
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.
Latest episodes

Mar 17, 2025 • 1h 5min
"Dirtbag Rich" - Blake Boles & I Talk About Extracting More Freedom From Life
In a lively discussion, Blake Boles, host of Dirtbag Rich, shares insights on extracting freedom from life. He explores the philosophical shifts around work, advocating for a broader definition that values passion over conventional success. The conversation dives into navigating fear and uncertainty when leaving stable careers for authentic living. Boles emphasizes community-building in a self-directed lifestyle and redefines money as a tool for freedom. Their engaging dialogue encourages listeners to embrace uncertainty and pursue personal growth.

15 snips
Dec 5, 2024 • 52min
Matt Yao Interviews Me
In this engaging conversation, Matt Yao, an explorer of writing and coaching, interviews Paul Millerd about his transformative book, Good Work. They dive into the shifting nature of work, urging listeners to prioritize meaning over traditional roles. They reflect on financial independence and the joys of self-employment, along with the pivotal role of creativity in everyday tasks. The duo also shares insights on sabbaticals and the balance between career and parenting, encouraging a spirit of experimentation in both personal and professional lives.

14 snips
Nov 6, 2024 • 1h 35min
Building A Life Around Good Work (Paul Interviewed by Abel James)
Abel James, a podcast host and musician from Austin, dives into transforming mundane careers into meaningful pursuits. He shares his own journey from corporate life to creative fulfillment spurred by personal challenges. The conversation emphasizes prioritizing passion over financial gain and balancing creativity with the responsibilities of parenthood. Abel advocates for redefining success beyond societal norms, encouraging listeners to embrace good work and authentic choices that lead to real joy and connection.

Oct 11, 2024 • 6min
Good Work is Live! (Audiobook preview)
Explore the journey of rediscovering passion through creative expression as the speaker shares personal anecdotes leading to their new book. Discover how a transformative experience shifted their focus from professional burnout to finding joy in writing. This reflection emphasizes the vital importance of pursuing meaningful work that truly fulfills us.

9 snips
Jun 26, 2024 • 44min
#175 20 Families as a "Traveling Village - Nikolaj Astrup on his experiment living in Thailand, Vietnam, and Japan with 20 families from around the world
Nikolaj Astrup shares his experience living in Thailand, Vietnam, and Japan with 20 families from around the world. Topics include communal living dynamics, intentional communal projects, community living experiments, homeschooling approaches, sustainable funding for projects, and reflections on leadership and community building.

15 snips
May 29, 2024 • 1h 2min
#174 Agency Is A Skill — Cate Hall on leaving law for poker, developing agency, deterministic vs probabilistic economy, risk, burnout, asking dumb questions, defining ambition, seeking real feedback, and the surface area of luck
Former Supreme Court advocate turned poker player and entrepreneur Cate Hall discusses leaving law for poker, developing agency, deterministic vs probabilistic economy, risk, burnout, asking dumb questions, defining ambition, seeking real feedback, and maximizing luck. She shares her inspiring journey of pivoting from a traditional career path to pursue fulfillment and success in unconventional ways.

22 snips
May 13, 2024 • 1h 25min
1 Year Dad Reflections - Conversation with Sky King & Nat Eliason
Nat Eliason and Sky King join Paul Millerd in a discussion on fatherhood, exploring challenges, sleep training, parenthood choices, financial realities, vaccine decisions, childcare expenses, balancing writing with parenting, and personal experiences during OBGYN appointments. The conversation dives into humorous struggles, insights, and reflections on unconventional paths of fatherhood.

55 snips
Apr 16, 2024 • 1h 7min
#173 Solopreneurship After Burnout — Justin Welsh on burnout, taking ownership of his time, struggling with a results oriented mindset, non-monetary success, becoming a top LinkedIn influencer, income goals, The Creator MBA, dealing with fears around money
Former startup executive Justin Welsh shares his journey from burnout to building a one-person knowledge business. Topics include struggles with a results-oriented mindset, non-monetary success, becoming a top LinkedIn influencer, setting income goals, The Creator MBA, and dealing with fears around money.

Apr 1, 2024 • 1h 9min
#172 Success In The Second Half Of Life — Henry Oliver on John Stuart Mill, Samuel Johnson, Penelope Fitzgerald, why we shouldn't dismiss Gladwell, writing, late bloomers, the importance of finding the others, Tyler Cowen's help and the lessons from Audrey Sutherland
Henry Oliver, a writer and brand consultant, explores late bloomers and the lessons we can learn from them. Topics include John Stuart Mill's influence, Samuel Johnson's dictionary creation, Penelope Fitzgerald's journey, the impact of writing online, Tyler Cowen's support, and the importance of finding like-minded individuals.

28 snips
Mar 25, 2024 • 1h 15min
#171 "All Work Is Noble," Montessori, and Kids & Work — Matt Bateman on starting growing up with the internet, digital and industrial literacy, studying philosophy and learning how to teach, starting the Guidepost school network, how to train teachers, how children learn and work, values in education, agency, and writing his new book
Matt Bateman discusses his journey from academia to Montessori education, emphasizing the nobility of all work and the importance of agency in education. He explores kids and technology, values in education, and the hidden value systems in schools. Reflecting on his experiences, he offers advice for parents and challenges traditional educational approaches.
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