Sam is a partner at The Ready - an organizational design consultancy operating fully remotely. He is also a prolific writer, passionate about personal development, self-managing organizations and adopting a more human, adaptive, and meaningful way of working.🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @samspurlinInstagram: samspurlinLinkedIn: linkedin.com/in/samspurlinSam's writing: samspurlin.com/writingSam's writing on Medium: samspurlin.medium.comNewsletter: thedeliberate.substack.com/p/landing-page⌛TIMESTAMPS(00:53) - The scripts that Sam grew up with (10:09) - Teaching and why Sam quit (17:10) - Claremont and letting go of the PhD (25:49) - Working pro bono to become a consultant (31:26) - Complicated vs complex systems, ego in the organizations (53:49) - Writing, podcasting, farming and retrospective meetings (01:02:02) - The trap of a "dream job" (01:05:27) - Closing remarks 📕Buy Paul’s Book (Published Jan 2022): The Pathless Path😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path? - Join 100+ Others In The Find The Others Community📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Derek Sivers has been a musician, producer, circus performer, successful entrepreneur, TED speaker, and book publisher. He has lived all around the world and has never let himself be too comfortable - constantly changing and following his inner ambition.🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @siversWebsite: sive.rsMy Favorite Derek Book: Anything You Want⌛TIMESTAMPS(00:54) - The scripts that Derek grew up with (05:45) - Comfort as a plateau that needs to be shattered (11:46) - Travel as a tool to change your life (17:26) - Beliefs and actions (22:48) - Learning from other people's approaches to life (27:44) - Derek's future and how to learn from when our lives go off track (33:53) - Scripts around having kids (45:03) - Retirement & Ambition (56:25) - Closing remarks 📕Buy Paul’s Book (Published Jan 2022): The Pathless Path😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path? - Join 100+ Others In The Find The Others Community📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Dror worked as a real estate private equity exec, startup founder, front-end developer, parliamentary advisor, and soldier. Having lived all around the world he is now based in NYC, writing as an “Economic Historian”.Having predicted that remote work is going to become the new norm back in 2015, he has just published a survival guide titled "After Office".🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @drorpolegWebsite: drorpoleg.comAfter Office ⌛TIMESTAMPS (13:30) - Living in Australia and China (23:10) - Writing and Work in Dror's life (27:46) - Remote Work and Real Estate (42:26) - Using information from the Internet - writing a top 5 book (49:42) - Unconventional Paths and The Disappearance of The Middle-Skilled Jobs (58:56) - Inequality, Luck, and Challenges for The US   📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Isabel is a writer who is very passionate about the creative process. She has some powerful original ideas about the relationship between the artist and their creation, trusting one's intuition, and why people should stop pretending.🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @isabelunraveledIsabel's Writing: https://mindmine.substack.com⌛TIMESTAMPS(0:11) Introduction (5:41) "The chronic state of performing" (12:00) Missing and rediscovering her passion for writing (34:38) Detaching your sense of self from the work (41:52) The inner child (53:02) Why people should just stop pretending? (1:00:30) How Isabel thinks (or doesn't think) about her future? (1:04:09) Closing remarks 📕Buy Paul’s Book (Published Jan 2022): The Pathless Path 😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path? - Join 100+ Others In The Find The Others Community📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Nick Maggiulli is a finance data analyst and writer. He is the author of "Just Keep Buying" and has a blog titled "Of Dollars and Data".🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @dollarsanddataBlog: Of Dollars and DataNick's Book: Just Keep Buying ⌛TIMESTAMPS(0:47) The scripts nick grew up with(5:35) Writing books and blogging(32:44) Building relationships in  the NYC finance scene(36:07) Why the writers shouldn't dumb down their books(37:33) Perceptions of money(1:07:26) Closing thoughts📕Buy Paul’s Book: The Pathless Path🤝Join Find The Others: A Community For People On Unconventional Paths📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Cécile has had a successful career in consulting, acquiring a senior position in a big company that has taken a leadership role in the energy transition in the UK. Although she was passionate about her job she decided to go on a yearlong sabbatical from work, traveling around the world and writing - creating space for her curiosity & creativity.Michelle has a background in sales but after a couple of years in the business she decided to go on a sabbatical that doesn't seem to have an end. When she isn't busy fending off people who constantly try to hire her, she runs a podcast with her sister - "Status Post Adulting Podcast" and she has written multiple essays, while slowly "getting famous for not working" in the meantime.🎥🍿 YOUTUBE: WATCH HERECécile:Twitter: @cecile_mcmWebsite: https://www.cecilemarion.org/Book a 1-on-1 Call With Cecile (Gift Economy): Book HereMichelle:Twitter: @mvarghooseMichelle's Essays: NewsletterPodcast: Status Post-AdultingMy Essay On The Ultimate Guide To Sabbaticals⌛TIMESTAMPS(0:00) Audio intro(2:27) Deciding to go on a sabbatical (25:29) "There is nothing to do" - rediscovering joy (30:05) Lowering the cost of living (46:58) How people change on a sabbatical - discovering writing (1:08:30) Getting famous for not working, the gig economy(1:11:17) The role of writing in Cécile's journey (1:15:37) Returning to work - closing thoughts📕Buy Paul’s Book (Published Jan 2022): The Pathless Path 😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path - Join 75+ Others In The Find The Others Community📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

David Senra is the creator of Founders Podcast and is obsessed with bringing alive the knowledge of the most driven, curious, courageous, and interesting founders throughout history.  He has spent almost all his time reading, re-reading, and recording one of the best podcasts on the planet right now. Links:Follow his podcast: @FoundersPodcastListen: Founders Podcast or Itunes⏳TIMESTAMPS2:58 The scripts David grew up with8:09 Working full time while in high school and during college20:47 Trial and error, finding his life’s work33:24 Why David thinks keeping his podcast behind a paywall was a mistake51:15 Nobody understands the scale of the Internet54:15 The time needed to succeed1:03:56 Ed Thorp - balancing being an entrepreneur with one's family life1:14:02 Lessons from David Ogilvy and Marvin Bower1:24:57 The necessity of taking risks📕Buy The Pathless Path (Paul’s Book, published Jan 2022): The Pathless Path😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path - Join 100+ Others In Find The Others 📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter (8,700 subscribers): Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality videos using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Visakan Veerasamy is an internet creator and writer, he is passionate about the future of the internet, ideas, and how people can be bolder on their creative journeys.  His mission is to build the greatest social graph of friendly, ambitious nerds that the world has ever seen.This is our second conversation and dives much more into his current work and how he thinks about the internet. 🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @visakanvWebsite: visakanv.com Buy Introspect: On Gumroad⌛TIMESTAMPS(0:00) Audio intro(2:27) Long-orbit friendships(7:34) Can rooting for people be learned?(8:54) Preemptive defensiveness vs live and let live(12:55) Agreeing with the letter but not the spirit(14:11) The conformist culture of the US(15:53) Having a positive vision vs just being against something(20:04) Posting trajectories, long-term engagement(28:38) Trying to replace income, burnout, and learning patience(36:22) Micro-existential crises(40:07) How is Visakan making money these days?(44:31) Charging based on value, not on prestige(46:41) "A homeostatic impulse" to always make the same amount of money, limiting beliefs(52:19) Pricing books and managing your expectations(58:10) How did it feel to get $1000 for a book?(1:00:36) People Visakan is following, shoutouts(1:13:52) Understanding the scale of the Internet and having low expectations(1:20:31) Persistence and heart is all you need(1:26:25) The Internet as a spiritual practice - dealing with negative comments📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Amy Tangerine is a long-time creator, entrepreneur, and mother. We talk about her path, starting a business that took off, her "third-life" crisis, learning to inject rest into her path, her relationship with her mother, having children, scrapbooking and building a business around work she loves. WATCH On YouTubeFOLLOW AMYHer Website: amytangerine.comTwitter: @amytangerineInstagram: @amytangerineFacebook: @amytangerineTIMESTAMPS0:00 Audio intro0:12 Introduction1:10 The scripts Amy grew up with2:35 Amy's parent's path and the ancestral trauma6:00 How Amy's parents inspired her11:03 Amy's vision of her future after graduating college13:50 The seeds of doubt about her path14:57 The 1/3 life crisis17:43 Keeping in touch with your creative side24:57 Scrapbooking & contemplation29:33 Suffering a miscarriage and writing a book37:13 The 3 F's - Fulfillment, Freedom, and Fun39:07 Creative freedom42:39 The challenges of working creatively44:39 Having kids48:16 Overthinking and worrying📕Buy Paul’s Book: The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality videos using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 people, 16 chickens, 2 trampolines, and 1 zipline.We talk about:Leaving her dream jobLiving in an intentional "off the grid" communityWhat she learned from her ambitious days as a museum industry leaderMarriage & kids on an unconventional pathWriting her novelWATCH On YouTubeFOLLOW NINAHer Website: NinaSimon.comTwitter: @ninaksimonTIMESTAMPS0:00 Audio intro0:12 Introduction1:37 The scripts Nina grew up with4:43 Did Nina see herself as creative growing up?5:39 Nina's education and why she hated her dream job at NASA12:17 Fitting your life into your job vs fitting your job into your life14:39 Nina's approach to money, building a marriage that supports entrepreneurship19:55 Writing books27:39 Giving herself a permission33:17 Making choices that are not "the right choice"38:37 The non-traditional paths and having kids46:08 Reinventing yourself, knowing when to leave52:42 Constructing backward narratives about our lives📕Buy Paul’s Book: The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality videos using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 YoutubeLinks Mentioned:@david_perell (Twitter)David's course Write of PassageFriday Find's LinksAct of Creation (Koestler)Denial of Death (Becker)Art of Loving (Fromm)Gutenberg Galaxy (McLuhan)The Managerial Revolution (Burnham)Tribe (Junger)Bullshit Jobs (Graeber)@culturaltutor (Twitter)📕Buy Paul’s Book: The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality videos using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trialEditing by Atman Pandya 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 YOUTUBELinks:Angie's Site: Angie Creates Her Experience in Write of Passage: From Fear To ThrivingAngie's Podcast: Angie Creates (English & Chinese)Timestamps0:00 Introduction0:15 Introduction & Angie's challenge1:06 Angie Challenging Relationship With Fitness6:48 Letting go of Fitness after launching a course10:40 Setting a deadline to quit fitness creator stuff13:35 Moving back to the US with Angie & mindsets16:05 Struggling to find a job and US business culture17:25 Success narratives from Paul's family22:15 Communities that accept you & Write of Passage24:05 Angie's experience in Write of Passage34:35 Freelancing for course creators36:15 We're having a kid!40:30 Self-employed life and kids42:30 Afraid of being a "full-time mom"43:45 Work, money & identity49:05 Paul & Ambition📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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/mykDRmuDvwI Links Mentioned: Davids SiteTime Management Not Mind ManagementJefferson Letter About TravelOn "Making It and 15 Years as a Creator Love Your WorkMini-LivesAUDIO TIMESTAMPS1:37 What are the scripts David grew up with?8:51 The impact of studying abroad12:21 Living in different places while hating vacations20:18 The moment David realized this is not how his life is supposed to be28:38 How did David feel at the beginning of his self-employment?34:42 Work identity and engagement41:53 Burning with curiosity and not having a choice but to follow it48:37 Is the self-employed path easier than it was before?49:35 "To be me for a living"57:03 Doing things for the sake of it1:00:36 Self-publishing books📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality videos using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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, and eventually became a strategy consultant at McKinsey.Relevant Links:Adam's Website and McKinsey EssayTom Critchlow's WritingVenkatesh Rao's The Art of GigTimestamps0:00 Audio Intro0:48 The scripts Adam grew up with3:54 Shifting from MIT to Brown5:33 Becoming interested in consulting7:25 What was it like from 1999 to 2002?9:08 Adam's path to becoming a partner at McKinsey11:56 Leaving McKinsey14:05 What kept Adam at McKinsey for 10 years?16:06 What do people get wrong about McKinsey?18:49 Decentralization and the emergent order21:46 The new ideas in customer experience Adam helped shape24:06 Going into the finance industry in 200925:23 Turning data into insights27:20 How to influence other executives to embrace the "hypothesis first" framing? 28:44 The 2 skills from the consulting world that are missing elsewhere30:28 Teaching the importance of feedback33:22 Development Group Leaders35:21 Lessons from working at a hedge fund42:01 Did the world of billions inspire Adam to go solo?42:56 Becoming a freelancer46:52 Should you clearly define the services you're offering as a freelance consultant?50:18 The role of Adam's writing51:44 Did the nature of Adam's projects shift over time?53:14 The best part of the self-employed life Adam didn't expect54:15 AI & The Future58:10 The forecasting contest📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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, FoundationsThe Art of Gig, SuperstructuresWATCH ON YOUTUBE: https://youtu.be/KC63HrF8V4EYou can find Venkatesh:on Twitter @vgron RibbonFarm (blog and substack)His consulting website: venkateshrao.comLinks Mentioned:How Karate Kid Ruined The Modern World (Cracked)Lords of StrategyWhat Theorising Is, Theorising Is NotTempo, by VenkateshJim KellerSquad WealthWe talked about:1:00 The scripts Venkatesh grew up with 5:05 Preparing for the leap, Dan Pink's books 10:48 Predictable income vs adventure18:58 Is $100 enough to build confidence in a project?21:08 Understanding the big consulting companies 27:18 The positioning vs people's school33:34 "Avoid polished deliverables" 42:17 Helping the executives take a step back 47:54 Systematic doubt and systematic confidence 51:40 What is "the clutch class" and why does it matter? 59:34 "What the clutch class is doing on evenings and weekends everyone will be doing in 10 years" 1:01:54 Keeping a 10-foot pole between your public identity and freelance gigs 1:03:38 How does Venkatesh work with clients? 1:07:53 The Yak collective and the future of indie consulting 1:12:34 Why the gig economy will outgrow the paycheck economy?📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 of work experience.  Someone at her company told her she wouldn't "make it"🍿WATCH ON YOUTUBEKyla's Website: Educator, Creator, Investor Follow Kyla: @kylascan on Twitter, Instagram, and TikTokPath Role Model: Cody Ko⌛TIMESTAMPS1:09 The scripts that Kyla grew up with2:26 Writing her first book5:01 Finding out that people actually want deeper ideas7:31 Kyla's mindest when she was graduating9:24 Why Kyla didn't like her "cool" job in LA?11:50 DMing Paul and quitting her job16:05 Approach to work in Kyla's age cohort17:19 Kyla's parents on her leaving her job18:05 Pushback and skepticism19:27 Positive surprises after going on her own path20:27 "The passion crisis"23:24 How to find things you care about?25:26 Gatekeeping and aging out27:27 Kyla's short vertical videos33:09 AI and the future of writing35:58 Doing, not doing, and bike riding38:17 Remembering the good ideas38:48 The vibes of the economy41:20 Influence and responsibility42:58 Favourite financial leader?43:50 Why Kyla doesn't like what the Fed is doing?45:33 Generations living in different realities47:00 How did the "vibes" of Kyla's path change?50:51 Kyla's biggest supporters51:23 Putting herself out there52:04 Fame, success, and imposter syndrome54:03 Charts in Kyla's videos54:50 Kyla's TikTok's as poems55:48 What do people get wrong about short-form videos? 56:46 Going from TikTok to YouTube57:27 Bread58:32 "Money is not our moral compass".59:15 What does Kyla need help with?📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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, like housing, healthcare, taxes, and insurance. 🍿WATCH ON YOUTUBELinks:Her How To Get A Mortgage CourseHer WebsiteThe Catastrophe of Success (Tennessee Williams)Small Bets Community📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trialAudio Timestamps:0:00 Audio intro2:10 What were the scripts Catherine grew up with?8:46 The differences in the experience of work between generations12:19 Applying to Emerson - the cold, unwelcoming Boston16:02 How Vassar teaches acting16:41 Auditioning in New York City after graduating17:16 Becoming disillusioned with a career path as an actress20:24 Producing her first play23:34 The American Booksellers Association30:24 Creating jobs for herself33:15 Working at Longreads38:00 Leaving Longreads39:30 After Longreads - moving to Austin44:17 Designing life with her husband48:18 How the system is incompatible with the new ways of life48:52 Leaving the US as a way to gain perspective49:42 "I'm breaking some law right now, I just don't know which one"50:37 Does work equal suffering? The IRS' definition of a hobby51:44 Why Catherine doesn't think in long time horizons52:59 Getting a mortgage as a self-employed person59:12 Small Bets & Dan Vassallo1:01:55 LLC vs. S Corp1:12:24 Healthcare in different states1:16:55 Catherine's course1:17:20 Tennessee Williams - The Catastrophe of Success1:23:24 Cathrine's path role models? 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 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.🍿Watch on YouTubeThis conversation was really special.Links:My interview with Jonny on The Curious Humans podcastPaul's Interview with Al Humphreys The Three Marriages (David Whyte)Jonny's TEDx Talk on Grief----📕Buy Paul’s Book (Published Jan 2022): 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 PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here (Sponsored Link, Includes discount)------------------📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: SubscribeFurther Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

🍿 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 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 2014Working full-time remotely for Duck Duck GoWhat people get wrong about remote workIndividual preferences & desire for freedomWhy she's writing a bookProductivity & remote workLearn more:Ali's Book "Remote Works" (Feb 2023)LinkedIn-------------📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 More About CoreyWriting on Psychology TodayHis personal website ------------------📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 scriptsHer creative interests vs. practical career choicesGetting into google and getting sucked into the tech worldQuitting her job and thinking she needed to found a companyShifting to freelancing and creating space in her lifeCreating and writing online and building an audienceCreating in a second languageHiring employees vs. hiring contractorsPursuing an academic path at the same time as a solopreneur pathHer personal site: Anne-Laure Le Cunff | Wellness, Creativity & CultureHer newsletter & community: The Maker Mind Newsletter by Anne-Laure Le Cunff (nesslabs.com)🍿 Watch on Youtube-------------📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 experiment with different ways of teaching things like market making, probability, thinking in bets, and the behaviors needed to "make it" in the trading pits.This conversation was a delight and I think you'll enjoy it. We cover:Ending up at Penn and not really knowing what he was going to doFiguring out he enjoyed math and financeGetting a job at SIGJoining the training teamLeaving finance to spend more time with his kidsBecoming a high school teacherHow he thinks about teaching & mentorshipHis 20-year journey in creating his game "Stockslam"Prefer Video? 👉 Watch on YoutubeLearn more about stockslam:TwitterWebsite📕Buy Paul’s Book (Published Jan 2022): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality videos using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 because he enjoys it so much. Check out this convo as we explore:Scripts Justin grew up withWhat he learned from his parents buying a SupercutsLaunching a successful Youtube businessHow illegible his success was to his familyHis struggles with hustle cultureFinding the work he likes doing…and moreJustin's mission is to enable creators big and small to land 1 million paid brand partnerships by 2032.You can find Justin here ⇒ Creator Wizard or Twitter📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 RebellionGary's Site: Breakthrough PlayFollow Gary on Twitter: Gwen GordonFreestyle love supreme (Hulu) 📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality videos using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 videosWe Don't Just Teach Content Marketing ... We Built Our Company With It (copyblogger.com)About The Kolbe A™ Index | Instinctive Strengths AssessmentVIA Character Strengths Survey & Character ReportsPamela Wilson: Mid-career Online Business Coach101 Essays That Will Change The Way You Think: Wiest, Brianna📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 WorksTwitter: @taragentileHow learning I’m autistic changed the way I work Finding A Way to Take Up Space A Conceptual Analysis of Autistic Masking: Understanding the Narrative of Stigma and the Illusion of Choice 📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessVideo Episodes & Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 them bilingually after becoming bilingual in Spanish herself during her time in Cuba. She's a self-described early AND late bloomer, having sped through milestones early on but now slowly figuring out what's next for her work and family. She understands many of the challenges of going off the default path—like the paradox of choice—and how decision-making and prototyping are skills to be learned and practiced while building a pathless path.She is from San Francisco originally but now lives in New York with her husband and kids.👉 Follow Aida on Twitter and Read Her Writing Links Mentioned:Life Is in The TransitionsLate BloomersLost ConnectionsThe Hilarious World of Depression📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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, guiding his vision of democratizing employment and growing decentralized communities. In 2014, John was awarded “40 Under 40” by the Denver Business Journal for his contribution to shaping the future of business. CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Become a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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:WebsiteTwitter @Malcolm_OceanSign Up For Complice and get one bonus weekCrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Become a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 education with a broader audience online.Follow Hannah:@HannahFrankman / Twitter@rebelEducator / TwitterLinks Mentioned:3 Reasons Homeschoolers Often Become Entrepreneurs - Foundation for Economic Education (fee.org)No, You Don’t Need to be “Qualified” to Homeschool Your Children - Foundation for Economic Education (fee.org)📕Buy Paul’s Book (Published Jan 2020): The Pathless Path📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Become a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 the most thoughtful perspectives on the future of work and global mobility. Currently, Lauren is Executive Director of Plumia, the mission to build an internet country for digital nomads at SafetyWing, a Y Combinator company that raised a $35 million Series B in 2022. She is also author of the book Global Natives and writes the Counterflows newsletter) about borderless living. She tweets @LaurenRazavi. SPONSOR: CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here Links Mentioned Path Role Model: Pia Mancini Minimum viable state Book Recommendation: Slouching Towards Bethlehem by Joan Didion Timestamps 2:01 Introduction 3:22 Lauren's Influences Growing Up 6:30 Lauren's Idea of Home 9:00 Paul on International Couples 10:24 Lauren on how she sees "place" & digital citizenship 12:44 Becoming a Digital Nomad 17:26 Paul's experience in Bali 19:34 Digital Nomads being self-reflective 23:51 The fear of asking questions about life 30:10 How everything changed in 2020 31:52 Why the remote work is here to stay 34:21 Asking better questions - Nomads and Settlers 43:52 Lauren's approach to writing - working with an editor 51:21 The most interesting experiments with countries/policies 58:23 The problem with the real estate 1:02:28 Rapid fire questions with Lauren 📕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 Podcast: Become a sponsor of the Podcast / Newsletter Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course Want to launch a course? Podia or Teachable are both great Web Hosting: Skystra Fast WordPress Hosting Host your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 was on his way.  His long-term vision is to build an alternative to traditional advertising in audio.We talk about this and a lot more including:Why he quit a good job to work at a smoothie barHow a cold email to Ryan Holiday changed his lifeGrowing up in HawaiiSerendipitous events that lend to him moving to AustinThe future of AudioLinks MentionsModern StoaSky's Podcast (Paid) or RMRK.appThe Gray Lady WinkedThe Brass Check@consumersky (twitter)CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up HereTimestamps1:41: Intro to Sky and where his name came from5:03: Sky's influences growing up11:34 Why he went to the corporate world17:12 Cold emailing Ryan Holiday & vision for 19:47 Sky's "quake moment"25:15 Moving to Austin and working for Aubrey Marcus30:44 Sky's desire to help people 32:55 Growing up in Hawaii36:10 Going to China at 1039:30 Everything anywhere all at once reflections44:40 The "true default path"47:30 Hiring someone & responsibility48:30 "what are you uniquely positioned to do?"49:20 Advertising Subsidy & Media incentives57:20 Meme farming & future of audio1:01:30 Bucky Fuller & specialization📕Buy Paul’s Book (Published Jan 2020): The Pathless Path 📲Connect + Follow PaulTwitter: @p_millerd Paul’s Newsletter: Subscribe to Boundless Paul’s YouTube: Subscribe 🙏Further Ways To Support The Podcast:Become a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 creating and writing, he slowly started to figure out a better path forward for him. After leaving the corporate world for a second time, Lawrence finally found a calling - writing on his blog: More To That where he uses visual storytelling to express his ideas of pursuing alternative paths, sharing ideas, and creating online.  Some of the topics we explore in this conversation include:  The influence of money and prestige  Burnout and reflection The importance of the right partner  Finding the right medium  The Arc of the Practical Creator How To Find Lawrence: Website @moretothat (twitter) CrowdHealth: You ditched the traditional path… why haven’t you ditched your traditional health insurance Experience the freedom and affordability of cash payments and community-funded healthcare with CrowdHealth. Use promo code “Boundless” during sign-up for a special discounted subscription offer. Sign Up Here  Audio Timestamps  2:26: Intro/Who is Lawrence  3:47: Scripts around creativity  5:37: Prestige and Money  8:56: Fear of ending up broke and homeless  16:55: Knowledge Work & Burnout  21:20: Having the right partner supporting you  29:38 How writing emerged as something important  32:44: The Arc of the Practical Creator: Stage 1  42:15: The Arc of the Practical Creator: Stage 2  50:48: The Arc of the Practical Creator: Stage 3  59:10: Rapid-fire questions with Lawrence  1:03:35: Outro/Where to find Lawrence  Buy Paul’s Book (Published Jan 2020): The Pathless Path  Connect + Follow Paul  Twitter: @p_millerd  Paul’s Weekly Newsletter on Work & Unconventional Path: Subscribe to Boundless  Paul’s YouTube Channel: Subscribe  Further Ways To Support The Podcast: I support the following services and recommend and/or use all of the following  Become a sponsor of the Podcast / Newsletter  Rate on iTunes or Spotify!  Want to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio Course  Want to launch a course? Podia or Teachable are both platforms I use  Web Hosting: Skystra Fast WordPress Hosting  Host your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 with money.  He runs The Money Workshop with people helping them explore the scripts people have with money and realized that people have one of two orientations towards the world: #1 The Money Path: “One day when I sorted this out I’ll get to do what I want” #2 The Life Path: “Do what you love and the more you follow it you will have your needs met with and without money” Which one are you? Learn More About Tim’s work here 👉 Different Space - Transformational learning & development by Tim Malnick New to Reimagine Work?  Learn more about Paul here JUST LAUNCHED: 📕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 PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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, startup advisor, and the author of an upcoming book about the business implications of augmented reality. He also hosts Tech News for MBAs ---- New to Reimagine Work?  Learn more about Paul here JUST LAUNCHED: 📕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 PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

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 PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Join Khe's Supercharge Your Productivity course: https://10k.radreads.co/join-syp11/yzrsv (affiliate)Get access to Khe's $10k training which will help you wander towards the pathless path: https://radreads.co/millerdFrom a live event where Paul & Khe talk about their shared journeys of self-employment, creating online & more 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Just launched my book, The Pathless Path!  Purchase the book here. This is the introduction of the book. I'll be releasing some clips of me reading the book and will eventually publish an audio book. 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Kris Abdelmessih has one of the most unique perspectives on life and works I've stumbled across in the past few years.  He uses his experience as a trader to look at decision-making and work investments through the lens of options, pricing, and other financial models.  I enjoy his perspective because unlike other financial types, he seems to have a proper appreciation of non-work / non-productive time.We explore his recent break from trading, his creative journey writing on the internet, and finding his people, and he challenges me to think differently about how I'm spending my time with my work.The conversation dramatically shifted how I'm thinking about the possibilities of my path.  If you are on a self-employed path, this is a must-listen:For Kris' newsletter: Party at the Moontower - (moontowermeta.com)------------SUPPORT BOUNDLESSSubscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation.🆕 I launched Freelance Consulting Skills Course.  You can find out more and sign up here.If you'd like to support the podcast, consider using my affiliate linksPodia - 14-day free trialTeachable - 14-day free trialWealthfront - $5k managed for freeConvertKit - First 1k subscribers for freeCharles Schwaab No International ATM Fees 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Howard Gray is the founder of Wavetable, a studio that helps brands and companies come together to develop fan-based experiences to help teams teach and share ideas. The two things that drive him are to "create space for people to do the work they want to do" and to help people "make sense of the world and overcome the tension of putting things out in the world" We dive into his idea of the formless path, why the creator economy is in danger of being hijacked, how he sees himself as a guide rather than as a creator, and why fatherhood is helping him "sharpen" his focus. Links Mentioned Howard Homepage Labels In, Labels Out Jobs, Vocations, Careers SUPPORT BOUNDLESS Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation. 🆕 I launched Freelance Consulting Skills Course.  You can find out more and sign up here. If you'd like to support the podcast, consider using my affiliate links Podia - 14-day free trial Teachable - 14-day free trial Wealthfront - $5k managed for free ConvertKit - First 1k subscribers for free Charles Schwaab No International ATM Fees 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

“You can’t study or learn your way into a new identity” - I love this quote from Darren Joe.  He’s been thinking about carving a different path from 2003 to 2004.  He said that he was driven by a natural drive to be independent and do his own thing.  I found this pretty impressive because in those years not many people were doing what he was doing. He recently published a book titled The Fail-Safe Entrepreneur.  In it he argues that almost all solopreneurs strive for three things: Freedom, Adventure, Meaning.  I definitely agree.  However, he says many fail to reach these aims because they ignore the shadow side of this path.  He details four things - FAIL: Failure, anxiety, instability, loneliness. We explore many things in this conversation including: Grappling with the achiever identity Longing for independence and freedom Parental approval Building Community Experiments Defining success You can buy his book the Fail Safe Solopreneur on Amazon ------------------------ SUPPORT BOUNDLESS Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation. 🆕 I launched Freelance Consulting Skills Course.  You can find out more and sign up here. If you'd like to support the podcast, consider using my affiliate links Podia - 14-day free trial Teachable - 14-day free trial Wealthfront - $5k managed for free ConvertKit - First 1k subscribers for free Charles Schwaab No International ATM Fees 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

In parts 1 and 2, I interviewed Michael about his plan to quit his comfortable consulting job and start a new path creating and selling courses online. Let's see how he reacts to his own quotes from a year earlier! ------------------------ The best way you can support me is to join in the conversation. Share thoughts on Twitter, send me an e-mail, and tell me what resonated or what you’d add or refer a friend: If you’d like to support further you can use my affiliate link for some of the platforms I recommend. Podia - 14-day free trial Teachable - 14-day free trial Wealthfront - $5k managed for free ConvertKit - First 1k subscribers for free Or if you want to fund my crypto house, you can send me some crypto here. 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Austin Church thought he was going to be a poet.  When that didn't go as planned, he joined the business world.  Six months later he was laid off in the 2008 recession.  Luckily, his firm hired him back as a freelancer and that completely changed his perspective on work.  Ever since he's been hacking a living, shifting roles as a freelancer, founder, entrepreneur, and coach.  We chat about his journey and more. Learn more about Austin and his great writing on freelancing here. --------- SUPPORT BOUNDLESS Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation. 🆕 I launched Freelance Consulting Skills Course.  You can find out more and sign up here. If you'd like to support the podcast, consider using my affiliate links Podia - 14-day free trial Teachable - 14-day free trial Wealthfront - $5k managed for free ConvertKit - First 1k subscribers for free Charles Schwaab No International ATM Fees 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Natalie Rachel went through her own experience with burnout before turning to help others.  She found that "with burnout, rest doesn't touch it," you need a deeper strategy.  We compare notes on our own journeys where we were surprised by burnout.  We thought it was something that resulted from working long hours.  Natalie says a better way to think about it is as "self-neglect of reflection." Resources Mentioned: Natalie On Twitter Natalie on the James Altucher Show Dr. Geri Puleo --------- SUPPORT BOUNDLESS Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation. I launched Freelance Consulting Skills Course.  You can find out more and sign up here. If you'd like to support the podcast, consider using my affiliate links Podia - 14-day free trial Teachable - 14-day free trial Wealthfront - $5k managed for free ConvertKit - First 1k subscribers for free Charles Schwaab No International ATM Fees 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Ben Hunt is a father, husband, former academic, author turned blogger, former hedge fund analyst, investment advisor, and farmer. And he’s also my podcast guest in this episode. His writing has been an inspiration to me as I try to carve my own path after leaving what he calls “Team Elite.” His philosophy of make, protect, teach focuses on local and bottom-up change in the world.  In addition, we also discuss: How losing his father changed his relationship with time Industrially necessary scripts and "the good egg" Why writing about work elicits strange responses How he thinks about narratives and politics related to work --------- SUPPORT BOUNDLESS Subscribe to the weekly Boundless newsletter to stay up to date on new episodes and join the conversation. I launched Freelance Consulting Skills Course.  You can find out more and sign up here. If you'd like to support the podcast, consider using my affiliate links Podia - 14-day free trial Teachable - 14-day free trial Wealthfront - $5k managed for free ConvertKit - First 1k subscribers for free Charles Schwaab No International ATM Fees 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here