#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,

[00:59] Paul: Welcome to The Pathless Path. I'm Paul Millerd, and in this podcast, we examine the invisible scripts that run our lives and dare to imagine new stories for work and life. Today I am talking with Catherine Cusick. I am super pumped to talk to you today, Catherine. I feel like you have so much to offer. You've gone into the weeds on all the technical parts of navigating your own path, legal, healthcare, getting a mortgage, all that.

And you've also been carving this path on your own and with your partner. Uh, I'm excited to dig into that because I'm in a similar experience of being a dual self-employed married couple.

[01:39] Catherine Cusick: Uh, my condolences. It's—

[01:42] Paul: I love it.

[01:42] Catherine Cusick: It looks fantastic for the logistical problems. It's otherwise fantastic.

[01:48] Paul: We'll, we'll dive into that, but I thought an interesting way to introduce you would be to read something you wrote to me, which kind of brings alive something that's energizing you. Do you mind if I read that?

[02:02] Catherine Cusick: I would love that.

[02:04] Paul: So you wrote, housing, healthcare insurance, and tax policies were designed for employees in ways that are now causing generation-wide disruptions in all those industries. Individuals blame themselves when those systems don't work, but they don't work by design. This is the stuff that really eats away at people when they worry about leaving their jobs or living the most meaningful life they feel called to live. Hell yeah. My plan is, my plan is to spend the next however long spilling some ink from this point of view. I now have years-long visibility into where some of these policies fall apart, and I want to articulate what I'm seeing because I don't think I'm alone.

I love this. Uh, you said you struggle with introductions, so I thought this might be a more fun way to introduce you. Um, So welcome to the podcast, Catherine.

[02:53] Catherine Cusick: Thank you, Paul. Yes. The things that I've written in advance are always much better rehearsed than the things that I just come up with on the spot. So that's very, very helpful.

[03:08] Paul: Before we dive into that, I want to start with a question I ask all my guests. What are the stories and scripts you grew up with that have shaped what you thought you were supposed to be doing and now how you're trying to make sense of that now.

[03:22] Catherine Cusick: Sure. So I was chatting with you off mic before a little bit about how a lot of things changed for me the year I turned 14. And what changed that year was really that I developed an interest outside of school. Uh, I went to a new school for 6th grade through senior year, so I did 7 years at the same school, uh, and had been there for half that time when I started my freshman year. But that year, I— my friends started doing a lot of theater, and so I started doing that with them. And it, it started me on an earlier path around acting and playwriting, which is a very long thread that isn't really reflected much of anywhere in my online presence currently.

So it's, it's interesting to talk about. Um, that was a side of me that was all about my social life and friends and doing things that were joyful doing things that were in the present and that involved, uh, my body and doing physical things that weren't sports. Um, and the other side of me, uh, was very diligent at school and very motivated by grades and A's and, uh, reward systems that were based on points and my GPA. And these were kind of two different versions of me. It was a bit of a bifurcation of my path early on where a lot of things that made me feel alive came from somewhere else. And at the same time, I really liked school.

I really liked studying. I had a lot of moments in my teenage years and throughout high school, my mother often would, would take— would try to pry textbooks from me and go hide them because she'd want me to go do something else. But I just wanted to read and I just wanted to do all of the reading and do all of my homework. And then every now and then I'd go to rehearsal and go have friends. And so that was something that started splitting my personality around age 14. And then that same year— so that's in my personal life, but in world events, uh, I was 14 in 2001, and I grew up north of New York City, and my father worked in the Empire State Building.

So he was in the Empire State Building a week or two into my freshman year of high school on 9/11. And came home safe, made the last train home, and was home by the time I had gotten home from school. And I think about that constantly because it was a— terrifying day. Um, there are a lot of peers who went to my school who had exactly the opposite experience. I had the lucky experience, and I think a lot about what, what could that other life have been, because it would have been an incredibly tragic and terrifying life. If he had not come home that day.

And I think about that as a systemic thing that shaped part of my life because it was very, it made a huge impact on me at the time. It was completely outside of my personal control as a 14-year-old. And a lot of that depended, the luck of that moment depended on what the World Trade Center symbolized. That the Empire State Building didn't.

[07:58] Paul: Right.

[07:59] Catherine Cusick: And that's a very random thing to me from my perspective that made me lucky. And it was a big moment and it was the beginning of very large world events kind of following me around and bookending my education. I also graduated in from college in 2009. So I graduated directly into the housing crisis and the financial crisis. And those kinds of things really made an impression on me at the time. They mattered a lot.

They changed the course of my life a lot. And they were giant events I could not have predicted that many people did not predict. That changed everything about my future. So I think that those, those events mattered a lot to me growing up. And I think they did shape what I thought a default path might have been. I think if those things hadn't happened at those times, my, my vision might have been more narrow or might have focused more specifically on me personally as an individual.

And I think it's part of why I start to try to connect these large systemic things that we come up against, especially in something like unemploy— in, in self-employment that aren't individual and that are shaped by larger forces that you run into a lot and that can change the course of your life in a lot of ways.

[09:45] Paul: Yeah, it's, it's so fascinating. I think I'm a couple years older than you. I graduated college in 2007, and us as the older millennials are sort of this lost generation in between two worlds. Like, we, we, we inherited the scripts of the boomers.

[10:06] Catherine Cusick: Um, absolutely.

[10:07] Paul: And the path sort of worked for them. Although there was a lot of like burying who they were as people to pull that off.

[10:16] Catherine Cusick: Oh, yes. My dad was born in 1944, so he's technically Silent Generation. There's a whole lot about, you know, his story is not my story, but oh boy, the burying.

[10:30] Paul: Right.

[10:31] Catherine Cusick: Of course. Of many things. Yeah.

[10:34] Paul: And then as we were graduating, I got lucky. I always wonder the what if, if I was graduating in your year, right? I think graduating in '07 was like this last hurrah before a weird new world started to emerge. Like it was sort of easy to get job offers. I was like reaching for further job offers and like everyone sort of like was set. And then us, we actually were fine in the workforce.

We didn't get laid off because we were all so cheap.

[11:11] Catherine Cusick: Like companies, another stroke of luck being cheap labor.

[11:14] Paul: Companies just didn't hire you. Right. And they did. And they just kept us and we're like, all right, just do a little more work. But that was fine when we were young. Sure.

So yeah, my, my questioning of the system, uh, lasted a little longer. What, what was it like for you in college? I know, I think you went to Vassar.

[11:36] Catherine Cusick: I did.

[11:37] Paul: So, which is a very liberal arts. People do a lot of different things. A lot of people do have connections at schools like that. What, what was your path? Like, what did you think you were going to do entering as a freshman? What did you end up doing leaving as a senior?

[11:54] Catherine Cusick: So Vassar, has a fantastic drama department, and the interest in acting went through into college and after college for quite some time. I was very funny using all of your prompts as writing prompts and questions that you've asked as things to reflect on throughout my life. I always forget how I approached my college search. And every time I remember it, I think it's really almost batshit. I was very driven and very present at school and did very well there, but I didn't think about college very much. I didn't care too deeply.

I didn't focus on the SATs. I showed up that day and took them, and I got, you know, an average score. And I thought it would be fine because I had a very good GPA. And then I think we had counselors, we had guidance counselors whose job it was to sit us down and talk us through a college search. And I hadn't thought about it very much. And then I ended up applying to one school.

I applied to Emerson at first, early action. So I picked one school and I was gonna try to go there, but that was a BFA. That would've been a Bachelor of Fine Arts in acting. And that's a very different kind of education than a liberal arts degree or a Bachelor of Arts. And I went— I had never been to Boston. I had never, uh, been anywhere with a really cold climate.

I went to go visit in, uh, the winter, in when it was incredibly windy, which I think was really helpful because I was like, oh, I can't live here because Boston was that much colder than New York for you. Boss, I was there at a time— I think I was just like in a wind tunnel. It was something very specific that day.

[14:17] Paul: The worst, like, 10 days of Boston, or like what?

[14:20] Catherine Cusick: Exactly. Yeah, I was definitely there. Boston was, you know, rolling up the welcome mat and saying, don't come. Uh, I had gone to do my audition for that, and I did— you know, you do a 2-minute monologue, you do a contrasting one, you do dramatic and you do comedic— and I did both of them And I ended it, and the person whose job it was to watch my audition and chat with me, her first question was, "Why do you want to come here? Why do you want to come to this school?" To this day, I don't know what I said to her because in my mind, my immediate thought was, "I don't. I don't want to come here." I lied in the moment, but I left that space and was like, well, this wasn't it.

This isn't it. This isn't where I should go. And I went back to the drawing board probably for really only a couple of weeks because I went on a tour of Vassar, which was a little over an hour away from where I grew up. And that was my main criteria, was that I didn't want to go too far from home. And I showed up at Vassar and felt like I belonged there very quickly. And I went on the tour a week before.

They had two rounds of early decision, so their first round had already been done and I missed that round. But they had a second round and that was due in like a few days after the tour. So I just went home and I filled it out and I sent them their application and I was like, yeah, if you say yes, I'm coming. And I got in on Groundhog Day, and I was done with my college search like a couple months later. And that's very different, I think, from a lot of how people approach their education. I, I really just picked a couple places.

My backups were, were just because I had to have a couple of them, and I never used them.

[16:31] Paul: I didn't, uh, have any backups. I only applied.

[16:35] Catherine Cusick: Yeah, I really, like, I really wouldn't have enjoyed those backups. I I just sent them things because I had to.

[16:41] Paul: How did you end up at American Booksellers Association? Was that your first job out of school?

[16:47] Catherine Cusick: So there was a break after I graduated. So for all of college, I still focused on drama and I studied drama and I was an acting major.

[17:01] Paul: Were you thinking you wanted to be in plays or something like that?

[17:05] Catherine Cusick: Yeah, I was going to pursue acting. And Vassar is a very smart and good school because they don't really track you that way. If you're going to be interested in theater and major in drama, you have to also do stage management. You have to understand lighting design. You have to also do costume design. You have to do the 360 degrees.

Technically around, uh, this whole experience. So I studied there, graduated, and then I lived close enough to New York City that I was going to audition and to try that route. As I think some— something like 60,000 20 to 22-year-olds show up in New York City to pursue acting, uh, every year. Something like that. I was one of them.

[18:05] Paul: That's wild. Yeah, I mean, it makes sense if you watch a Broadway show. Like, everyone is so talented. It's pretty wild.

[18:13] Catherine Cusick: Oh, yeah. Yeah, I mean, that is a— so that's a career where there's an oversupply. And what's really interesting about the oversupply in acting in cities like New York or in London or in Los Angeles is that it's oversupply of anyone who's in your type. Uh, so my competition for roles becomes people who look, sound, and behave like me, who are my age, who are— who present gender in the same way as I do. Um, and what happened there was that I— so I was, you know, 22, a young 22-year-old woman, and every script I got, everything that I read, all of the sides I'd get to go into auditions to read parts for The writing was atrocious. Just atrocious.

The roles that were available to young women who are in their early 20s who have a certain vibe, um, are sad. It was, it was a very sad and disappointing landscape where there just were not— there were so few well-written well-done roles that were complicated and interesting people that I would want to be, or a story I would want to tell versus everything that I had studied, which is the best of all playwriting in all of the world, where a great play is some of the best writing on the planet. And then I show up into the commercial reality of that at that age, and it was nowhere near as inspiring.

So another thing about that that I think you and I have in common is that I, at the time in my early 20s while I was pursuing acting, I realized over a couple of years that, um, that, that profession, despite the fact that I love it and that it's my first love and that I will always love actors specifically, the profession is very dependent and you need permission from other people to do that art. You need to be accepted into things. You need to get past gatekeepers. You needed to have an agent. You needed casting directors to get it and to get you and to think you were doing something special and unique. Um, and you were very dependent on writers because you're dependent on the writing being good if the show is going to be any good.

So I veered very hard into writing myself and into creating stuff for myself, vehicles for myself, vehicles for my friends, just trying to write more often. I ended up producing a play in 2012 near Times Square and in a space— here's a beginning story of why I start getting really interested in policies and technicalities that matter a lot. I was in a space that if you— it was 99-seat theater. And if you put one more chair in it, that changes what production code you're on and it changes what budget you're allowed to have. You need at least a $50,000 budget to have a production at that level. And it's about the number of chairs in the room.

[22:24] Paul: Wow.

[22:25] Catherine Cusick: That's an Actors' Equity technicality of producing. But so I was doing all of these things and I was coming to this realization that I was dependent on writers and gatekeepers. I was writing a lot myself in those years. I was reading constantly and libraries were really what was like saving my sanity and frankly saving me from depression a lot. So, so I came to some conclusions eventually. Another, another thing about producing and self-producing this production in 2012 on this same specific code, it was called the Showcase Code at the time.

Actors' Equity is a union for actors and they create levels, tiers of production codes. The Showcase Code also had a specific thing in it where you couldn't charge more than $18 for a ticket, no matter what you were doing or where it was or what your costs were, what the expenses were. The pricing was fixed. And by the time I finished doing that production, I looked at the money where I had lost money and I, uh, put together— I was like, oh, the economics of theater don't work. Um, or at least they don't work in— at this— at the tier that I can currently access at age 24, however old I was at the time. Uh, the economics of theater don't work the higher up you go either.

That's why Broadway tickets are a jillion dollars and why The audience for them is shrinking all the time because so few people can afford it. But I looked down and saw the economics of this don't work. This isn't a viable pathway right now. I'm going to need to pay my rent. I need a job. So I went to Craigslist and there was a job at the American Booksellers Association listed there, and they needed people who cared very deeply about reading and writing to work there.

So I applied.

[24:49] Paul: That's awesome. What, uh, what stands out about that experience? I think I'm more interested in talking about like where, how you ended up at Longreads, but what were some of the lessons you took away from the book publishing industry? So another set of gatekeepers.

[25:07] Catherine Cusick: Haha. Another set of gatekeepers. It was fantastic because it, it brought me. Very close to the business side of publishing and to the, the economics of selling books and the margins of books. So for those who don't know, which I think is 99.99% of the universe, the American Booksellers Association is the trade association for independent bookstores. In the United States.

Um, I worked there from 2013 to 2017 as something like a field rep, and I covered half the country. There were two of us. Uh, but by this time in history, the number of independent bookstores had gone significantly down since it had historically in time. But don't worry about the American Booksellers Association because they have an endowment from having existed for 100 years. And that's what was paying my salary at the time. That said, my relationships— I was a relationship manager and my relationships were with the owners and managers of independent bookstores in the United States.

My regions were the New Atlantic region, the New England region, the Great Lakes, and the Midwest. Uh, so it was about 1,000 stores, and my job was to stay in touch with our membership and to give them anything that they needed and to share resources with them from the American Booksellers Association, which provided education and, um, small business resources for people who were trying to make that business work. It's another very tight margin situation. If you're making a 2% margin and you own a bookstore, you're doing gangbusters. You're doing fantastic. The amount that you're profiting is just like heads and shoulders over colleagues in the joint down the street that is going to close in a year because the economics don't work.

And it brought me really close to how it works with publishers, uh, setting the prices for books, that the prices are written on the inside flap, that the bookseller doesn't set that price. It brought me really close to how important it is to have If you're an independent writer or if you're a new debut writer, you want frontline booksellers at independent bookstores to know about you and to evangelize you because those are some of the most powerful people in getting the word out.

[28:11] Paul: Maybe I need to meet these people.

[28:14] Catherine Cusick: Yeah. Hey man, I know some.

[28:17] Paul: So how did you— I mean, this all sounds like fascinating experience, especially where you ended up now. You're sort of, you're in these like industries that have weird economics dying and you became super curious about the economics of that. Were you always interested in math or were you just like, I'm going broke, I should probably figure this out?

[28:41] Catherine Cusick: Those things are not mutually exclusive. Uh, I love not going broke. I've— to this day, I haven't gone broke. It's great. It's going great. Yes, I've always— and I've always been very good at math.

So this goes back to the bifurcated personality. I still wanted to go home and do all my homework. I still wanted to, you know, get my 5 on AP Calculus. And did and enjoyed it thoroughly. I have pretty strong feelings about how genders get tracked out of STEM and STEAM industries. I know exactly why and when I got tracked out of math, and it was linear algebra at Vassar.

[29:37] Paul: Oh, interesting.

[29:39] Catherine Cusick: A woman teacher.

[29:40] Paul: I skipped linear algebra because I, I just like, my brain is not wired for it.

[29:46] Catherine Cusick: My brain is not wired for it either. I think it's a very— it, it's a completely different kind of thinking. Um, and I can only say that the way that that class was taught was basically hazing, that like, if you can't get it, then you're not fit for math. If it's challenging for you, then you're not fit for math. And I was like, well, I'm fit for the drama department, so I'm gonna stay there. Uh, they, they're at least still welcoming me and saying I can be here.

So that's a very different story. But I was always interested in math. I always loved it. I was always interested in things working or not, in what makes things work or not. And money is a very important part of what makes someone's creative life work or not. I always cared about how are actors paying their bills.

If 95% of Actors' Equity membership is unemployed at any given time in the year, how do you— how is that working? You know, who's financing this entire industry? Because Who's paying for the 60,000 people to move to New York City and pay New York City rent? Somebody's paying for it. This is part of why a lot of these industries have trouble with accessibility and who gets to practice these art forms.

[31:19] Paul: What brought you to Longreads?

[31:23] Catherine Cusick: So I had been at ABA for 4 years. I had invented new jobs for myself.

[31:31] Paul: Nice.

[31:32] Catherine Cusick: I took over there.

[31:33] Paul: That's a very, very common sign of people that eventually become self-employed. They're either jumping to different jobs very often or creating their own work.

[31:45] Catherine Cusick: From 2015 on, I made up all of my titles. And so I figured I should just keep making it all up. If I'm going to make up the job, I might as well. run the place. So in 2015, I started doing a second job and I, I was fighting an uphill battle for years trying to get a raise, frankly. Um, and that was coming.

[32:13] Paul: Looking back, is it just like, oh, I should probably just go to a more profitable company and that might be easier to get a raise?

[32:20] Catherine Cusick: Well, it took me some time. It took me a couple of years. To, to let that sink in because I also cared a lot. It was a really cool job.

[32:32] Paul: That's awesome.

[32:33] Catherine Cusick: Um, I was really interested in the people. It was the first place where I had colleagues who were all really smart and with it and lovely to be around, and I cared about all of them. So I, I really wanted it to work. But I was doing more and more work and getting more and more responsibility and looking around me and noticing things that needed to be done and then doing them. But there was no relationship between that and my compensation. There was no incentive to make things better or to fill gaps or to create things that needed to be made.

There was really an incentive to sit still and to not do those things. But so I took over social media management for them. No one was doing it, wasn't really being done. It was divided among 5 people, I think, and each person reluctantly was doing it on each day of the week. They would, they would do musical chairs for whose job it was and no one wanted to do it. So I decided I wanted to do it and I took over the ABA Book Twitter account and the IndieBound Twitter account.

Um, because IndieBound was a, a program of the American Booksellers Association. That is a, that's an alternative to Amazon that now has turned more towards Bookshop.org. But I was just, you know, on Twitter at work because it was my job. And then a tweet went by from a man named Mike Dang, who was the editor-in-chief at Longreads at the time, saying they were hiring a social editor. And I just happened to look at my feed right when he sent it, and I happened to be following him, probably just because I was such a huge fan of Longreads. Longreads was the thing that I'd read on my free time.

And I was like, oh, this is my favorite website on the internet. I'm doing this job. I—

[34:47] Paul: That's awesome.

[34:48] Catherine Cusick: I wrote, I opened my email, I opened my personal email account, wrote him an email in 5 minutes that said, I would be great at this. You should chat with me. I think it was very, very boring. It wasn't even really like a resume. I might have sent a resume, but I just sent it to Mike Dang. And then months later, that worked out.

I didn't hear anything for a month, so thought nothing had happened, but then it just took a long time.

[35:19] Paul: One of the interesting things, long reads and long form in the early 2010s were super, like, those were, that was like where you could find the best writing on the internet.

[35:36] Catherine Cusick: 100%. Yeah.

[35:38] Paul: Like 15 years ago, it was legitimately hard to find like good, deep, thoughtful writing on the internet. And those were like some of the early threads. I actually ran a Facebook group called Media Feast where people were only allowed to post long reads.

[35:56] Catherine Cusick: I feel like I remember that.

[35:58] Paul: You were in that group?

[36:00] Catherine Cusick: I remember that that group existed. I was just very around and many, many people ended up crossing my screen at some time.

[36:11] Paul: Yeah, but yeah, that's so cool. And what, at Longreads, you're involved in social, is that, did your perspective on like work and your own path start to change?

[36:23] Catherine Cusick: Probably, yes. It still feels so recent that it's unformed. But when I applied for that job, I was just so enamored with it and so excited and just wanted every— I wanted nothing more than to do that because I came on in 2017 and that was a time when Longreads had been just starting to publish original work. And Longreads was originally a curation service. It was originally You know, founded by Mark Armstrong, and he created the Longreads hashtag on Twitter, and it was about sharing, um, often long-form journalism from elsewhere. But they, uh, the company got acquired by Automattic in 2014, uh, and a lot of investment came into Longreads, and they had a lot of room to expand.

Um, and under Mike Deng as editor-in-chief, they were producing and commissioning a lot of writing and a lot of new work. But the perception was still that Longreads is a curator. Um, so there wasn't enough eyes, there wasn't enough awareness that this was a place where original work was coming from. And they wanted to be getting more pitches, they wanted to get more essays submitted, they wanted more people to read what they were putting together because the editorial team It was a bit of a golden era, I think, while I was there. But it was from, you know, before I was there, 2015-ish to 2019-ish, there was really fantastic writing there. And my job was to be an evangelist for it and to grow the audiences for it.

And I'm like, I really don't know what a better job is than that. All I do is read fantastic new writing and get really close to the creation of that, and then share it and, and encourage people to engage with it. Because if you're the writer, do you want to promote your work? It's challenging. It's hard for a lot of people to promote their own work, and it's very difficult to do self-promotion. It's challenging.

Um, but you want to be read. You want people to engage with your ideas. So someone like me is really useful to have.

[38:59] Paul: What— when did you start thinking about potentially forging your own path?

[39:05] Catherine Cusick: Um, probably throughout 2019. There was a lot going on behind the scenes in 2019. Anyone curious about it can can go ahead and Google what was going on at Longreads in 2019. It's a long story. It ends with a number of layoffs and it ends with some chaos. And I was ultimately laid off, but I was laid off in May of 2020 because a lot of that really brilliant editorial team was just not going to make it financially through.

[39:45] Paul: Yeah.

[39:46] Catherine Cusick: The pandemic. Um, but I— but that job, because it was owned by Automattic— Automattic is a distributed company, so I was remote from 2017 on. I was doing all of my work online. I could log in from anywhere. I was location independent since 2017. So being location independent and not showing up in an office does really help encourage you to think differently and to be able to rely on yourself and to be like, well, I'm already doing all of my work in a location-independent way on the internet.

Maybe there are multiple ways to be doing that, and some of those can be on my own.

[40:29] Paul: And when did— so you left. What did you do when you first were let go of Longreads?

[40:37] Catherine Cusick: I isolated for the next several months. I, I was I grew up in New York and lived in New York and then moved to Austin in 2018, late 2018. So I had just moved, um, and I moved with my husband. And the main— one of the primary reasons I moved was because at the time, compared to New York, housing costs were more affordable here in Austin. So I was moving, I was taking my remote job and my location-independent job and choosing a place to live with a high quality of life. Uh, I was very burned out by New York and really wanted to be somewhere more like Austin, which has just a fantastic energy and wonderful people.

[41:39] Paul: There's a lot of New York refugees here.

[41:42] Catherine Cusick: Yeah, it's— it—

[41:43] Paul: you—

[41:44] Catherine Cusick: this is a great place to come if you're a New York expat, and, and it's not as politically fraught as coming from California. But so I moved here to buy a home, and this is a whole other thread that has been in the background the whole time. Because while I was location independent at Longreads, I could work remotely, I could work whenever I wanted to asynchronously. I was making more money. I made more money at Longreads, like significantly more money than I was making in my previous position, which was something I had wanted at the time. And it was stable.

It was a set amount. In the background, this was also a 1099 position. This was a contracting position. So this is part of why I've had to figure out all of these things behind the scenes, because that's just what the form said. We can, we can go long and deep into the misclassification of employees and that trend in technology especially. But Uh, for, for me, I wanted the job.

I was doing the job. It was a full-time job. It took full-time to do. Um, and I made full-time money. So I wanted to take that, move somewhere where I could afford a home, and use the stability of having had that gig for a long time having had an anchor client that just kept repeating in a very, um, a very stable-looking line, and to turn that into homeownership, because I was always very, very clear that that was something I wanted from the moment I left college and was like, oh, how do I pay the rent? I wanted to replace the rent with a fixed mortgage, and I wanted the mortgage to be really, really low.

I wanted it to be— I always envisioned myself with a partner. I always envisioned having somebody else here with me, but I also envisioned this needs to be something that can be handled on one income, and it needs to be handled on a modest income because I am a very— I only like art and I only care about writing and creative people and theater and businesses that have terrible financials and low margin. So I need to have a very low overhead and I gotta lock that in. And I, we, I mean, it's a very long story and we can get into this, but I, you know, finally achieved that also in May of 2020. We closed in March of 2020, a week into, okay, we're gonna shut down the world for a couple of weeks. I'm, you know, we'll come back.

[44:57] Paul: But good timing though.

[44:58] Catherine Cusick: Yeah, you know, right in there, that's when, that's when the closing happened.

[45:02] Paul: It was better than, better than 2021 when housing prices went bananas.

[45:07] Catherine Cusick: But, uh, I mean, it was by the skin of our teeth. It was, it was minutes away from falling apart and not happening, and it had taken me a decade to do Yeah, I'd love to hear more about how you and your husband think about that.

[45:22] Paul: Do you explicitly say to each other, okay, we want to design a life that can work around one income or piecing together one income? What are your guiding principles?

[45:34] Catherine Cusick: Yeah, so one of the best things about meeting my husband was that We have been on the same page and have had the same values from day one, right away in our first conversations. Just very, very deep, clear matching values. My husband, uh, is named Brian Donahoe, and he is a musician. He's a professional musician, a lifelong musician. I'd call him a decorated and accomplished musician. He's worked with very, very fancy people.

He has a very strong and interesting, meaningful career. And his whole life up until meeting me was trying desperately to find someone to be with who'd understand everything about what's chaotic about that life. Um, and because I'd come from the angles I'd come from, I understand the economics immediately. I just understand, like, yeah, if you get certain phone calls, you take that phone call. If you have the opportunity to show up in the middle of the night to go play with one of your heroes, You're gonna do that and you're gonna come home at 5 in the morning and that's what's gonna happen because that's what you're called to do. Um, so things like that were so important to us.

[47:16] Paul: That's so beautiful. I think, uh, my partner and I, she's very into art and creating and I just see that as so central and important to like who she is and, oh yeah, she's She supports me similarly, and it's, it's so powerful to have like those things, right? The things that can't be like purely monetized or optimized or captured. Sure, you might make some money doing it, but knowing that those are, um, worth pursuing are such powerful anchors, especially in a relationship. And absolutely, I mean, similar, similar to You, I think finding my partner Angie, like just finding someone that understands like the weird way I've been living is like, yeah, I'm down.

[48:05] Catherine Cusick: Yeah, of course. As somebody who can, you know, who can roll with it and who can be in the present moment with you and understand why you care so much and why it's so important, why I have to do it this way. You know, I think it would just be, What an incredible waste of talent to meet someone like my husband, look at him and say, like, why aren't you home by 5? Well, because that's just not what that industry is. It's, it's what Daniel Vassallo calls a stochastic industry, uh, where a lot of random chance just comes into the picture a lot and you go with it. Or you can't do that job.

And some people have to do that job. It's their only choice.

[48:58] Paul: Yeah. And I think in some ways the artists are really becoming more important. I think it's hard to see, but I think they're becoming more important in terms of navigators for people because the entire world is becoming more probabilistic or stochastic.

[49:15] Catherine Cusick: Sure. Yes.

[49:16] Paul: We're moving from like these predictable paths, which live in our imagination and at one time could be lived out in reality, but can no longer be lived out in reality. And it seems like that is a big interest for you because like our systems are not designed to support these lives, especially in the US. Like one of the biggest hacks is basically to leave the US because everything just gets a little easier.

[49:47] Catherine Cusick: Yeah, so I've heard. I've, I've, it's very interesting to me at this point how, uh, I've lashed myself to the ship of America and I'm very, very interested in the United States and in making things about the United States work.

[50:08] Paul: I think it's, it was super valuable for me to leave the US because I was able to appreciate some of the things I missed. The entrepreneurial culture, the culture of being generous and helping people without an expectation. That is very unique to working in the US, harder to find in other places. So I definitely missed that being abroad. I did not miss the healthcare bureaucracy. Why would you?

And just like all the other stuff I have to deal with. I basically joke to people, I'm breaking some law right now. I just don't know which one.

[50:47] Catherine Cusick: Listen, man, you're like, you're just miles ahead of a lot of folks because I also have jokes that it's just like, I can't tell you how many laws we're all just breaking, like, all of the time. And that's part of why law enforcement is a, a big topic because who, which laws are we enforcing and who, yeah, who is getting disproportionately hit by that versus like the fact that we're breaking a law right now. We just don't know which one it is because it's probably archaic and it was a policy that was created, you know, maybe 67 years ago because that year some specific thing was going on and then no one took it off the books and it's just still there.

[51:36] Paul: Yeah. And you actually shared something which was pretty interesting. It was IRS specifications sharing whether something is a hobby or a business. And one of the—

[51:46] Catherine Cusick: the IRS hobby loss rules. Yeah.

[51:48] Paul: Yeah. And one of the ways you can tell if something is a hobby and not a business is if you don't get satisfaction from it. Literally explicitly in the IRS, right? So like, I mean, this is ingrained in our culture too, that like work is suffering, right? And like, it's in the IRS code, right? Exactly.

And a lot of these things like made sense at one point, but like just aren't really working anymore. Yeah, maybe not. But like these things just aren't really working at the edges anymore. Do you think like, are you short like, are you long-term optimistic about these things that like things will shape up and be oriented around embracing these paths? Or do you think like basically politicians just want to turn everyone into full-time employees?

[52:44] Catherine Cusick: It's a good question. I don't think in long-time horizons. And that's probably—

[52:52] Paul: that's probably similar and could be a down— byproduct of this path, right?

[52:57] Catherine Cusick: It might very well be. I really subscribe to research and evidence that human beings are horrible at predictions. We try to do it all the time because we really want to mitigate uncertainty because emotionally our limbic systems hate uncertainty. So we really want to try to reduce it. But we live in worlds that are super interconnected and have just larger and larger complex things and systems crossing over all of each other all the time, that there's always— everything always exists all at once, whether you're aware of it or not. So I don't think too far out.

Yeah, the longest I think far out is that mortgages come on 30-year time horizons and like that. That's in my background. That's in there. I'm going to pay that bill for a long time.

[53:58] Paul: Let's start there.

[54:00] Catherine Cusick: Sure.

[54:01] Paul: How do you get a mortgage as a self-employed person?

[54:04] Catherine Cusick: First, you're a masochist. First, you want pain and you go directly towards the pain.

[54:14] Paul: So you figured it out, right?

[54:16] Catherine Cusick: I did, but it took years.

[54:19] Paul: Right. And you help people figure it out. What are some of the— so like, what are the like things people should do to make this easier for themselves?

[54:31] Catherine Cusick: Yeah, so because I was so obsessed with the concept of home, the feeling of stability, so driven by that and by having your housing feel secure, I was driven for a very long time, for years and years and years, to make getting a mortgage work. I applied 3 times and was rejected twice. Uh, I did not figure it out the first 2 times, and only when I got the information correcting my second attempt, when I got feedback on the second attempt, did I figure out what I needed to change. for the third attempt to go through.

[55:21] Paul: And, and what was that feedback?

[55:23] Catherine Cusick: So the feedback was, um, when I first applied, I had a W-2 and I had a normal application process. I just didn't make enough money. And it was very simple. They were just like, you don't make money. You work in odd industries. Uh, your margins are too low.

You are not, uh, able to access this tier of quality of life. And I was like, great, I should go get more money. I went and got more money. One of the ways I got more money was becoming an independent contractor. I made more money. But then, uh, we applied for the first time— my husband and I, when we were engaged, applied together, uh, right before we were getting married, uh, to buy a place in 2018.

The feedback we got from that was very bespoke, um, and very specific to us. And this is hint number 1: we went to a credit union. Um, we went to UFCU.

[56:27] Paul: And is that just because they're more local and like thinking— yes, um, in their community a little more?

[56:34] Catherine Cusick: Yeah, then I think they have missions, and I think the missions are important. The mission statement matters. For credit unions in a way that the major big-name commercial banks that spit out conventional mortgages for breakfast, like, they don't have a mission about educating the community. But credit unions do. So we got feedback on our tax returns and somebody pointed at lines in it and the parts of it that were, um, that were holding us back and that were keeping underwriters from approving us.

[57:19] Paul: Nice. What are the— do you remember those lines?

[57:22] Catherine Cusick: Oh yes, they were my entire— I re-engineered my life to make those lines look different for the next 2 years to make sure that I could get approved.

[57:32] Paul: What are they?

[57:33] Catherine Cusick: So the big difference is that a lot of the ratios that mortgage underwriters are looking at are based on your adjusted gross income. And adjusted gross income means something different when you have a W-2 than it does when you're self-employed, because the tax strategy for being self-employed, which even if you're not self-employed— yeah, exactly— is to write off your expenses, um, and to, to, to claim qualified business expenses because it adjusts your gross income. So you're taxed on a lower income because you're proving on paper, well, so much of this money went back out the door, it's not in my bank account, so I can't give it to you.

But if you are trying to minimize your tax burden by claiming every business expense that you're entitled to, that you're— that are qualified for your industry, that lowers your adjusted gross income, which lowers your borrowing power, and thus it affects any kind of loan you would ever want to get.

[58:51] Paul: So what, what do you do? Do you just not Do the, do you file a different type of form or how do you do that?

[58:58] Catherine Cusick: You file the same form. The, what's interesting about it, as we're making jokes about like not knowing what laws you're breaking, it's tax fraud to not claim those business expenses. If you have a receipt for a business expense and you needed to buy a new computer and your computer is important for your career. If you don't report that business expense, that's tax fraud, even though it would mean that you pay more taxes and the IRS gets more money. But so what you have to do is literally change your behavior. I need to not buy that computer this year because I can't have that receipt because I can't report it because if I report it, it will adjust my gross income and this will lower my borrowing power.

[59:49] Paul: This is even for credit unions?

[59:51] Catherine Cusick: Yeah. Oh, this is anywhere. And this is, this is still scrutinizing 2 years of financial history because that's what they'll want.

[01:00:00] Paul: All right, so we're probably scaring people about, um, going to work on their own now. What are some of the things you've learned that maybe aren't as scary as people think?

[01:00:11] Catherine Cusick: Sure. So, I mean, And part of what I hope to be doing with the stuff that I'm working on now, and I think the reason you— where you found me and what community you found me participating in, I am in a community that Daniel Vassallo runs called Small Bets.

[01:00:38] Paul: Yeah, he's been a past guest.

[01:00:39] Catherine Cusick: He has been a past guest.

[01:00:40] Paul: His episode's great.

[01:00:41] Catherine Cusick: I heard his episode. I prepared for this. I also listened to Angie's episode. I went in on the backlog. I, uh, so I was in the first cohort of Small Bets because I find, uh, the way that Daniel expresses specific things that he thinks are very counterintuitive and refreshing. Uh, his take is very interesting, so I wanted to hear what he had to say, and I joined that group very early.

But that entire philosophy is just about, um, creating small bets in the world and having a portfolio of small bets. Um, and one of the things that I created was based on a prompt that I got from that community to think about, like, well, what's What's one of the hardest things you've ever done that you did, that you accomplished? And can you teach someone else how to do it? And so immediately, like, yeah, qualifying for a mortgage as a self-employed applicant was the hard— one of the harder things I've ever done. And there is a way to do it. And so on the one hand, I apologize for 20 minutes ago making it scary how all of these things interconnect.

But to help solve that and to help resolve some of that tension, I'm trying to now create resources that spell out what I did so that you can skip the first 2 rounds where I got rejected just for not having the right instructions. Uh, there are instructions. These things do exist. There are pathways. There There is a pathway to starting your own company that's just with DBAs. There are pathways that are through LLCs.

There are steps to these things, and you can just follow them in order, and someone just needs to write them in a clear way so that you can follow those steps.

[01:02:54] Paul: Yeah, I think there, there is still a lack and a huge opportunity, and maybe you're going to filled this void of people with those skills of knowing how to do these things that also speak the language of self-employed people.

[01:03:10] Catherine Cusick: Yeah.

[01:03:10] Paul: Um, like I'm navigating whether to turn an LLC into an S corp now, and I don't re— like, I know the information is out there. I don't know how to assess somebody for being good at this or not, or even like what to do next.

[01:03:29] Catherine Cusick: You and I should chat because I know what you should look at. And I, I, I started an S corp. I— my current company is structured as an S corp right now and has been for 2021, uh, for 20— gosh, for 2022, because it's almost 2023 now. Time is scary. Um, I am going to revoke the S election for next year because I finally watched it for the last 8 or 9 months since I incorporated this LLC. I now see what it looks like and how it plays out into your balance sheet and into your profit and loss statement and the way that you have to— the way you structure paying yourself a salary Uh, to me is not worth it in the end.

It, it erodes your profitability.

[01:04:27] Paul: How so? Can you bring that alive a little more?

[01:04:30] Catherine Cusick: Yeah. Um, or I mean, and this is my opinion because I also think that an S corp, depending on what you're making, all of this stuff matters what the numbers are.

[01:04:44] Paul: Yeah. So I'll, I'll give some context. So LLC, LLC, basically you're getting an EIN from the government that is like a designation of your company as a legal entity. You can open bank accounts with that. But pretty much if you're a solo operator, you're sort of like you can flow the money in between all your different bank accounts. You're just sort of keeping an inventory and accounting of your expenses and then just mashing that up at the end of the year.

S corp is sort of a corporation that takes all your money and pays your expenses and then distributes profits to you in the form of a salary. And my understanding of that is that the costs go up because you need to pay for more paperwork, more administration.

[01:05:33] Catherine Cusick: Yes.

[01:05:34] Paul: And yeah, you're also just doing different things with money in terms of either paying yourself smaller amounts or keeping money, and there's different deductions that you don't qualify for. So yeah, would love to hear some of your reflections. Like, what, uh, were there like one or two things where you're like, oh, this is totally less than I expected, I'm going to take a different designation?

[01:05:59] Catherine Cusick: Yes. So here's where I fell on this. The rule of thumb is that if you're— if you want one number, if you're making more than $80,000 in a year, an S corp makes sense and is tax efficient.

[01:06:17] Paul: Less than $80,000 or more?

[01:06:19] Catherine Cusick: More than $80,000.

[01:06:20] Paul: More than $80,000.

[01:06:22] Catherine Cusick: Okay. You're between $60,000 and $80,000. We're in a gray area and we talk about it. If you're under $60,000, this makes no sense at all. It just makes no sense at all. If you're in this $60,000 to $80,000 universe, and that's where I am, and that's where, um, that's where I am hovering since leaving my job.

So here's what happens. You do need to come up for, for an S corp, you need to pay yourself a reasonable salary. What is a reasonable salary? Well, there are CPAs and folks on the back end who will spend lots and lots of time, um, helping you to determine what this number is. And it's an important number because there are— it'll trigger IRS audits if you go too low.

[01:07:13] Paul: Yeah.

[01:07:14] Catherine Cusick: If you had a job, uh, before you went and did all of these entrepreneurial things and you Uh, if whatever your job title is, whatever you call yourself now that you feel like you've made up your own title, there's still ways to, um, benchmark what the market rate is for that skill set. And you need to kind of be within the realm of that market rate.

[01:07:45] Paul: Got it.

[01:07:46] Catherine Cusick: So In my case, being within the realm of that market rate, because my skill sets are interesting and they are odd and they have gotten me a certain tier of money already, that means that I can't pay myself the reasonable salary I would like to. I would like to pay myself something like You know, I wanna make up a number. I wanna pay myself $15,000. I wanna like pay myself like a part-time employee. Yeah. Right.

And leave the rest of it in the, in the business and invest it. I wanna do it differently, but I have to pay much more than that to myself because of my benchmark.

[01:08:31] Paul: Right.

[01:08:32] Catherine Cusick: And then that erodes my profitability. Got it.

[01:08:34] Paul: So, so you have to pay yourself a reasonable salary, 60 to 80, gray area below is probably LLC is better. Is there— now, is there an argument for just setting up an S corp in case you make more money, um, and then just not taking the election?

[01:08:51] Catherine Cusick: I'm not sure that you can set it up as an— you have to take the election.

[01:08:56] Paul: Oh, okay.

[01:08:57] Catherine Cusick: Set up the S corp. An S corp is just a tax election.

[01:09:01] Paul: Got it.

[01:09:01] Catherine Cusick: That's all it is.

[01:09:04] Paul: Got it. And yeah, so I think you have to make Do you have to make that designation by like July 15th or something?

[01:09:11] Catherine Cusick: Yes, that's the latest date that you can do.

[01:09:14] Paul: Okay. And are you, are you paying for a provider to manage this for you? Like Collective or something or doing it yourself?

[01:09:23] Catherine Cusick: I'm working with a company called Collective.

[01:09:26] Paul: Collective. Yeah. Yeah.

[01:09:27] Catherine Cusick: Which is a fantastic, fantastic company for this. Use case. And if you are in that zone, uh, where you're making more than $80K, run, don't walk to them, because their, their pricing is fantastic. And they roll it all up together. They'll do taxes, they'll do all the accounting, they'll do everything for a rate that is very fair. And they're, they're truly fantastic.

What happens when you start into thinking and setting things up and making elections, being like, I want to do this now because I'll grow in the future. Well, in the meantime, you're racking up losses and those stay on the balance sheets, and then you just look like you're not making a profit. And the IRS will only let you do that for 4 years in a row.

I'll send them an email. I'll send it to my rep and just be like, I had a chat with Paul and I think that you should, um, make— I think you should help it, uh, be more of a no-brainer for Paul to do an S corp because—

[01:10:53] Paul: yes. Collective, we need you. Me and Catherine are onboarding so many people onto Solo Pass. There's going to be an explosion.

[01:11:03] Catherine Cusick: We're doing the deep emotional work for you.

[01:11:08] Paul: This is great. So, yes, pardon me for going into super technicalities, but some people—

[01:11:13] Catherine Cusick: Well, this is my life. I mean, the technicalities matter a lot.

[01:11:19] Paul: So what about, have you dug into employing your spouse in an S corp as well? Because like my wife does work with me sometimes and there's actually a reasonable case that you could like pay your spouse as well and then do other stuff with healthcare, which is probably an excuse to dig into like healthcare stuff.

[01:11:39] Catherine Cusick: Well, yeah, sure. Well, so now, um, you know, I'm not getting any dollars from Collective, but Collective is also fantastic for this. No one is paying me to say that. Um, if you wanted to go that route, you can. Uh, my spouse and I are very good. One of the great things about meeting Brian and the fact that he is a musician is that I am just not in that lane.

We aren't in each other's lanes, and they don't cross very much, and we have very independent work. We pursue them separately. That said, I still sent you an example of one time where we did work together, um, but that for the fun of it, because why not. But, um, we keep things pretty separate, and I am also very fascinated and interested in economics and the business side and, and revenue and everything about profitability. And my husband is a classic, like, would very much rather not think about it. Used to file his taxes like by October, whenever, always was doing extensions.

And I was like, yep, those days are over. We're doing it now. I do it in February when I'm bored. Because I want to. So we have very different approaches to, to how much we care about all sorts of things. But yes, it's very possible to, to handle these things together and to combine them, especially if it makes sense for your taxes.

[01:13:23] Paul: Yeah. What, um, should people be as scared, um, about healthcare as many people are? Like, I think, like, it's not great for self-employed people, but I think people's projection of it is far worse than the reality of it. Like, the Obama healthcare plans are decent.

[01:13:41] Catherine Cusick: They are decent. And I will also do my, um, unsponsored plug. I'm just not sponsored enough, y'all. But I, I'll do my unsponsored plug for healthcare.gov. I started, you know, I've had healthcare.gov— well, I've had Marketplace plans since 2017, so I've done this 5 times.

[01:14:03] Paul: Same.

[01:14:03] Catherine Cusick: I'm gonna do it 6— for the 6th time, like in a week. Um, but the first year or two, because we moved in 2018, so the first year or two I did it in New York. And New York has the worst— they have a state exchange and it's trash. It's, it's just trash.

[01:14:22] Paul: I call them hope and pray plans. Like, the New York plans are so terrible. I've done 4 states now too. I've done New York, Connecticut, Massachusetts, and now Texas.

[01:14:32] Catherine Cusick: Texas. So you have an even bigger sample size than I do.

[01:14:37] Paul: Massachusetts is by far the best value for price.

[01:14:41] Catherine Cusick: Um, well, and they've been at it the longest.

[01:14:43] Paul: Texas is probably second, which would probably surprise people. Connecticut's pretty bad, and New York is just like, oh my gosh, New York is like— I call them hope and pray expensive cocktail place.

[01:14:56] Catherine Cusick: I mean, I mean, listen, one of the reasons I needed to not live there was because cocktails are a very important part of like getting through life in New York, just drinking it all away.

[01:15:08] Paul: You want to have high-priced cocktails, not high-priced insurance.

[01:15:12] Catherine Cusick: Yes, there's the tagline for the commercial cut. But, um, yes, so the thing about Texas is that Texas, um, would really like everyone to pull themselves up by their bootstraps and thus does not have its own state exchange. Which means that you can get plans through healthcare.gov, the federal marketplace. Healthcare.gov is a good website. I'm going to go out on a limb and have my unpopular opinion. It's a good website.

It's a better experience. I started doing this in 2017. Things have improved. That's a very unpopular thing to say. I'm sorry.

[01:16:00] Paul: It's very good.

[01:16:01] Catherine Cusick: You know, it's still a government website and a lot of folks will hate on government websites all day long. It's gotten better every year.

[01:16:10] Paul: Yeah, it's actually very good. The service is excellent. Very good. You can call someone and get somebody on the phone in 30 seconds. In Connecticut, they still have an exchange that is like, it's terrible. It's awful.

[01:16:23] Catherine Cusick: I could never get anyone on the phone in New York. I mean, And my plans in Texas have been better. My premiums have gone down. Like what coverage we've— the coverage that becomes available each year keeps improving. One of the main things that I encourage everybody to do, whether you're in a state with an exchange or whether you just— whether you're in a state like Texas where we have the most uninsured Americans of any state, and you can go on the healthcare.gov site, there are searches that— there's a search option where you don't have to fill out the form to look at these things. You just put in your zip code and it'll show you the same interface.

You'll see the same information. You don't have to fill out the form first and you'll see what we're talking about. And then you can use filters to just narrow it down. And my favorite filter is to use the ratings. So I only look for plans that have higher than 4-star ratings, and it's worked out every time. So there's always going to be trash coverage in some places or terrible catastrophic options.

But then there are great ones and there are tax advantages to paying a better premium for better coverage.

[01:17:46] Paul: Yeah, I love that. Yeah. So don't be scared of healthcare. Maybe be scared of getting a mortgage, but there are workarounds there.

[01:17:54] Catherine Cusick: You don't have to, I mean, you know, I, I'm trying to help with this and if you, if you're scared of, let's put it this way. If I've just scared you about it, send me an email or DM me on Twitter because I will just, I'll talk you into it now.

[01:18:08] Paul: I'll post the link to your course, um, as well, which I think is, um, $15, I think. I will definitely be buying that if I consider buying a home at one point. Um, I'd love to, um, ask you about, um, Tennessee Williams' essay you sent me. Really awesome. I just read this. It's The Catastrophe of Success.

So I thought I might read something, um, from his essay, which is so cool. Once you know this is true, that the heart of man, his body, and his brain are forged in a white-hot furnace, for the purpose of conflict (the struggle of creation), and that with this conflict removed the man is a sword cutting daisies, that not privation but luxury is the wolf at the door, and that the fangs of this wolf are all the little vanities and conceits and laxities that success is heir to—why then, with this knowledge, you are at least in position Of knowing where danger lies. I love this so much. It talks about him getting famous and just sort of like losing his inner passion and going on a journey of reclaiming it. What does this essay mean to you?

[01:19:24] Catherine Cusick: I mean, number one, that's how a playwright uses a paragraph like that. That's how, how brief. Yeah. He can say something so grand and so full of meaning and just making sure that every single word counts and you're using the full extent of your imagination to write something. So that's one. But I read this essay probably when I was a teenager.

I don't know how old I was at the time, but this essay really— it just got to me at a useful and impressionable age. And I read it one time early on, and I've kept it in the back of my head for decades since, because I have a very deep belief, um, in the uselessness of chasing fame and, and the fact that fame has backfired if you listen to the self-report of so many of any of your heroes in any cultural or artistic frame, anyone who you respect who has achieved a level of fame, fame almost always, mostly logistically means that you've lost privacy. And like, the reality of it is often really depressing It's challenging. It makes you question the meaning of life and the purpose of what you're doing. It makes you question the work you're doing, your art, your place in the world.

It's a very— all of the self-report that I've ever read, starting with that, has said to me, this is not a state of being that's really worth aspiring to. And many of the people like Tennessee Williams who can write things like that weren't trying to do that. They were trying to, in his case, trying to tell the truth or trying to just like really create something that meant something deep to them, to express something about their lives that was important and meaningful. And the fame comes from whether if they hit some truth that does resonate with a lot of people this is just a distraction that happens to people who are great at what they do or who make something that resonates a lot. And, and this— that essay really was the one. It's like 3 pages long and it just makes so much sense to me.

He describes, um, a life where he was suddenly catapulted into living out of hotel rooms and being waited on hand and foot and how empty that felt. And he has a great line in it about how nobody in this life should be cleaning up anyone else's messes. And that if it's worse for anyone, it's probably worse for the recipient. Yeah. You should do things for yourself and you should struggle because that's what humans, that's what we're designed to deal with. So might as well stick with the struggles you have and you don't need them to be significantly worse.

Life is already very hard, so you might as well just try to do the work you're trying to do.

[01:23:00] Paul: What do you aim at instead of fame?

[01:23:02] Catherine Cusick: The truth is a big one. And I identify as a writer when I'm being ambitious and strong and have a good self-image. And I— my husband identifies with music and he is a composer, so we both write, but we write different content and mine has language and his has instruments. But you want to make something that feels true. And whenever I'm writing anything or revising something, anytime I'm spending all of my time rewriting a sentence over and over and over, my editor mind is asking myself, is that true? Do I mean that?

Is that what I mean? What do I mean? Say something more specific. Try again. And then at the end of that interrogation, maybe I have something that resonates or that's thoughtful. And that feels important to me.

That feels like an important thing to try to do because the things that aren't true feel wrong. And I'm trying to get things to feel right and to feel true to me. And that is usually what I'm trying to do most of the time. I love that.

[01:24:22] Paul: Yeah. Wanted to shift to some rapid fire questions. All right. Since you were listening, you probably heard some of them, but who's a path role model you've had?

[01:24:34] Catherine Cusick: Oh, that's a great question. I'm not picking one.

[01:24:40] Paul: Yeah, you can have multiple. No rules.

[01:24:42] Catherine Cusick: Yeah, there's an archetype. The archetype is character actors. Oh, interesting. Character actors. That's always who I wanted to be. That's the kind of career I wanted to have.

I think it's the career that my husband has the parallel of in music because he's a guy who can get plugged into the session and he will make that session amazing, whatever room it is. You don't want to be the front runner. You want to be somebody who's unique for being authentically who you are. Character actors were never being known for their appearance, unless it's unique. They're known for their work, and they're respected for the body of work. And the way that that gets expressed is that they work over and over and over and over again.

Because people keep calling them because they're wonderful to be around, they're wonderful to work with, and they do an amazing job at their work. Those are definitely— that's the career I've always wanted to have.

[01:25:53] Paul: Who's a good example of that?

[01:25:55] Catherine Cusick: Um, one of my favorite actors of all time is Michael Shannon. Yeah, yeah, Shannon is a great one. Michael freaking Shannon is just Truly a genius. What an incredible actor with so much range and now has come in. I mean, he, he really hit a different tier and he's much more famous now. He's more well-known and he's been in like franchises.

I guess he's, he's played very well-known villains. But his entire career and some of the deep cuts of his work are just like something else.

[01:26:40] Paul: What is something you've read that's inspired you? Read, listened to, watched lately that's inspired you? That's a good question too.

[01:26:54] Catherine Cusick: There are so many, so I want to pick something really good. There— the— my favorite play of all time, since I don't know how many folks are interested in theater or drama or that form of literature. So hopefully this is a source or a type of information that folks don't know so they can discover this now. There's a play by Jez Butterworth called Jerusalem. Mark Rylance. Played the lead in that, and he is another perfect example of a character actor with a career the length of your arm.

Jerusalem is the best play I've ever seen and the best writing, some of the best writing that anyone has fit into 80 pages that I've ever read.

[01:27:44] Paul: That's one. Amazing.

[01:27:45] Catherine Cusick: Yeah. Thank you. Something that probably others might not say.

[01:27:51] Paul: What's next in your journey? What sort of bets are you making now in Dan Visallo's language?

[01:28:00] Catherine Cusick: So I'm in this community, the Small Bets community that Dan Visallo started, and I've been slowly creating new resources always asking myself and prompting myself with the same question of like, what's something very hard that I've had to conquer in my life, or something very thorny and difficult that I've run into again and again? Have I figured any of them out? And if so, can I download whatever it was I learned that helped me do it out from my brain and from my experience and put it out into the world in a way that might be helpful. And that is what I'm trying to do now. I've been doing— within that community, he has guest classes, and he tapped me to teach one that's about what to expect when you go into self-employment in the beginning, especially if you have a full-time job, if you're an employee, if you dream of this life and you haven't made that leap yet.

What can you expect when you make this kind of giant lifestyle change. And Daniel is a fantastic lightning rod for many frequently asked questions about self-employment. And then he, bless him, punts those in my direction because I have a lot of material that I've, I've put into, in his case, a speaking and webinar format to walk through, you know, how do you incorporate? When do you incorporate? How do you get health insurance? How do you qualify for life insurance?

How do you qualify for disability insurance? How do you secure housing? How do you get a lease or a mortgage? What happens if you die? Like, then, then what? What How do you take care of the people in your family?

And all of the same questions that you're so eloquent about when you deal with the uncertainty and the emotional, psychological baggage of like, can I even do all of these things? My answer is usually a resounding yes because they can be done and they have been done. And so I'll just put out into the world in 30 slides in 90 minutes, like, here, here's how I went about those things. Here are the questions I asked at the very beginning, and here's my response to what I ended up doing. And things like, I tried the S election, I watched what happened for 9 months, here's why I'm gonna reverse that decision. And if my circumstances were different, why I'd encourage someone like Paul to consider it.

You know, think things like this. So I'm trying to build a bunch of resources now taking what I've been prototyping behind the scenes in the community and trying to, number one, make a lot more of my writing public, uh, to write down more of my thoughts and opinions and instructions around these things so more people can access them. A lot of it for free, hopefully. A lot of it as a gift to the world. And then some of it, um, to try to create options where you can support me while I am also navigating all of this and my dear husband who doesn't want to look at our taxes.

[01:31:35] Paul: I love it. Well, it was so great to talk with you today. I feel like we could have went another couple of hours getting into the technicalities of these things. But yeah, you're a great resource. I'm really excited to continue sharing what you create and share out there. Kudos to Dan.

There will be very more soon. Brought you into his fold. But yeah, keep sharing. Um, this stuff is super valuable. I've gotten a lot of questions about it over the years, and I'm happy to point people to a valuable resource. Uh, thank you so much for joining the podcast today, Catherine.

[01:32:12] Catherine Cusick: Anytime. I'm so pleased that I could come. Thank you.