Paul Millerd

The Pathless Path with Paul Millerd

Business EN ↓ 202 episodes

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,...

Author

Paul Millerd

Category

Business

Podcast website

pathlesspath.com

Latest episode

Feb 25, 2026

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Episodes

#127 The Art of Quitting & Reinvention - Nina Simon on living "off the grid" in an intentional community, taking "turns" in marriage and work, having kids on an unconventional path & leaving her dream job at NASA 04.01.2023

At each professional crossroad, Nina Simon has made the choice most likely to disappoint her mother. She left an electrical engineering job at NASA to design spy museum exhibits, said goodbye to a museum directorship to start a global movement for more inclusive cultural organizations, and now has put down her CEO hat to write crime fiction. Her first novel, Mother-Daughter Murder Night, will be p...

#126 Hearts on Fire - David Perell on curiosity, being a citizen of the internet, taking himself seriously, childhood obsessions, building Write of Passage, ambition, and money 15.12.2022

This episode was a delight. I've been following David's journey since 2017 and he was one of the fellow internet weirdos I saw on a similar path that didn't quite make sense. I've been inspired by how many people David has helped onboard as "citizens of the internet" through his course Write of Passage.  I'm rooting for David and I think you'll want to as well by the end of this episode. We filmed...

#125 Angie & Paul - We're Having a Kid (and other life updates) 13.12.2022

Angie and I talked about our journey (mostly hers) over the last two years including her leaving fitness, moving to the US, enrolling in Write of Passage, finding her community, and initial traction as a freelancer. 🍿 WATCH ON YOUTUBE Links: Angie's Site: Angie Creates   Her Experience in Write of Passage: From Fear To Thriving Angie's Podcast: Angie Creates (English & Chinese) Timestamps 0:0...

#124 Can You Ever "Make It" While Self-Employed - David Kadavy on Doing Work You Love, Self-Publishing, Traveling & Perspective, Mini-Lives & Living as An Expat 05.12.2022

David talks about his self-employment journey, discussing topics such as graphics design, studying abroad, work identity and engagement, self-publishing books, and advertising on Amazon. He reflects on his experiences and explains how he shifted from a traditional job to self-employment, including how he experienced a new reality after leaving his job. We talk about how hard it is to ever "make it...

#123 McKinsey Partner to Indie Freelancer - Adam Braff on writing online, the gig economy, consulting skills, consulting 28.11.2022

Adam Braff grew up in a house where writing was always encouraged. His mother published a newsletter, and his father was a data analytics consultant. He started out as a lawyer, but after the dot-com boom led to a surge in demand for consultants, he decided to make the switch. He now runs his own consulting firm and writes regularly on a variety of topics.  Braff himself became interested in consu...

#122 Indie Life & The Future of Work - Venkatesh Rao 23.11.2022

This episode was a delight. Venkatesh Rao is the creator of Ribbonfarm and has been writing about the internet, technology, and gig life. This conversation focuses on his recently published book, The Art of Gig.   If you are thinking about working independently, becoming a freelancer, or are interested in consulting, you should definitely buy his book: The Art of Gig, Foundations The Art of Gig, S...

#121 Carving Your Own Path In a "Vibecession" - Kyla Scanlon on leaving her job, writing online, TikToks as Poetry, and The Passion Crisis 14.11.2022

I believe that Kyla Scanlon is one of the most talented all-around creators. She is transcending the assumptions about what people want, especially with things like short-form videos. Her TikToks are synthesized, thoughtful, and funny, setting a new bar for what people want in an information age. We talked about her journey growing up in Kentucky, writing online, hacking into the finance industry...

#120 How Do You Buy A Home While Self-Employed? Catherine Cusick on her path, acting, economics of Broadway, longreads, independent book sales, buying a home, digital media & how to navigate hostile US self-employment regulations, 07.11.2022

The legible story is that Catherine is a writer, producer, and digital media consultant. She helps creative people connect with new audiences, usually writers, usually online. But she hasn't had a W-2 job since 2017. Before that she worked as an actor, worked at a company called Longreads, and then has done a bunch of solopreneur experiments over the past five years. Her recent interest is writing...

#119 Goosebump-inducing Waves of Knowingness - Jonny Miller on grief, friendship, living abroad, founding a company, remote work, Rolf Potts, David Whyte, poetry, and finding work that matters. 27.10.2022

Enroll In The 5th Cohort of Nervous System Mastery: You can get $250 OFF using the code PATHLESS => nsmastery.com Jonny Miller is a dear friend and I've had the privilege to get to know him closely over the past four years on our own journeys. We've lived in Japan, Indonesia, and Mexico together. When we met we were both single but now are both married in cross-country relationships and have na...

#118 A Better Future for Healthcare - Andy Schoonover on Crowdfunding for Healthcare, Search Funds, Buying A Company, Work-Life Balance, Bitcoin & Problems With Healthcare 24.10.2022

Andy Schoonover is the CEO of one of the sponsors of this podcast. After talking with him I actually thought he'd be a great guest on the podcast. He has a fascinating story from going from search-funder post-MBA grad to forming his own healthcare company. Can his company fix healthcare? Can anyone? Time will tell but I'm rooting for him. Join CrowdHealth: You ditched the traditional path… why hav...

#117 The Truth About Remote Work - Ali Greene on being a remote leader, leaving the default path, stories and taking breaks, living in different countries, & writing a book 17.10.2022

🍿 Watch on YouTube Ali Green has been a remote worker since 2014. It took her a couple of attempts to fully unpair from the office and even when she had a fully remote job it took her another year to lean into her freedom. Now she's writing a book about what she's learned leading teams, living in different countries, and working remotely. Quitting her job and inventing a "story" Experiences worki...

#116 From The "Holler" to Therapist to Creator Coach - Corey Wilks Psy. D. On Helping People Thrive 11.10.2022

Dr. Corey Wilks is a Licensed Clinical Psychologist and Executive Coach with over 15 years of psychological experience. In 2020, he stopped practicing therapy and ventured into entrepreneurship. Now, he coaches entrepreneurs and creates content to help people be more intentional with how they live, work, and create. His latest project is Intentional Life Design, a 5-week live cohort-based course f...

#115 Creativity as a Compass - Anne-Laure Le Cunff on Leaving Google, Freelancing, and Combining Creativity & Neuroscience, 03.10.2022

In this episode, I talk with fellow creator and curious human Anne-Laure Le Cunff. She left her job at Google and embarked on an entrepreneurial journey about one month before I did in April 2017.  We compare the lessons we have learned over the past five years as well as talk about: How her mother's experience as an immigrant influenced her work scripts Her creative interests vs. practical career...

#114 Training Elite Wall Street Traders - Michael Steiner on his time at SIG, using games to train market makers & becoming a high school teacher 26.09.2022

Mike Steiner found himself on Penn’s campus at a young age not really knowing what he was supposed to do next. Thanks to helpful roommates, he started to figure out how to take advantage of the opportunities around him. He started getting more interested in math, statistics, and finance. He eventually ended up interviewing in New York and ending up at the famous training firm Susquehanna Investmen...

#113 Beyond Hustle Culture & Helping Creators Make Money - Justin Moore from Creator Wizard on his journey as a Youtuber, creator, brand agency founder, musician, and now Sponsorship Coach 19.09.2022

Today I’m talking with Justin Moore - he and his wife was what he calls “OG Youtubers.” From creating content to landing sponsorships to building his own agency, he’s seen every angle of the creator economy. a lot over the last ten years. In the past couple of years, he walked away from the agency and has stumbled into a new path, one he’s finding a lot of joy following - helping other creators ge...

#112 The Power of Play In Work & Life - Gary Ware is Leading A Playful Rebellion 12.09.2022

Gary Ware is someone that inspires me. I've seen him give two walks, both at the World Domination Summit in 2018 and then in 2022.  In each, he stood out for his ability to show up as himself and share playful and powerfully true stories about his journey.  I love when I get to meet people like Gary and this interview was no different.  You can feel his positive energy flowing through the screen (...

#111 The Art of Self-Management - Claire Emerson on Quiet Achievers, Her Unconventional Path, Finding Digital Mentors & Overcoming Procrastination 06.09.2022

Claire Emerson is a writer and project consultant who helps business owners execute their best ideas. She is the curator of Flourish newsletter and the creator of Implement My Course — a free 10-day email course on how to apply what you learn without procrastination poisoning your progress.  Links Mentioned: Anna Macko - Crypto Queen (@lovingnotworking) • Instagram photos and videos We Don't Just...

#110 The Very Online Quasi-Wandering Monk - Tasshin Fogleman on Metta, Monasteries, Leisure, Work, Twitter and Finding Work That Matters 24.08.2022

I spoke with Tasshin Fogelman about his life's work to bring more love into the world, how he navigates life as a modern online monk, what he learned from spending time at the monastic academy, and what he see's as work worth doing. You can learn more about his work here: https://tasshin.com/ 📕Buy Paul’s Book (Published Jan 2020) : The Pathless Path 📲Connect + Follow Paul Twitter: @p_millerd Pau...

#109 Autism at Work, Early Blogging & Unconventional Paths - Tara McMullin 02.08.2022

Tara McMullin is a writer, host of the What Works Podcast, and also cofounder of a podcast production studio.  She's been working with small business owners for more than 13 years and has a deep understanding of what makes them tick.  She’s recently written about realizing she was autistic and how that has impacted her role in the workplace. 🍿 Watch On Youtube 🔗 Links: Tara's Site: Explore What...

The Nonlinear Life Path: College at 16, Med School in Cuba & Starting Over After Kids - Aida Alston 27.07.2022

Aida Alston is no stranger to alternatives to the default path. From testing out of high school at 15, to finishing college with no debt, then going to medical school for free in Cuba, Aida has been walking her version of a pathless path for a long time. But she's at a transition point now. She decided not to pursue clinical practice as a physician—again turning away from the default path right in...

Fixing The Healthcare System For Indies x Web3 - John Paller 19.07.2022

John Paller is a Denver-based entrepreneur and the Founder of Opolis , a Digital Employment Cooperative for independent workers. He is also the founder of ETH Denver, the world’s largest Web3 and Ethereum festival. Prior to discovering Ethereum in 2015, John spent more than 15 years in talent acquisition, HR Technology, and employment systems, building multiple successful enterprises. John brings...

How To Set Goals & Do Things That Matter - Malcolm Ocean 12.07.2022

Malcolm ocean is a fellow wanderer of the pathless path and as is such - is hard to describe. He runs a software company, Complice which helps people turn big goals into day-to-day actions. More broadly from my vantage point, Malcolm appears to be one of the most deeply curious humans alive about how we make things happen at the individual and group levels. Follow Malcolm: Website Twitter @Malcolm...

Lessons From Homeschooling, Skipping College & Carving Her Own Path - Hannah Frankman 28.06.2022

Hannah is awesome and you should listen to this podcast.  She grew up homeschooled, is an endlessly curious person, has a deep sense of agency, and is a pro at carving her own path.  She's done a ton of things including writing, coaching, and working at startups and has created jobs for herself, negotiated working remotely (before it was cool), and has done a ton of other things.  She recently fou...

What Do Digital Nomads Tell Us About The Future? - Lauren Razavi (Executive Director, Plumia) 22.06.2022

Lauren and I first talked when I was locked down in Taiwan in 2021.  It was amazing to connect with another nomad and writer after weeks of not seeing people.  I was also a bit stuck in my book writing process and she gave me a ton of helpful hints to take my book to the next level. I was excited to interview Lauren because she just finished her own book, Global Natives about her own experience as...

Growing up in Hawaii, Corporate Detours & The Future of Audio - Sky King 14.06.2022

This episode is with Sky King, the founder of Modern Stoa, a podcast advertising company for podcasters.  His path is fascinating - he grew up in Hawaii, rarely wore shoes, was heavily influenced by Asian culture, had a father who was retired, and somehow ended up in a massive corporation right after college.  In 2016. he became fascinated by how the media was shaping the 2016 US election and deci...

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