#146 Separating Work & Identity - Simone Stolzoff on the myth of a "Dream Job," last-minute around the world trip, journalism, work, identity, writing his book, knowing when to quit, and the dangers of turning passion into a livelihood

[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 to Simone Stolzoff. He is a writer, recently published a book, should be out by the time this podcast is released. Called The Good Enough Job. He explores topics I love, uh, our relationship with work.

And the more people writing about this, the merrier, because it means there's more people I can hang out with and nerd out with on these topics. Uh, we'll dive into his story. He was definitely on the default path, but took an adventurous route through that path. He did some traveling abroad, due to a last-minute ticket he booked and explored writing but also design. And I'm intrigued by how he paired those. We'll also just talk about the journey of writing a book, how his experience— he went the traditional published route compared to mine— and how he feels about that.

Welcome to the podcast.

[02:10] Simone Stolzoff: Thanks, Paul. It's great to be here.

[02:12] Paul: So we've been talking on the side for years. It's fun to talk about this with you and Now we'll both have books out there. Um, I was lucky enough to read a copy of yours a year ago, and I was just pumped that more people are writing about this. I think you were hitting an angle which is really worth talking about, which I don't think many writers actually, um, hit it correctly in terms of like the deeper questions of like, what is a life? Like, what should— how should we be spending our time as adults? But before we dive into that, I want to just explore your personal journey.

And the question I always start with is what are the stories and scripts you grew up with around work? Could be broader around success, things like that. But what were some of the stories you grew up with?

[03:04] Simone Stolzoff: Yeah, so my parents got divorced when I was very young and they both remarried early. And so I had 4 parents raising me since I was, you know, 5 or 6 years old. And so there were 4 different models of what work could be like. I grew up in San Francisco, but sort of pre-dot-com, pre-tech kind of finding its sex appeal. And my dad and my mom biologically are both psychologists. And I am example A, you know, the result of 2 psychologists coming together.

And then my stepdad founded San Francisco Jazz Festival. So he's in the music presenting world. And then my stepmom is a lawyer. So there's sort of this spectrum of like art on one hand and like traditional professions on the other hand. And just to fast forward through my own experience, I studied poetry and economics in college. And so that tension between the pursuit of art and the pursuit of commerce has been a theme throughout my whole life.

[04:02] Paul: It's interesting, and feel free to say you don't want to talk about this more, but it's interesting to see two psychologists kind of go in opposite directions. Like a a lawyer is like even more conservative, whereas jazz is basically improv, right? So does that kind of describe the two differing personalities of your parents as well?

[04:22] Simone Stolzoff: Yeah, you know, I imagine this is probably pretty common among children of divorce, but, you know, their two lives are pretty different now and it's hard to quite picture them together, you know, and I'm very happy that they both remarried and I love my stepparents, my stepsiblings that I inherited. Through those marriages, but it's amazing how much we're sort of a result of our context and the people that we spend time with. And now it's hard for me to imagine my dad and my mom together, even though I'm obviously the result of that.

[04:53] Paul: Who was the biggest influence on you growing up?

[04:56] Simone Stolzoff: I'd say my older brother. I had an older stepbrother who was 6 or 7 years older than me. And so when I met him, I was about 5 years old and he was already a teenager. And in the way that many older brothers do, I inherited his mix CDs and his taste in culture and his perspective on how to live. And also, I think interestingly, my brother was working from a young age. He was washing dishes in the back of a music venue, and he was always sort of thinking about how to sustain himself.

And I grew up with a fair amount of privilege. I went to private school in San Francisco. It was a relatively sheltered experience. And my parents always told me, you know, you can be whoever you want to be, you can do whatever you want to do. But there was something I appreciated about my brother's sort of self-sufficiency and the way that he operated in the world that I always looked up to.

[05:56] Paul: A lot of people are told you can do whatever you want to do when you grow up. I think I was told it. What I think I realized when I was older is there was a lot of hidden assumptions behind that, which is basically like, you can do whatever you want as long as you fit it in a full-time job and employment and continuously throughout adulthood. Were there assumptions like that or were your parents really like, go do whatever you want?

[06:20] Simone Stolzoff: Yeah. I mean, so 3 of my 4 parents have graduate degrees and my stepdad is a college dropout. And so I think in some ways I inherited this perspective of like growing up in a certain neighborhood in San Francisco. Most of my, my friends' parents were doctors and lawyers or maybe in the business world in some respect. I think going to graduate school was just sort of something that I always assumed that I would do. And the sort of peer group I had was a very sort of like high-achieving, very academic group.

I went to this high school that was called University High School, which tells you about everything that you need. It was very like pre-professional, very like academic in its orientation. And then I went to college at Penn, which is a very pre-professional school as well, where Wharton, the business school, is sort of the dominant culture. And so even though nothing was explicit about what I had to do or the path that I was on, there was like an implicit assumption that you, you know, go to private elementary school and then private high school and then go to the best college that you can possibly go to and then get the highest paying job that you can possibly get and work your way up a career ladder. And it wasn't until I was about 24, 25 that I finally found out for myself that you're able to break from that script.

[07:46] Paul: Yeah. You had this interaction with somebody, Anis Mojgani. I could be getting her name wrong, your senior year of college. Tell me about that.

[07:56] Simone Stolzoff: Yeah, so Anise is a poet. He's actually the current poet laureate of the state of Oregon. And I was a poetry nerd. Like, in college, my biggest community was the spoken word and slam poetry group. And I had the opportunity to interview Anise for an article that I was writing. And so I called him up and, you know, this is me, I was 22 years old, about to embark on this unknown future.

I was calling this guy who was like my professional idol, and I was expecting him to sort of tell me the follow your passion pep talk. You know, I wanted him to say, you know, go out and pursue poetry and see where that takes you. And he didn't. He was actually very frank with me and He said, you know, some people do what they love for work and some people do what they have to for work so they can do what they love when they're not working. And neither is more noble. And I think that last part is really key.

It's like really what stuck with me is this nobility aspect of the way that we tend to revere people whose careers and their identities neatly align. You know, the astronauts or the painters or the social entrepreneurs. And here was, you know, my idol, a professional poet no less, telling me that it's all right to have a day job. And, you know, of course, being the naive 20-something I was, I didn't heed his advice. I was looking for a vocational soulmate. I went out searching for a dream job.

But on the other side, you know, a decade and a half later, I can really see the wisdom in that. And I think a lot of the world is coming around to that idea as well. That having a job that's more of a means to an end is nothing to bat an eye at.

[09:46] Paul: What— so you say professional role model, but it sounds like you weren't seriously considering becoming a poet or something. What was that about?

[09:58] Simone Stolzoff: Yeah, I think, you know, I throughout my entire college and early career was always hedging. I was trying to optimize for optionality so that I could, you know, continue to keep as many doors open as possible. And so I studied poetry, but I also studied economics just in case, like, I wanted to go that route and I wanted to pursue something creative, but I ended up becoming a copywriter in the business world because that felt sort of like the most, like, palatable way to be a creative and also have the stability of a firm or an agency behind me. And so I think there was a lot of fear there. There was maybe not confidence in my own ability to make it as a creative, or maybe this like more strategic sort of externally validated motivation that said, okay, like your poetry is cute, but like go get a business job like all of your friends.

And especially at a place like Penn that, you know, so many people go through the on-campus recruiting process and, Even my friends that did, you know, do theater or were urban studies majors ended up going to work for, you know, Goldman Sachs or BCG for their summer internships, just because it really just deferred a lot of dreams. You know, it was hard to feel comfortable with uncertainty when so many other people around me were on a prescribed path.

[11:28] Paul: It's hard to turn that down too. I think, I mean, my college was not like this. We didn't have access to like the elite companies, but in grad school it's easy to get an impressive job. So I think a lot of Ivy League schools are like this. Like pretty much everyone, if they really want it, can get like an impressive job to the adults around them. Right.

And that's so hard to turn down. You did go copywriting though, so that's not exactly one of those like prestigious, impressive paths. How were you thinking about your path at the time?

[12:04] Simone Stolzoff: Yeah, I mean, I think there were two influences. One was I was literally on job sites looking for writer and the word copywriter kept popping up. And the second was that I was watching Mad Men at the time and Peggy was this like amazing copywriter and I was like, oh, maybe I could do that. It's sort of like a mix of like business and creativity. And, you know, I, I like in retrospect, I can see all of these different kind of pivots in my career. Being influenced by like the media I was consuming in that particular moment for what I thought was like cool or prestigious or something that I wanted.

[12:41] Paul: Yeah. Did it deliver?

[12:43] Simone Stolzoff: I'd say yes and no. I mean, I think there— so I moved back to San Francisco, joined an agency, was a copywriter, and there's something amazing about that period in your life where it's like the first time where you're earning a consistent income. And I had so little responsibility. I was living with 3 of my best childhood friends in a house in the Haight-Ashbury District. And it almost didn't matter what I was doing for work at that phase of my life. I was like, this is magic.

Like every 2 weeks, just these numbers show up in my bank account. And I was going to concerts all the time. And I was just like, my social life was so much more important than my career at that point. And then it came to a head sort of unexpectedly where my best friend from college was a professional soccer player at the time. And he was living abroad. He was living in Sweden, and he gave me a call and said, hey, I don't know how I got here, but I'm on this like Flyertalk forum, this like travel blog, and there is this glitch on Priceline.com.

And if you buy this very particular itinerary from San Francisco to New York, New York to Milan, and then 8 days later from Prague to Ho Chi Minh City, you know, it made no sense. But this very specific itinerary The whole ticket was $200 and he was like, you know, I saw it's leaving from San Francisco and so I'll call you and tell you.

[14:10] Paul: How far were you into your career? Like after school?

[14:15] Simone Stolzoff: I'd worked probably 14 or 15 months, so less than a year and a half. And yeah, it was the golden ticket, you know, and like there was probably some like latent acknowledgment in the back of my mind that this wasn't the path for me. And you kind of just open your eyes to opportunities that persist. But really, like, I was pretty happy with my job and I was just more happier, more happy by the prospect of buying a one-way ticket and traveling around the world.

[14:44] Paul: Yeah. And that's not something you thought of before that?

[14:48] Simone Stolzoff: I mean, yeah, I had dreams of, you know, while I'm young, before I have a mortgage or a serious relationship, I want to, like, see the world. But it wasn't explicit until this ticket came around. You know, Travis literally called me in the middle of the night. It was 3:00 AM, and I thought about it for about 30 seconds, and I bought the ticket, and then I submitted my 2 weeks' notice at work, and in a month I was at the airport.

[15:14] Paul: You know, that's pretty dramatic. Like, where does that courage to take that leap come from?

[15:21] Simone Stolzoff: Hmm, great question. I think it's a mix of this experience that I had when I studied abroad in college, which was my first time really living on my own by myself. And I learned in that moment that like, I had a lot more agency and autonomy over the course of my life than I thought I might have. You know, I was sort of like a goody two shoes, you know, I was pretty square, I followed the rules, I jumped through whatever hoops were put out in front of me. But just that 8 months living in Buenos Aires in Argentina showed me two things. It showed me how other people live and the world out there, and two, how much I liked going to the beat of my own drum.

And so the decision to quit my job, end up traveling the world for 11 months, almost an entire year, is a natural extension of that curiosity and that thirst for novelty and autonomy that I that I had.

[16:28] Paul: How were you thinking about your life during that trip? Were you thinking, okay, this is a 1-year break. I'm going to go back and restart my career. What were the thoughts?

[16:37] Simone Stolzoff: Yeah. I mean, I think this is maybe similar to some time that you've had abroad, which was, I thought that the trip would give me all the answers. I was like, I'm going to go and then travel, just like recreate for a little bit. And then I'll figure out sort of the direction of my life and where to go from there. And the truth is it didn't. Like, I didn't come out on the other side of 11 months with like, okay, I'm going to go to journalism school and then I'm going to do that for a few years and then I'm going to leave journalism and enter design.

And on the side of my design job, I'm going to try and write a book. Like, there was none of that. But I think what it did was help cultivate a comfort with ambiguity and the unknown. Like, there were little things about that trip, like I was in Nepal when the earthquake in 2015 happened. And, you know, I'd done a little bit of like culture writing on the side, even when I was working at the agency. And I started pitching stories from what I was seeing on the ground in Nepal because it was this, you know, international disaster.

And I had this unique perspective on it. And that was really my start in like journalism, like reported journalism, you know. And there are friends that I made along the way in that trip that I've worked with or stayed with and had other professional experiences. But I really wasn't looking at the time through the lens of career. I was looking at this traveling that I was doing through the lens of how can I suck the marrow out of life? How can I be a 25-year-old with my clothes on my backpack and be able to say yes to as many different opportunities excite me?

[18:20] Paul: I love Kevin Kelly's idea that countries should basically subsidize a year abroad for people. Like, travel is one of the most valuable experiences. Right now we're just subsidizing really expensive college and it just keeps getting more expensive because subsidies increase prices. But would you agree with his take? Like, do you think this is just something every young person should do no matter what?

[18:46] Simone Stolzoff: Yeah, I thought about this a lot and how, like, prescriptive I can be about the benefits that travel has had in my own life. And I actually do think that everyone would benefit from it. I don't think it's an overreach to say that just some sort of experience where you can get out of your bubble, the, the growth line is so steep. You know, you can literally just go around introducing yourself and try and figure out who you want to be in each of those. Interactions, there's no period of my life that has shaped me more into the person that I am than that year I spent quote unquote doing nothing.

[19:27] Paul: I love that. So you came back and you sort of threaded together this really unique combo of journalism, writing for companies, working in design. Uh, was that very emergent? Did you have any sort of intention behind that?

[19:42] Simone Stolzoff: I knew that I liked writing and I knew that I wanted to be surrounded by creative young people. And outside of that, I didn't really have a plan or like a vision for what my career might hold. You know, I came back and I started working for this like startup journalism publication that was hosted on Medium in its early days. I don't know if you remember Medium used to have these sort of like in-house in-house publications. It was called Timeline. It was about like bringing relevance to, to history.

But it was only, you know, I worked there for maybe 4 or 5 months and then some friends of mine were starting a company that was like, I thought, very soulful. It was a way to pick up homemade meals from people in your neighborhood that like to cook. It was called Josephine. And I was like, oh my God, I want to work with my friends that are like doing the startup thing. And so like, I left the Timeline job. I go work for Josephine and I was doing marketing and communications, you know, and in many ways that was like the best job I've ever had because it was like my two friends, Matt and Charlie, and running this company and, you know, there were 8 of us and like raising money and we were all like in our 20s and we had no idea what we were doing.

It was just sort of like the— I wish I was like a gonzo journalist at the time because it felt like You know, who gave the teenager the keys to the plane, you know? And, but I realized that like, you know, maybe the marketing world wasn't for me and I wanted to be writing the stories, not pitching them to journalists to write about us. Then I ended up going back to school. I went to journalism school for a year to like square my hips towards what I thought was gonna be my path, which was being a magazine reporter. And I did that for a little bit and then I got restless again, you know, and left journalism to go work for IDEO, which is this consultancy. And yeah, so it's been a very meandering path, you know, the, the drunkard's walk of my career.

[21:48] Paul: What is journalism school like? I'm just curious about what the energy was in journalism in the mid-2010s. Like, I'm picturing like the mood was not the most optimistic, but maybe, maybe I'm wrong.

[22:05] Simone Stolzoff: Well, there's this kind of weird mix where on one hand it's like, you know, all of these publications are hemorrhaging employees and traditional print media doesn't know what to do with itself and the pivot to video that didn't work out, yada yada. At the same time, there are all of these like exciting upstart publications and new mediums. You know, I remember in journalism school, VR journalism was going to be the next frontier. And like The New York Times was putting out like a VR video every single day. And there were these new hot publications like BuzzFeed and Quartz that were doing new things when it came to telling stories and Vox. And I was like, I want to be there.

I want to be at the forefront of new media. And here we are in 2023 and like, yeah, they're all shutting down. BuzzFeed is all shutting down, you know. But I think of all of like the people that I've worked alongside, journalists are still my favorite. They are, they tend to be very like curious and creative and good conversationalists and like give a shit about something, you know? And in other industries like tech or consulting that I've worked in, there was a lot more apathy.

[23:16] Paul: Interesting. Yeah. What, um, And as that journey progressed, uh, what was, how was your relationship to work, uh, and writing evolving?

[23:30] Simone Stolzoff: Yeah, I mean, I think the most clear inflection point was in 2018. I was working as a staff writer, um, at like, you know, a hot New York-based publication and a recruiter from this consultancy idea reached out to me. And, you know, like, never say no to the interview. I was like, okay, I'll go along with this. I'd heard of IDEO. I think I'd watched like David Kelly's TED Talk or something, and I sort of started interviewing for them.

And, you know, I was covering work that was like my beat. And they had this small consultancy within the firm called Design for Learning that did a lot of like higher ed and K-12 consulting. They wanted to expand to think about, you know, corporate space and the future of work, quote unquote. And I was intrigued. I sort of like passively went through the interview process and then I had these two paths ahead of me. You know, one was to continue to be a staff writer at a publication on the work beat, a job that I had like, you know, rearranged my life in order to be able to get in the door for.

And the other was, you know, the, the other door number 2, you know, is this world of design that I knew next to nothing about for a company that had like a fancy brand. And it really sent me for an existential loop. On one hand, it's like, oh, the agony of having to choose between 2 attractive job offers. You know, like, I don't expect much sympathy. But on the other hand, like, it didn't feel like I was choosing between two jobs. It felt like I was choosing between two versions of me.

And I think out of that struggle and the tumult of trying to make this decision was the first kernel that ultimately led to the book is, you know, how did our jobs and our identities become so entwined? And maybe there is a way in which separating yourself from your output or separating your self-worth from your work can actually lead to a healthier relationship to work and to life.

[25:46] Paul: So that led you to work for IDEO?

[25:49] Simone Stolzoff: So yeah, I ultimately took the IDEO job, which ironically, you know, in retrospect was probably the best thing that happened to my writing career. Because I was, you know, no longer turning out articles every single day. I was working on projects with interesting people, but the job was, you know, a means to an end. It was like something that it was easier for me to kind of clock in and clock out. I left my work laptop at work, and it was in those first few months where I was thinking about, okay, how can I keep my writing muscles from atrophying? That I started working on this book project as a way to just have an accountability to continue to write, to continue to think in stories and narratively.

And I'm very grateful for IDEO because if I was working a journalism job, I definitely wouldn't have had the capacity or the space to be able to explore something that has ultimately become my proudest professional achievement.

[26:49] Paul: Yeah, that's such an interesting insight. And I think this is the major flaw in chasing your passion. Well, I don't think the idea of chasing your passion is a bad thing. I think it's the fact that most people take that to mean find the job doing what you think you love. And then in the process of doing that, you have to deal with all this other stuff and it's inevitably going to drain your energy. I was never able to conjure up enough energy to actually do anything substantial.

On the side of work. I was just too drained, but I also didn't have the frame of thinking about it that way. I was always trying to find jobs I loved or find the next dream job. And it's such a challenging thing. And it was in the air in the 2010s. The 2010s were like meaningful work, dream job, you can have it all.

The millennials are taking over the world. Like, what happened?

[27:52] Simone Stolzoff: Totally. Yeah. I mean, all of these young tech CEOs that looked like they were maybe around our age, and there was so much excitement with WeWork sort of like plastering "Always do what you love" on the walls of their coworking spaces and their mugs. And I believed it, you know, I mean, people did.

[28:10] Paul: Yeah, it was broad. People believed it. It was, it was a collective. Belief. Like, there wasn't— people weren't getting tricked into this. People were—

[28:21] Simone Stolzoff: and I think that's what makes this topic that you and I both explore so rich is it's nuanced. It's not follow your passion or don't follow your passion, you know. And we do work more than we do just about anything else. And how we spend those hours matters. You know, I like what you say about You try and optimize for liking your job. And I think like coming into writing the book, I think I had more of a hot take.

You know, I was like, work is bad. We do it too much. Our whole world is centered around work. Like, ah, there has to be another way. But on the other side of, you know, 3 years of work and reporting, I think my hot take is tempered into something more mild, which is, you know, it's— there's no problem in identifying with what you do or getting meaning from your job. It just can be risky when it is the sole source of identity or the sole source of meaning in your life.

As so many, especially tech workers, have found out in the last few months and years, it just doesn't lead to a diversified or resilient sense of who you are.

[29:29] Paul: Hey there, it's Paul, and thanks for listening to The Pathless Path podcast. I wanted to take a quick break to ask you a small favor. I'm really loving doing this show and for the first time have the support to help me take it to the next level. Unfortunately, it's still pretty hard to spread the word on podcasts, but that's where you can help me out. If you enjoy these episodes, I'd really appreciate it if you could leave a review on Apple or Spotify or simply share the episode on social media or with some friends. Finally, if you're enjoying this conversation, You probably like my book too.

It's been read by thousands from around the world, and each week I get notes saying how much the book helped people on their paths. You can grab the audiobook read by me or other versions in the link in the show notes below. Let's get back to the show. Yeah, and I went through a similar thing when I left my job. I was just like, F work. I just want to like run away and like live in a cave.

But eventually I developed a love for writing and I was like, ooh, this is interesting. I'm excited to do this. I'm not tied to making money from it. It feels worth doing. What if I design my life around this? Even if I have to make money doing other stuff, this is substantial and worth worth living for.

And that's really hard because I think what you discovered as well, and what I discovered is that a lot of this is just like mental models people have. People think, oh, I need to be able to monetize the thing I love. That's not promised for anyone. I didn't make any money from writing for 7 years.

[31:21] Simone Stolzoff: Totally.

[31:22] Paul: If I never made money from my book, would I still be writing? 100%. I love it. I'll keep doing it. I don't care if I make money. It's vital.

It gives me this connected state which I didn't know existed before. And I think that's possible for many people. It's just that people underestimate how much, like, just Being in a job or being in a workplace that isn't enabling them the space to do that work will just chip away at that energy to actually find it.

[32:00] Simone Stolzoff: Totally. And that's what I fear about so much of the dominant narrative right now around like side hustles and side grinds and monetizing your passion is once you turn what you're passionate about into your livelihood, it can really change your relationship to your passion. I'll just bring up one quick study that I write about in the book, and it is a psychological study that looked at preschoolers and specifically it was trying to study their motivation. And so they went into this preschool and they observed preschoolers during their free time and they saw the kids that liked to draw. And then they took the kids that liked to draw and they broke them into 3 groups. For Group 1, they said, if you continue to draw, at the end of this experiment, we'll give you this good player award.

It was literally like an award with their name and a ribbon. And if you draw, we'll give this to you. The second group of preschoolers, they didn't say anything up front, but if they drew during the experiment, then they received the award. And then Group 3, no award, didn't say anything before or after. So they do the experiment. They come back to the classroom 2 weeks later to observe the students during their free time.

The students in groups 2 and 3 drew just as much as they drew before and after the experiment. But the students in group 1, the students who were told that if they drew, they would receive an award, drew at much lower rates than they did before the experiment. And the takeaway is pretty straightforward. Like when you convert your passion into work, it drains your motivation to do it often. And, you know, we know this about like the difference between reading a book for school versus reading a book for pleasure, or going on a drive because you have to versus going on a drive because you want to. When you're only attaching yourself to the extrinsic motivation, to the external rewards, it really changes your experience of the behavior itself.

[34:01] Paul: Yeah. And I don't even know if that's categorically true, that if you try to make money from your passion or something that really brings you alive, it will undermine it. I think it's that people have— it's wishful thinking. They think that it's just going to work smoothly, right? The reality is, as soon as you try to make money, you're doing other stuff. Right?

Like, if you're trying to make money from writing online, you might be handling with like billing processors and accounting and like weird glitches with email processors and things like this, right? It's, it's all the other stuff that gets in the way. And then the pressure to make money. I think most people expect, oh, I can make money from my thing. And then That's like a whole other thing. That's where I always advise.

I don't know if you can make money doing what brings you alive and what you feel connected to, but at least step one is trying to figure out if you can actually find something like that.

[35:07] Simone Stolzoff: Totally. And I think that's the difference, right? If you stay connected to your intrinsic motivation, to the drive, to the reason why you wanted to become a writer in the first place, Yeah, like, go for it. Why not? You know, but the problem is when you lose sight of that vision and you forget why you took that leap and you are trying to troubleshoot the email bug or you're spending 90% of your hours focused on monetization as opposed to creation, then it's very easy to make your passion or something that you have a lot of pleasure in feel like a drag.

[35:48] Paul: Like you're going through the book launch process right now. Do you enjoy that part?

[35:52] Simone Stolzoff: It's a completely different job. Like I had no idea how many different jobs being a quote unquote author was like. I was obviously familiar with like writing and reporting because my background is in journalism, but the promotion side, especially with a traditional house, is like nonstop. You know, it's, it's this weird message of like, no one is gonna advocate for your book more than yourself. And like, you have this like bar set from your advance that like, I'm not gonna make any money until I sell a certain number of books. And therefore, like the market never sleeps.

There's always one more sort of post I could be doing on social media or one more interview I could be doing to this small radio show in this random town, you know? And I think, It's hard to know when is enough, you know? And I think that's ironically, you know, the title of the book is The Good Enough Job. When you work for yourself, sometimes those lines between when you are and aren't working become harder and harder to draw.

[37:01] Paul: So how do you know when to stop now?

[37:03] Simone Stolzoff: I think there are a few things. One is understanding sort of the seasonality of this type of work. And right now I'm in a season of working. You know, I am in a grad. The book comes out soon. There is a limited amount of time that I have to prepare for this launch.

The problem is that often the sort of season can just expand like a gas to, like, take up as much space as you allot for it. And so my antidote to that is in July I'm going to Turkey with my partner and then we're going to Italy and we're not going to be working at all.

[37:48] Paul: Nice.

[37:49] Simone Stolzoff: And so like my sort of mentality is, okay, in May, in June, I'm going to focus on trying to get the word out about this book. And then I have like a structural backstop to protect me from going further than that. The second is to like think about ways in which you can create some of those structural barriers in the course of your day. You know, I think like anyone can have the intention to like work less or to like have more balance in their life. But what I found is what actually helps with that is like trying to outsource that willpower as much as possible and have obligations to the people I care about where I have to be present and I can't be like on my email when I'm going on a walk with my best friend or I am exercising in a certain way. That allows me to like unitask and not have one eye open like a shark trying to think about whether like my tweet got enough engagement.

Just having those other containers of my life where that have different metrics of success beyond like book sales has been really helpful for not only my ability to regenerate and recharge and be clear in what I am doing when I'm on the clock, but also just cultivating different aspects of who I am. And, you know, like, yes, my name is on the book and I am an author, but I am also like an Ultimate Frisbee player and a chocolate chip cookie fanatic and like someone who likes to spend his Saturdays in Golden Gate Park. And I'm trying not to let the fact that I have this big sort of thing in my professional realm take away from all those other sides of who I am.

[39:30] Paul: I think you should change your about page to that.

[39:34] Simone Stolzoff: I am a chocolate chip cookie connoisseur.

[39:37] Paul: No, seriously. I think it, I think in today's world, these kind of intros are like way more interesting and people are like, it, it's like a curiosity trigger. It's like, oh, that's interesting. What does that mean? Are there all like, all these questions arise.

[39:53] Simone Stolzoff: Um, yeah, I love that.

[39:56] Paul: What, at what point in writing the book did you think, oh crap, I might leave my job?

[40:02] Simone Stolzoff: Yeah. I mean, one of the great ironies is I'm writing a book about the culture of overwork and work-centricity in America, and I'm doing it on the side of a full-time job. And that irony is not lost on me. You know, like I examine some of that tension in the book itself, and I ended up taking a leave from work to focus on the book for a few months. And then I realized, you know, actually what I want right now is to be able to square my hips towards this project that is more meaningful to me. And, you know, maybe there will be another corporate job in my future, who knows?

But for right now, I want to be able to do fewer things more deeply.

[40:44] Paul: What was it in that time you took off though? Was there a felt sense? Was there a just excitement? What about it?

[40:52] Simone Stolzoff: Yeah, I mean, it definitely, there was like an expansiveness also, like my partner and I left and we went to Spain and that's where I took my book leave. And so just being in a different context really helped facilitate that. Um, and there was also this like finite nature of it, which made me appreciate it, I think, which is like kind of like being a second semester senior in high school where you're like, I have this like time-bound period, like I'm going to enjoy it where I like, those were some of the most fun months of my life, you know? And then I came back to work and I was like, okay, let's see if I can continue to do this. And quickly it became clear that the answer was no. And so I made a plan to leave and I've been working for myself for about, you know, 8 months now.

And it's interesting, like I'm sure you've seen this in a lot of people that you've talked to. When you work for yourself, we can often be our own worst micromanagers. You know, like we can be the ones cracking the digital whip. We don't need someone to say, you know, make sure that your butt's in your chair and you're at the office. And so it's had me have to put into practice a lot of the wisdom I learned from the experts that I talked to for the book and how to make sure that even on this quote unquote Pathless Path of doing my own thing, that I'm not and continuing to act out a lot of the internalized capitalism and corporate expectations that I've inherited.

[42:20] Paul: Like what, what, uh, what were some of the biggest challenges?

[42:24] Simone Stolzoff: I think the biggest one is just knowing when to stop, even when the work is not done. Um, there's this guy that I spoke to for the book who's this religious scholar named Caspar Terkyle, who's an amazing, amazing thinker and guy. Yeah. And he does this thing every week that I really look up to. And every Friday afternoon, he sends out the same tweet, which is, "The work is not done, but it is time to stop." And I just love that so much. It's like so profound and hard to actually believe, you know?

And I— and when I was first starting out finishing the book, working full-time on it, weeks where I like hit my writing goal, I would feel great. And weeks that I didn't hit my writing goal, I would feel like crap. And I realized that I was just sort of like rising and falling with the roller coaster of my professional accomplishments. And I needed to have other mechanisms in order to help me be the person that I wanted to be. Because what inevitably happened in those early days is like, I wouldn't get as much work done, be as productive, and therefore I would like work longer. To be, try and make up for it.

And it becomes this like vicious cycle where like, I'm not doing my best work. I'm trying to push on through and it's not actually helping my work or my life or my relationships.

[43:47] Paul: Yeah. I've told people they need to fire the manager in their head if they're going, going to stay on this path. Uh, so were you working just like regular Monday through Friday after you quit your job? I always find this so fascinating because My impulse is like not to work. I've never struggled with like not doing enough. Yeah, I'm just like, whatever, I don't really care.

[44:10] Simone Stolzoff: Totally. And, you know, you become the envy of my eyes. I see Paul taking another walk around Austin.

[44:18] Paul: Well, I don't think I'm doing anything special. I think I've always been wired by this. And I think what's actually enabled me to get more done counterintuitively is actually leaning into that. Like, I am very like, I can get more done if I wander without a plan. And then I'm just like, oh crap, like this idea, I need to like spit it out and nothing like— and this comes from like the capitalism. Like, I think like the basic criticism of capitalism is like not really that persuasive.

But the interesting take on capitalism is that it shapes our reality and then our consciousness of like what our own, like our own human natural tendencies. These haven't changed like for thousands of years. We start thinking like, oh, I'm supposed to work 8 hours a day, 5 days a week.

[45:12] Simone Stolzoff: Totally.

[45:13] Paul: Then my lived experience now is I can work less, but then work like 5 hours on a Saturday and like do something I'm really excited by and proud of.

[45:26] Simone Stolzoff: Yeah.

[45:26] Paul: And there's this sort of magic you need to think, tinker about with that.

[45:31] Simone Stolzoff: Yeah. I remember in the very first draft of the book, I sent you the introduction and there was a line that said something like, the 40-hour week and 2-day work week are relatively arbitrary. They were negotiated before and they can be negotiated again. And you were like, this, this fires me up, you know? And it's true because like, It's fake. It's, yeah, it's fake.

And a lot of it is just like anachronistic at this point. Like in an industrial age when you're maybe making widgets on an assembly line, yes, there is like more of a direct relationship between the number of hours that you put in and the amount of output that you get. But in a knowledge economy, in this new world that we're living in, there isn't a direct relationship. And it's actually by taking that walk or giving your brain the space it needs for ideas to bounce off of each other, that actually produces better work. And I think so many offices and so many industries are still working with that industrial model of how work gets done.

[46:34] Paul: Yeah. And it's a lot of it's fear. We grew up with these models. This is how the world works. This is how you're a good person. And then these people eventually become leaders and then there's opportunity to change.

It's like, we can't do something different. Like right now we're in a really interesting period because We don't have a 5-day work week anymore, but our concept is that we still do. Nobody is going to offices. I'm talking, we're talking about knowledge work, right? And these are the people listening to the podcast anyway. Knowledge work, 80% of people are working remotely on Fridays now.

We basically have a 4-day work week. Everyone knows that like everyone's using this Friday for like errands and like excess personal stuff. Going into their life. And that's a good thing.

[47:23] Simone Stolzoff: Totally.

[47:24] Paul: These are people that are going to work for these companies longer. They're going to spend more time with their kids and family. They're going to be happier. And this story just isn't being told as much. I think you dive into it a bit with some of the remote work and some of the stories in your book. But yeah, it's kind of crazy.

We have this fake debate. Should people return to the office? It's over. Hybrid work is here. Most people are working 3 days a week in an office and have much more flexibility than before. And that is freaking beautiful.

[47:58] Simone Stolzoff: Yeah, I, I'm reminded of this conversation that I had the other day with a doctor. This is like an attending doctor at a big hospital. And I was asking him about the sort of residency model and like How is it possible that, like, making residents work 24 and 36-hour shifts is, like, good for anyone? And, you know, he gave me a few arguments about, like, continuity of care and fewer pass-offs. And we sort of, like, dug into all of them one by one. But after, like, digging into it, the truth came out, which is basically like, this is how I did it and this is how, like, my boss did it.

And like, it's like Greek life pledging, you know, it's like I went through the wringer and therefore like the next generation should too, as opposed to like actually returning to first principles of like what makes sense.

[48:51] Paul: I call this sufferism. I suffer and thou shall suffer too, right? And this goes back to like religion, and it's sort of this conservative strain of energy that is very deeply embedded in the US. And it's not aligned with politics. Pretty much everyone believes it, especially over the age of 50, which is that how can you trust people if you're not monitoring them, you're not controlling them? Can you really trust people?

And there's this really interesting quote in an Ezra Klein podcast where he's interviewing somebody about like the welfare state, and she just said matter-of-factly, she's like, it doesn't really matter with a lot of the things we're doing We just can't give people something for nothing. Food is like that. Just not politically viable because the majority of people not politically aligned, just vast majority of people just don't, don't want people to get a free lunch. Like, and so much of that fear is embedded in the work society of like, what if people like, what if people do X? What if people don't work? Like all these fears.

And it's so weird once you're outside of it because my existence triggers a lot of people. I'm sure you've faced this since you've become self-employed or when you were traveling abroad. Aren't you worried about X? What if you can't get another job again? It's like so much fear. Where do you think that comes from?

[50:27] Simone Stolzoff: I think, you know, like many of people's anger or fear comes from projecting their own insecurities. I mean, I think at like a structural level, there's a framing that has been really helpful for me to think about, which is in America, we have this core mythology, which is the American dream and how anyone can sort of work their way up and become an owner one day. But one of the results of this mythology is that the majority of Americans identify with the ownership class, even if they themselves, the likelihood of becoming an owner is very unlikely. Everyone, not everyone, but a lot of people believe that they're just one lucky break away from being, you know, a millionaire or CEO or the boss.

And because of that, a lot of people vote and believe in ways that don't actually align with their best interest because they're looking out for their— the future version of themselves that is the owner of the company that everyone is going to be like freeloading off of, you know. And I remember first reading this idea from this historian. I was like, that makes so much sense. Like, even though, like, the math doesn't work out that everyone can be an owner, everyone believes that they can be, you know, the Donald Trump of the world, and therefore they want to make sure that no one is getting a free ride, even if that person is them.

[51:58] Paul: Yeah. Did I, did I send this to you? This is a quote. This is from the organization, Organization Man, published in the 1960s. It's Holly White's book. And yeah, he, he was talking about this in the 1960s.

He's like this. Knowledge class, I think he was calling knowledge workers or whatever he was calling it at the time. He's like, they don't see themselves as workers. They just see themselves as future owners. Right. And this has instilled through all of society.

It's almost everyone. And it's not even that they're not voting in the right ways in their own interests. It's that it has become the air we like exist in that we don't even see it. It's kind of crazy.

[52:48] Simone Stolzoff: Totally. It definitely feels like a sort of like seeing the Matrix moment when you can realize that that mentality is all around us.

[52:57] Paul: Yeah. And then what I've realized is me stepping off that path with being around people who are still on a very like upward trajectory, at least imagined sort of career trajectory narrative. Is that my existence, I don't really have any goals. I'm just bumbling along. I'm not like growing, aiming. I'm just sort of floating in the same space over and over again.

I trigger the anxieties about like, oh crap, what if this is not true? Is there another way? And the possibility of other paths is terrifying for some people, I think. So we just sort of collectively agree never to talk about it. Have you had any weird reactions people have had around work as you brought this topic up?

[53:44] Simone Stolzoff: Yeah. I mean, I have a lot of friends that are in like the finance world or come from like more traditional paths. And the question that I get a lot is like, so like, tell me like really, like how much money is there in writing a book? Or like, what is the sort of like ROI on the time you spend on the book? Yeah. And like, it's, it's, I mean, I, I come from that world as well in a sense, and I understand the desire to want to put like economic terms on things and see if it makes sense.

But what gets lost in that line of questioning is just the spiritual value of being able to do things that we want to do with our time, you know, like in and out of the workplace and like, Like, for example, sucking the marrow out of life, as you said. Yeah. I mean, sure. Like, there's a potential financial upside of writing a book and maybe people will read it and maybe people won't read it. And I think you and I are both so glad that we did it because we got to learn about ourselves. What, what is it like to strip away all the artifice?

And just be confronted with a blank page. Like, what are the ways in which I have been kidding myself in terms of my own sort of grandeur and dreams of what I'm able to do? And that humbling experience I wouldn't trade for any amount of money, you know?

[55:17] Paul: Yeah, that's the secret of writing a book about work is you can sort of solve your own work relationship in the process. Like, I had a really breakthrough moment at the end and it brought me to tears, but I really felt like at peace after writing my book. Um, it was pretty cool. And what you're really doing, and this sort of makes sense to me, is saying I'm willing to light money on fire in the short term to explore the possibilities of life and sort of lean into a different mode of being. Does that resonate?

[55:51] Simone Stolzoff: Yeah, I mean, I probably don't go as far as like David Perel did where he was like, I'm basically going to have my parents put a down payment on my future and go all in and not think about money. You know, like I'm sort of at a phase now where I'm thinking more about like my family and that side of things. And so the, even the language of like lighting money on fire kind of freaks me out, but I am consciously foregoing higher current earning potential in order to pursue a path that feels more aligned with my values.

[56:27] Paul: Which is not a normal thing in our worlds. Like, I am sure the majority of your Ivy League classmates are not actively embracing lowering earning potential.

[56:39] Simone Stolzoff: Totally. Because it's hard. I mean, with lifestyle creep and the sort of expectations that you have and then just loss aversion of thinking, oh my God, I was making $100,000, $200,000 a year. Like, what will happen if I no longer get validated in that way? Is, is an existential question. You know, it's, it's hard to walk away from both the ways that our jobs compensate us monetarily and non-monetarily as well.

[57:08] Paul: And, but what's, what's keeping you on this path? Are you excited to stay on it? Do you want to stay on it?

[57:16] Simone Stolzoff: Yeah, I do. And I'm maybe, you know, like, obviously you are on the sort of The Pathless Path, so you don't, have a full vision for—

[57:25] Paul: I think we're all on a pathless path though. Like, that's my whole thing is like, I think, I don't think any of us can pretend to know what we're doing. We just sort of have these stories we tell ourselves like, oh, if I'm in this career, I can keep going. It's like, but the jobs keep changing too. It's like—

[57:42] Simone Stolzoff: Totally. That's a great way to think about it. I think like I have a lot of openness at this phase in my life and I sort of know what the next 2 months of my life are going to look like. And I have very little idea what life is going to look like after that. And I've cultivated a fair amount of peace with that disposition.

[58:05] Paul: That's awesome. Um, and what, what are you thinking about next in terms of like continuing to explore this work topic? Is there something else? Like, what is the curiosity rabbit hole you're thinking about now? What has the conversations about the book kind of surfaced for you?

[58:24] Simone Stolzoff: Yeah, great question. I think my next sort of topic that I'm going to sink my teeth into isn't actually directly related to work. I've been fascinated by the experience of, of doubt as both like an emotion and as a thing that we have to manage in our lives. And that's what I've been like thinking about recently when it comes to what another book might be, or just a topic that I'm really interested in and learning more about. You know, the cliché is that you sort of like write the book that you need to read. And I think at this phase in my life, The Good Enough Job was the perfect book for what I wanted to explore in my life.

And I'm excited for maybe another few years of thinking about something completely different.

[59:16] Paul: Yeah, I love this one quote you pulled out. Annie Dillard's quote, "How we spend our days is how we spend our lives." And you pointed out that this is not the complete quote. And this sort of like sums up work culture these days is like we just gravitate to these things that sort of fit how we want the world to work. But she goes on and she says, "How we spend our days is how we spend our lives. What we do with this hour and this one is what we are doing." The life of the spirit requires less and less. Time is ample and its passage sweet.

It's really just a call for acceptance of like living in the present. Have you been able to embrace that?

[01:00:01] Simone Stolzoff: I have certainly been able to embrace it more than the version of myself 10 years ago, like worrying about whether I'll get a promotion was. You know, that whole section from that book is so beautiful. She talks about like, what is the value of a day spent reading? And maybe it's hard to like put your finger on what is the value of that, but a life spent reading, now that is a good life. And yeah, what a great metaphor for how we can choose to spend our time and really the freeing of the guilt and the shame from being able to do things that aren't immediately productive or monetizable.

[01:00:43] Paul: Yeah, I feel this very powerfully now. For the last 9 and a half weeks, I've mostly been spending my time cuddling with a cute baby, which is my daughter. And to me, it is like the culmination of everything I've worked towards. This is the only goal that matters. To me is like having the space to do this and do it with presence has just been so beautiful. And I am technically working now, but I'm working with somebody who's become a friend and deeply curious about similar things.

And this is very energizing for me. And like, it's just so beautiful. I feel so lucky. Um, and I love that other people are exploring this. Um, what else do you want people to know about the book?

[01:01:34] Simone Stolzoff: Yeah. I mean, I think one thing that I want to make clear is that I, like Simone, I don't have the answers, you know?

[01:01:43] Paul: Me neither.

[01:01:44] Simone Stolzoff: This, like in both of our books, like they're not very prescriptive books. You won't find 10 easy steps, you know? And I think—

[01:01:53] Paul: Did you get any pressure to put in like a how-to?

[01:01:57] Simone Stolzoff: A little bit, you know, but I tried to make it clear that this book is more of a meditation than it is an advice column, you know? And I think in actuality, deeper healing can come from narrative, from stories. And I definitely found this to be true through the course of reporting the book. It was by diving deep into these different characters' narratives that I was able to see myself and reflect on my own relationship to work in a way that is so much deeper than saying, you know, step 1, this, step 2, this, step 3, that. And I think we both came to similar realizations in the process of writing.

[01:02:40] Paul: Yeah. And do you think it's worth searching for a vocational soulmate, as you put it?

[01:02:45] Simone Stolzoff: I think some people would benefit from doing so and others would not. And this sort of comes full circle to the Anis Mojgani quote. You know, some people love what they do for work and some people do what they have to for work, and neither is more noble.

[01:03:02] Paul: Yeah, I've been trying to remix the Michael Pollan quote, which is like, eat not too much, mostly plants. And I've been applying it to work. It's like, work not too much, mostly on things that matter to you and helping and caring for other people. It seems like you've sort of landed in a similar vibe, which is that like, treat work with lightness. Like we're putting too much weight on it. Treat it with lightness.

See how it fits in your life. Does it provide meaning? Keep going. If not, maybe lean back a little. Does that resonate?

[01:03:39] Simone Stolzoff: Yeah, I love that. You know, not too much, mostly plants. I think that is a good way to approach most aspects of our life, you know, and I hope that reading your book or reading my book might inspire people to see that on the other side of prioritizing work is the time and energy and space to prioritize all these other things that inevitably matter to you.

[01:04:09] Paul: Yeah. And I, I think it's a good companion to my book. My book is like my personal journey. And I think what you do is provide, you have a number of stories of other people and you go in depth in terms of how other people are relating. And my dream is that we have like in 10 years, 100 more books like this. It, I think it's an emerging space about exploring relationship to work and not making it about like passion or crushing it.

Um, and yeah, these stories inspire people, so I appreciate you writing it. And where should we send people?

[01:04:46] Simone Stolzoff: Yeah, you can learn more at thegoodenoughjob.com. And I'm @simonestolzoff on Twitter or wherever else you want to do your reaching out. I'd love to hear from you. And just a note to say that I, in many ways, was inspired by Paul's approach to work, approach to gratitude and generosity. And I don't think this book would've been what it is if not for the sort of inspiration and, and friendship that we have had on this parallel path.

[01:05:21] Paul: Awesome. Really appreciate you. Uh, it's all, it's all a journey. We're all supporting each other. Um, hope you keep going with this or explore wherever your curiosity's taking you, doubt or wherever that leads.

[01:05:33] Simone Stolzoff: Uh, amen.

[01:05:35] Paul: Pump. Congrats on publishing the book. I will link that up. Uh, thank you for coming on the show today, Simone.

[01:05:42] Simone Stolzoff: It's great to be here. Nice to see you, Paul.