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

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

The Pathless Path with Paul Millerd

November 7, 20221h 34m

Audio is streamed directly from the publisher (media.transistor.fm) as published in their RSS feed. Play Podcasts does not host this file. Rights-holders can request removal through the copyright & takedown page.

Original episode page

Show Notes

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 YOUTUBE

Links:

📕Buy Paul’s Book (Published Jan 2022): The Pathless Path

📲Connect + Follow Paul

🙏Further Ways To Support The Podcast:

Audio Timestamps:
0:00 Audio intro
2:10 What were the scripts Catherine grew up with?
8:46 The differences in the experience of work between generations
12:19 Applying to Emerson - the cold, unwelcoming Boston
16:02 How Vassar teaches acting
16:41 Auditioning in New York City after graduating
17:16 Becoming disillusioned with a career path as an actress
20:24 Producing her first play
23:34 The American Booksellers Association
30:24 Creating jobs for herself
33:15 Working at Longreads
38:00 Leaving Longreads
39:30 After Longreads - moving to Austin
44:17 Designing life with her husband
48:18 How the system is incompatible with the new ways of life
48:52 Leaving the US as a way to gain perspective
49:42 "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 hobby
51:44 Why Catherine doesn't think in long time horizons
52:59 Getting a mortgage as a self-employed person
59:12 Small Bets & Dan Vassallo
1:01:55 LLC vs. S Corp
1:12:24 Healthcare in different states
1:16:55 Catherine's course
1:17:20 Tennessee Williams - The Catastrophe of Success
1:23:24 Cathrine's path role models?


NEW: The Pathless Path Hardcover Premium Edition

📘 My 2nd Book Good Work: Learn More
📕 Buy My First Book, The Pathless Path (65k+ Sold): The Pathless Path
😁 Join 500+ In My Cozy Community: Pathless Path Community


📲Connect + Follow Paul

🙏Further Ways To Support The Podcast:

  • Accounting, Taxes, and Payroll for Your S-Corp (Ideal for $60k+ income): Collective
  • Looking for alternatives to traditional health insurance in the US? Check out Crowdhealth
  • I use Transistor to host this podcast. It rocks. Launch Yours Here
  • I record high-quality videos using Riverside: Sign Up Here
  • I use and love the Readwise reader for notes and highlights: Join Here for a 2 month trial

Topics

careerspaul millerdunconventional pathsdigital nomadcreator economyyoutubetwitter people
← All episodes of The Pathless Path with Paul Millerd