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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

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.

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

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

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

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

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

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

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

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

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

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

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

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

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

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

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

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

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

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

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

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

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

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

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

Paul talks about why he is passionate about the future of work and shares some of his personal journey

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

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

#1 - Why do I care about the future of work?

Although Noel claims he lacks wisdom, he has a lot of it. He describes his career as “eclectic.” Starting his career in the 1980’s the environment around him (greed, money) influenced him to question what he was really trying to accomplish. He took a long term perspective and tried to focus on what he did not want his career to be at sixty — which he put simply as not doing “the things he wanted to do”. Although on a more corporate track early on in his career, he tried to continuously reflect on what mattered — even if it raised some eyebrows in among his peers.

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

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

#2 Noel Boyland on “doing the things you want to do” in your career

David was born abroad then moved to the US at a young age, all while being raised to believe that the path to success rests solely on going to school and getting a “safe” job with a big company. For the last 11 years he did just that, and by traditional measures of success, it looked like things were going well. Unfortunately, starting on Day 1 of his first job, he could never shake one, recurring feeling: “I really, really, really don’t like this”.In December 2017, after a lot of saving and planning, he worked up the courage to quit his job, build his retirement house in France, and focus on building a life around a freelance career.Forget the big house and fancy cars, his new measure of success is the amount of control he has over his time. He is using his time to explore his passion for learning new things, particularly in technology and programming, as well as helping others who are also looking to forge their own path away from the cubicle farm.Support the podcast: https://www.patreon.com/thinkBoundlessCheck out more episodes: https://www.think-boundless.com/podcastIdeas, questions, guest ideas? paul@think-boundless.com

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

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

#3 David Vaucher on Ending His Career to Start His Life

Chris is the founder of uncommonly and an avid fan of the long-running CBS television show Survivor. A former teacher, marketer, and management consultant, Chris has an eclectic mix of skills and professional experience. Chris has worked with over a dozen Fortune 500 clients spanning multiple industries including Media & Entertainment, Publishing, Insurance, Pharmaceuticals, and Corporate Social Responsibility. He is obsessed with inspiring great leadership and creating incredible learning experiences that change the way people think and operate.Learn More:Chris' Website: www.un-commonly.comHis Youtube Channel: https://www.youtube.com/user/TopherDean87Links:*Podcast: www.boundlesspod.com*Support: www.patreon.com/boundless*Show Notes: https://wp.me/p9AOW1-cY

📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

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

#4 Chris Donohoe on "uncommon" leadership, starting his own firm and "limitless creation"

“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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📘 GOOD WORK: LIVE! => Learn More
📕 Buy Paul’s Book (50k+ Sold): The Pathless Path
😁 Join Hundreds On Unconventional Paths: Pathless Path Community

📲Connect + Follow Paul

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

The Shadow Side of Solopreneurship - Darren Joe

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