Steph Smith - Carving a 21st Century Career & Life (Podcast)

[01:37] Paul: Today we're talking with Steph Smith, who is a remote worker, works for The Hustle, manages their Trends product, has also worked remotely for several years. Has taken a very different path, I think, than many people, doing a number of different things. You're working on your own side stuff. You recently written an ebook. You taught yourself how to code in the past several years. So I'm excited to dig into all that, how you kind of thought about approaching work in your career early in your life and what you're thinking about now, as many people are kind of moving more towards how me and you have been working for the the past few years.

So welcome to the podcast, Steph.

[02:27] Steph Smith: Thanks so much for having me.

[02:29] Paul: Uh, so you're, uh, in San Diego now. How do you decide where to go next?

[02:36] Steph Smith: Uh, it's, it's funny cause I have people kind of ask me that question too. And they're like, oh, of all the places you've been, like why San Diego? Or like in the past, like why Bali or whatever? And I think, um, when you first start working remotely, or at least when I first started working remotely, I was like, I felt like I had to go to all these incredible places, and incredible places being really flashy, or like, whoa, I've never heard of that, or that's really exciting. But then you realize that working remotely just means you can be wherever you want to be at a given time. You just have flexibility, and that doesn't mean you need to maximize the coolness factor of a place.

And so I just, after a while, realized that, and then would maximize for certain things, right? So for a while I was living in Bali just because I felt like that was the easiest place to live. It was the easiest place for me to get a lot of work done, for me to kind of network and be around like-minded people. So for a while I was maximizing for that. I ended up in San Diego because of a relationship. But that's another example of where just like, you know, things change in your life, priorities change, and then the flexibility is amazing because you can do that, right?

Like I can go and like have lived in Bali for years and then just go and switch to San Diego and it's cool. So that's why I'm here now. But in general, I think the theme is just like, you can be wherever you want to be as your priorities change. And it doesn't need to be like the flashiest or the coolest place. Like, it's actually great that I can actually be a little bit more stable at this time.

[04:00] Paul: Yeah. So I think people of Bali have a very clichéd view of what it's actually like there. So I spent some time there as well, and I was actually blown away in a very positive way of what exists there. A lot of people that are either working on their relationship or work or trying to get to a healthier relationship with it. It's very integrated to the local community as well. I mean, though, there are a lot of Westerners there, but to me it seemed kind of like a beta version of like what a city could look like if remote work was really widespread.

How are you thinking about that now in terms of what you're seeing, what you experienced there, and what Uh, like you're seeing trickles of it in the US and it's like, some of this has been done in other places and it is possible. Yeah.

[04:52] Steph Smith: That's, it's so funny that you mentioned that about Bali because for a while I spent like around 2 years traveling remotely, um, before going to Bali because I kind of avoided it for the reason that it has these clichés. And I was like, man, I don't want to go to Bali and, you know, like be that remote worker. And, and like I had heard certain things about it, but I went there and it was exactly, uh, kind of what you're describing, which is just like, an amalgamation of really interesting people that ended up in the same place and had certain things that they were trying to optimize for. And that's why you just got this really interesting group of people that were working towards similar things. And I think you're going to see that with now the whole world going remote, at least for now. And I think it'll continue into the future.

You'll just see that people will start to congregate in different places that have different sets of values, or even just simple things like people who had to work in cities that never really were city people will now go into smaller towns and stuff. But then you'll also see in Bali, Bali's not the only remote work segment that existed, right? There was people who lived in Chiang Mai or Medellín or Lisbon, and they all had slightly different vibes just because a certain type of person was attracted to that place, but also like the types of people who, who kind of were there already. And so I think we're going to see a lot of that where people just start gravitating to certain places and, you know, you're surrounded not just— you're not surrounded by people who, you know, you happen to grow up with or whatever, but just you actually gravitate to a place where there's like-minded people.

And that'll happen all over in the States, in Europe, you know, Africa, everywhere.

[06:32] Paul: Yeah, it's, it's definitely an exciting future. It's I think it's exciting for me just because it's like, oh, there's more people potentially to hang out with in the future. And I think one thing that I was always scared of is kind of, okay, you get this house, then you, you're settled in, in a commute and a job and you, your sphere of who you see and who you're involved in just kind of shrinks. Um, and it's exciting to see new possibilities emerge.

[06:59] Steph Smith: Totally.

[07:01] Paul: Uh, so I want to go back. Um, you said that you spent a lot of your childhood traveling the world, spent, or maybe not a lot, but you traveled the world playing chess as a child. Uh, so what, uh, what did you learn from that experience and how did that kind of shape your, uh, view of, uh, the world?

[07:26] Steph Smith: Yeah. So I, yeah, I did travel a lot playing chess, mostly in North America, but it was like international points. But the— it wasn't so much the traveling at that time that like opened my mind because it was mostly in North America, but more so just like chess is this like incredible game where, you know, you can compare chess to other games like poker. Poker has a lot of luck, um, and it's also like an incredibly hard game to master. But chess is a game where like there is a right answer, right? Like unlike many things in life, with chess like there is an optimal move.

And it's, it's, you know, there is so many moves that it's hard to, you know, become a true master and the best at it. But the, the thing that I'm getting at is that with chess, especially when you're young, you kind of learn this concept that like if you work towards something, like if you study it, if you, you know, play games every weekend for like many years of your life, you will get better. And another interesting thing for me is I started— I played chess when I was very young, and I also was a female. And so I'd be sitting like at a chessboard against like a 50-year-old man for 3 hours.

And like just that, that kind of experience, I think it doesn't have to be like a female versus male or things like that, but just this experience of like when you're really young and you learn to like become really good at something, um, so much so that you're kind of like displacing traditional norms. You just kind of realize that like if you spend time with something, like you will improve at it, and that That's not just true of chess. Chess is a little easier to visualize, right? Because there is like, you have a rating and you improve your rating and you win and lose. But the same thing is true with other skills in life. And so that was really, I think back to it now with that view, I don't think I thought of it exactly that way as a child.

But it is something that I think has shaped me where now I look at stuff and people are always like, oh, you learned to code? How did you get the confidence to learn to code? And I was like, oh, well, I think actually just being a kid and playing chess, like, taught me that you truly, if you spend enough time with anything, you become better at it and you can become an expert at it.

[09:31] Paul: Yeah, that's such an amazing lesson. And it's probably the age thing, right, that was more dramatic than the gender thing. Just, it must have been disorienting then. Let's say you're going to college, and I imagine people told you, oh, if you put in 25 years here, you can then have the right to do X. Right.

[09:52] Steph Smith: Yeah.

[09:52] Paul: That's a very traditional view of how we think about like competence. Um, you probably didn't agree with that. Did you have any tension with that? Did you ever see yourself as climbing any sort of traditional path?

[10:08] Steph Smith: So I've always been tied actually surprisingly to certain kind of like, uh, symbols of, of like status and certain In terms of like, I've always, you know, especially when I was younger, I wanted to be successful. I wanted to be rich. I still want some of those things. You know, I think all of us do to some extent, but slowly over time, I just, or maybe even quickly at certain points in my life, I just recognized that like, just because I want the same things as certain people doesn't mean that my path there has to be the same. And then that really was like around the time, like during slash just after college when I realized that like, the path that everyone was following, including me at a point in time, was like, it just didn't make sense for me. And it was, I think, some of those earlier experiences that shaped me that like, wait, you don't actually have to approach things this way.

And I know from certain experiences that you can become extremely skilled without spending like 30 years towards something. And you can actually completely pivot things in your life. I didn't always play chess. I went from playing chess to playing soccer to playing other things. And I realized that you can be kind kind of this hybrid individual. And so I think definitely there have been times where I've chased certain things that many other people chase and go the very typical path.

And then I just realized that not only is that not necessary for someone, but for someone like me and given my approach to things in the past, it really just didn't jive for me. And so that was kind of like, a moment for, or moments where I was like, oh, actually, like, let me just explore other things. And when I started to explore those other things, I realized like that those different approaches actually were more optimal for my life, my skills, my, you know, happiness.

[11:59] Paul: Was there a moment or a shift where you kind of consciously made that decision of I'm going to do things my way, or at least try to discover a different way?

[12:10] Steph Smith: Yeah, it was, it was really when I started looking for a remote job in 2015. So I went to university, did like full 4-year degree, actually really enjoyed it. And I think it's funny because like now looking back, it feels like it was like always like a certain thing that I would end up diverging from this path. But at that time, like, I don't think that's true. Like I was, I was in university, I finished university, I went and got a consulting job and although things at times felt like a little uncertain, that's true, I think, for everyone. And so I think there's like very possibly an alternate world where, you know, I would have ended up in consulting and spending like many years there and things like that.

But at that time, I do remember just feeling like, so I was working in Toronto, 2-hour, you know, back and forth commute and like just working in an office, all these like traditional, very classic, things that many people up until like March 2020 were like, the whole world was doing. And so I just remember feeling like this, like this can't be it, right? Like, you know, I can't actually be spending the next 20 years doing this. And so a friend of mine sent me a company that I'm sure you're familiar with, Remote Year. And at that time, when you're so ingrained in like this traditional path of being like, I'm in consulting and I'm going to become like a senior consultant at this Step and all this stuff. And you've never heard, like, I had never heard of something like Remote Year, which is this concept for people listening, like where you go and you live in a new country every month.

So that at the time was like so far-fetched. And I didn't even realize that there was all these remote workers. Like, this isn't also not that long ago. This is 2015, which now remote work is like on every headline of LinkedIn and like, you know, like all of these big publications. But at that time, It really was surprising for many people. And even like years later, it was still surprising for many of my friends and people that I was in contact with.

But in any case, that was the moment where, when I was sent that like Remote Year headline, they were recruiting for their second year. I didn't end up doing it, but it was this like aha moment of, wait, what? Like people, people actually do this. And then I spent the next year kind of pursuing like, how can I do that? But that was, I think, really a moment where I realized, like, you know, those moments that your world is just like a little bit shifted or reshaped and you're like, hold on. So that was it for me, I think.

[14:35] Paul: Yeah, it's amazing how much these things have changed. I graduated college in 2007, and when I was researching careers, like, LinkedIn was not even a thing yet.

[14:47] Steph Smith: Exactly.

[14:48] Paul: There was, there was no Twitter. If you wanted to find out information about a company, you go to their career site and they wouldn't talk about their culture yet. This was like 2010s and that's kind of all you knew. And it's been really interesting as I kind of write about work and think about these things, seeing people starting pretty much with like your age core. I think you're like 7 or 8 years younger than me. But basically you graduated out of college and then you're going to this office, but then you're on Instagram and seeing like, oh my God, there's 50 other possibilities for living life, or picture, or people are writing about how they're working differently on Medium.

And I think 2015, 2016 was kind of an imagination expanding time for me too.

[15:42] Steph Smith: Yeah.

[15:44] Paul: But I'm also, I'm also a bit worried. I think people like you are probably always going to be okay. Like if you had graduated with me, you probably, you might have spent 6 or 7 years in the corporate world, but now a lot of people are just going off on their own and either don't have that discipline of learning something you probably picked up from chess or the ability to understand like how do you level up or get feedback or improve. So not much of a question there, but are you seeing a lot of like younger people reach out to you, some of your classmates curious about how they can follow your path?

[16:22] Steph Smith: Yeah, so I think it's a great point that you bring up because I've definitely seen both in terms of like when I was living in Bali and people would end up there and, you know, not really know exactly what they were doing there other than they were like planning to you know, become a digital nomad or whatever. And then also I do have friends who, you know, have reached out and been like, oh, I wanna do what you're doing. I think what I would call out there is that many people who end up doing that are really just like copying someone else's life or like you're saying, like they see someone on Instagram and they're like, I wanna be there, right? I wanna like be taking pictures like them, or I want to, have the freedom like them. And it's okay because we all learn from one another.

Like, I also, when I— like, to your point, in 2015, like, many of the things that got me excited were seeing that other people were doing X. But I think what a lot of people kind of go astray in is just like, you, you can't just like model your life off of someone else. It's like, the whole reason that I went remote and have done many of the things that I'm doing are because I wanted to like redefine what my life was, right? Not necessarily go adhere my life to what, you know, someone else's is. And so I think that's where a lot of people go wrong. And then if you don't have that like internal motivation to like reshape your life, you're not actually gonna get like, you're not actually gonna be able to replicate someone else's life.

Because if someone, if there's like, you know, some very cool entrepreneur who went and like did all these amazing things and built up this business and lives remotely and all these things like, there are many, you know, pieces, many years, many like, you know, pivots, many like hard struggles that that person went through to get there. And you're only seeing like where they are now. And so many people are like, I want to be like that person, but their motivation is just to be like that person. They don't have like an inner, you know, like core to be like, I really want to like maximize my life. They just want to be like someone else. And therefore like they're not gonna end up like that person because they're not gonna be able to like, yeah, like rescale and like pivot and all these things.

So I just, I think we are gonna see a lot of people who, and we did even in the last couple years, of people who would like end up in Bali and, you know, with like $2,000 and be like, I'm gonna figure it out. And I'm like, honestly, kudos to you, but like, you gotta figure it out. Like, you gotta sit down and like go to the coworking space every day and you know, go on Udemy and all this stuff. But anyway, I'm going a little bit astray, but I, my point is that I think where people do go wrong is that they try to just be like someone else, but your goal should really be like, how do I create the best, most fulfilling life for me and see where that ends up?

[19:09] Paul: Yeah. I think it's surprising how many people have been inspired by Tim Ferriss' 4-Hour Workweek. But the real challenge, like you're saying, is actually finding your own path. I mean, for me, like, I am just not wired like Tim Ferriss. I can't do the crazy hours. So I need to figure out how do I actually design the life and the work and the type of work such that it actually fits with the energy I have and the type of things I want to do.

And the, the other thing nobody tells you is that your identity becomes a bit scrambled. Like, I went from a very easy-to-understand person— Paul works in consulting, makes good money, is a successful person that went to these schools. Now I'm Paul somewhere. We have no idea what he's doing.

[20:03] Steph Smith: Yes.

[20:06] Paul: And that unsettles other people. Because it's easier 'cause they want to know exactly where you stand, what you have, what kind of status you have. But it can be hard yourself to figure those questions out. How have you kind of thought about like who you are? Maybe it's a little more rooted for you because you still have that routine with a full-time job, but how do you think about like who is Steph? Are you a worker?

Are you not a worker? How do you define your life?

[20:37] Steph Smith: It's so funny that you mentioned that because I think— oh, sorry, I think I cut out for a second. Are we still here?

[20:44] Paul: You're still here.

[20:45] Steph Smith: Okay, great. Sorry, I don't know what happened there. But yes, so it's a great question because I even realize this more so now than before because when— now that my identity has been kind of diluted in some way and it's not locked into something, right? Like, I don't know what I am. Am I a writer? Am I a coder?

Am I just like Am I someone who works online? Am I a digital nomad? I don't know. I guess I'm partially many of these things, but it's funny because when you no longer have clarity as to what you are, people still will find a way to label you, right? So like many people now think of me as this like content person. And it's funny 'cause it's like, I don't think of myself as like a content person, but it's interesting because that just like, once you've pulled away from like what, you can, like, what you label yourself as, people will still find a way to do that.

And that almost like shines light on how easy it is to just get locked into things, right? Like, because the whole world is pushing you to get locked into something because people just like associating themselves or other people with status or with labels because it's just easier for our brains to like get our heads around that concept. And so that's almost like That experience over the last couple years has almost just reminded me of how much I shouldn't try to label myself or I shouldn't try to push to have these rigid walls or labels because I think that's just restrictive.

And I think Paul Graham has this quote, "Keep your identity small." And he actually talks about different things in this lens, but I like using this example, because I think once you start like becoming something, right, like I'm a writer, I'm a consultant, I'm a whatever, you became very tied to that, both in terms of like your inability to see like other opportunities out there, but also like your like need for that, right? Like you're like yearning to be labeled as something, right? And then if you are that way, like if I honestly, I feel like this would have happened had I stayed in consulting for like couple more years, I would have like really felt like a consultant. I would have felt like I had spent so much time in this. I would have been making good money and just feeling like that would have become my identity.

And I think what's interesting with the new shift from like, you know, everyone being in an office online is like a lot of people are now getting a little peek into that where they're kind of like, whoa, like, so I was a consultant, but now like no one, like I'm not going into work. I'm not like wearing the suit. I'm not doing all these things. And it's like, wait, so consultant really just means like I make spreadsheets and PowerPoints. Like, that's— I mean, I'm not like, you know, diminishing that because that's what I did for many years, and I still don't think I do anything more important than that. But do you get what I mean?

Like, it's— people are just pulling back the curtain, right? It's a ritual that became an identity, and now that the ritual is gone, people are now seeing that, wait, like, this is my identity? And like, did I really want to be this? Like, or do I really need to be this, I guess? And so I think it'll be interesting when people kind of like have the opportunity to reflect on that.

[23:54] Paul: Yeah. So I've been writing about this relationship with work struggle for 3, 4 years. I would say when March hit, I had a 5x jump in people reaching out to me and steady for the past 5 months. It was, it kind of blew me away. Um, I didn't really expect it. But maybe I should have given some of my own path.

But yeah, it's been really interesting. I think the identity thing, especially if you're a remote worker or doing other things, or let's say you're even a parent, right? If you say I am a consultant, that is really useful. If you're in a conversation with somebody that wants to hire a consultant, you should not tell them you're a writer or a wandering nomad. Yeah, but once you start to believe I am that person, you're, you're not going to see other opportunities, right? So one of the things I did when I was freelance consulting at first was just try to get different kinds of work.

I did like a TA at a university and it was very low pay, and if I had defined myself as a consultant, there would have been like too much shame of like taking this low salary doing that, but That was what I wanted to do. And that really helped. Like, I, I'm definitely floating in like nebulousness of identity right now, which is, which can be a bit overwhelming at times, but that's why I do things like this to find the others like you.

[25:27] Steph Smith: Yeah. And I think I've done the exact same things and that's to your point. It's, it's exactly like that relationship with status or your current like label or current identity. That stops you. So I like, when I wanted to work remotely, I was a consultant getting paid relatively well. And I had a very clear path, but I also like, I did like stints, you know, contract contracting stints with like social media, like even like working a support role at one point, like helping doing like things in SEO and all these things that now have led me to have like a marketing role, which I'm like very happy with.

But at the time, like, if I was this consulting person who thought I was important and restricted myself with certain levels of status, like I would have never done those things. And then I would have never ended up where I am.

[26:16] Paul: So I think you've discovered something I have too, which is you wrote that learning to write is learning to think. And learning to write and write publicly and do it often has probably been the most important thing I've done, um, since I've gone on my own 4 years ago. Um, when did you start writing, uh, online, and when did you start to see that it's pretty magical what can happen from that?

[26:46] Steph Smith: Yeah, I started writing online, I guess, uh, very end of 2018, early 2019. Um, so before that, I'd worked at a company and at the company, I ended up leading the publications team. So that kind of like brought me a little closer to this like world of online content. But even then, at the time when I was like leading that publication team, it was more so like, okay, this is how you grow content online. It wasn't like as an individual. So I didn't even fully recognize the like power of writing online until I started doing it myself.

And I just started writing online at the time because I had, certain things I wanted to say. And I saw this like gap online, not necessarily a gap in terms of like, oh, I'm going to become this writer and have this attention. But like, how come no one's talking about this? Or like, you know, everyone, the first, the very first article I wrote that actually got some traction was just like this guide to remote work that's not trying to sell you anything. And it was just this thing where I was like, I've been working remotely for years. And like, I feel like this, there's this very like strange view of it, or like the way that it's written about is inaccurate.

And so that's all I wrote is just that. And then that got some traction. And then I was like, huh, like, there is actually this like gap online for people to just be like honest and also just like intellectual. And, you know, you don't need to know everything. You don't need to like write for the New York Times or for Forbes. You can just like, if you're thinking about things that other people also find interesting, there's a lot of people that you can reach.

You know, there's this like age of now infinite leverage, people say, right? But really, it's just this ability to just you know, connect with not just the people immediately around you, but the billions around the world. So I just started writing online, and then I got, I think, a little luckier than most people in terms of like how, you know, people responded to my work and how quickly it scaled. But then once you— honestly, like, there's just an inflection point, which I'm sure you recognize, where you do start to just like reach other like-minded people and start engaging in conversations online that, you know, are, you know, in some cases much like more stimulating than the conversations you're having in person. And then from there, I just, you know, I just wanted to continue expressing myself online. So I did that.

[29:03] Paul: Yeah, that's, that's pretty funny. I think a similar drive for me, about 2016, 2017, I was reading about the future of work and it was mostly like really crappy content. Market from platforms trying to get you to sign up that were saying like the future of work is about flexibility. And it was like, this is nonsense. Like none of what they're talking about is like the lived reality of what it's actually like to be a remote worker or those things. I think it's gotten a lot better, but you still see like so many of these things.

And that really motivated me. It was like, okay, let's talk about what this is really like. You have these talent platforms that are writing, it's about flexibility, but it's really about all these other things we're talking about here— identity, figuring out where to live, how to design your life, and all that. How did you try to push a different perspective when you were doing some of the writing or content marketing at Top Towel?

[30:06] Steph Smith: Uh, so I mean, Top Towel was very focused around just like, how do we, you know, among the sea of content online How do we really focus on just expertise? And so we were focused on, like, I mean, Toptal itself as a company was like a network of experts, you know, within like the development space or designers or whatever. But we did have a publication that, you know, focused on kind of like this future of work thing, although that was more of like, just by nature, a corporate blog. And so I think I didn't actually have the, Nothing against Top Towel, I had a wonderful experience running that team, but I didn't actually have this creative freedom fully to talk about remote work in the ways that I actually thought of it and things like that, because it was a corporate blog. But that was the beauty of when you do have your own publishing space, you can say whatever you want.

It doesn't have to have this ulterior motive. The reason that there's so much content marketing online and why it's so bad is because it has an ulterior motive. And it's not always like the sinister motive of like selling something to you, but it's that they want to get more page views or that they actually have a team of only 2 writers and they're trying to get out 10 pieces of content a week. So it's just the incentives don't line up. But once you start publishing on your own, especially if you're not publishing to like make money and monetize it in some way, A, you can like publish whatever you want. right?

And there's no motive behind it, but also you can publish at the rate that you want, which is, I think, actually an underrated thing of many independent creators, that it's really wonderful because I'm only going to put out something if I think it's good, and if I think it— if the world needs it, right? I'm not gonna— like, I actually haven't published in many, many, many months because I haven't had the time to put something good together, and so I've actually just opted to not publish instead of, you know, hitting some sort of publishing cadence. And so I think that actually is, that's why you see so many independent writers have just like much higher quality thinking, not necessarily because they're like all the time, but because they have the right incentives in place to put the best quality content online.

[32:17] Paul: Right. So your experience at Toptal, I've written, speaking of like, as an independent, you have permission to write. I wrote this piece on talent platforms. I used to work at one. I've worked with them. I'm pretty pessimistic on the ability of like any single talent platform to scale and really kind of change how we think of gig work in the short term.

I think there's probably some missing pieces, but basically they're outsourcing a lot of the work for like scoping and things to the freelancers, which is just really, really hard. Did you leave Toptal more or less optimistic about talent platforms and the roles they play in the gig economy.

[33:05] Steph Smith: So I think you're right that they, they like serve a purpose right now in that the world is completely, you know, distributed, and someone in like Wyoming doesn't know how to, you know, get in contact effectively with someone in like Bulgaria, right? Like, they have that ability. We have like the infrastructure online to connect those people, but they don't know how, right? Like, and it's difficult. So that's really like the what the talent platforms do for people. What I think will become true, and you're already seeing this, is that anyone who's really, really, really effective at what they do will not need a talent platform.

And so, it'll be really hard for the talent platforms to really keep their level of quality and service, because In the end, like, again, the best people will go out and do their, their own thing. And that'll continue to be true because instead of something like Toptal or Upwork or Fiverr facilitating that engagement, there will be many other services that allow, you know, you to be discovered, whether it's like your online content or just— I'm sure there's gonna be many other things that kind of like surface in that environment. And so I think that they'll always have a place. Am I convinced that they're going to, you know, take over the world and be the next, you know, Apple or Google the way some people say? I'm not as convinced because again, like, I think the best, the best people won't utilize those platforms.

[34:36] Paul: Yeah, I think they're probably not VC-scalable, but probably are nice niche businesses in certain industries or functions. But we will see. Yeah. So speaking about creating your own connections and not needing a talent platform. Maybe share a little bit about how you landed your current role.

[34:57] Steph Smith: Yeah, that's, yeah, that's actually a perfect segue. So I got my role through writing online. So I wrote, started writing for my blog in early 2019. By mid-2019, I had written a couple different articles. I think 2 or so by that point had gone like pretty viral. Trending on Hacker News and many tens of thousands reading them.

And for the second one, this guy, Gary Tan, he's a VC, tweeted it. And Sam, the founder of The Hustle, had seen the tweet. I think he had seen some of my work before that. And I think he commented just something along the lines of, "Love Steph's work," or something like that. And then immediately after, DM'd me and was basically like, "Hey, how do we get you?" part of our team. And I had been a fan of The Hustle for a long time.

We used to advertise with them at Top Towel, and I worked on the growth team before leading the publications team. So I had not only heard of The Hustle, but I'd read their stuff for many years. So having been at The Hustle for, or sorry, at Top Top by that point for 3 years, I was already kind of ready to do something new, and it was perfect timing, and trends was just, launching at the time. And so anyway, to your point, that was, you know, that's a perfect example of how if you're writing great stuff online or just doing things that can get you discovered, you will, because we have this age where you can like discover people in this way. And so yeah, that's how I got my job, through Sam seeing my writing.

[36:33] Paul: Yeah, and how are you thinking about work As you're, I mean, you're, first of all, like everyone should go to your website and check out like your personal dashboard.

[36:47] Steph Smith: It's, oh yeah, my open page.

[36:49] Paul: It's so cool. Um, you track like all these stats about your life. I do not have the discipline to do that, but I find it, uh, very cool. Um, but one thing I see as a trend, um, in your story is you're creating more of your own stuff, you're putting out your own book and you've just done, had a lot of success with that recently. How are you thinking about kind of your future path and roles and how you're thinking about maybe balancing stuff you do on your own with full-time work?

[37:23] Steph Smith: Yeah, so I'm very happy at The Hustle currently, but the long-term goal, right, like when I'm talking at least like, you know, in the next decade, I do want to eventually just be doing something on my own, whether that is my own fun projects only, or starting a larger company. I'm not sure, right? To me, that's too far out where it could go either way or a completely different way. But for now, I'm happy with my full-time role. But the thing I love about this, and I've written about this, is that because I have a full-time role that I actually really enjoy, and Sam is the type of founder that is super supportive of me doing things outside of just that, I have this like not just freedom, but like this mental freedom to like, I know I'm getting income. I know I'm like, I'm set there to go and explore whatever the hell I want.

And so for now, a lot of my projects, you know, there are people who really like, they don't have a job and they need to make their side projects like their income. And that's wonderful for them. But for me, it's super fun to be able to just create like whatever the hell I want, right? So like a lot of my projects are just me like waking up one day and being like, oh, I really want to create like a directory of untranslatable words, so I went and did that, right? Or like I wanted to create this book because I wanted to do that, right? Like it ended up doing well financially, but it was just something where I was like, huh, like I actually know a lot about this subject, like maybe I should, you know, put that together and share it.

And so for now, I'm in this phase where I'm happy, I'm getting paid, And it's more of just this like exploratory, like, I have the skills, so why not go create things because I enjoy it. In the future, I do hope to create like something a little more of my own, right? Something that like does make its own money, does either have passive income or is building towards some like larger company. But I think to kind of like going back to some of the things we've talked about, there's all these like very regimented like norms of how you may exist within the world, right? Like, so you're either like, are you an entrepreneur or do you work for at your own job or are you like a maker or online creator? I kind of think of myself as like some medley of all those things.

And right now it's, there's the priority is just to like continue enjoying and exploring. But in the future that'll shift, right? And I think in the future I do want to create something more of my own.

[39:45] Paul: As you've started to make money, have you noticed you've been bolder in your job as well?

[39:51] Steph Smith: Bolder in what way?

[39:53] Paul: I don't know. I mean, I think a big thing for me when I went self-employed, I kind of went without a plan. But when I started making money and especially making money in different ways, I had this mental ease. And you talked about this a little, but it was like, okay, I can survive. I can take care of myself. I'm going to be okay.

Um, and that led to me getting a lot more creative about how I live my life and like taking time off without making money and things like that. So, um, yeah, I get, I guess it's more around those things. Um, and maybe it doesn't have to do with your job, but it has to do with other things.

[40:36] Steph Smith: For sure. And it does, it does have to do with my job just in general, where to your point, like I'm confident. That if I was fired today, and also like you wiped my entire slate of like projects that I've done so far, if I wiped everything and started new, I have learned the skills to go and make money if I need to, right? Like I have this confidence that I truthfully only would say I've got in the last year or so. Like if you were to ask me 2, 3 years ago, maybe other people had that confidence, and would have told me, no, Steph, you'll be fine. But I only have like developed this like true internal confidence that like, I'll be fine in the last year.

And so to your point, like once you have that confidence, you can go and take jobs that you're like, okay, this job may not be like super lucrative or like maybe it might even end up sucking, but it might end up being amazing, but I'm going to try it. Cause it has this like potential to be amazing versus something where if you're a little less sure of yourself, you're going to go into and take roles that are comfortable or consistent and things like that. Also, when I was at TopSell, I was leading a big team and part of me was like, "Oh, I'm going to continue being a leader." I actually made the decision to go and become an individual contributor again because I'm not really that scared about my career trajectory anymore. I'm not worried about, "Oh, will I ever get a leadership role again?" Will people not see me in, in a certain light?

And so I do think it gives you this freedom, which is amazing, to just do what you want to do at a given time, um, and also be a little more risky with your decisions. Because it's not even just having this like financial base that you've developed, but it's this, this concept where you're confident that no matter what, if, if everything was wiped clean, that you would be able to like start over fresh and everything would be fine.

[42:36] Paul: I love that. I think, I mean, for me, that's wealth, is having that and knowing you'll be okay. That's so cool. What— maybe you can leave us with some cool untranslatable words. So, I mean, I've been learning Chinese and it's kind of mind-blowing how so many things are— it's— you can't, you can't even translate. You can't even start to translate these words.

And it exists between so many languages. It's probably been one of the coolest things I've experienced just from traveling more. But yeah, I love this and it's— it always fascinates me. Do you have any untranslatable words that are kind of top of mind these days?

[43:32] Steph Smith: I just pulled up— so I wrote an article on this, and I love talking about the subject. I've done talks on it because I think it's so interesting, because a lot of people think that we have a certain vocabulary and we use that to articulate what we want to say. But what they don't realize is that the things that we have available to us— like, words are a tool— actually influence the way that we think. And there's like— I wrote an entire article about about how like there's examples of how having different words for specific colors actually allows you to see different colors and things like that. Where I just think it's so interesting when you start to recognize like that words are not just like a tool for you, but something that shapes you. And then if you realize that, okay, if that's true, what are all these like words that exist in other places that like I can learn from?

Anyway, I think it's just like a really interesting concept, which is why I've created a tool around it and written about it. And some of the— so some cultures are so, I guess, further removed from other cultures, like they're more distinct. Some of them being like the Japanese, if you've ever been to Japan, I assume you have. For anyone who hasn't, it's like, it's just a different world. And I don't just mean like, because it's it's technologically advanced, it's a different world. And because of that, the Japanese have many more untranslatable words compared to other countries.

But I'll pull up— I have like a list of some of my favorites, and some of them can be as simple as like the German have a word— I'm gonna butcher all of these pronunciations— but like Abendrot, which means the color of the sky when the sun is setting. Like, we literally just don't have a word for that, and it's so interesting. It's like, do these people, because they have a word for this, actually pay more attention to that thing? I don't know, but I think it's interesting. The Hungarian have a word for like— it's translated as like Donald Ducking, and like, this is just like a comical one, but it's like someone wandering around their house with a shirt but no pants. Like, things like that, which are just— it's so funny that things like this exist.

Or like, in Japanese, there's There's two words which I think are kind of like opposites in a way, but one of them is to stand in a bookstore and read a book without buying it. We've all been there. And then the other one is to acquire so many reading materials but let them pile up without actually reading them. So it's like the opposite, but they have a word for both of these things. Another one, like Nintendo, many people are familiar with the, you know, the company, but Nintendo actually means like to leave luck to heaven or to leave one's fortune in the hands of fate. And so we We have like words that we can use in English to like describe these things, but I think it's just so cool that there's individual terms.

And just to leave you with one that's like a little— to really just like nail home this point is like in Japanese, there's a word for unfortunately for like suicide work, which just means like— because exactly, which unfortunately because they have a certain work culture or they have for the last several decades, many more people compared to anywhere in the world have literally died at their desk, right? And that's what they call it, they call it work death. And so they have charities for this stuff, but they have a word for it, right? Because it's enough of a thing in their culture for them to like, you know, to no longer have to like use like 10 words to describe something, they'd rather just, you know, have something simple to be a descriptor. Whereas I think, I can't remember which language it is, But one of the Scandinavian countries actually— oh, it's Danish.

They literally have a word for work happiness, which I think is so interesting. So anyway, it's just— it's this amazing thing where you start to recognize these intricacies in culture and how we engage with each other. And I just think that if we had certain words for work happiness, would our view of work change, right? Versus something like— unfortunately, the Japanese have work, you know, maybe having a word for work death actually shines light on this, this concept. So anyway, that's, that's my little rant, but I love this stuff.

[47:47] Paul: I think we need to create a word that would mean thriving from remote work.

[47:54] Steph Smith: Yeah.