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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.

The Pathless Path with Paul Millerd

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:

Dennis Owen on LinkedInThe Pathless Path by Paul MillerdThe New Retirementality by Mitch AnthonyOutlive by Peter AttiaDie With Zero by Bill PerkinsJust Keep Buying by Nick Maggiulli
Chapters

 • (00:00) - Introduction and Guest Background

 • (01:36) - Early Career in the Airline Industry

 • (05:11) - Transition to Asia and Cultural Experiences

 • (07:47) - Volunteer Work and Personal Life

 • (15:31) - Retirement Philosophy and Activities

 • (21:55) - Creating Opportunities and Continuous Learning

 • (32:32) - The Reality of Retirement

 • (32:49) - Finding Meaning Beyond Money

 • (35:05) - Adapting to Technological Changes

 • (37:59) - Retiring in Chiang Mai

 • (42:14) - Balancing Health and Wellness

 • (43:57) - Embracing Lifelong Learning

 • (50:24) - Navigating Financial Decisions in Retirement

 • (58:42) - The Importance of Purpose and Learning

📘 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 Paul

 • X: 
@p_millerd • Instagram: 
@pathlesspaul • Paul’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): 
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

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 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:

Boundless LifeBoundless EducationRekha on LinkedInRekha on Instagram

 • (00:00) - Introduction to the topic of location-independent education

 • (02:14) - Rekha's background and early influences

 • (04:33) - Career beginnings and feeling unfulfilled

 • (09:01) - Transformative experience during pregnancy

 • (18:07) - Origins of Boundless Life

 • (25:35) - Breaking traditional education assumptions

 • (41:38) - Building community and relationships in Boundless

 • (49:08) - Funding model and future growth

 • (01:00:53) - Future plans and expansion

📘 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 Paul

 • X: 
@p_millerd • Instagram: 
@pathlesspaul • Paul’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): 
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

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 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

 • (10:13) - Career journey and exploration

 • (16:23) - Building authentic connections

 • (22:38) - Spiritual influences and meditation practice

 • (50:03) - Attentional co-piloting coaching session

 • (01:17:47) - Closing thoughts and contact information

📘 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 Paul

 • X: 
@p_millerd • Instagram: 
@pathlesspaul • Paul’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): 
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

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'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

 • (02:11) - Diving into Personal Financial Stories

 • (05:29) - Spending Rules and Financial Philosophies

 • (11:54) - The Wealth Ladder Explained

 • (19:48) - Navigating Career and Financial Growth

 • (30:23) - The Impact of Wealth on Lifestyle

 • (41:14) - Inflation Adjusted Wealth Levels

 • (42:26) - Fears of Going Broke

 • (43:04) - The 4% Rule and Retirement

 • (46:14) - Coast Fire Explained

 • (50:39) - The Emotions of Money

 • (54:33) - Creative Paths and Financial Decisions

 • (01:00:29) - The Future of Writing and Publishing

 • (01:05:35) - The Impact of LLMs on Content Creation

 • (01:08:49) - Reflections on Financial Advice

 • (01:16:56) - Concluding Thoughts and Farewells

📘 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 Paul

 • X: 
@p_millerd • Instagram: 
@pathlesspaul • Paul’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): 
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

How much money do you need to quit? I debate with Nick Maggiulli (and rabbit holes: wealth > income, why COAST FIRE rocks, and more...)

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

📘 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 Paul

 • X: 
@p_millerd • Instagram: 
@pathlesspaul • Paul’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): 
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

Following Your Inner Compass - Lawrence Yeo on his creative journey, sharing ideas, self-publishing, and playing the long game

In this episode, I have a conversation with my friend Jack Moses. Three years ago, Jack emailed me after reading my book, declaring he was dropping out of college. Over time, I've been amazed by his life's actions, from embracing hustle culture to diving deep into spirituality. Recently, Jack led a retreat in Thailand, inspiring me with his courage and optimistic outlook. Join us as we discuss spiritual journeys, trusting our paths, and taking bold steps early in life.

You can check out his podcast too

 • (00:00) - Introduction to Jack Moses 

 • (00:54) - Jack's Journey: From Hustle to Spirituality 

 • (01:14) - Meeting in Chiang Mai 

 • (02:52) - The Impact of Travel 

 • (07:34) - Returning to School for Football 

 • (08:18) - Navigating the Real World vs. School 

 • (16:02) - The Challenges of Hustle Culture 

 • (19:20) - Writing and Creativity 

 • (23:42) - Spirituality and Personal Growth 

 • (31:53) - Human Design and Life Strategies 

 • (40:22) - Launching the Hardcover Version 

 • (41:23) - Living in Mexico During COVID 

 • (43:28) - The Pathless Path and Finding Flow 

 • (44:25) - Balancing Work and Family 

 • (45:24) - Exploring Synchronicity and Consciousness 

 • (46:53) - The Journey of Writing and Creativity 

 • (52:11) - Navigating Relationships and Freedom 

 • (01:09:22) - The Decision to Move to Asia 

 • (01:11:37) - Publishing and Creative Independence 

 • (01:13:16) - Final Reflections and Gratitude

📘 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 Paul

 • X: 
@p_millerd • Instagram: 
@pathlesspaul • Paul’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): 
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

Hustle & Flow - Jack Moses on dropping out of school, hustle culture, spiritual paths, finding flow, and travel as transformation

Personal updates about life, including his recent move back to Asia, reflections on work and career paths, parenting experiences, and insights into education and self-publishing. I share the challenges and joys of parenting, how I think about decisions in regards to kids, and evolving thoughts on publishing and creative projects.

Topics
00:00 Introduction and Life Updates
05:32 Reflections on Career Paths and Work Culture
08:43 Family Relocation and Adjustments
11:06 Traveling with Children: Tips and Experiences
14:40 Advice for New Parents
17:34 Approach to Education for Children
20:33 Self-Publishing Journey and Future Projects

📘 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 Paul

 • X: 
@p_millerd • Instagram: 
@pathlesspaul • Paul’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): 
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

Paul Q&A Episode - Moving to Asia, Parenting, Preparing for Kids, Pathless Hardcover Art Edition

Hello! I'm back! Expect a slow ramp, but there are new episodes coming!

I talked with Nat Eliason about his journey as a writer, from early experiments with ideas to fully embracing writing as a career. We discussed the challenges and rewards of moving from nonfiction to fiction, the trade-offs between traditional and self-publishing, and the importance of audience engagement. We also explored how AI is impacting writing, strategies for gathering feedback, and fiction’s role in addressing societal issues. Nat closed by sharing his vision for the future of his writing and the opportunities ahead.

Links & book info!

 • Husk Special Direct Sale: 
Buy here • or 
https://shop.nateliason.com/products/husk • Husk on Amazon: 
Buy here • or here
 • More of Nat's stuff: 
His Website • and 
newsletter

📘 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 Paul

 • X: 
@p_millerd • Instagram: 
@pathlesspaul • Paul’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): 
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

Becoming A Writer - Nat Eliason on his upcoming fiction release, traditional publishing vs. self-publishing, AI tools, tinkering, readers, launch plans

Links:

PodcastBlake BolesDirtbag Rich Site • : https://www.blakeboles.com/dbr/

Episode Desription
Paul Millerd is a 39-year-old writer, ex-consultant, and advocate for ditching the default path in favor of what he calls “the pathless path.” (pmillerd.com / @p_millerd)

Paul walked away from a promising corporate consulting career—think McKinsey, prestige, and six-figure salaries—to pursue a life of writing, experimenting, and global wandering. He describes how he initially struggled with unlearning his achievement-oriented mindset, why the idea of good work (work that energizes) became his guiding principle, and how his first self-published book, The Pathless Path, briefly and unexpectedly earned six figures.

We discuss the philosophical basis of work and money, how to avoid the traps of both scarcity and overachievement, and how the value of exercising your freedom is limited by how others exercise their own freedom. (In other words: if you're free to hike on a sunny Wednesday afternoon, and no one's available to go with you, are you really free?)

Paul and his wife have a young daughter, and they struggle to find and live near other, like-minded families. We talk about how online communities help Paul stay connected while living nomadically between Texas and Taiwan and how online self-education was invaluable to his success. We conclude with a discussion of navigating fear and uncertainty on the pathless path.

Throughout the conversation, Paul stays refreshingly honest about the tensions between freedom and stability, the allure of easy money, and the ever-present temptation to fall back into old habits of achievement and validation. Energized by this conversation, I ended up talking more than usual about the tricky balance of factors that leads to a Dirtbag Rich existence.

📘 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 Paul

 • X: 
@p_millerd • Instagram: 
@pathlesspaul • Paul’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): 
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

"Dirtbag Rich" - Blake Boles & I Talk About Extracting More Freedom From Life

This was a fun episode. A friend, Matt Yao, reached out to see if he could interview me about my recent book, Good Work.

We first connected when he called me in the summer of 2022. He was in the middle of my book and knew he needed to quit his job. 

Over the last few years, he's been on a transformational journey, experimenting with writing, coaching, and several other side quests.

Hope you enjoy this conversation.

You can learn more about Matt here: Matt Yao

📘 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 Paul

 • X: 
@p_millerd • Instagram: 
@pathlesspaul • Paul’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): 
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

Matt Yao Interviews Me

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 Paul

 • X: 
@p_millerd • Instagram: 
@pathlesspaul • Paul’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): 
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

Podcast Update Nov 2020 - The Pathless Path

Lyt når som helst, hvor som helst

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