaSky's Podcast (Paid) or RMRK.appThe Gray Lady WinkedThe Brass Check@consumersky (twitter)CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up HereTimestamps1:41: Intro to Sky and where his name came from5:03: Sky's influences growing up11:34 Why he went to the corporate world17:12 Cold emailing Ryan Holiday & vision for 19:47 Sky's "quake moment"25:15 Moving to Austin and working for Aubrey Marcus30:44 Sky's desire to help people 32:55 Growing up in Hawaii36:10 Going to China at 1039:30 Everything anywhere all at once reflections44:40 The "true default path"47:30 Hiring someone & responsibility48:30 "what are you uniquely positioned to do?"49:20 Advertising Subsidy & Media incentives57:20 Meme farming & future of audio1:01:30 Bucky Fuller & specialization📕Buy Paul’s Book (Published Jan 2020): The Pathless Path 📲Connect + Follow PaulTwitter: @p_millerd Paul’s Newsletter: Subscribe to Boundless Paul’s YouTube: Subscribe 🙏Further Ways To Support The Podcast:Become a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
📘 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

20 snips
Jun 7, 2022 • 1h 6min
The Arc of The Practical Creator - Lawrence Yeo
Being an undeclared major till his senior year of college, Lawrence didn’t really know what he wanted to do. After looking up which jobs make the most money, he decided to declare as an economics major, leading him to explore Investment Banking. While he didn’t end up working in investment banking, he was still pulled by the power of prestige, something he says “is a drug, and is most potent” when you are young and looking at schools. Over a number of years and experiments with music and creating and writing, he slowly started to figure out a better path forward for him. After leaving the corporate world for a second time, Lawrence finally found a calling - writing on his blog: More To That where he uses visual storytelling to express his ideas of pursuing alternative paths, sharing ideas, and creating online.
Some of the topics we explore in this conversation include:
The influence of money and prestige
Burnout and reflection
The importance of the right partner
Finding the right medium
The Arc of the Practical Creator
How To Find Lawrence:
Website
@moretothat (twitter)
CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here
Audio Timestamps
2:26: Intro/Who is Lawrence
3:47: Scripts around creativity
5:37: Prestige and Money
8:56: Fear of ending up broke and homeless
16:55: Knowledge Work & Burnout
21:20: Having the right partner supporting you
29:38 How writing emerged as something important
32:44: The Arc of the Practical Creator: Stage 1
42:15: The Arc of the Practical Creator: Stage 2
50:48: The Arc of the Practical Creator: Stage 3
59:10: Rapid-fire questions with Lawrence
1:03:35: Outro/Where to find Lawrence
Buy Paul’s Book (Published Jan 2020): The Pathless Path
Connect + Follow Paul
Twitter: @p_millerd
Paul’s Weekly Newsletter on Work & Unconventional Path: Subscribe to Boundless
Paul’s YouTube Channel: Subscribe
Further Ways To Support The Podcast: I support the following services and recommend and/or use all of the following
Become a sponsor of the Podcast / Newsletter
Rate on iTunes or Spotify!
Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course
Want to launch a course? Podia or Teachable are both platforms I use
Web Hosting: Skystra Fast WordPress Hosting
Host your own community" Circle 14-day free trial
📘 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 1, 2022 • 35min
Podcast Update! Re-branded as The Pathless Path & LIVE Q&A From Youtube
I offer a short little update on the next steps for the podcast and include a live Q&A I did on youtube last week.
Video link: https://youtu.be/CGbw7Q8hoys
📘 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