#120 How Do You Buy A Home While Self-Employed? Catherine Cusick on her path, acting, economics of Broadway, longreads, independent book sales, buying a home, digital media & how to navigate hostile U

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

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The Pathless Path is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Russ Roberts, Kevin Kelly, Khe Hy, David Senra, Derek Sivers, Joe Hudson, Luke Burgis, Ben Hunt, Dan Vassallo, Steph Smith, Alex Pang, Visakan Veerasamy, Michael Ashcroft, Kyla Scalon, Trung Phan, Justin Welch, and more.