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