All Episodes
Displaying 61 - 90 of 187 in total
#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
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 museu...
#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
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...
#125 Angie & Paul - We're Having a Kid (and other life updates)
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 ...
#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
David talks about his self-employment journey, discussing topics such as graphics design, studying abroad, work identity and engagement, self-publishing books, and adv...
#123 McKinsey Partner to Indie Freelancer - Adam Braff on writing online, the gig economy, consulting skills, consulting
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...
#122 Indie Life & The Future of Work - Venkatesh Rao
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 ...
#121 Carving Your Own Path In a "Vibecession" - Kyla Scanlon on leaving her job, writing online, TikToks as Poetry, and The Passion Crisis
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 sh...
#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,
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...
#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.
Enroll In The 5th Cohort of Nervous System Mastery: You can get $250 OFF using the code PATHLESS => nsmastery.comJonny Miller is a dear friend and I've had the privile...
#118 A Better Future for Healthcare - Andy Schoonover on Crowdfunding for Healthcare, Search Funds, Buying A Company, Work-Life Balance, Bitcoin & Problems With Healthcare
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...
#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
šæ Watch on YouTubeAli 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 ...
#116 From The "Holler" to Therapist to Creator Coach - Corey Wilks Psy. D. On Helping People Thrive
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 ventu...
#115 Creativity as a Compass - Anne-Laure Le Cunff on Leaving Google, Freelancing, and Combining Creativity & Neuroscience,
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 mont...
#114 Training Elite Wall Street Traders - Michael Steiner on his time at SIG, using games to train market makers & becoming a high school teacher
Mike Steiner found himself on Pennās campus at a young age not really knowing what he was supposed to do next. Thanks to helpful roommates, he started to figure out ho...
#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
Today Iām talking with Justin Moore - he and his wife was what he calls āOG Youtubers.ā From creating content to landing sponsorships to building his own agency, heās ...
#112 The Power of Play In Work & Life - Gary Ware is Leading A Playful Rebellion
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.Ā In each, he stood out for his abili...
#111 The Art of Self-Management - Claire Emerson on Quiet Achievers, Her Unconventional Path, Finding Digital Mentors & Overcoming Procrastination
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 Impl...
#110 The Very Online Quasi-Wandering Monk - Tasshin Fogleman on Metta, Monasteries, Leisure, Work, Twitter and Finding Work That Matters
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 tim...
#109 Autism at Work, Early Blogging & Unconventional Paths - Tara McMullin
Tara McMullin is a writer, host of the What Works Podcast, and also cofounder of a podcast production studio.Ā She's been working with small business owners for more t...
The Nonlinear Life Path: College at 16, Med School in Cuba & Starting Over After Kids - Aida Alston
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 ...
Fixing The Healthcare System For Indies x Web3 - John Paller
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, t...
How To Set Goals & Do Things That Matter - Malcolm Ocean
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 in...
Lessons From Homeschooling, Skipping College & Carving Her Own Path - Hannah Frankman
Hannah is awesome and you should listen to this podcast.Ā She grew up homeschooled, is an endlessly curious person, has a deep sense of agency, and is a pro at carving...
What Do Digital Nomads Tell Us About The Future? - Lauren Razavi (Executive Director, Plumia)
Lauren and I first talked when I was locked down in Taiwan in 2021. Ā It was amazing to connect with another nomad and writer after weeks of not seeing people. Ā I was a...
Growing up in Hawaii, Corporate Detours & The Future of Audio - Sky King
This episode is with Sky King, the founder of Modern Stoa, a podcast advertising company for podcasters.Ā His path is fascinating - he grew up in Hawaii, rarely wore s...
The Arc of The Practical Creator - Lawrence Yeo
Being an undeclared major till his senior year of college, Lawrence didnāt really know what he wanted to do. After looking up which jobs make the most money, he decide...
Podcast Update! Re-branded as The Pathless Path & LIVE Q&A From Youtube
I offer a short little update on the next steps for the podcast and include a live Q&A I did on youtube last week. Video link: https://youtu.be/CGbw7Q8hoys
The Money Path or The Life Path? - Tim Malnick
Tim Malnick has always lived between the two worlds of business and creative/activist circles. Ā In his twenties, he stumbled into a creative group of young people, of ...
Music, Entrepreneurship & Embracing Non-Work - Paul Canetti
Paul Canetti is a professor at Columbia Business School and sits on the Strategic Advisory Board of Riverside Acceleration Capital. We explore his initial passion for ...
The Magic of Writing with Sasha Chapin
I talked with writer and writing coach Sasha Chapin about the role of writing in our lives, how we think about writing, and how he specifically helped with my process ...
