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Lyt når som helst, hvor som helst 

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

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

 • (00:11) - Life Updates and Creative Challenges

 • (01:12) - The Journey of Writing a Memoir

 • (05:14) - Revisiting Family Stories

 • (08:25) - The Emotional Rollercoaster of Writing

 • (10:29) - Balancing Motherhood and Creativity

 • (13:09) - The Struggles of Working with Others

 • (26:48) - The Impact of Miscarriage

 • (34:08) - Rethinking Work and Parenting

 • (42:17) - Struggles of Citizenship and Homelessness

 • (42:43) - Emotional Turmoil and Support

 • (43:07) - Guilt and Parenting Challenges

 • (45:45) - A New Beginning in Thailand

 • (46:40) - Balancing Work and Family

 • (57:01) - Exploring Financial Literacy

 • (01:12:23) - Publishing Journey and Cultural Differences

 • (01:23:21) - Future Plans and Reflections

Angie Finished Her Memoir! - Angie and Paul on the creative process, parenting, travel, writing, life challenges, and books

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

 • (01:39) - Introduction and Missing Guest 

 • (02:28) - Podcast Plans and Initial Banter

 • (02:49) - Reflecting on Past Conversations

 • (03:38) - The Journey of Self-Employment

 • (12:12) - Life Updates and Health Challenges

 • (16:05) - Parenting Reflections and Future Plans

 • (19:38) - Balancing Work and Family Life

 • (23:58) - Navigating Challenges and Personal Growth

 • (30:02) - The Role of Fathers and Emotional Resilience

 • (33:35) - The Impact of Miscarriages and Moving Forward

 • (36:47) - Reflecting on a Challenging Project

 • (38:17) - Book Sales and Audience Insights

 • (39:57) - Future Plans and Creative Inspiration

 • (40:51) - The State of Online Creation

 • (50:21) - AI and Its Impact on Creativity

 • (01:00:04) - Balancing Work, Family, and Creativity

 • (01:05:26) - Fun and Games: Dictator or Hustle Bro?

 • (01:08:26) - Concluding Thoughts and Future Outlook

Michael Ashcroft on Getting Lost and The Joys of Dad Life

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

 • (00:43) - Ali's Journey and Paul's Influence

 • (01:50) - Defining the Pathless Path

 • (03:43) - Living the Pathless Path

 • (06:21) - Daily Life and Nomadic Living

 • (19:40) - Traveling Village and Family Life

 • (23:07) - Education and Raising Kids

 • (27:05) - Ship, Quit, and Learn Framework

 • (31:21) - Balancing Priorities and Curiosity

 • (32:05) - Living a Minimalist Lifestyle

 • (32:52) - Creative Paths and Family Support

 • (35:26) - Cultural Differences in Marriage

 • (38:54) - Economic Growth and Middle-Class Ideals

 • (42:06) - Questioning the Traditional Career Path

 • (44:34) - The Inspiration Deficit and Meaningful Work

 • (48:38) - Challenges of the Creator Journey

 • (55:56) - The Pathless Path Community

Click here to watch a video of this episode.

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What's After BigLaw & Consulting? - Allie Canton & Paul Millerd On Reinvention, Parenting on The Pathless Path & as Parent

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

 • (00:43) - The Religion of Work

 • (02:44) - Steven's Early Career and Family Background

 • (06:20) - Navigating the Tech Industry

 • (19:13) - Leaving Silicon Valley

 • (23:35) - Life After the Career-Ending Move

 • (32:27) - Financial Shifts and Creative Solutions

 • (33:39) - Navigating Personal Crises

 • (43:00) - The Role of Community and Religion

 • (55:02) - The Power of Permissionless Income

Commit A Career Ending Move - Steven Foster on Permissionless Paychecks, Communal Living & Battling Life's Challenges While Pathless

Click here to watch a video of this episode.

Mentioned in the episode

Andrew Taggart’s websitePathways to the Dao (Andrew’s Substack)Leisure: The Basis of Culture by Josef PieperSecular Monks (article by Andrew Taggart)Why Buddhism is True by Robert WrightPierre Hadot (Philosophy as a Way of Life)The Pathless Path by Paul Millerd

 • (00:00) - Introduction

 • (03:04) - The Evolution of Work Philosophy

 • (07:07) - The Role of Telos in Modern Life

 • (14:01) - Personal Journeys and Realizations

 • (36:36) - Writing as a practice and medium for understanding

 • (47:56) - Rethinking Karma Yoga in Modernity

 • (50:34) - The Mundane Nature of Daily Tasks

 • (56:58) - The Spiritual Journey of Work

 • (58:40) - Introspection and the Reality of Work

 • (01:10:28) - Balancing Objective Conditions and Inner Peace

 • (01:27:29) - The Concept of Inner Purification

 • (01:34:51) - Final Thoughts and Future Projects

The Yoga Of Work - Andrew Taggart

I took questions from people for episode 200. Enjoy!

Click here to watch a video of this episode.

 • (00:00) - Introduction and Podcast Background

 • (02:30) - Future of Education and Teaching

 • (04:51) - Thoughts on Being a Prophet

 • (05:31) - Current Pulling Forces and Changes

 • (07:52) - Special Hardcover Edition Plans

 • (09:27) - Managing Financial Anxiety

 • (11:13) - Business Lessons from Corporate Life

 • (14:06) - Evolving Perspectives on Parenting

 • (16:37) - Self-Love versus Self-Improvement

 • (20:12) - Building Community and Future Plans

 • (22:15) - Courage and Sustainability on the Pathless Path

 • (26:22) - Practical Advice for Going Off the Beaten Path

AMA Episode 200 - I answer questions on parenting, courage, being a prophet, taking risks, and money

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

 • (00:58) - Early Career in the Airline Industry

 • (04:33) - Transition to Asia and Cultural Experiences

 • (07:09) - Volunteer Work and Personal Life

 • (14:53) - Retirement Philosophy and Activities

 • (21:17) - Creating Opportunities and Continuous Learning

 • (31:54) - The Reality of Retirement

 • (32:11) - Finding Meaning Beyond Money

 • (34:27) - Adapting to Technological Changes

 • (37:21) - Retiring in Chiang Mai

 • (41:36) - Balancing Health and Wellness

 • (43:19) - Embracing Lifelong Learning

 • (49:46) - Navigating Financial Decisions in Retirement

 • (58:04) - The Importance of Purpose and Learning

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

 • (01:36) - Rekha's background and early influences

 • (03:55) - Career beginnings and feeling unfulfilled

 • (08:23) - Transformative experience during pregnancy

 • (17:29) - Origins of Boundless Life

 • (24:57) - Breaking traditional education assumptions

 • (41:00) - Building community and relationships in Boundless

 • (48:30) - Funding model and future growth

 • (01:00:15) - Future plans and expansion

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

 • (09:35) - Career journey and exploration

 • (15:45) - Building authentic connections

 • (22:00) - Spiritual influences and meditation practice

 • (49:25) - Attentional co-piloting coaching session

 • (01:17:09) - Closing thoughts and contact information

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

 • (01:33) - Diving into Personal Financial Stories

 • (04:51) - Spending Rules and Financial Philosophies

 • (11:16) - The Wealth Ladder Explained

 • (19:10) - Navigating Career and Financial Growth

 • (29:45) - The Impact of Wealth on Lifestyle

 • (40:36) - Inflation Adjusted Wealth Levels

 • (41:48) - Fears of Going Broke

 • (42:26) - The 4% Rule and Retirement

 • (45:36) - Coast Fire Explained

 • (50:01) - The Emotions of Money

 • (53:55) - Creative Paths and Financial Decisions

 • (59:51) - The Future of Writing and Publishing

 • (01:04:57) - The Impact of LLMs on Content Creation

 • (01:08:11) - Reflections on Financial Advice

 • (01:16:18) - Concluding Thoughts and Farewells

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

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
 • (13:07) - Reaching out to Ryan Holiday

 • (17:14) - The research process and learning from Ryan

 • (24:43) - Skiing, Australia and finding his own voice

 • (39:45) - Animal courtship

 • (43:04) - How Ryan Holiday manages his team

 • (51:04) - Ambition and learning from past models

 • (01:02:32) - Downsides to fame

 • (01:03:23) - Where can we find Biilly?

#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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