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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

Jeff Hittner of Your Project X and Paul talk about their favorite 10 career myths. They dive deep into the beliefs and mindsets that drive these beliefs while making an argument for people to reflect at a deeper level to shift past the default to contemplate a wide range of options

Readable Version: Top 10 Myths

Myth #1 - "Once I land my dream job / make $X a year, I'll be happy" (2:35)

Myth #2 - "I need to find my passion" (7:15)

Myth #3 - "I should never take a pay cut" (14:15)

Myth #4 - "You should have a 'steady' income" (20:40)

Myth #5 - "I have to know what I need to do before I change directions" (26:15)

Myth #6 - "An extended break is irresponsible" (32:30)

Myth #7 - "It's fine to take a risk when young, but not when you have kids" (40:35)

Myth #8 - "I should go to grad school to figure out what I want to do" (46:15)

Myth #9 - "I can't make a change now after years in this field" (55:20)

Myth #10 - "I'll be happy once I'm running my own business" (1:04:54)

Links Mentioned:

How to Get Unstuck In The New Year • , Jeff Hittner On Quartz
Self-Determination Theory • , Deci & Ryan
 • Comparing 
Passion & Purpose • , Thrive Global

Jeff Hittner leads Your Project X, a social venture with a mission to help 1 million people find more purposeful work. He has more than 18 years experience as an entrepreneur, consultant and changemaker. He is the founder of five social ventures, including IBM’s Corporate Social Responsibility (CSR) consulting practice globally. In 2011, he developed the curriculum for one of the first MBA’s in Sustainability in the US, at Bard College, where he was the Leadership professor. He was also two-time Chairman of the Carnegie New Leaders at the Carnegie Council for Ethics in International Affairs.

Jeff’s passion has always been at the intersection of education and entrepreneurship. Prior to your Project X, he ran a career transition program for 64 New Yorkers, built global education programs including a blended learning initiative for high school dropouts in Latin America and career discovery programs for youth in Europe. Jeff received his Masters in Cultures and Development Studies from the Katholieke Universiteit Leuven in Belgium, and a Bachelor of Business Administration from The College of William and Mary in Virginia where he was an elite gymnast. As a thought leader, Jeff has been published in a dozen major publications, including Forbes. Jeff lives in NYC with his wife, Grace, and one-year-old son, Rivington.

For More With Boundless:

Consider supporting the podcast on PatreonJoin 110+ People Carving Their Own Paths In The Slack CommunitySet Up A Curiosity C﻿onversation With PaulJoin The Free 3-Week Self-Employment ChallengeLearn More
📕 Buy Paul’s Book (50k+ Sold) 1. : 
The Pathless Path
 2. 😁 
Join Hundreds On Unconventional Paths: Pathless Path Community

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 • Twitter: 
@p_millerd • Instagram: 
@pathlesspaul • Paul’s Newsletter: 
Subscribe to Pathless • (23k+ People)
 • Paul’s YouTube: 
Subscribe
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 • Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): 
Collective • Looking for alternatives to traditional health insurance in the US? 
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10 Career Myths We Should Stop Believing (Jeff Hittner)

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

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

📘 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...)

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

📘 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 Inner Game of Work: Pranab Sachi on Codependent Origination, Rob Burbea, Quake Books, Attentional Co-Piloting, Michael Taft, and "Non-Success"

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

Uri Bram is the CEO of The Browser which runs regular newsletters to help people find good articles, podcasts, and videos to read. He has been living as a digital nomad for over seven years and also runs The Browser as a remote company.

We chat about Uri’s own journey, what it's like working with Robert Cottrell (who reads 10-12 hours a day), his early experiences becoming a kindle best-selling, how he thinks about running a remote company and some of his favorite reads worth checking out.

Articles/Books mentioned

 1. In Praise of Idleness and Other Essays, Bertrand Russell

 2. Derek Parfit, Reasons and Persons

 3. Leadership & Solitude, William Deresiewicz

 4. Disadvantages of an Elite Education, William Deresiewicz

 5. Seeing Like a State, James Scott

 How Ghost Is Structured for the Long-Term
 6. The Great Works of Your Life, Cope

 7. Ada Palmer, 
Ex Urbe
 8. Susan Bryson, Aftermath

 Salary Negotiation: Make More Money, Be More Valued 9. , Patrick McKenzie

-------------------------

To find ways to support Boundless, Click here

Subscribe to a weekly e-mail on life, work & the creative 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 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

Curating Goodreads Remotely (Uri Bram, CEO of The Browser)

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