#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 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:

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

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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?