The Pathless Path with Paul Millerd

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.

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Links:

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

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?

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