The Pathless Path with Paul Millerd

The Pathless Path with 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.

Episodes

February 25, 2026 86 mins

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
  • (01:09) - Life Updates and Creative Challenges
  • (02:10) - The Journey of Writing a Memoir
  • (06:12) - Revisiting Family Stories
  • (09:23) - The Emotional Rollercoaster of Writing
  • (11:27) - Balancing Motherhood and Creativity
  • (14:07) - The Strugg...
Listen
Watch
Mark as Played

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
  • (02:37) - Introduction and Missing Guest
  • (03:26) - Podcast Plans and Initial Banter
  • (03:47) - Reflecting on ...
Listen
Watch
Mark as Played

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 burn...

Listen
Watch
Mark as Played

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 lifest...

Listen
Watch
Mark as Played

I took questions from people for episode 200.  Enjoy!

Click here to watch a video of this episode.

  • (00:00) - Introduction and Podcast Background
  • (03:28) - Future of Education and Teaching
  • (05:49) - Thoughts on Being a Prophet
  • (06:29) - Current Pulling Forces and Changes
  • (08:50) - Special Hardcover Edition Plans
  • (10:25) - Managing Financial Anxiety
  • (12:11) - Business Lessons from Corporate Life
  • (15:04) - Evolving...
Listen
Watch
Mark as Played

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...

Listen
Watch
Mark as Played

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:


  • (00:00) - Introduction to the topic of location-independent education
  • (0...
Listen
Watch
Mark as Played

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 referenc...

Listen
Watch
Mark as Played

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 sp...

Listen
Watch
Mark as Played

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 vers...

Listen
Watch
Mark as Played

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 ...

Listen
Watch
Mark as Played

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 Cul...

Listen
Watch
Mark as Played

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, s...

Listen
Watch
Mark as Played

Links:


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, experi...

Listen
Watch
Mark as Played
December 5, 2024 51 mins

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 lea...

Listen
Watch
Mark as Played

You can follow Abel's podcast here: Abel James Show


NEW: The Pathless Path Hardcover Premium Edition

📘 My 2nd Book Good Work: 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

Listen
Watch
Mark as Played
October 11, 2024 5 mins

Check out and purchase Good Work here: https://pmillerd.com/goodwork

Or from Amazon directly: https://amzn.to/4gwRSCN

Listen
Watch
Mark as Played

Cate seemed to be fully entrenched on the default path — she had graduated from Yale and became the Supreme Court advocate on her way to becoming a partner in her law firm. But she didn't want to live the lives of the people around her. She pivoted hard, you could almost hear car brakes squeaking as she made the turn, and over a year she became the number one female poker player in the world. She later started art and perf...

Listen
Watch
Mark as Played

Popular Podcasts

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    Dateline NBC

    Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

    Post Run High

    Post Run High features conversations with high-performing founders, athletes, artists, health and science experts, and leaders about what it really takes to succeed. Through honest, post-movement conversations, guests share how they’ve navigated challenges, built resilience, and used movement as a tool for clarity, discipline, and growth. Each episode explores the mindset behind performance — what keeps people going when things get hard — and offers tangible advice listeners can apply in their everyday lives.

    The Buck Sexton Show

    Buck Sexton breaks down the latest headlines with a fresh and honest perspective! He speaks truth to power, and cuts through the liberal nonsense coming from the mainstream media. Interact with Buck by emailing him at teambuck@iheartmedia.com

    The Interface

    Stop doomscrolling. Start decoding the tech rewiring your week - and your world. The Interface is the BBC's fiercely informed, fast and funny take on how tech is changing everything. Hosted by journalists Tom Germain, Karen Hao, and Nicky Woolf, each episode unpacks week-by-week the unfolding story of how technology is shaping all our futures. No guests. No jargon. Just three sharp voices debating the tech news stories that matter - whether they shook a government, broke the internet, or quietly tipped the balance of power. As TikTok shifts geopolitics, Trump drives digital shockwaves, Elon Musk expands his space-internet empire and AI reroutes the routines of everyday life - the trio ask: what world are the tech titans building for us? And do we want to live in it?

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.

  • Help
  • Privacy Policy
  • Terms of Use
  • AdChoicesAd Choices