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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

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"

In this episode Cody Royle and I discuss what sets high performing NFL organizations like the Patriots and the Giants (and others apart from the rest). Cody is the author of Where Other’s Wont: Taking People Innovation from the Locker Room into the Boardroom. His book is available here: http://amzn.to/2E5R88kCONTEST DETAILS: I am giving away two of Cody's books for free. Just retweet this episode with the hashtag #boundlesspod or send a screenshot of you subscribed to the podcast to paul@think-boundless.comLinks:* www.boundlesspod.com* www.whereotherswont.comSupport the podcast & join the community:* www.patreon.com/thinkboundless

📘 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

#5 Super Bowl Minisode - Cody Royle on The Patriots and what business can learn from sports

Janet is one of my favorite people. We have a similar belief that people are capable of more than they believe and that alternative paths are more realistic and the reality than people realize.Not a fan of default paths from an early age, one quote stood out from Janet that she has continuously asked herself throughout her life:“The conventional path is not going to work for me, what can I do instead?”Janet first started “hacking” life in high school when she decided that the standard curriculum wasn’t for her. Despite pushback from parents, teachers, and peers, she followed her curiosity and negotiated an alternative path — avoiding things like Math to go deeper with teachers in social studies, religion and politics.Her next “hack” was to apply to college in Canada. Starting with the constraints that she wanted to avoid debt and that her parents would support the equivalent of in-state tuition she looked for different options and found a way when her uncle convinced her to look at Canadian universities. Although taking a non-conventional path, she learned a lot about being able to adapt that would help her later on in her career. Full writeup: https://think-boundless.com/2018/02/07/934/Janet: http://www.careerjanet.comLinks:* www.boundlesspod.comSupport the podcast & join the community:* www.patreon.com/thinkboundless

📘 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

#6 Janet Matta - Rock Star Career Coach On The Alternative Paths We Fail To See

Growing up all Cody thought about was sports. He saw his path as becoming a professional Aussie Rules Football player. However, after competing at the highest level of the sport, he quickly saw felt his “talent just fell away” at the age of 18. He struggled to live in the moment and stewed on the fact that everyone around him seemed much more talented. While this period would help him realize that he was better suited as a coach than a player, it took him a few years to make that realization.

Show Notes

Support the Podcast: Patreon

Podcast Information: #BoundlessPod

Paul: @p_millerd & Cody: @codyroyle
Cody's Book: Where Others Wont

Book Recommendations:

Legacy: What The All Blacks can teach us about the business of lifeOriginals by Adam Grant • and 
A Dozen Things I Learned From Adam Grant
Links:

altMBA • Simon Sinek: 
Start With WhyNetflix CultureHow Netflix's Culture Got Patty McCord FiredBoundless Podcast: Episode 3

📘 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

#7 Cody Royle on The Talent & Performance Secrets of The Sports World

I discovered Tom by reading a piece he wrote on freelance consulting. I was fascinated with his approach and how similar it was to mine - especially coming from a completely different perspective - digital marketing & content. We talk in depth about how he thinks about content in today's world, his thoughts on personal branding, how writing helps him create and leads to serendipitous connections and how he manages a diversity of interests. We also geek out about our love of all things Ribbon Farm and Venkatesh Rao.

His Advice For Careers: Go work somewhere interesting rather than something that is safe. Earlier in your career, Tom pushes people to sacrifice revenue or stability in favor of learning and growth.

Podcast Information: #BoundlessPod

Support: Support The Podcast For $1 a Month

Links:

Tom Critchlow • & 
@tomcritchlowField guide for Independent Consultants • by Tom Critchlow
The Consultant's Grain • by Tom Critchlow
Seeing Like a State: How Certain Schemes to Improve the Human Condition Have Failed Venkatesh Rao on The Knowledge Project PodcastBlockchain Man • by Taylor Pearson
RibbonFarm Blog

📘 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

#8 Tom Critchlow on Personal Branding, Freelance Consulting & The Future of Work

Billy used to be an avid skier, working odd jobs and traveling between the northern and southern hemispheres trying to catch the best skiing. In 2018 he e-mailed Ryan Holiday and pitched him on doing some work for him for free. In a couple of months, he was hired as Ryan's research assistant. Billy is one of the most curious people I know and we dive into his journey. 

🎥🍿 YOUTUBE: WATCH HERE

Links:

 • Twitter: 
@bpoppenheimer • Website: 
billyoppenheimer.com • Billy's 
Newsletter
⌛TIMESTAMPS

(00:56) - The scripts Billy grew up with
 • (13:45) - Reaching out to Ryan Holiday

 • (17:52) - The research process and learning from Ryan

 • (25:21) - Skiing, Australia and finding his own voice

 • (40:23) - Animal courtship

 • (43:42) - How Ryan Holiday manages his team

 • (51:42) - Ambition and learning from past models

 • (01:03:10) - Downsides to fame

 • (01:04:01) - Where can we find Biilly?

📘 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

#141 Ryan Holiday's Secret Weapon - Billy Oppenheimer on growing in Philadelphia, almost going to law school, role models, working with Ryan Holiday, his research process, the notecard system, skiing, and the downsides to fame

#141 Ryan Holiday's Secret Weapon - Billy Oppenheimer on growing in Philadelphia, almost going to law school, role models, working with Ryan Holiday, his research process, the notecard system, skiing, and the downsides to fame

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