The Pathless Path with Paul Millerd

1 hour 26 minutes
Angie Finished Her Memoir! - Angie and Paul on the creative process, parenting, travel, writing, life challenges, and books
Check out Angie's book in Chinese: mit886.com
More about angie: Angiecreates.io
Click here to watch a video of this episode.
- (00:00) - Welcome to the Pathless Path Podcast
- (01:09) - Life Updates and Creative Challenges
- (02:10) - The Journey of Writing a Memoir
- (06:12) - Revisiting Family Stories
- (09:23) - The Emotional Rollercoaster of Writing
- (11:27) - Balancing Motherhood and Creativity
- (14:07) - The Struggles of Working with Others
- (27:46) - The Impact of Miscarriage
- (35:06) - Rethinking Work and Parenting
- (43:15) - Struggles of Citizenship and Homelessness
- (43:41) - Emotional Turmoil and Support
- (44:05) - Guilt and Parenting Challenges
- (46:43) - A New Beginning in Thailand
- (47:38) - Balancing Work and Family
- (57:59) - Exploring Financial Literacy
- (01:13:21) - Publishing Journey and Cultural Differences
- (01:24:19) - Future Plans and Reflections
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 Paul
- X: @p_millerd
- Instagram: @pathlesspaul
- Paul’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): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
- I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial
25 February 2026, 2:56 pm
1 hour 11 minutes
Michael Ashcroft on Getting Lost and The Joys of Dad Life
I chat with Michael on parenting, getting lost, the pathless path, hustle culture, travel, and more. This is his 4th appearance on the show.
Find more about Michael here: https://michaelashcroft.com/
Or explore his writings on expanded awareness: https://expandingawareness.org/
- (00:00) - Introduction / Teaser
- (02:37) - Introduction and Missing Guest
- (03:26) - Podcast Plans and Initial Banter
- (03:47) - Reflecting on Past Conversations
- (04:36) - The Journey of Self-Employment
- (13:10) - Life Updates and Health Challenges
- (17:03) - Parenting Reflections and Future Plans
- (20:36) - Balancing Work and Family Life
- (24:56) - Navigating Challenges and Personal Growth
- (31:00) - The Role of Fathers and Emotional Resilience
- (34:33) - The Impact of Miscarriages and Moving Forward
- (37:45) - Reflecting on a Challenging Project
- (39:15) - Book Sales and Audience Insights
- (40:55) - Future Plans and Creative Inspiration
- (41:49) - The State of Online Creation
- (51:19) - AI and Its Impact on Creativity
- (01:01:02) - Balancing Work, Family, and Creativity
- (01:06:24) - Fun and Games: Dictator or Hustle Bro?
- (01:09:24) - Concluding Thoughts and Future Outlook
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 Paul
- X: @p_millerd
- Instagram: @pathlesspaul
- Paul’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): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
- I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial
31 December 2025, 3:55 am
1 hour 27 seconds
What's After BigLaw & Consulting? - Allie Canton & Paul Millerd On Reinvention, Parenting on The Pathless Path & as Parent
Allie and I discuss our shared experiences of leaving traditional career paths to explore more authentic lives. Allie, a former lawyer, talks about navigating parenthood, part-time work, and her numerous interests while stepping off the default path. We chat about how Allie was inspired by 'The Pathless Path,' the ship, quit, and learn framework, and our upcoming experiments with nomadic living. Allie also talks about burnout, and alternative ways to live meaningfully.
Follow Allie's writing and podcast on Substack: Practically On Purpose
- (00:00) - Introduction and Guest Overview
- (01:41) - Ali's Journey and Paul's Influence
- (02:48) - Defining the Pathless Path
- (04:41) - Living the Pathless Path
- (07:19) - Daily Life and Nomadic Living
- (20:38) - Traveling Village and Family Life
- (24:05) - Education and Raising Kids
- (28:03) - Ship, Quit, and Learn Framework
- (32:19) - Balancing Priorities and Curiosity
- (33:03) - Living a Minimalist Lifestyle
- (33:50) - Creative Paths and Family Support
- (36:24) - Cultural Differences in Marriage
- (39:52) - Economic Growth and Middle-Class Ideals
- (43:04) - Questioning the Traditional Career Path
- (45:32) - The Inspiration Deficit and Meaningful Work
- (49:36) - Challenges of the Creator Journey
- (56:54) - The Pathless Path Community
Click here to watch a video of this episode.

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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 Paul
- X: @p_millerd
- Instagram: @pathlesspaul
- Paul’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): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
- I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial
20 November 2025, 12:35 pm
1 hour 7 minutes
Commit A Career Ending Move - Steven Foster on Permissionless Paychecks, Communal Living & Battling Life's Challenges While Pathless
In this episode, I have a deep conversation with Steven Foster, who opens up about his career journey from Silicon Valley to embracing a pathless life. We dive into his essay 'Commit a Career Ending Move,' reflecting on how modernity has turned careers into a form of religion. Steven shares his personal challenges, including severe health issues and family crises, and how embracing a more communal and nature-focused lifestyle has helped him navigate these obstacles. This episode is an exploration of redefining work, faith, and finding a deeper purpose beyond traditional career paths.
- (00:00) - Introduction to Steven Foster and His Career Journey
- (01:41) - The Religion of Work
- (03:42) - Steven's Early Career and Family Background
- (07:18) - Navigating the Tech Industry
- (20:11) - Leaving Silicon Valley
- (24:33) - Life After the Career-Ending Move
- (33:25) - Financial Shifts and Creative Solutions
- (34:37) - Navigating Personal Crises
- (43:58) - The Role of Community and Religion
- (56:00) - The Power of Permissionless Income
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 Paul
- X: @p_millerd
- Instagram: @pathlesspaul
- Paul’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): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
- I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial
13 November 2025, 1:46 pm
1 hour 37 minutes
The Yoga Of Work - Andrew Taggart
Click here to watch a video of this episode.

Mentioned in the episode
- (00:00) - Introduction
- (04:02) - The Evolution of Work Philosophy
- (08:05) - The Role of Telos in Modern Life
- (14:59) - Personal Journeys and Realizations
- (37:34) - Writing as a practice and medium for understanding
- (48:54) - Rethinking Karma Yoga in Modernity
- (51:32) - The Mundane Nature of Daily Tasks
- (57:56) - The Spiritual Journey of Work
- (59:38) - Introspection and the Reality of Work
- (01:11:26) - Balancing Objective Conditions and Inner Peace
- (01:28:27) - The Concept of Inner Purification
- (01:35:49) - Final Thoughts and Future Projects
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 Paul
- X: @p_millerd
- Instagram: @pathlesspaul
- Paul’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): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
- I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial
8 September 2025, 12:00 pm
30 minutes 14 seconds
AMA Episode 200 - I answer questions on parenting, courage, being a prophet, taking risks, and money
I took questions from people for episode 200. Enjoy!
Click here to watch a video of this episode.
- (00:00) - Introduction and Podcast Background
- (03:28) - Future of Education and Teaching
- (05:49) - Thoughts on Being a Prophet
- (06:29) - Current Pulling Forces and Changes
- (08:50) - Special Hardcover Edition Plans
- (10:25) - Managing Financial Anxiety
- (12:11) - Business Lessons from Corporate Life
- (15:04) - Evolving Perspectives on Parenting
- (17:35) - Self-Love versus Self-Improvement
- (21:10) - Building Community and Future Plans
- (23:13) - Courage and Sustainability on the Pathless Path
- (27:20) - Practical Advice for Going Off the Beaten Path
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 Paul
- X: @p_millerd
- Instagram: @pathlesspaul
- Paul’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): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
- I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial
4 September 2025, 5:22 am
1 hour 2 minutes
How To Retire Well: Dennis Owen on Moving Abroad, Building Community, Volunteering, Adapting to New Cultures, Creating Routine, Consulting After Retirement, Managing Money Mindset Shifts, Staying Current with Technology, Health Habits, Navigating Expat Li
In this episode, I talk with Dennis Owen about his journey from a long career in the airline industry to building a purposeful and active retirement in Chiang Mai, Thailand. Dennis shares how he intentionally “retired to” a new life filled with volunteering, consulting, and community involvement, rather than just leaving work behind. We discuss the challenges of adapting to a new culture, the importance of routine, staying curious, and the mental shift from saving to spending in retirement. Dennis emphasizes the value of purpose, continuous learning, and building a diverse community, while also sharing practical tips and book recommendations for anyone to continue to reinvent their path after work.
Click here to watch a video of this episode.

Topics Covered:
- Transitioning from a long career to retirement
- Moving abroad and adapting to a new culture
- The importance of “retiring to” something, not just leaving work
- Building routine and community in retirement
- Volunteering and giving back
- Consulting, ghostwriting, and staying mentally active
- The mental shift from saving to spending
- Staying current with technology and learning new things
- Health, wellness, and daily habits
- Navigating practical challenges of living abroad
- Book and resource recommendations for retirement and reinvention
- Advice for finding purpose and meaning after work
LINKS:
Chapters
- (00:00) - Introduction and Guest Background
- (01:56) - Early Career in the Airline Industry
- (05:31) - Transition to Asia and Cultural Experiences
- (08:07) - Volunteer Work and Personal Life
- (15:51) - Retirement Philosophy and Activities
- (22:15) - Creating Opportunities and Continuous Learning
- (32:52) - The Reality of Retirement
- (33:09) - Finding Meaning Beyond Money
- (35:25) - Adapting to Technological Changes
- (38:19) - Retiring in Chiang Mai
- (42:34) - Balancing Health and Wellness
- (44:17) - Embracing Lifelong Learning
- (50:44) - Navigating Financial Decisions in Retirement
- (59:02) - The Importance of Purpose and Learning
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 Paul
- X: @p_millerd
- Instagram: @pathlesspaul
- Paul’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): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
- I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial
25 August 2025, 12:00 pm
1 hour 6 minutes
Worldschooling 2.0: Rekha Magon on Location-Independent Schooling, co-founding Boundless Life, Lessons during bed rest, rethinking family in a digital age, travel, freedom, and raising global citizens
In this video, I talk with Rekha about Boundless Life and the idea of location-independent education. We cover her background, what led her to start Boundless Life, and how the program works for families who want a different approach to learning and community.
For more:
- (00:00) - Introduction to the topic of location-independent education
- (02:34) - Rekha's background and early influences
- (04:53) - Career beginnings and feeling unfulfilled
- (09:21) - Transformative experience during pregnancy
- (18:27) - Origins of Boundless Life
- (25:55) - Breaking traditional education assumptions
- (41:58) - Building community and relationships in Boundless
- (49:28) - Funding model and future growth
- (01:01:13) - Future plans and expansion
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 Paul
- X: @p_millerd
- Instagram: @pathlesspaul
- Paul’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): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
- I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial
5 August 2025, 3:59 am
1 hour 21 minutes
The Inner Game of Work: Pranab Sachi on Codependent Origination, Rob Burbea, Quake Books, Attentional Co-Piloting, Michael Taft, and "Non-Success"
In this episode, I interview my friend Pranab Saachi, and we get specific about the ideas and influences that have shaped his thinking. We talk about codependent origination from Buddhist philosophy, the concept of “quake books” that have shifted his worldview, and his own approach to “attentional co-piloting” as a practical alternative to traditional coaching (which he then has me try out live on the call).
Pranab references teachers like Michael Taft and Robert Burbea, and explains how Internal Family Systems and Joe Hudson’s Art of Accomplishment have factored into his work. We also discuss his abandoned “Non-Success Podcast” idea and why he’s more interested in experiments than achievements.
Connect with Pranab here: https://www.pranabsachi.com/
Click here to watch a video of this episode.

Some topics we talked about include:
- Codependent Origination (Buddhist philosophy)
- Quake Books (life-changing reads)
- Attentional Co-Piloting (Pranab’s coaching approach)
- Michael Taft (meditation teacher)
- Rob Burbea (Buddhist teacher)
- Joe Hudson & Art of Accomplishment
- Internal Family Systems (IFS)
- The Non-Success Podcast (Pranab’s project idea)
- Tim Ferriss, Wait But Why, Siddhartha, and more
- (00:00) - Introduction and background
- (10:33) - Career journey and exploration
- (16:43) - Building authentic connections
- (22:58) - Spiritual influences and meditation practice
- (50:23) - Attentional co-piloting coaching session
- (01:18:07) - Closing thoughts and contact information
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 Paul
- X: @p_millerd
- Instagram: @pathlesspaul
- Paul’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): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
- I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial
28 July 2025, 2:30 pm
1 hour 19 minutes
How much money do you need to quit? I debate with Nick Maggiulli (and rabbit holes: wealth > income, why COAST FIRE rocks, and more...)
In this episode, I'm pumped to welcome back Nick Maggiulli to the podcast (https://youtu.be/deMXbaI-Ir4). We dive into various topics about money and financial independence, with a focus on Nick's endorsement of the 'COAST Fire' strategy, something I accidentally embraced after quitting my job.
Nick shares his personal stories of financial challenges growing up and how these experiences shaped his approach to saving and spending. We debate the right time to take financial leaps and discuss how data-driven trends are making more Americans wealthier today. Nick introduces his wealth ladder concept and explains how it can help you live life on your terms.
His new book is here: https://www.amazon.com/Wealth-Ladder-Proven-Strategies-Financial/dp/0593854039
I loved his first book too: https://youtu.be/WWXPNK06r-k
Click here to watch a video of this episode.
- (00:00) - Introduction and Guest Reintroduction
- (02:31) - Diving into Personal Financial Stories
- (05:49) - Spending Rules and Financial Philosophies
- (12:14) - The Wealth Ladder Explained
- (20:08) - Navigating Career and Financial Growth
- (30:43) - The Impact of Wealth on Lifestyle
- (41:34) - Inflation Adjusted Wealth Levels
- (42:46) - Fears of Going Broke
- (43:24) - The 4% Rule and Retirement
- (46:34) - Coast Fire Explained
- (50:59) - The Emotions of Money
- (54:53) - Creative Paths and Financial Decisions
- (01:00:49) - The Future of Writing and Publishing
- (01:05:55) - The Impact of LLMs on Content Creation
- (01:09:09) - Reflections on Financial Advice
- (01:17:16) - Concluding Thoughts and Farewells
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 Paul
- X: @p_millerd
- Instagram: @pathlesspaul
- Paul’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): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
- I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial
21 July 2025, 1:38 pm
1 hour 11 minutes
Following Your Inner Compass - Lawrence Yeo on his creative journey, sharing ideas, self-publishing, and playing the long game
Lawrence is one of my favorite creators. He shares with passion, vulnerability and care.
I chatted with Lawrence Yeo about his new book, 'The Inner Compass,' exploring themes of self-reflection, creativity, and the journey of writing and self-publishing. We discuss the importance of engaging with the world to gain a deeper understanding of oneself, the role of ambition in creative work, and the dynamics of traditional versus self-publishing.
Click here to watch a video of this episode.

To find his book and support his work:
BOOK: https://compass.moretothat.com
SITE: https://moretothat.com

CHAPTERS
00:38 The Journey of Self-Reflection
01:12 Creativity and Connection
06:38 The Nature of Creativity
08:55 Success and Inner Fulfillment
16:51 The Risk of Authenticity
18:51 Self-Publishing Insights
36:51 The Power of Short Books
38:06 Self-Publishing vs. Traditional Publishing
39:58 Creative Intentions in Writing
42:07 Overcoming Fear in Publishing Choices
44:17 The Pathless Path: Choosing Your Journey
47:48 The Next Book: Exploring Money and Identity
52:05 Innovative Approaches to Book Launches

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 Paul
- X: @p_millerd
- Instagram: @pathlesspaul
- Paul’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): Collective
- Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
- I use Transistor to host this podcast. It rocks. Launch Yours Here
- I record high-quality videos using Riverside: Sign Up Here
- I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial
8 July 2025, 11:21 am
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