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:

Her How To Get A Mortgage Course
Her Website
The Catastrophe of Success (Tennessee Williams)
Small Bets Community

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

I use Transistor to host this podcast. It rocks. Launch Your Here
I record high-quality video using Riverside: Sign Up Here
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

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

X: @p_millerd
Instagram: @pathlesspaul
Paul’s Newsletter: Subscribe to Pathless (26k+ People)
Paul’s YouTube: Subscribe

🙏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

The Mighty Meekness of Masculinity: Part 8 - A History of Christian Moral Progress

Every Square Inch Podcast

Outro

The AI-powered Podcast Player