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 published in 2023 by William Morrow. Nina lives off the grid in the Santa Cruz mountains with 20 peop...
Jan 04, 2023•1 hr 9 min•Ep. 127
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 this in David's epic studio - I highly recommend watching this one on Youtube Links Mentioned: @davi...
Dec 15, 2022•1 hr 22 min•Ep. 126
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 0:00 Introduction 0:15 Introduction & Angie's challenge 1:06 Angie Challenging Relationship With Fitn...
Dec 13, 2022•56 min•Ep. 125
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" on a solo journey and how you are constantly starting from day 1. 🍿 YOUTUBE : https://youtu.be/my...
Dec 05, 2022•1 hr 18 min•Ep. 124
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 consulting during the first dot-com boom. He transferred from MIT to Brown in order to study linguistics, ...
Nov 28, 2022•1 hr 2 min•Ep. 123
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, Superstructures WATCH ON YOUTUBE: https://youtu.be/KC63HrF8V4E You can find Venkatesh: on Twitter @vgr ...
Nov 23, 2022•1 hr 21 min•Ep. 122
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 from a non-target school, and ultimately deciding to become self-employed with less than two years o...
Nov 14, 2022•1 hr 4 min•Ep. 121
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 and speaking about how to navigate systems that make self-employment harder in the United States, l...
Nov 07, 2022•2 hr 34 min•Ep. 120
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 navigated finding work that matters, getting married, and living in foreign countries together. 🍿 Wat...
Oct 27, 2022•2 hr 57 min•Ep. 119
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 haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash ...
Oct 24, 2022•1 hr 23 min•Ep. 118
🍿 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 working remotely since 2014 Working full-time remotely for Duck Duck Go What people get wrong about remot...
Oct 17, 2022•1 hr 13 min•Ep. 117
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 focused on helping people overcome limiting beliefs, think bigger, and do work that matters. Find Mor...
Oct 11, 2022•1 hr 25 min•Ep. 116
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 choices Getting into google and getting sucked into the tech world Quitting her job and thinking she...
Oct 03, 2022•57 min•Ep. 115
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 Investment Group (SIG). As a part-time trainer at first and then in a more central role, Mike started to expe...
Sep 26, 2022•1 hr 11 min•Ep. 114
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 getting paid as a sponsorship coach. He turned down a buyout offer for his course and newsletter becau...
Sep 19, 2022•1 hr 14 min•Ep. 113
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 (or earbuds!). 🍿🎞️ Watch This Episode on Youtube Links Mentioned: 📕Gary's book: Playful Rebellion Gar...
Sep 12, 2022•57 min•Ep. 112
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 Teach Content Marketing ... We Built Our Company With It (copyblogger.com) About The Kolbe A™ Index |...
Sep 06, 2022•51 min•Ep. 111
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 Paul’s Newsletter: Subscribe to Boundless Paul’s YouTube: Subscribe 🙏Further Ways To Support The Podca...
Aug 24, 2022•1 hr 14 min•Ep. 110
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 Works Twitter: @taragentile How learning I’m autistic changed the way I work Finding A Way to Take Up ...
Aug 02, 2022•1 hr 1 min•Ep. 109
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 front of her. She's been a full-time stay-at-home mother since then to her two children, raising th...
Jul 27, 2022•2 hr 32 min•Ep. 108
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 a breadth of experience in fundraising, investor relations, community outreach and crypto economies,...
Jul 19, 2022•52 min•Ep. 107
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_Ocean Sign Up For Complice and get one bonus week CrowdHealth: You ditched the traditional path… wh...
Jul 12, 2022•2 hr 38 min•Ep. 106
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 founded Rebel Educator which is a media brand that aims to share more about homeschooling and alternative ...
Jun 28, 2022•1 hr 20 min•Ep. 105
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 a nomad (since 2013!) and also the past, present, and future of the movement. I think she is one of t...
Jun 22, 2022•1 hr 10 min•Ep. 104
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 decided it was time to act. From a cold email to Ryan Holiday to helping build Aubrey Marcus' podcast, Sky...
Jun 14, 2022•1 hr 8 min•Ep. 103
Being an undeclared major till his senior year of college, Lawrence didn’t really know what he wanted to do. After looking up which jobs make the most money, he decided to declare as an economics major, leading him to explore Investment Banking. While he didn’t end up working in investment banking, he was still pulled by the power of prestige, something he says “is a drug, and is most potent” when you are young and looking at schools. Over a number of years and experiments with music and creatin...
Jun 07, 2022•1 hr 6 min•Ep. 102
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 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold) : The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul Twitter: @p_millerd Instagram: @pathlesspaul Paul’s Newsletter: Subscribe to Pathless (23k+ People) Paul’s YouTube: Subscribe 🙏Further Ways To Support The Podcas...
Jun 01, 2022•35 min•Ep. 101
Tim Malnick has always lived between the two worlds of business and creative/activist circles. In his twenties, he stumbled into a creative group of young people, of which “none of them following the obvious path.” This gave him a lot of confidence that different kinds of paths were possible and enabled him to offer a diversity of perspectives that he was able to bring to many different environments. One of the things he spends a lot of time on now is helping people transcend their relationship ...
Mar 28, 2022•1 hr 8 min•Ep. 100
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 music growing up, how he became an accidental founder, and how he's exploring his relationship with work after exiting his startup. He was named one of Inc.'s “30 Under 30” and has founded multiple software businesses including MAZ and ClickEasy (originally Bounce House), both of which were acquired in 2021. He is an angel investor...
Mar 21, 2022•59 min•Ep. 99
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 in the book. Check out Sasha here: Sasha Chapin (imsashachapin.com) & Buy Paul's Book https://think-boundless.com/the-pathless-path/ 📘 GOOD WORK: LIVE! => Learn More 📕 Buy Paul’s Book (50k+ Sold) : The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow Paul Twitter: @p_miller...
Feb 12, 2022•47 min•Ep. 98
