The Pathless Path Podcast
Conversations with people on unconventional paths covering topics such as life design, meaning, creativity, digital nomadism, writing online, reinvention, and parenting
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201 episodes Angie Finished Her Memoir! - Angie and Paul on the creative process, parenting, travel, writing, life challenges, and books Michael Ashcroft on Getting Lost and The Joys of Dad Life What's After BigLaw & Consulting? - Allie Canton & Paul Millerd On Reinvention, Parenting on The Pathless Path & as Parent Commit A Career Ending Move - Steven Foster on Permissionless Paychecks, Communal Living & Battling Life's Challenges While Pathless The Yoga Of Work - Andrew Taggart 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 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 The Inner Game of Work: Pranab Sachi on Codependent Origination, Rob Burbea, Quake Books, Attentional Co-Piloting, Michael Taft, and "Non-Success" Lawrence Yeo: Listening To Your Inner Compass Climbing The Wealth Ladder With Nick Maggiulli Hustle & Flow - Jack Moses on dropping out of school, hustle culture, spiritual paths, finding flow, and travel as transformation Paul Q&A Episode - Moving to Asia, Parenting, Preparing for Kids, Pathless Hardcover Art Edition Becoming A Writer - Nat Eliason on his upcoming fiction release, traditional publishing vs. self-publishing, AI tools, tinkering, readers, launch plans Matt Yao Interviews Me #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 The Six Pillars of Agency: Insights from Poker Pro and Entrepreneur Cate Hall Justin Welsh: From Burnout To Solopreneur (Podcast) 1 Year Dad Reflections - Conversation with Sky King & Nat Eliason #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 #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 Rethinking Work & Education via Montessori Schools - Matt Bateman David Pakman: Long-Term YouTube Careers, Loving Work, Rest & Breaks, Fatherhood & Politics #170 Apprenticeships, Sabbaticals & "Good Work" — Steve Schlafman & Matt Yao on slowing down, deprogramming, unlearning, learning from others, deciding to quit, going on a sabbatical, not being jealous anymore, competitiveness and enoughness, finding good work, ambition, the apprenticeship, Downshift, decelerator, marriage, family and reframing money Creating Margin For Life & Running a "Calm Company" | Justin Jackson (Pathless Path Podcast #168 Building With "margin for life" — Justin Jackson on lessons from running a skate shop, optimizing for profit, running a "calm company," co-founding Transistor, having kids early, designing margins and how money actually does make him happy #167 Wandering in the Wilderness — Dom Francks on confronting fragility, his love of nature, the disconnect from nature, working as a software engineer, viewing yourself as a piece of poetry, how we're always embedded in nature and being guided by intuition #166 Breaking Free of the Rules — Rick Lewis on being a child actor, dropping out of college, being a professional juggler, street performing and a clowning, the corporate world as an outsider, breaking rules, parenting and how to reinvent yourself #165 Gardening in the Digital Ecosystem — Kevin Espiritu on his fascination with the early Internet, how Poker broke his brain on money, starting his YouTube channel, Epic Gardening, taking a long term perspective, how to structure a video, transforming his YouTube channel, introducing new people to his audience, the probabilistic mindset and what he learnt from poker that helps him in his life Joe Hudson on The Art of Transformation In The Modern World | Pathless Path Podcast #164 Transformation For High Achievers — Joe Hudson on growing up with an alcoholic father, living around the world, transformation and self-discovery, becoming comfortable with yourself, emotional fluidity, expressing emotions, and the art of parenting The Strategic Independent: Tom Critchlow on Blending Consulting, Courses, and Creativity The Unscripted Journey: How Erin Doppelt Learned To Trust Her Inner Wisdom To Build An Intentional Life The Future of Indie Consulting & Life - Venkatesh Rao From Selling Steel to Tech CEO: Jovian Gautama on Leveraging The Internet Money & The Creator Economy (How To Get Rich) - Steph Smith | Pathless Path Podcast Daniel Vassallo - The Self-Employment Meta Game (Podcast) Why I Turned Down A $200k Publishing Offer From The "Holler" to Therapist to Creator Coach - Corey Wilks Psy. D. On Helping People Thrive Jenny Blake on Saying "No" to Something Good, Free Time and Pivot | The Pathless Path Podcast What Do Digital Nomads Tell Us About The Future? - Lauren Razavi #162 Money, Work, Parenting & 1 Month In Taiwan - Angie & Paul on money scripts, cultural differences, being Taiwanese in the US, being American in Taiwan, perceptions of work in their families, life with a newborn, impostor syndrome, remote work and travel #161 9 Year Identity Crisis?! - Tom Critchlow on being stuck, indecisiveness, going to wander, taking every 7th week off, strategically dropping the ball, hiring an editor, and fear of finishing his book #160 - Why Manifesting Works — Erin Doppelt on how living in Israel and India changed her life, "snapshot manifestation", why women should work aligned with their menstrual cycle, entrepreneurship as freedom for women, pregnancy, and her new book Living Intentionally After "Enough" - Bilal Zaidi on leaving Google, emigrating to the US, the intensity of New York, writing poetry and spoken word, and travel vs. vacations (Pathless Path Podcast) From Rugby to Writer & Book Influencer: How Ben Mercer Reinvented Himself #157 Parenting & Our Future - Paul & Angie Check-In on Five Months of Parenting, Unexpected Happiness, Parenting Scripts, and The Time Bucket Exercise from Die With Zero Ali Abdaal on Identity, Prestige, Quitting Medicine | The Pathless Path Podcast Kyla Scanlon on the Passion Crisis, Vibecession, and Quitting Her Job To Bet On Herself | The Pathless Path Podcast #155 Homeschooling = Future of Education? - Hannah Frankman (Repost) Luke Burgis on Mimetic Desire, The Three City Problem & Academia | The Pathless Path Podcast Melvin Varghese: The Creator Therapist | The Pathless Path Podcast Why Sheryl Sandberg is Wrong — Dawn Baker on The Art of "Leaning Out" | The Pathless Path Podcast #154 Learning to "Lean Out" - Dr. Dawn Baker's Journey from Medicine to 'Leaning Out', Embracing Unconventional Paths, Living Off-Grid, and Homeschooling #153 Beyond Mimetic Desires - Luke Burgis on the temptations of conformity, contemplating life in Starbucks, thick desires and thin desires, letting go of control, the importance of play, learning from different work cultures, his stay in Rome and becoming a father Goofing Off On Purpose - Kevin Kelly on owning his time, staying optimistic about the future, raising children, and his new book Excellent Advice for Living | The Pathless Path Podcast Derek Sivers on Ideas That Are Useful, Not True, Booking a One-Way Flight, Living on a Kid's Not Adult Schedule & "True Ambition" | The Pathless Path Podcast Anna Gát Reinvented Herself and Digital Intellectual Culture (The Pathless Path Podcast) #151 Culture Without Culture War - Anna Gát on growing up in Hungary, emigrating at the age of 30, staying curious as we age, Interintellect, building a startup, bad advice and trusting your gut, her article in 2018, culture without culture war, creating your own gatekeepers, and success in the UK vs US #149 "I will sell out Madison Square Garden" - Danny Miranda on starting a blog at 14, following your intuition, discipline, meditation, his podcast, retreats, masculinity, compassion, "The True Path", thinking big, and trusting The Universe #148 Embracing Post-Traumatic Growth - Jessica Depatie on her Korean background, shadow work, producing a documentary - "Dark Night of Our Soul", expanding your perspective through travel, what does it mean to rest, defining growth, the hero's journey, and memes #147 You Can Love Cooking Too - Myles Snider on intuitive cooking, living in Argentina, working in Tulum, food industry scripts, health myths, the beauty of "slow cooking" #146 Separating Work & Identity - Simone Stolzoff on the myth of a "Dream Job," last-minute around the world trip, journalism, work, identity, writing his book, knowing when to quit, and the dangers of turning passion into a livelihood #145 Capitalist by Day, Spiritual by Night - Alex Hardy on achievement, Wall Street, tech startups, exiting his company, pride & suffering, his sabbatical, suppressing his curiosity and rediscovering his passions #143 The Art of Living - Kyle Kowalski on how to have an existential crisis, synthesizing the art of living, curiosity as fuel, his relationship with money, "killing himself to work" and "purpose washing" in big companies #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 #140 Tom Peters - Fired from McKinsey to Top Business Thought Leader #139 Compounding Memes - Trung Phan on his great grandfather, living abroad, the expat community in Asia, writing, working at The Hustle, children and work, balancing his various activities, going solo, and playing the long game #137 Life as Conversation - Russ Roberts on his relationship with his father, starting the EconTalk podcast in 2006, Adam Smith, why people want to be "lovely", aiming high, why it's hard to have fun, misunderstandings of the academic world, and moving to Israel in his 60's #136 Complexity & Complicatedness - Sam Spurlin on playing hockey, why he quit teaching, studying at Claremont, leaving a PhD program, working pro bono too start his career, complicated vs complex systems, how to deal with ego in organizations, remote work failures, podcasting with his brother, and the importance of a retrospective meeting #135 Beyond Comfort - Derek Sivers on why great musicians shake things up, ambition, and moving to a new country as a superpower, lessons from Singapore, and the scripts around having children #134 The Office-Based Reality is Over - Dror Poleg on entrepreneurship in Israel, studying in Australia, working in China, Future of Remote Work and The Real Estate Business, How To Write A Top 5 Book in Almost Any Category, The Disappearance of The Middle-Skilled Job, Inequality and The End of The Offices #133 Creation Without The Ego - Isabel Unraveled on writing, "the chronic state of performing", detaching your sense of self from the work, finding the inner child, paying attention to your emotions, trusting your intuition and why people should stop pretending #132 Making Money Simple & Smart - Nick Maggiulli on blogging into a new career, writing for smart people, building relationships in the finance world, the lifestyle creep myth, dying with too much money, and money emotions #131 The Art of Sabbaticals - Cécile and Michelle on finding "forgotten hobbies", writing online, improving their relationship with money, abundance mindset and rediscovering joy #130 You Have One Life - David Senra on finding his life's work, trial & error, the necessity of talking risks, mortality, balancing his entrepreneurial endeavours and family life and what can be learned from reading hundreds of biographies. #129 Friendly Ambitious Nerd World-Building - Visakan Veerasamy on Long-Orbit Friendships, Preemptive Defensiveness, "Hot Streaks," Writing A Book, Making $1000 for one copy & Negative Comments #128 Crafting A Life You Love - Amy Tangerine on working in fashion, carving her own path, starting a business, a third-life crisis, scrapbooking as contemplation and learning from and inspiring her children #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 David Perell on The Scripts of School and Becoming an Internet Citizen | The Pathless Path Podcast #125 Angie & Paul - We're Having a Kid (and other life updates) #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 #123 McKinsey Partner to Indie Freelancer - Adam Braff on writing online, the gig economy, consulting skills, consulting #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, #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. #118 A Better Future for Healthcare - Andy Schoonover on Crowdfunding for Healthcare, Search Funds, Buying A Company, Work-Life Balance, Bitcoin & Problems With Healthcare #115 Creativity as a Compass - Anne-Laure Le Cunff on Leaving Google, Freelancing, and Combining Creativity & Neuroscience, #114 Training Elite Wall Street Traders - Michael Steiner on his time at SIG, using games to train market makers & becoming a high school teacher #112 The Power of Play In Work & Life - Gary Ware is Leading A Playful Rebellion #111 The Art of Self-Management - Claire Emerson on Quiet Achievers, Her Unconventional Path, Finding Digital Mentors & Overcoming Procrastination #109 Autism at Work, Early Blogging & Unconventional Paths - Tara McMullin The Nonlinear Life Path: College at 16, Med School in Cuba & Starting Over After Kids - Aida Alston Fixing The Healthcare System For Indies x Web3 - John Paller Malcolm Ocean on Rationality, Goals, Self-Awareness & Motivation as a Self-Employed Entrepreneur Hannah Frankman On Why Homeschooling Matters & Why It Helped Her Skip College Lauren Razavi on Digital Nomads and The Future of Global Mobility & Digital Citizenship (The Pathless Path Podcast) Sky King on Growing up in Hawaii, Quitting to Work At a Smoothie Bar & Building The Future of Podcasts (The Pathless Path Podcast) Lawrence Yeo On The Arc of The Practical Creator, Creativity & Finding Work That Matters (The Pathless Path Podcast) Podcast Update! Re-branded as The Pathless Path & LIVE Q&A From Youtube The Money Path or The Life Path? - Tim Malnick Music, Entrepreneurship & Embracing Non-Work - Paul Canetti The Magic of Writing with Sasha Chapin Khe Hy - Tales From The Pathless Path The Pathless Path Launched! (reading of the introduction) How a Trader Models The Solo Creative Journey - Kris Abdelmessih (Podcast) The Formless Path - Money, Fatherhood & Creativity (Howard Gray) How To Tame The Shadow Side Of Solopreneurship - Darren Joe (Podcast) Six Months In The Creator Economy - Michael Ashcroft (Part 3) Accidental Freelancer To Brand Consultant, Founder & Freelance Coach (Austin Church) Burnout & "Living At Work" In 2020 - Natalie Rachel Ben Hunt on Industrially Necessary Paths & How To Live In The Now Money Fears, Self-Employment & Living Abroad With Kids - Jenni & Lisa Dazols A Sabbatical Every Seven Weeks - Sean McCabe What happens six months (and three months) before you quit? - Michael Ashcroft Who are digital nomads? (Professors Rob Litchfield & Rachael Woldoff) Quitting To Teach History to 500k+ on TikTok (Michael McBride, Creator of Idea Soup) Amy McMillen - Leaving a Path That Makes Sense (Podcast) Oshan Jarow: The Reality & Possibilities For Work Packy McCormick - Making Newsletters Fun (Podcast) Curating Goodreads Remotely (Uri Bram, CEO of The Browser) Steph Smith - Carving a 21st Century Career & Life (Podcast) Packy McCormick - Bringing Fun To Newsletters Since 2019 Podcast Update Nov 2020 - The Pathless Path Angie Wang - My Partner On This Crazy Journey Amy McMillen - Wandering In Uncertainty & Writing A Book (Mid Pandemic) Will Bachman: Building an Independent Consulting Practice With a 5-Decade Success Mindset Reflection with Andrew Taggart on Work & Life Laurel Farrer on The Global WFH Experiment & The Long-Term Promise Of Remote Work Diania Merriam on Imagining The New American Dream Longform Thoughts: Why Organizations Undermine Creativity & Potential Amir Salihefendić on trust, communication & deep work in building a remote company A Remote Company With 40 Vacation Days?! (Amir Salihefendić, CEO Doist) Moataz Ahmed on Freedom, Creativity & His Journey To Overcome Laziness Visakan Veerasamy On The Curious Humans Of Twitter & Creating His Own Work Alex Pang on Working Less, Rest, Leisure & The 4-Day Workweek Geography & Culture Side Hustle Experiments w/ Rohith The Phases & Emotional Journey Of Making A Work Shift (Stephen Warley) Andy Sparks on Writing, Entrepreneurship, Success & Life As A Lake Good Writing & Doing Work That Matters (Andy Sparks, CEO Holloway) Alex Hillman on Coworking That Works & The 10K Independents Project Ben Brooks on coaching, trust, the art of management & entrepreneurship Should Everyone Have A Coach? (Ben Brooks, Founder of Pilot) John Zeratsky on what living on a boat for 18 months taught him about work, belonging, comfort & money Hannah Wei on her nomadic life, competing in her first Muay Thai fight, dealing with burnout & tinder experiments Alastair Humphreys on microadventures, long-term travel and busking his way through Europe Ben Keene on dreaming, starting a tribe & living on an island with three kids Heather McGowan on learning, adapting & identity in the future of work Richard Sheridan On Building A Life And Company Filled With Joy Building a mission-driven career (Jerel Bonner) How to fill your morning with purpose and joy (Craig Kulyk) How Wesley & Tanya Are Co-Creating a Life and An "Actually Slim" Dress Shirt Company Chris Kirkland on Running TokyoCheapo.com, Living In Japan, and Lessons On Entrepreneurship & Living Nomadically Martha Balaile on creating inspiring art filled with magic Reimagine Work & A Short Update From Paul Gabi Macra's journey from the basketball court to the yoga mat Christine Bader on "Learning To Quit" & Life Reinvention Building & Investing In Calm Companies (Tyler Tringas) Paul on success, storytelling, learning & experiments (UX Gorilla Interview) Launching Uncommonly: One Year Later (Chris Donohoe) Guest Episode: Joe Dumars x Adam Grant x Cody Royle Learning, Self-Employment & Making Business More Human (Mike Tannenbaum) The Top 10 Career Myths We Should Stop Believing Mini Episode: Five Things Before You Leap: Lessons From The Self-Employed Bryan Victor, Unconventional Singaporean on creating his own education through wedding planning, year-long travel & creating a visual animation studio Tash Walker On Why Companies Should Adopt A 4-Day Workweek Why every company should adopt the 4-day workweek (Tash Walker) The Real Gig Economy: Sarah Kessler, Author of Gigged Screw The Cubicle With A Side Of Pineapple (Lydia Lee) How A Remote Company Enables Freedom, Trust & Digital Dance Parties (Wade Foster, CEO of Zapier.com) "My Name Is Nemo and I Don't Do Small Talk" Ervin Ling On Escaping The Corporate World At 30 To Travel The World Ted Bauer: The Absurdity Of The Corporate World & Real Future Of Work Shayne Spencer on the "dumb idea project" and how failing econ helped him start his firm YuTing Chiu on cultural sound differences, building instruments & creative expression Jacqueline Jensen on sabbaticals, rethinking work and building a "calm company" Dr. Laura Gallaher on humor at work, leadership at NASA after crisis, and building a business traveling the world Andrew Taggart, Practical Philosopher on how "total work" has taken over our lives Podcast Update, Digital Course Experiment & Moving To Asia Tony Triumph on growing up entrepreneurial, moving to NYC with $300 and building incredible relationships Rohan Rajiv on learning through 3500+ daily blog posts Reflections: One year of freelancing, experiments & other people's reactions Luke Kanies on his journey from commune to CEO and why people hate working for big companies Candace Cabrera Moore, fearless yoga entrepreneur on building a global business, brand & community Boundless Podcast - Stephen Warley on the biggest shift since the industrial revolution (Episode 19) Boundless Podcast - Nita Baum on how to "be free" and self-employed (Episode 18) Boundless/Unleashed: Paul on the future of work, freelancing and his media diet (Episode 17) Damien Peters on blogging, wealth, and building a remote business from Spain (Episode 16) Connor Gillivan on entrepreneurship, selling on Amazon and working with freelancers (Episode 15) Jen Morilla on breaking plates, grief and traveling the world with purpose (Episode 14) Boundless Podcast: Romy Rost on leadership, freelancing & coaching as a skill (Episode 13) Boundless Podcast: Tanya Alvarez on resilience, entrepreneurship & community (Episode 12) Boundless Podcast: Pauri Pandian - Tennis as a career, coaching & healthy masculinity (Episode 11) Boundless Podcast: Ben Dubow On State Department Rejection To Propaganda-Fighting Startup Founder (Episode 10) Boundless Podcast: Amma Marfo on Combining Humor, Creativity & Writing (Episode 8) Tom Critchlow on Personal Branding, Freelance Consulting & The Future of Work Cody Royle On The High-Performance Secrets The Business World Should Steal From Sports Janet Matta, Rock Star Career Coach On The Alternative Paths We Fail To See Super Bowl Minisode - Cody Royle on The Patriots and what business can learn from sports Chris Donohoe on Quitting The Corporate World & Founding His Own Firm David Vaucher on Ending His Career to Start His Life Noel Boyland On Building A Career & Life That Matters Episode 1 —Boundless Podcast — Why I care about the future of work