How a Trader Models The Solo Creative Journey - Kris Abdelmessih (Podcast)

[01:35] Paul: Today I'm talking with Kris Abdelmessih. He's a former trader and writes an amazing newsletter and blog called Moon Tower Meta. He writes about his experiences working as a trader and how he looks at life and work through the lens of options pricing and valuing different things in life. I've been exchanging emails with him for while, and we decided to have a conversation exploring some of the ideas we're both excited about. This conversation was a ton of fun for me. He pushed my thinking further and has really set me off, uh, in a number of different directions, thinking differently about my path.

I think you'll definitely enjoy this. Uh, let me know what you think and enjoy the conversation. If you were like somebody entering the work place now, how would you be placing your financial bets in terms of like your energy and time? And maybe you're thinking about this now as you've kind of tried to think about the next chapter of your path too.

[02:44] Kris Abdelmessih: Yeah. Oh, um, where would I start as a worker? So here, I'd actually prefer to— let me step back. I would actually go a little earlier than that. There is a very influential interview that I listened to was this woman named Kathleen Mercury. She's an educator here in the US.

I believe she's in the St. Louis area. And she teaches board game design. To gifted and talented kids in, around the middle school level. And she was an educator for a long time before that, and then she kind of added this as an experiment, let me try this out. And then she's become this person who has built like this amazing curriculum to teach this.

And, um, anyway, I point people to that interview with her because She talks a lot about the reason— it has nothing to do with, like, the necessarily the importance of board game design. It's like, that's not the point. The point is that, um, she thinks that it's very, very important to bring out sort of like the design thinking creative process in all of us. And the reason is expression and sort of asserting your creativity in the world is a way to own your life. Like, it— that's, you know, it's kind of— we'll go back to the idea that it sounds like snowflakeism, but it's— I think there's a lot of truth in it. It's this idea that, like, you are the only— you are the best person at being you.

And if you have some control, and control only comes from differentiation, and differentiation comes from creativity. And I think everybody, my own view, I have a 5 and an 8-year-old. I tend to believe that my life tends to be surrounded by kids, kids that are sort of all around me. I'm kind of involved with kids around here all the time. And I think all kids are creative. I think you're just born creative.

There's a, there's a thread of the school knock the creativity straight out of us. There's a kick, there's a kick that the will to learn straight out of us as it beat us down. Um, I'm, I'm biased on an anecdote of one. I feel like it very much did that to me. I was very bored in school, um, and I saw it as just this tournament and it wasn't really about learning. And I think that re-grabbing the idea that we are supposed to learn, and learning is about creativity ultimately, um, and amplifying that is the key to having control over our lives.

So when you come out of school, I don't have a prescription for what you should do out of school, but you should do something that you are uniquely able to do. And I don't mean that— and again, I don't really mean that in the snowflake way— but you don't want to let yourself yourself be totally commoditized. You need to care about what you're good at, and you need to find a way to amplify that and express that in some way. Otherwise, you are a slave.

[06:15] Paul: Yeah, I think that sums up a lot of how I'm thinking about it now. I think what I tried to do out of school is basically— there's these stories we cling to around work. And it's really seductive to go try and fit into those stories. However, over time you become that story and you kind of lose track of your own decision-making and you're making decisions downstream of the story rather than like who you are. Whereas I find self-employment now, I have to wake up every day and be honest with myself. There's no employer or coworker to blame and I have to say, oh, I'm actually good at this, I should keep doing this, or I'm enjoying this, I should try and keep getting better at this.

It's, and I think, I mean, maybe you and I got lucky too because the world is set up to reward highly analytical people.

[07:16] Kris Abdelmessih: Right.

[07:17] Paul: So in some ways, I don't know if I lost my creativity as much as I kept getting rewarded over and over and over again for being a good synthesizer and analytical thinker. And over time, I started to think that was me. I'm like the, the person that can make sense of complex information better than other people and do that incredibly well.

[07:38] Kris Abdelmessih: Um, although I think that's— I mean, the analysis, yes, it's analytical, but, um, I— that is very much a form of creativity. I mean, it's kind of funny, I think trading is one of the most creative of things a person could probably do. It's super creative.

[07:56] Paul: Yeah. Because you're searching the edges for the new ideas, right? You're trying to expand the possibility space.

[08:02] Kris Abdelmessih: Exactly. I mean, the very idea of like, here's a computer in a room, go sit in it and make money come out of thin air is a very creative endeavor. So I don't— I mean, to me, like, you know, creativity can come from this you know, a romantic place about arts, but it also comes out of analysis.

[08:26] Paul: Well, I think I had a very— my idea of creativity was like Creativity Inc., which is like formal roles blessed by gatekeepers. You now have permission to be a creative individual, right?

[08:40] Kris Abdelmessih: Yeah.

[08:40] Paul: And I think this has happened with work. Work has basically been destroyed as a word. We only think of work as something you can get paid for. We've taken this Japanese concept of ikigai and created our wishful thinking diagram, which like maps with like, oh, what you can be paid for. And that's not what the topic was about at all. It was reason for being right.

And one of the things I love doing is writing. And that's like, I protect that now. That's my creative space. I can't fund my life doing that right now.

[09:16] Kris Abdelmessih: Right.

[09:18] Paul: But it's vital for keeping me going. And it took me a long time to figure this out. But I think you're right around creativity. Being a parent is probably the most creative thing you could possibly do.

[09:34] Kris Abdelmessih: Yeah. Well, it feels like you're operating in space. I mean, it's like There's no, there's no, you know, like the guidelines or, you know, even like today, it's like my kids come home at 1:45 and I'm like, okay, what are we gonna do today? Totally open-ended question every single day.

[09:56] Paul: Yeah. And so creativity is all around us. Just the creativity of navigating bureaucracy, figuring out how to buy things online is you have to be somewhat creative. And I think part of my journey was realizing, oh, moving around all this information and creating a slide and telling a story, oh, I'm actually being really creative. And I don't need to get permission to do that in other aspects of my life.

[10:24] Kris Abdelmessih: Well, you can— I think that you can think about that as far as like, is it— if a job is a creative job, would be if there was 10 people in your role, how different all of those roles would look. As versus, like, you're a— if you're a, uh, if you're working at McDonald's, then 10 people are going to do the role, it's going to look the same. You know, they might make the people around them feel differently and all that, but ultimately the job that to be done will look the same at the end, or very similar. Um, but any kind of job like you've had before 10 people are all going to be vastly different outcomes in what they're creating. So that's a, you know, a big hint that it's creative to start with.

[11:09] Paul: Yeah. What, so what do you see like with other parents? I think I see a lot around kids, like parents have like, they love the story. The default path story of work is so, it has such a hold over our imaginations. And I see so often kind of an unwillingness to imagine outside of that and like just take that story and then make these very straightforward decisions. Like my kid needs private school.

The most important thing is grades. I need, they need to achieve and succeed. Do you see that like with a lot of parents in the culture around you?

[11:53] Kris Abdelmessih: So I would say that I'm going to preface this by saying that I live in the Bay Area, and which comes with its own culture. I live in a fairly well-to-do town in this culture. It's, it's, it's, uh, you know, so this is like, you know, my sample is not enormous of what's going on, but my sense is that all the parents are— all the parents that I speak to care about Is school kind of doing right by their kids as far as, you know, no parent thinks you're supposed to be sitting there doing a bunch of memorization.

[12:34] Paul: Yeah.

[12:35] Kris Abdelmessih: No parent thinks, like nobody believes this. There's nobody that thinks, like that straw man is like, I don't even know anybody who thinks that. So it's a silly argument. You know, everybody understands that you want your kids to be doing projects. You want them to be unleashing your creativity. I think everybody gets that.

I think that— but the question is, everybody understands this intellectually, but what do you do with that?

[12:59] Paul: Yeah, that's such the hardest part.

[13:01] Kris Abdelmessih: It's the hardest part. And the reason— so I'll tell you what we— for example, like, you know, my 8-year-old, he goes to code school and he goes to, like, we host chess class for the neighborhood at my house. And like, we do all this, what, what I would just call enrichment, right? And I would say that's a fairly conventional way of attacking the problem is like, hey, let's expose our kids to like interesting things and see what happens from there. The more— I mean, you have the, the more crazy experiments that are out there where it's, um, a buddy of mine just sent me an article and I forgot the name of the school, but it's the school where the schools where you go and it's like completely child-directed. Like, I'm not talking about Montessori.

There's like one school in the country that still does this, and it's like you just go there and you basically do whatever you want. And, you know, the outcomes for the kids that go to these schools— and granted, I'm sure that that's hardly a random sample of people— but the outcomes for the kids to go to the school are kind of— they're like fine. They seem like well-adjusted and they're happy, but it's not like they end up go necessarily— they're gonna go make lots of money or whatever it is. It's like, hey, the kid when he was 9 years old was like very mechanically minded and became a mechanic. And it's like, that's— and it— and the question is, is like, what was that outcome like for the kid? Was this a good outcome?

Is there a bad outcome? Did the parents think this is a good outcome or a bad outcome? I mean, to me, I'm like, this is a fish that was a fish that lives in water. So are we going to judge whether the water is bad or whether the fit is right? I don't, you know, I don't know what we're going for here.

[14:47] Paul: Yeah, and I think a lot of this conversation gets wrapped up in numbers, right? It comes back to what we originally talked about. It gets wrapped up in like incomes, uh, class, opportunities, ability to like make a good wage. Um, and I think what I've enjoyed about what you're writing about is You're basically saying, okay, yes, you should think of these things maybe as financial investments, as options through life, but that you should also value options that can't be quantified.

[15:20] Kris Abdelmessih: Yeah. Well, so the funny thing is, is like everything actually comes back to— everything comes back to accounting, right? It's like the problem is like money is like this super lossy symbol for your happiness. On the one hand, I'm like, people that are like, "Oh, money doesn't buy you happiness." I'm like, "Dude, I know what being broke is like, and that sucks." That will buy you unhappiness. Having no money will make you unhappy. But yes, of course, there's a major declining utility to making money.

So the question is, is how do we, um, kind of separate these things? My big thing with this idea is, um, it's a— which is something I haven't written about yet, it's kind of like an in-progress thing— but is the idea— I don't know where I heard it, the concept, but it's, it's basically miswanting.

[16:18] Paul: I think miswanting.

[16:21] Kris Abdelmessih: So I think what's— what happens is, um, our desires are so unconsciously derived from one another because we are born copiers. I don't say that in a bad way. I mean, we're literally built to copy.

[16:41] Paul: It's a good survival, uh, program, right?

[16:45] Kris Abdelmessih: So we're— right, so the, this, the copy program compiles automatically. And what happens is we don't know, we can't tell the difference between what we should copy and what we shouldn't. Or sorry, I should say our default is to copy everything that we see or that gets glorified. And we're not super introspective about it until we touch the stove. For example, If you ever have— for me, I know this for me, I don't like fancy things, like to own things. I drive a beater car and all stuff.

The reason is not because I have— like, look, I'll go to a car show and I'll look at beautiful cars and I love it. I love looking at beautiful cars, all that. But the thing is, is I know that if I ever bought a nice car, it would own me. I wouldn't want to park it anywhere because I would be afraid that its perfection would be sullied by somebody bumping up against it, or I would worry about, am I treating this car right? Like, this is the same way I play the guitar. I wouldn't even buy like a super fancy guitar.

And I'm kind of like, I don't even feel like I— then I have to worry about it. And to me, like, those are things I don't want to spend my mindshare on. But I didn't learn this until sort of like I owned a house at one point that was fairly high maintenance. And I learned that I don't want some— I don't want fancy high maintenance shit.

[18:27] Paul: Yeah, but so a lot of people, a lot of people discover that but don't have that awakening, right? They just shift their story. So what is it like? The— is it your way of seeing the world, like thinking of things like very analytically and trade-offs and at the margin that enabled you to then go, oh, I'm going to backtrack this trade.

[18:52] Kris Abdelmessih: Yeah, it's a lot of it, a lot of it is sort of, it's paying, just paying a lot more attention to how things make me feel. Yeah. Um, it's actually sort of not analytical. Um, it's really trying to, you know, I kind of like those words that are get— that you get used a lot about like that person's energy, that person's vibe. Like, you know, my wife uses— we'll say things like that a lot. And over time, I've sort of started adopting that.

And because I think that sometimes I can't understand it, but I just— lands— it just lands me in the right spot. So I don't— I don't, you know, I can't put my finger on it, but I don't like this. I don't like the feeling of this. And I also try to be super aware about not, um, like the derived things. I, I do try to be a little bit introspective about why do I want this, um, why do I want, you know, what, you know, did this, uh, I think a lot of that also is, is just, I don't know, as I've aged, I just realized how much barnacles of the things that I were told just like live in my brain, and I'm just undoing it all and trying to be like, oh my God, I still probably up to a couple years ago, I was still telling people that, you know, I like this or I like that, and I'm like, I haven't liked that so long.

[20:26] Paul: I've had, I've had the same experience. I think for me, living in Taiwan, when I moved to Taiwan And now my wife is Taiwanese. We met when I moved here. We have such different automatic scripts that like, I'm like pre-filtering stuff and being like, wait, do I actually think this? Is this my American programming? Because in a relationship, you have to work these things out and agree on a direction.

So you need to figure out where they're coming from. But when I first arrived here, I became so aware of this American idea machine in my brain just telling me what I should do, how I should feel. Oh, you're a lazy piece of crap because you're walking around in the middle of the week and you haven't made money in a month. I'm like, where is that coming from?

[21:12] Kris Abdelmessih: Right. You know, I'll get— I have a kind of a one— I have a— I feel like it's an interesting example because probably a lot of people feel this way, but— or may have felt this way, but Um, my— I have a beast of a last name. It's this 11-letter last name. My wife's maiden last name, um, is H-I-N-H, so it's 4-letter last name, simple Asian Vietnamese name. And I, I felt strongly about her taking my last name, and she was like, yeah, that's, that's not normal in a lot of Asian cultures. To— yeah, well, I just, I just wanted her to do it because I was like, that's what you should do.

And now I feel pretty awful about like digging my heels in on that because I'm like, man, that's— you— she went from a 4-letter last name to like an 11-letter monstrosity, right?

[22:12] Paul: So yeah, what's the added time in her life she's not going to spend writing her name?

[22:18] Kris Abdelmessih: That's right. You know how long it took me to finish Scantron tests? The worst. Uh, so I— it's one of those things that I, I feel bad about that. And the entire reason I wanted her to take it was just all this fucking programming that like, oh, you're supposed to take the other person's last name. And, um, and I would have back then probably thought that it was crazy to not do that.

And now One of my close friends named their daughter's last name— named her daughter— their daughter's last name is a portmanteau of him and his wife's last names. And I'm like, that's— I think that a couple of years ago, probably more than a couple, probably 10 years ago, I would have thought that was absolutely insane. And today I'm like, oh, these are two people that like pretty much were not following anybody's script and decided that this was the thing that felt the most right to them.

[23:16] Paul: Yeah. Well, 500 years ago, people didn't have last names. People started— this is in the book Seeing Like a State— people started getting last names because people needed to figure out who was who. So a lot of names, like in England, for example, my last name is Millerd, but it comes from like Miller. From England, and more than likely my descendant was like John the Miller in the town, right? It was just like an identifying name, and every culture has these different things.

Yeah, we got married in Taiwan and no one has the other names, right? Because you everyone keeps the, the, the male name, right? So like, my wife's mom has her side's name and her dad has his side's name, but she has her dad's last name. So it was like nobody takes the other name. Like nobody even asked when we registered here. So it was like, yeah, of course she's going to keep her name.

[24:29] Kris Abdelmessih: Right.

[24:29] Paul: So it didn't even— yeah, but to the US, it's like, oh, everyone was like, well, why didn't she take your name? Right. It's like, well, her name isn't even in English letters. It's in Chinese characters, so you can't read it anyway. Yeah, right, right.

[24:50] Kris Abdelmessih: I think that the whole like a lot of the stuff that you talk about or write about, what's interesting to me is that it, um, what's great is that it's mo— it just dives beneath the surface and like, we do things this way, but why? You know, it's just kind of like first principles in a way.

[25:12] Paul: Yeah, that's what I've tried to do. I, I went through a similar thing. I, when I left my job, my income just disappeared. So I got super freaked out about money, really financially insecure, and I had this scarcity mindset. So I basically just cut all costs like crazy and like obsessed over money. My biggest realization over the next year was that I didn't miss anything and I valued time way more than I imagined.

Like a free hour for me is I think on average worth way more than most other people for me. And that's illegible to other people. But then over time, what I realized is that there's an enormous psychological cost to obsessing over minimizing your spend.

[26:04] Kris Abdelmessih: Yeah.

[26:05] Paul: And that's really what motivated me to try and like earn more money and be more pragmatic about making money.

[26:13] Kris Abdelmessih: You know, um, so what you said there is the, the thing about exploring or trying to discover these things, like, it's kind of this unpacking of all that, um, detritus that is kind of stuck in our heads. It's, it's actually just from— you lived in a different way, like, you, you ended up You had a good job and you went to having no money and you tried this and you tried that. And actually, if you just try living a bunch of different ways, you will very quickly narrow in on what matters to you and what doesn't. The thing that happens is the people that are most likely to have all these preconceived notions, I feel like are the ones that are on a track and haven't actually been that derailed. I mean, one of the things that's shocking to me, one of the— probably one of the most shocking things I've ever— that I can ever, um, that I see on a day-to-day basis is close-minded older people.

It's, it's— we take it for— we, we just assume a lot of them that they will be close-minded. And I'm like, I don't even— I don't understand how you could be close-minded. Like, how did you get through your life not dealing with, um, horrible— like, you know, just something that really, really sucked, or having a gay kid, or having— like, like, how did you get through your life and not get exposed to things that would make you super empathetic? So when I see a closed-minded older person, it is literally shocking to me.

[27:53] Paul: But it does seem more prevalent though. Like, I know what you're talking about. I have these experiences. I sat around a table with some older people and they were talking about work and they started talking about people getting screwed by work. Their buddy that got laid off a year before he got a pension, this guy that got fired and like within 6 months he had to like move and sell his home. Another person who like died immediately after retiring.

And then they start like talking to me and I'm like, yeah, it's crazy, right? Then they were like attacking the straw man of what they thought I stood for, which is like nobody should work. I think, I think there's two things happening. I think one is that the story was so powerful and so convincing to them that they feel the need to protect it. And I still see this with young people too, though there's more cracks and there's more evidence that there are other stories happening. Maybe Instagram.

Has a role in this. But two, like, there was actual real suffering. Being a woman in the workforce for a boomer sucked. You definitely got sexually harassed and dealt with discrimination. Being a man in the workforce as a boomer sucked. You couldn't actually share vulnerability.

You couldn't be your full self at work. And you were expected by society to play this role, which isn't, probably isn't the best single-player role to be in, or single-mode role to be in. So I think there's just this like anger. It's like, I had to go through this and you should too. And I almost think we need like this mass cultural ritual to like honor all the suffering people went through to work. And be like, all right, let's move past that.

Right. Like, my life is so good because of the broad economic prosperity that has occurred. And nobody wants to stop and acknowledge that, like, my life is possible. Like, people are more happy to like, let's just pretend things are still the same way they were 40 years ago. Right. And to me, it's like, oh my God, the possibilities are incredible now.

[30:23] Kris Abdelmessih: Yeah. Well, you're the, you know, you're also, you have your, the, your path has made you see that, okay, you were, you have discovered that you don't need to be dissatisfied. So, that's really, really empowering.

[30:45] Paul: Exactly. And when I entered the workforce, I thought work had to suck, right? Maybe you had the same thing. I entered the workforce in '07 before the Google-ification and meaningful work idea around work. It was like kind of work's a necessary evil. You might find something you like doing, but like more or less you got to work.

Work kind of sucks. Put in your time and shut up about it. Mm-hmm. Yeah. And I discovered basically through creative experiments on the side that, oh my God, I can actually like what I do.

[31:18] Kris Abdelmessih: Right. Yeah. I mean, I was sort of lucky in the sense that I don't think that I, I liked— I mean, I was really scared the first week of my job to the point where I was almost like, I may need to quit because I don't like coming out of college after like a week. Yeah, it just felt like the whole thing felt incredible.

[31:41] Paul: Did you go right into trading?

[31:43] Kris Abdelmessih: Yeah, my first day on the job, I was on the floor of the American Stock Exchange. I remember it was like, I can remember my anxiety of starting a new job the last day of the end of my summer after I graduated from college and I was going to start a full-time job the next day. I can remember the night before I had a bit of an obnoxious piercing that I had to remove from my face. So it was like, you know, I just remember that night and I was like, I gotta go be an adult now. And that first week was pretty miserable and I was physically uncomfortable. I didn't know what the hell was going on around me.

Super intimidating. I was just scared. And but conceptually, I loved the idea of what I was going to be doing. To me, I was like, I'm going to go play a game for a living. So I thought it was the coolest idea. But, and I was lucky in that I pretty much always liked my job.

I always liked what I did.

[32:59] Paul: Well, it's kind of self-employment. You have some skin in the game, right? If you have a long—

[33:07] Kris Abdelmessih: yeah, your salary and bonus. I mean, it's not— I mean, you know, that kind of job, it wasn't, you know, it wasn't until 8 years later that I actually was self-employed, like prop trading type stuff. Yeah, I was a prop trader, but that didn't come until 8 years later. You know, it was, it was a job. I mean, it had, it had politics, and it had, um, so it's still pretty hard to get fired. It was hard to get fired.

It would have been hard. Yes, it would have been hard to get fired.

[33:36] Paul: Yeah, I think that's kind of what differentiates things, right? If you're a prop trader and you're losing consistently, you're just going to be cut off, right?

[33:46] Kris Abdelmessih: Right.

[33:46] Paul: Um, self-employment too, like if you don't make money, you're done.

[33:51] Kris Abdelmessih: Yeah. Yeah, I mean, I've had a full— my last, you know, there was definitely times where I didn't make money and, you know, but, and that was, I mean, that could be stressed, that was a little bit stressful, but overall, I'd never really questioned what I was doing. It wasn't until very recently.

[34:20] Paul: Well, nobody asks you if you're self-employed like me. People ask me all the time, why are you doing this? Why don't you get a job? Why aren't you doing this? Why don't you have a house? When you're on, when you're working in a job, nobody, literally no one will ever ask you, why are you doing this?

[34:39] Kris Abdelmessih: Right.

[34:40] Paul: And if you're making, if you're making good money, No one will ever ask why you're doing what you're doing, right? So I have the same thing. No one ever asked me and I never thought about it until I, until I started asking and I didn't have an answer at all. I didn't have like even the start of a good answer. And I think that curiosity is what kind of led me out of my path. So maybe this is a good way to talk about like pricing.

Decisions. I think this is the fundamental thing people are missing, is that they see what I'm doing in self-employment and they're mispricing the cost. But also, there's a real cost. The cost of what I went through of like a year or two of just kind of like experimenting in life, dealing with financial scarcity, That was really hard. That was costly financially and a lot of mental space that some people don't have. But I think they're dramatically underpricing the upsides of such experiments in their life.

And I don't know why. I think I know why that is because I never thought about it. This way before. Um, but yeah, do you think that's somewhat accurate?

[36:08] Kris Abdelmessih: I think so. I think it's extremely accurate, but I think that it has to be caveated, of course. But I'll tell you why it's— I think it's accurate. If, um, part of it is because of the selection bias in the first place of being the person— like, if you think you can, if you're the kind of person that even has enough confidence to go and take the leap, you're like not a random sample of the population at all. Yeah, you are, you are somebody that believes in themself.

[36:46] Paul: So it wasn't even that. I think what did it for me is I went several months, uh, without work while I was dealing with an illness for 2 years. And that like snapped my connection to like showing, like needing to continuously work through all my life.

[37:04] Kris Abdelmessih: Right.

[37:05] Paul: So, so it was more the fact that like, I did that before, I'll be okay again. I can go take, I honestly thought of my time off as like, I'm gonna take a year off. I'm probably gonna really struggle to make money. I guess totally not confident about what I was doing. Um, but you're right, I think probably deep down I knew, okay, you were confident enough given my background, I know how to make money, I could find work, I'll figure it out. If not, I'll take a job at a bar.

[37:39] Kris Abdelmessih: Yeah, so what I was going to say is the reason, the reason they opt— I mean, what they're mispricing there was the fact that decisions are two-way doors, right? So you can— but here's the thing, I just left. I mean, I just had to walk through all this in my head. Like, I just left a very high-paying job for— and it's also a job with people that I worked with and known in some of these cases for 20 years. In other words, like, if I went back to doing what I was doing, there is a good chance I would not even get close to what I was making before. And that's because I have all this goodwill built up with people who trust me.

And if I were to just go somewhere else, I'm not going to have that benefit of the doubt. You know, if I were to have a tough year with the people that I work with now, it really wouldn't matter that much. They'd be like, It's a tough year, they get it. Nobody else is going to have patience for that, even if I have a lot of experience. So in other words, my two-way door is like, I probably can't ever go back to what I was doing before and make anywhere near what I was making. But could I not starve?

[38:57] Paul: Yeah.

[38:58] Kris Abdelmessih: So it's like, if your worst-case scenario is like, you go back and you make— here's the thing. One, is like, if you're working a job and you feel dissatisfied enough that you think it's worth leaping, if you leap and you fail, or you realize it's not— the grass isn't greener, whatever it is, and you go back, you will go back knowing that the grass isn't greener, and that will make an enormous difference. Like right now, I don't have a job right now. So It's kind of funny because I was telling my wife, I was like, man, if I had a job getting paid anything, I would feel super rich because I'm like, wow, because I was just living without making any money at all. I would be so, you know, there would be this sense of gratitude as far as like getting paid something just because I know what it's like to not get paid anything.

So I think that one, it's like there's this two-way door thing that people sort of undervalued. It's You can go back. You might not make what you were making before, but you can go back to doing something. That's one. And I think the other thing is this idea that you might actually learn something about yourself.

[40:19] Paul: That's the—

[40:20] Kris Abdelmessih: Like, you get space. Like, space is— people are undervaluing space.

[40:26] Paul: Yeah, I think that is incredibly valuable. We, like, life is filled with infinite distractions. And when you're working a full-time job, I think the thing people underestimate is going back to your energy comment, how much of their actual creative energy gets stolen from them such that they can't actually enter that introspection, reflection space. And that's exactly what I experienced when I came to Taiwan. This was 2018, and my freelance work just dried up. People were like, remote work won't work.

We can't do that. You need to be on site. So, so I just didn't have any work, but I had plenty of time and space to think about what I was doing. The money thing's interesting too. I got offered 50 grand less than my last job for another full-time job. And they were selling me on, well, this is what you say you're really passionate about.

We can get you back up to your former salary in 5 or 6 years, we think. And I was like, this is crazy. If I really care about what I claim to care about, I can just go do it on my own and work less. And the funny thing is, I've, in, this is my 5th year, I still have never made that amount yet with money. I still have never made the $50 grand less amount annually. And it doesn't matter.

Like, I've kind of like, I've realized I can be very happy. Like, my target is like, 40 grand US per year. And that's like a perfect life for me, right?

[42:18] Kris Abdelmessih: Well, here's the thing, you also—

[42:21] Paul: I found out principles by going to the bare bones and then building back.

[42:26] Kris Abdelmessih: That's right. But also nobody can— A, you always have the option to go take a higher paying job if you want. But the other thing is the thing that you have is it can't be taken away from you. Yeah, exactly. I mean, basically you have a pot, you have a pile of equity in yourself that currently is— it's a small pile of equity, but it has tons of optionality depending on how you, how you decide to, um, actually— all right, so this is— I'm gonna—

[43:01] Paul: okay, yeah, let's dive into optionality.

[43:04] Kris Abdelmessih: No, no, I was gonna I'm going to say, let me throw this concept out. Okay. This is a little, it could be a little bit long-winded because it's something that I'm tuning. So do you know, actually I'm giving, I did a talk this summer for On Deck about finance stuff, right? I did this thing and I did this example. I have this, this idea that sometimes you see prices that don't make any sense.

And that happens all the time. Everything today feels like it doesn't make any sense. And of course, a fool looks at a price that doesn't make any sense and says, that's dumb. But anybody that knows anything about how markets work says when they see a weird price, they recognize that what has happened is that there is information that they either lack, there's information that they are underweighting, but there is something going on that they do not see. They basically don't see the whole picture. And that weird price that they're seeing is a clue to them that they should go find out more information.

It should not be like a prompt to be prompt to say that's stupid, it's a prompt to learn. So my example of this, which I think is powerful, comes from portfolio theory. And I'll show you where I'm going with this. See, if you have two stocks, like I have this example where I have— you have a stock that makes sunblock, I call it Sun, and you have another stock called Rain that makes umbrellas. Sun makes 10% in a year if the year is sunny, and it loses 2% if it's a rainy year. Rain makes 2% in a rainy year, but loses 2% in a sunny year.

Okay? So if you look at rain, it just looks like the rain stock is like, why would anybody want that stock? It's a coin flip. It loses 2% or gains 2%, depending on whether it's sunny or rainy, and it's 50/50 to be sunny or rainy. Why would anybody want that stock? Nobody should want it.

So if you look at rain in isolation, it looks idiotic to want it, but who wants it? Well, the sun shareholder wants it because the sun shareholder realizes, wait a minute, if I put half my money in sun and half my money in rain, the worst thing that can happen is I break even. It's actually even more counterintuitive than that because if the Sun shareholder put 70% of their money in Rain, which is the coin flip stock, and 30% of their money in the good stock in Sun, they actually make money every single year. Now, this is a very unintuitive idea. The point of the idea is that you cannot look at anything in isolation because there is somebody smarter out there that can see the whole picture and sees how this thing, which looks stupid in isolation, actually fits in really well with a portfolio.

The reason that's interesting is because the value of that weird thing that looks like— in other words, the value of something in isolation is the floor of what it's worth. You could build your company and you know what your cash flows are and you know how Paul Millerd does, but somebody else out there might look at what you do and be like, you know what, if I combine with what Paul does with what I do, the combination is better than the individual parts. And the thing is, an employee does not get the advantage of that. The equity owner gets the advantage of that. You want to be the owner of rain because there is always an option that that thing is worth more in a portfolio context than what you can actually see directly. And that idea to me is— and I think everybody talks about the typical, like, you'd rather own than be an employee in general, but because of the optionality.

But that part of the optionality, think about the number of combinations. We are like exploding in combinations in the modern world. The more combinations there are that are possible, the more valuable that option is that your thing is worth more in a portfolio context. Wow.

[47:49] Paul: Yeah, I, I totally follow. Everything you're saying, but I think the part that's profound is the end, right? So if you, and you could probably map that to your own life, right? If, and I think this is kind of what's happening, I'm experiencing, I find my life so good that it's really hard to understand how, but if you applied it to that, I'm kind of taking this portfolio approach to my life of like all these different like meaning buckets and shifting it such that I'm earning these unexpectedly consistent positive returns. I don't know if that maps to kind of what you're saying, but I could also see it as like how you're thinking, how you're thinking about work as well.

[48:44] Kris Abdelmessih: It does map, but it's a little bit different in the sense that You know what, a more straightforward example of that would be a person who's a pretty good writer in some way, but on their own, if they were just trying to monetize their own blog, it's probably not gonna pay. But there might be somebody else out there that says, you know what, the way you write, matched with what we do is a major sort of value added. Like, I think about, like, one thing I've thought of is education in options or finance, right? I could go out there and I could probably make a course. I sell the course and you would make some amount of money. I have— there's a lot of reasons why I don't want to do it that relate to, like, the fact that I kind of don't care about, like, well, here's the thing, like, well, now you're a self-help guru for, uh, financial, uh, newsletter Twitter.

[49:51] Paul: Um, you could just turn it into us, uh, how to apply options to your life decision-making.

[49:57] Kris Abdelmessih: Yeah, kind of. There are people out there. I mean, I don't like to actually be— I, I don't, I don't love to, like, batter people with that sort of that, like, wonkiness about it. But when I think about the when I think about this problem of just thinking about what I could do, and I was thinking, oh, I could probably go make an options course, but then it will make some certain amount of money, but where's the real payoff on if I create an options course? I was thinking, who is the most valuable? What is the way if I cared about trying to make the most amount of money possible with the option knowledge in a course setting?

It wouldn't be selling the course. It would be probably walking across the street here to Robinhood and being like, let me build education for you. And that would be— in other words, the value of the education is the person it pairs best with is the broker, because the broker is the person who can monetize that in a real way. Monetizing education directly is like not a very good way to make money, but having education be the complement that is commoditized so the broker can make more money is how the value of the education goes up.

[51:18] Paul: So I need to put you on my personal board of advisors. Well, I think, I think there's two things. I think you're You're perfectly right and people don't think this way. And I think they don't think this way because a lot of what I'm seeing is like solo creators like myself. And perhaps something you're undervaluing in your model of this is the absolutely thrilling experience of creating your own stuff. So I wouldn't want to work with Robinhood because that—

[51:53] Kris Abdelmessih: Well, I want to back up one second on that. I completely actually get what you're saying. I was saying that if I was going to make a— the only— the main— if I wanted to make a course and make the most amount of money off of making a course, that's the route. I mean, that was the caveat. But if I wanted to just do it for— it's kind of funny because I can make a course and a lot of the things that I actually do on the education where I'm trying to educate people is I would want to keep it free just, just out of like my own principle. And if it was good enough that people wanted to pay for it because they thought it was actually going to help them trade— it's a weird market to me because I'm like, I'm not, I'm not a guy that thinks that people should be like at home day trading.

Uh, I, I, I mean, I'm so jaded at this point that I feel like the going out and spending your time trying to throw darts at things, um, is not a good use of anybody's human capital. And if that is the thing that you love, go work with a team that's actually a professional at doing this. That's what you should do.

[53:02] Paul: So are you arguing that technical analysis has not magically, uh, um, rehabbed itself for crypto? I see all these like technical analysis chart.

[53:18] Kris Abdelmessih: I don't know, I'm like, oh my God, I'm a horrible person to ask about that because I grew up— my trading background and everything absolutely pooh-poohs on technical analysis to the point that if anybody saw you even— if you mentioned anything that was technical analysis related, you immediately got discredited. So you were— and, and that, you know, the bad part about that is it's— it is super close-minded, and, um, it's super close-minded. But it— you know, you have to make your choices of how you want to allocate your time. I mean, I'm literally working for the best traders in the world. Yeah, if they think that this is a waste of my time, like, who am I to be like, no, I want to be open-minded about this, right?

[54:06] Paul: If they were like, you need to start learning about this, you You invest a little energy in it. Yeah. But yeah, let's, so let's return to that a little. I, and I think what I was getting to is maybe you're underpriced. So it sounds like you're not underpricing the creative thrilling side of creating your own thing and owning that. But I do think from my perspective, it's probably a blind spot of what you're proposing.

Which is that I, I'm probably underestimating the potential of running my own thing and all the creations I have now. I think I've got in— I'm trying to challenge myself on this over the next year. I think I've become too protective of my own stuff because of my past path. Like, I'm so fearful of like creating another job for myself. Because of kind of the rut and stuckness I was in that I've like put up blinders when like obvious financial opportunities emerge. And like, I, all the stuff I opt into, like I totally want to work in.

And an extension of that is there are options available to you because of how you're psychologically wired that full-time employees have a hard time seeing. Like, I'm running an online course teaching people strategy consulting skills, which is basically how do you take information, synthesize it, structure it, and tell a persuasive story. There are tons of knowledge workers that want to learn this at an extremely high level. However, the— I love teaching this and I love coaching people on this. I love making sense of it. I did it for free for years and I got really good at it.

However, if I just went and became a strategy consultant, I could make 4 times what I'm making now doing this. So this is kind of a hidden opportunity for a lot of people with my background because 98% of people aren't going to do what I'm doing because They rather just make the crazy salary from working the full-time job.

[56:31] Kris Abdelmessih: And the fact, and that is your opportunity, the fact that like you have a lower cost of personal capital.

[56:41] Paul: Right. And, but over the, but I also, I feel like I'm playing with house money a little bit and maybe that's the wrong use of that phrase. Phrase, but I think people's time horizon is totally off with how they're thinking about work now. Everyone thinks taking, going from $250K to $0K the next year is like absolute failure. But what they really should be looking at is over 25 years, what are the, like, what are the things I want to earn in? And like basically take bets such that like maybe 17 years from now, you make $10 million.

[57:24] Kris Abdelmessih: That's right. So, what do you think?

[57:25] Paul: That's what I—

[57:26] Kris Abdelmessih: you're nailed. This is exact. I feel very, very strongly about what you said there, right there.

[57:32] Paul: And well, I think this is what I've realized in the last year or two. It's like I'm basically building all these capabilities of unlimited upside and stacking in these weird portfolios of the future. And I'm investing in myself at the same time and like unleashing these creative things and becoming happier. It seems like too good to be true.

[57:53] Kris Abdelmessih: So I'm going to, I'm going to tell you a story that's going to— I'm going to tell you a financial— this is like kind of the context of like what you actually DM'd me about. I will give you the financial analogy of what you just said, and it's, and it's probably one you haven't heard. So that idea about making— and you put it in context for me. You're making $250K and you make no money the next year, you're a failure. Okay? So that idea reminds me of an aphorism that I heard when I was at Sussk.

And that was, if you make money every day, you're leaving money on the table.

[58:43] Paul: I love that. That resonates.

[58:46] Kris Abdelmessih: So let me give you an example of that in practice to make it sort of more concrete. So when I was on the floor, a lot of the time I worked for a firm and I had a ton of capital behind me because I had all their capital, whatever. But there's a lot of people down there that are just trading their own money down on the floor, right? They are going to take much less risk, they trade much smaller, and all that. For them, it was important to make money every day. For me, it didn't matter.

I cared a lot more about my weekly or monthly P&L than I cared about my daily P&L. What that meant was there were trades that I could do, and here's an example. It's this. Let's say something is worth $5 and I give you the chance— it's the same thing as— oh, sorry. You know what? I got even a better one.

The bookie. Everybody thinks that a bookie's job is to balance order flow, okay? So to get the line exactly where it is and then just sit on both sides of it and collect the vig. That's not That, that's, that's not what they do. A bookie, a well-capitalized bookie, wants the line to be wrong so that there's a lot of edge on one side. And if you actually, like, so, so like, if the, if the line on the 49ers was really, really wrong and the 49ers were just totally cheap and they could put the line like that and not have anybody come in and try to buy the 49ers from them, they would prefer that because they would say, you know what, I want to amass a massive long position in the 49ers for this weekend if I could.

And so maybe the 49ers— let's say if it was the 49ers are worth 50 cents on the dollar, rather than saying I'm going to buy at 45 and sell at 55, they realize they can amass a giant position buying at 35. And if somebody came in, kind of like a small player came in and was like, I want to pay 45 for the 49ers, they'd be like, fine, I'll sell you a little bit at 45, knowing they were kind of making a bad trade because it was worth 50. But the point is, the broken line allows them to amass a giant position. Now, the position is much, much riskier, because the 49ers could lose and they didn't, whereas the first guy that makes the balanced market makes money no matter what, but the second guy makes way more money, but sometimes he loses.

So the point was these guys that were on the floor, they would often make a good trade and then they would just not maximize how much money they can make by doing a bad trade right after. It's like, I bought something for a bargain and I sold it a little bit higher. Whereas we'd be like, I'm going to buy as much as I can at the bargain and I'm just going to hold it until the whole market readjusts to the right price. And if that means I'm going to sweat a bunch of risk, so be it. But in the long run, I'm going to make way more money doing that than trying to balance the flow. So in your analogy, it's I'm going to be okay not making any money next year because I'm thinking about the long run.

I'm thinking about how do I make the most amount of money over my career, not how do I make sure I make money every day. And if you try to make money every day, you are not going to be— you cannot optimize for the long run.

[01:02:33] Paul: Yeah, and I think this is where our stories distract us. Our stories are so powerful that we miss the fact for literally billions of people right now, the risk of ruin in the next couple of years is almost zero.

[01:02:48] Kris Abdelmessih: Right.

[01:02:49] Paul: Yeah. And we, that is to me, I call it the inspiration deficit, which is basically if all these people would realize this, it's all this possibility and creativity unleashed. And I don't want to sound utopian, but I mean, I see it everywhere. And people say, oh, it's just an American thing. I walk around my wife's hometown and every third car is a $70,000, $80,000 imported luxury vehicle.

[01:03:25] Kris Abdelmessih: Right. Wow.

[01:03:26] Paul: Because the cost of housing for most of these people was low. The cost of living is still low. What do you do what do you do with the excess cash? All I see in that, and I've got my wife on board with this, and we point at cars and we calculate the number of years we can travel around the world.

[01:03:46] Kris Abdelmessih: All right.

[01:03:47] Paul: It's like, look at that one. That's 4 years of travel.

[01:03:51] Kris Abdelmessih: Right. And actually, that's a great— that you should— and you should actually advertise that way of thinking a lot more Actually, people are pretty crappy at that relative, uh, relative value sort of thinking.

[01:04:06] Paul: Well, a lot of people think that a week vacation costs $4,000, therefore a year vacation costs $200,000, right?

[01:04:15] Kris Abdelmessih: Right.

[01:04:16] Paul: Um, but yeah, well, and these trade-offs are invisible unless you've actually experienced it firsthand, right? So the same kind of career thinking goes on here, um, in Taiwan and many other countries. The funny thing is I have these curiosity conversations every Wednesday, and the scripts are pretty much the same everywhere now. It's like work full-time job and save money for a house. There's variations on that, but people aren't seeing how much more options we have now.

[01:04:53] Kris Abdelmessih: Yeah, I think one of the things that makes it hard, one of the things that does make it hard to, um, really internalize a separate script is just, um, it's just hard to go, it's hard to do things on your own. Like if you think about like, yeah, you know, I've just kind of like written a post about like world schooling and stuff like that, but you know, is something that's on our mind, but it is definitely really really hard. I mean, the problem is like, it's come off of our mind because of COVID but, um, but it's kind of a hard thing to do because it's so out there to do that. And I think that it would not feel so out there because once you start researching into it, you find the communities that do that. And then you realize like there's a playbook for all these things.

[01:05:44] Paul: Well, you just solve problems as they emerge. Like bad things happen.

[01:05:49] Kris Abdelmessih: Yeah.

[01:05:50] Paul: So I've got, I've gotten bit by a dog. I've gotten a parasite. Um, I was fatigued mysteriously for a month. Um, I've gotten a scooter stolen. And so these bad things happen, but then you actually just react.

[01:06:08] Kris Abdelmessih: Yeah.

[01:06:10] Paul: It's not that you can design around them.

[01:06:13] Kris Abdelmessih: Right. And it's not, it's not like not doing the these things doesn't happen either. I mean, you have a house and, you know, one day your, you know, your roof cracks. It's like your foundation— it's like there's, there's actually— I had the thought today that it was kind of— it's like, you know, you know, the birthday problem, like, you know, 50/50 that somebody's got— okay, like, I had that, you know, the math behind that is like the n to the, you know, something to the nth power is like 1 minus some, some probability to the n. And I was thinking today I'm like coming out of my driveway and I was thinking, it's amazing to me, given all the complexity around us, like you have a home and these people go to school and that person works there and like your life is just kind of complex.

And I was like, it's amazing to me by birthday problem math that you're not putting out a fire in one of these complexities every single day. I'm like, every day that I don't put a fire out feels like a miracle to to me because I'm like, how does that happen? I feel like the odds of a fire every single day should be close to 100% when, when there's so many things that can go wrong in a modern life. Yeah.

[01:07:19] Paul: Yeah, it's— and well, I think this is the thing that blinds people is that in some ways, like, I am not a critic. I might be a critic of the default path, but not in the way you think. I actually think the default path of like structuring your life around the full-time job is probably one of the greatest innovations we've ever discovered in the modern world. The ability to live a rather good life by only giving up 40 hours of your life per week is absolutely incredible. And the fact that it operates so smoothly for so many people, is it's like it would blow people up, like blow people's minds 200 years ago.

[01:08:10] Kris Abdelmessih: Yeah, I agree with you.

[01:08:13] Paul: But my biggest argument is that this blinds people from what they might actually want or enjoy more.

[01:08:23] Kris Abdelmessih: Yeah.

[01:08:24] Paul: Well, I think, yeah, it's kind of a local maximum. On a larger, on a larger plane.

[01:08:33] Kris Abdelmessih: Yeah. What, what about, what do you think about, um, one, one thing that's kind of interesting to me is, uh, the concept of sort of premature optimization. So the, the, I, like, I was pretty clueless in college. It changed majors a whole bunch, and college is this very expensive place, and Um, it feels like in a way it feels like it's in the wrong order to me. Like, I would want to go to college now. I think a lot of adults— I think a lot of adults feel that way.

It's like they'd want to go to college when they're 40. Like, I don't want to— I don't want to go take tests, but like, I want to go learn stuff now.

[01:09:14] Paul: Imagine how curious people would be instead of just getting drunk every week, right?

[01:09:19] Kris Abdelmessih: Totally. It would just be so— it would be so interesting. Now. But that— it feels like a weird thing to me because I would say the great thing about it is, for me, 100%, the best reason, the best thing that came out of college was the fact that I grew up in a pretty provincial place, which is central New Jersey, and I went to college and met people from all over the world. And To me, that is and always will be the single most important thing about college, is that it opened my eyes. I was so close-minded when I went to college.

I was like so close— it was so close-minded.

[01:09:58] Paul: I think me too.

[01:10:00] Kris Abdelmessih: And, um, college opened, opened me up a lot, and that was 100% the value of it to me, was it was a chance to get the hell away from my upbringing. Um, but I do, I do find that there's so— it feels like there's so much at stake. You graduate from college, you go get a— you go get a job, you end up on a path, and it's like a— like, trading worked out for me, but I always say it was a historical accident because while I did like it, I actually I think the personality of the job was not really my personality. I think I was a much more optimistic person before I found trading. And I'm kind of in the process of— I'm probably far along in that process now. I started a couple of years ago where I'm trying to knock a lot of the skepticism that it builds for me.

Like, trading is like a very, very skept— you have to be— I mean, everybody's out to get you, and it is. You have to be a very skeptical kind of person, and, um, you have to try to poke holes in everything, and you have to ankle bite, and you have to say, actually, that's not how that works. Like, but I wasn't good enough to be able to separate that from how— from how life works.

[01:11:30] Paul: I think I experienced a very similar thing. Like, I was good at consulting. I'm really good at the sense-making analytical stuff, but there was this cynicism that grew in me, and I just became so cynical about how organizations worked. I became like the facts guy that like challenged everything intellectually. And really the past 5 years for me have just been like a softening back into like a lot of, oh, I was actually this optimistic, like more go with the flow kind of person when I was younger. Right.

Yeah, it's weird. I think I desperately tried to break into consulting even though people told me I couldn't, I went to the wrong school. Schools, and I broke in. I landed at McKinsey as a research analyst when I was 23. And once you're in that game, it'd be stupid not to try and like succeed on that path. Yeah.

[01:12:40] Kris Abdelmessih: Like, it was a golden ticket. Yeah.

[01:12:43] Paul: And like, my parents didn't go to college. And like, Then my boss is like, oh, I went to this program at MIT. Have you thought about grad school? You could probably easily get in. And I'm like, what? All right, all right, let's go, let's go do that.

Then I'm going to MIT, then I'm like bouncing around all these other consulting firms. And then in my last job, I was like fighting with my boss because I want to get paid more, although I'm getting paid more than I ever imagined making. And that was the awakening for me. I was being miserable because like I thought I was underpaid and I thought everyone in my office was like, ah, they're jerks, their system's rigged. I haven't made half of what I made there in 4 years and I didn't want the money. I just started playing a game that I was around.

Like the game though is stupid. And to other people, they're like, I feel the same. Yeah. And that's probably why you, our writing probably resonates for each other. But other people see my life as like giving up that. And I just see it as like, oh, I kind of did that.

Like, that's not me. I'm like restarting over again, right? Um, I'm at like year 4 or 5 of like a 25-year journey that I actually want to be on.

[01:14:16] Kris Abdelmessih: How did you, how did you, um, so like right now it's kind of funny, like today I was just speaking to one of the moms out on the soccer field today and, um, you know, I met her last week and our kids have become friends and stuff and I was just I was chatting with her today, and then, you know, I get that question like, so what do you do? I'm like, so I don't do anything. And I'm like, I don't even know how to answer. In the beginning, when you first— I don't have an answer to the question. I'm like, literally, I don't do anything. I did finance for a while, and it's still like, I've only— I only quit this year.

So I was like, you know, I, you know, I left my job earlier this year, so it feels Like, it's not that dramatic to say that, but I could also see myself like— like, I don't know if I'm ever going to be in a path where I'm going to tell somebody that I do something that they're going to actually put in the proper box or put in a box or anything. I have no idea.

[01:15:17] Paul: Yeah, I think society is moving in a direction in which this kind of path where will not be as weird 10 years from now. Pragmatically, I still struggle with that question every time. I take two approaches. One is a pragmatic one of just trying to give an answer and move on to other stuff. Yeah. And then some people are genuinely curious, and then I basically just tell a more drawn-out story.

But for the pragmatic Typically, if I'm dealing with somebody that's a bit older, I say, oh, I'm a freelancer and I work with companies and do consulting. And then they say, oh, nice, how's business? Oh, business is good.

[01:16:03] Kris Abdelmessih: Good.

[01:16:04] Paul: Then move on. Because when early on, I was— that question was so central. To everything I was thinking about. And I would try to answer it honestly. And what I discovered is that article you shared this morning, people get really angry at me when I'm like, oh, I'm just wandering and trying to explore, dabble in different work. And like, people would start digging and like, people would get mad at me or like argue against me.

[01:16:39] Kris Abdelmessih: Is that in every geography?

[01:16:43] Paul: No. And that's for different reasons, right? When I'm traveling in Taiwan, people are more curious about what— white dude, you look different than everyone else. Where are you from? And they're actually genuinely curious about where I'm from. When I'm in Asia, people more want to know, where are you from?

What are you involved with here? People ask, are you a student here? Because A lot of people come here to study Chinese. But yeah, America is the strongest. People are obsessed with work and money and people hate to hear that, but like people are obsessed with it. Yeah, it's a hard question to answer because you don't want to trigger the other person.

I think visa, coined this phrase. It's like preemptive disarmament.

[01:17:40] Kris Abdelmessih: Yeah.

[01:17:41] Paul: So like, what I try to do is preemptively make sure I'm not going to trigger the person I'm talking to.

[01:17:49] Kris Abdelmessih: So you do that by sort of— I mean, an easy way to do that is to kind of like, oh shucks, I'm just, you know, I'm, you know, I can, I can My thing is I would, I just would self-deprecate, like, ah, I'm in a lost place right now. And I also, like, I can also be like, I'm having a midlife crisis, and it's kind of like a funny thing to say that nobody really pushes on.

[01:18:15] Paul: Yeah, I try to avoid that. I find generally people don't actually like self-deprecating humor. I have a very pragmatic response now. So I pair the two worlds. So I give, I say I have a business, I run my own business doing things online, and then I pair it with things I'm interested to, as if it's like an invitation, right? Like I have my own business, I do a bunch of things online.

I freelance. That's like, That, so the person can then take the first part of that answer and say, oh, okay, it makes sense, freelance consulting, okay. And then I say, yeah, I write online, I build online courses, I host a podcast. And those are kind of the cues to be like, oh, I heard about these online courses. And then we can have a conversation. The majority of people, especially from the US, don't want to have that conversation.

And I don't want to trigger an existential crisis for anyone.

[01:19:26] Kris Abdelmessih: Yeah.

[01:19:26] Paul: I want to talk to people like you who are just so curious about this stuff.

[01:19:33] Kris Abdelmessih: Yeah. And I would say I feel like my experience of that—

[01:19:38] Paul: So I would challenge you to play with it. I would A/B test different responses and see what kind of reactions you get.

[01:19:46] Kris Abdelmessih: Um, I feel like living here, it's like people are a lot more open to it.

[01:19:52] Paul: Yeah, definitely.

[01:19:54] Kris Abdelmessih: Because like in the Bay Area, it feels like—

[01:19:56] Paul: because earnings are probably so high, right? And like everyone kind of has solved their like basic, um, security fund if they got laid off.

[01:20:07] Kris Abdelmessih: Yeah. But yeah, I feel like out here it's a little— it's more forgiving in that way. But like, yeah, if I was in a— I spent a lot of time in another place, I would— I feel like I would have a harder— and I spent a bunch of time like in Texas this summer. I feel like even there would be a harder question to answer. The Bay Area is like, everyone's like gets it. If you're like some like hippie doing some random shit, it's all good.

[01:20:32] Paul: Yeah, the Northeast is a little harder.

[01:20:35] Kris Abdelmessih: Yeah, it's interesting. The, uh, in the beginning before you were earning money, what did you say?

[01:20:43] Paul: That was hard because it was like what I am now.

[01:20:47] Kris Abdelmessih: I mean, I don't earn any money.

[01:20:48] Paul: Well, my own insecurity was just dominating the question. I, so my first 9 months I made a bunch of money freelancing.

[01:20:55] Kris Abdelmessih: Okay.

[01:20:55] Paul: Um, so I mostly just said I was freelancing.

[01:20:59] Kris Abdelmessih: Okay.

[01:20:59] Paul: Um, so, and then when I moved to Taiwan, basically for like a year straight, I made like $10,000. And that is when I started really like, oh, I'm a full-time vagabond who, and like that's when I discovered people get pissed at you.

[01:21:28] Kris Abdelmessih: And —like you're insulting your parents. Yeah.

[01:21:33] Paul: They then will take, they'll then try to search for things to attack me. Like, oh, where'd you work? Oh, you can do this. A lot of people say you can do this because you, why, right? You can do this because you worked at MIT. I don't think there's any causality between my past work and what I'm, doing now, I think there's probably a correlation against certain skills and aptitudes and intelligence I have for sure.

But it is not because I worked a certain place I'm able to do it. Actually makes it harder to do these things.

[01:22:17] Kris Abdelmessih: Right. I mean, they're also kind of keying off— I mean, they're also like, they are picking up on the fact that it's like Oh, you got an, you know, you went to MIT, like you have options in life.

[01:22:29] Paul: Right. Yeah. That's, and, and that is, that is true. But the people I talk to who are actually curious about taking different paths in their life aren't interested in those things. The only people interested in those things are the people solidly on the default path. Correct.

Right. Because I've talked to people, all different incomes, all financial status. And the reality is 90% of people I talk to who are making high incomes think the amount of money I left with is absolutely insane. They think it's way too small. Wow. Yeah.

Like the numbers people give me are insane to me. They're like, oh yeah, maybe if I had $2 million, I'd consider stepping away. And I'm like, what the heck? Right. I was like, one year of cost of living and I'm good.

[01:23:28] Kris Abdelmessih: I think it's because, so one of the reasons for that, like I think one of the reasons people think that is—

[01:23:34] Paul: Well, you did a survey on this, right?

[01:23:36] Kris Abdelmessih: Well, I did the survey on what people consider to be rich, but I think what happened, I think it's really hard to, because when people have to envision this question of like, I'm gonna leave my work. It's because they don't imagine their life unchanged in all the other ways it would be unchanged. Like, you wouldn't, you wouldn't have all these like giant bills that go along with your current life.

[01:24:03] Paul: Well, I didn't imagine it either. This is the crazy thing looking back. I had no plan. I had no clients lined up. I quit my job in New York City. It, it only took me 3 weeks to realize I'm like, oh my God, I need to do a budget.

So I like, I had like mint.com set up for like looking at how like number goes up. But I'm like, oh my God, I'm like exporting the data. I'm doing the math. I'm like, what am I doing in New York City? Right. So I sublet my apartment.

I stopped going out to eat. I didn't buy new stuff. I didn't like— I moved to Boston. I moved into a house with 3 other 20-somethings. We had 1 bathroom. I lowered my rent to $800 a month.

I started, I started biking everywhere. Right. And I lowered my costs by like $3,000 a month within like within 4 months of quitting my job. Yeah. But I totally get how that's invisible to people because I didn't, I didn't plan anything, right? I'm like, I felt so stupid afterwards.

And then like I moved to Asia and I cut to the bone even more. Like I was in Taipei, I was not going to nice restaurants. I was getting $2 dumplings every day. Yep. And I have this moment I've written about where I was in this store. I was crazy rainstorm and I'm like, I finally need to buy like sandals.

I can walk around the rain. I'm walking around in Poya, the CVS of Taipei, and they're like, it's like 150 NT, it's $5. I'm like, I shouldn't do it. I'm like doing laps. I go back to the sandals. Ultimately I walk out.

And didn't get the sandals. I think that month my cost of living was like $950 and I wasn't making money at the time. But I then realized that was when I was like, the cost of this is too much. Like, I got to try and at least make money, right? Right. Wow.

But I was also incredibly happy at that time. I wasn't like obsessing over money all the time. But it was a cost. Yeah. I was just reading books all the time, go to the park. My life was wonderful.

And a lot of those like realizations and ahas, like I've written about and like a couple months later when I had nothing to do, I bought a course in which I've now made over $100 grand from, or I built a course. You built one, right? But I only built that because like friends were asking me about it and I was like, you know, I'm gonna build a course. There wasn't even the online creator economy yet. And I didn't make any money from that for 6 months. But it's all these random things I just did during this period, which enabled me to survive over the long term.

[01:27:11] Kris Abdelmessih: I mean, listening to, listening to that, it sounds, that sounds very frightening.

[01:27:16] Paul: It, it was, I felt stupid. That's the thing. You can, deep down, I knew I was on a path I needed to follow, but I'm also walking around the park reading that book and then having thoughts flow into my head like, you're an idiot, Paul. You're so stupid. Your friends are making more than you. Failure.

You have friends working at amazon.com right now. Think about like if you just took a job at Amazon, like how much you'd be making. And so you still have those thoughts and it's terrible, but it's also amazing at the same time. So is there that—

[01:28:05] Kris Abdelmessih: actually, I was going to ask you right about that. So one thing is like, so right now, Right now, um, because I have no idea what I'm gonna do, there's this, um, restless anxiety energy, uncertainty. Like, there's a lot of just— yeah, crap. And it's, it's not— and it's not stressful, it's just, it's there. It's like, I'm like, what the hell? And there's, you know, there's like opportunities that kind of come along along where it's like, I could, you know, somebody will ask me like, would you have any interest in coming back and doing this or doing that?

And it's like, there's a part of you that's like, you could— I could make all that go away and just go into numb mode because you could go back and you could take a job and it would like quiet all that. Yeah. And, um, I actively don't want to quiet all that because it's like, to— it sounds like what you just said is like, I know that I, I need to, I need to feel this. I need to go through this because I think that the other side will be— I'll know more about myself.

[01:29:19] Paul: Yeah, so you're crazy like me.

[01:29:22] Kris Abdelmessih: Yeah, it is, it is crazy. I mean, it's not— I'm not crazy like you because you did this It was way riskier when you did this. My wife has a job. Like, when you did this, it was crazy. I mean, I'm not— I don't put myself in the same class of people taking a giant risk. My wife works, so it's not, um, uh, it isn't the same.

And I don't give myself anywhere level that, that level of credit for taking a risk.

[01:29:50] Paul: No, I don't think you should downplay it though, because I think what you're experiencing is almost like universal. When you transcend against the default path, there's tremendous amount of shame you need to go through. And it doesn't actually matter how much money you have. The shame is the same amount.

[01:30:15] Kris Abdelmessih: Yeah, because I think, I think what the shame is about, well, at least to other people, not to me, Because the shame to other people, I think, is probably that it's like, hey, you're capable and you're wasting your capability, right? That's where the shame comes from. But I've, you know, the way I— for me, I don't really— I don't even— I don't buy into that because to me, I'm like, yes, the economy has said my highest and best use use is this, but we've never tried to figure out what my other highest and best uses are. And I'm also like irrationally perhaps confident about the fact that there might be a higher and best use for me than the thing that stopped giving me the feels.

[01:31:08] Paul: Yeah, and I, I think that's where I am. I think, I think about role models, right? So like a really profound book for me is Tuesdays with Morrie. And what I'm aiming at really is kind of like his vibe at the end of his life. Like, how do you cultivate that kind of like energy and community around you? How can you be at the end of your life and have other people say like, oh, wow, like, man, still living?

So I'm really aiming at aliveness. But I think you're downplaying some of the things you do. Like, think about like following your journey, like I think the summer you created for your kids is something they'll probably talk about for the rest of your life, their life. I hope so.

[01:31:52] Kris Abdelmessih: I mean, I have no idea, but—

[01:31:55] Paul: Right. And who knows how kids can always turn on you, but yeah, there are. But yeah, why isn't the work of being a parent high-value work?

[01:32:11] Kris Abdelmessih: Um, yeah, I guess I never— I don't really— in a way, I don't really think about it that way. Um, but again, it's also— I don't have— it's weird. It's— and you know what, when I, when I, I remember I was hanging out, I had this like night out. It's kind of funny, like there's this group of dads that I hang out with like every month. We get together and one of these guys' backyards. And half the dads are unemployed.

And in a lot of cases, it's like they're just super wealthy. And in the other half, the dads are in, you know, high finance or tech jobs and they're making a bunch of money. But they look at the dads, even the ones that that like myself, who have, it's not like I'm, you know, I don't have like Bay Area wealth the way people do around here. And they look at those dads and they're envious. And so it's just kind of interesting dynamic because career gets sort of talked about a lot in this circle and everybody's kind of aware of the treadmill, like all the, and there's no straw men, going on in these conversations because it's a bunch of guys in their 40s that, that like are pretty introspective about some stuff. And what's interesting is I remember this conversation with this one guy who left his, his gig.

He hasn't had a job in like 9 years and he's been like bouncing from one entrepreneurial thing to sort of the other, but he doesn't know where his supper is coming from exactly. Now, this guy, when I was telling him that I was thinking I was going to quit soon, the big thing he asked me about that is like, when you think about that, I was kind of telling him I have anxiety around that and all that. He was like, is the anxiety coming from you or is the anxiety coming from having to explain it to other people? Yes, this is huge. And I said Oh no, I'm 100% certain that this is the right thing for me. I don't question that at all.

[01:34:23] Paul: I'm— So you've gotten to the center of it. This is the question I ask people, which is the most, uh, the hardest question for people is, will your parents still love you if you do this? Right. Um, and it really gets to the heart of it. And if it's not your parents, it's typically like your spouse. Because people talk to me and they'll say, I'm like, who are you?

Have you told anyone this? They're like, oh no, I can't tell my parents. I can't tell my spouse I'm thinking this. Right?

[01:34:57] Kris Abdelmessih: Yeah. So that's really, that's really heavy. People are talking to you in a very, very delicate place. Holy shit. Right.

[01:35:08] Paul: And this is what makes me so passionate about exploring these these things because I feel like I have a responsibility to help these people make sense of it. And this is something that's— so this is something that's helped me deal with this uncertainty and become even more sure about my path is basically these letters I get from people writing or these conversations. And I think the solution to this uncertainty really is leaning into what is your positive version of freedom in like Eric Fromm's sense. I don't know if you're— are you familiar with that idea? I'm not. So Eric Fromm wrote at the beginning of World War II, he's trying to wonder why are people so willingly just joining Nazism or socialism around the world, or fascists.

And his argument was that this freedom thing is rather new. Up until the early 1900s, we oriented through the world through like a church. And the church told us what to do, or our community told us what to do and how to behave. Now people are free and they don't actually know what to do. So like, wow, negative freedom in his mind was like the freedom from control, right? So like, people experience this negative freedom of like the freedom from control of oppressive hierarchies.

And to the most part, we're still obsessed with freedom from oppression in society and politics. However, the opposite side, he said, of this was like a positive freedom, which is what is our deeper relationship with the world such that we are deeply connected to both ourselves, other people, and the world at large. And this is not really something that gets anyone fired up. So there's no political vision for this. And there's— it's really hard and disorienting to actually do this. So a few of the things he said that work, one was like ritualistic group modes.

So he used examples of like tribes. They have these ritualistic group experiences which bind I was going to say like an AA meeting. Yeah, exactly. Two is conformity. He said this is mostly a trap because it's not actually your own vision. It's a vision that you're opting into.

He said the third mode was creative union. So finding some way to create. And I think this is why creativity is so important. It can be— this is probably what you experience in writing. Writing helps you make sense with the world and connect with, like, your vision of what the world is. And you don't know where that's going to take you.

[01:38:07] Kris Abdelmessih: Um, actually, you, you were the one who gave me the language to understand my own writing because you were the one who told me that writing to find your people. Yeah. And it was, by the way, that was one of the— I've actually told that to like 3 other people since. And the reason is that, um, that phrase was, it was, it was so powerful to me because I was like, why do I— I've asked myself before, why do I write? Why do I write? And I would have these like these theories.

I was like, the clarify my thinking, to educate other people, be like all these things. And then the second you said that, I was like, you know, when you know something is like so right that everything else was definitely wrong. Yeah, that was the feeling I had when you said that. I was like, holy shit, that's like, that's it. That was, that's, that was, that was the whole thing.

[01:39:02] Paul: Yeah, this clarified for me a couple years ago, um, when somebody just, somebody I cared about angrily responded to one of the things I'm writing. And I really had to do some reflection. And I realized, like, I'm not writing for him. And I wrote this whole thing that was like, I'm not writing for you. I'm not writing for you who succeeded on the default path of life and crushing it. I'm pumped that you're killing it, but I'm trying to explore something else.

I am writing for the curious weirdos who think there might be more possible ways to to live a life. And yeah, I've— a lot of people can't see this, but I have a very clear strategy. When I'm older in life, I want to be surrounded by curious, loving people in an engaging way. And I think the best way to do that is start building it now. So I have curiosity conversations every Wednesday. I've talked to over 250 people from around the world about their relationship to work.

And they typically reach out based on stuff I'm writing. So I'm in this broader conversation with the world and it basically creates this virtuous loop, which is essentially my positive vision of freedom. As long as I can keep that loop alive and engaged and energized, like that's it. That's life. Right.

[01:40:26] Kris Abdelmessih: I think you're right. And I think you're right.

[01:40:30] Paul: And it's almost too simple to be true. And like any profound wisdom, but all the other stuff is just around the edges. Like the strategy consulting course, like that helps me make money to keep that alive. Right. And like other ways of making money, the stories I tell people about what I do and where I'm going, any goals I pick, they're all incidental to this deeper engine. Right.

[01:41:00] Kris Abdelmessih: It is that, um, actually, I love, I love that you use the word engine. I don't know, it's like literally makes me think of like, uh, it's, it's like a, like a deck, one of the deck builder card games. But it's like, it's totally, it's totally what it is. It is the, um, I often think, I actually think, often think about things in terms of like what you're saying, like the engine It's a, it's a, um, every— if you ever get like, whenever, whenever you get a game, like every game is sort of a skin or a theme on it. Like this game, like we're moving around pieces because we're gonna drill for oil or something, or we're gonna do real estate over here, whatever. But like when you go past the skin, it's always like, what is the underlying engine of what's going on here?

Yeah. And it's very interesting because who you are outwardly is, um, like visible skins, but the engine that's under— underneath it all, the thing that binds it all together, is the fact that you have this positive creative vision, which is— God, I have to— I feel like I have to think about that for a while because it's really— it's really kind of heavy. Like, it takes— it feels like it's going to take a lot, like, a lot of, like I'm going to burn brain cells trying to think through that one. Yeah, because it sounds exact— it sounds right to me. So it— I have to like— it could use some remixing.

[01:42:28] Paul: I think it's very specific to my journey and what I'm perfectly wired to be doing. So it probably could use some broadening to be more applicable to other people, but Yeah, I think a lot of the most important things in life are really simple. It's just, it's very hard to learn them in your body rather than your mind.

[01:42:52] Kris Abdelmessih: Yeah, man, that's, that's so true. I, I, I agree. So true. It's the— it is very— it's like, I mean, that's super resonant to me because of the same thing I said before with like trying to just trust how the vibe of the way this feels or this person feels and trusting, trusting that, that, that like your feelings are actually doing a great job of capturing, um, all the illegible stuff that we can't articulate, but your feelings are actually doing a great job of guiding you.

[01:43:29] Paul: Yeah. And I mean, my wife is trying to do the same path. She left her job with almost no money to her name and just started on this solo journey. And she's still trying to figure it out. And she's a little more introverted than me, so she doesn't get the energy from connecting with people through her writing, but she still likes a lot of the same stuff. And she hasn't really discovered her, like, engine yet.

But we're both kind of aiming We're aiming around a life in which work kind of fits what we want to live. So we're like boldly going to try and live the life and then working backwards to see what fits. Right. And it's really hard. And people will be like, oh, you can't do this when you have kids. It's like, yeah, I'm, I'm prepared.

It's going to level up the degree of difficulty, but I was going to say, I still want to play.

[01:44:23] Kris Abdelmessih: I was going to say that's the, what you're It's so crazy to me because what you're telling me, like, what you're telling me seems— the methodology of like envisioning a life and working backwards to how do I have the life that matches the energy or the creative union that you're trying to create, that sounds like what you would come up with if you were to actually hurt your brain and give it some thought. I think thinking is hard. I always say thinking is exhausting and it's really hard. That's what this is. This is like, you've thought a lot to figure this out and it's painful. What you said there about trying to work backwards, to me, I'm like, isn't that literally the definition of living?

Isn't that what living is? Isn't risk Living. I mean, that is living.

[01:45:23] Paul: Yeah, well, John Stuart Mill called this experiments in living, and he said it was the most important thing to discovering originality and genius, right?

[01:45:33] Kris Abdelmessih: That, that, that's actually what life is like. Yeah, it's not, you know, it's not a— life is not this like recipe that you follow. It's really this, this like—

[01:45:43] Paul: well, and I, I think what's happening—

[01:45:46] Kris Abdelmessih: you try to get there according to— or you, you see how you want to live, and then you're trying to make your life work with the way you need it to work for you.

[01:45:55] Paul: Well, I think that's how life was for most of history. But what's happened is we have these really good, kind of like off-the-shelf life modes. You can just like, by default path and not have to worry about those questions. All I'm ever saying is that like, I get a kick out of thinking about those questions, which other people I think are saying are, um, probably overpricing. And I'm like, I actually want to try different modes and see what emerges. And I find this fun.

Other people are like looking at it and being like, this is crazy.

[01:46:43] Kris Abdelmessih: Yeah, because they look at it and they think think like it's, they think it's a distraction.

[01:46:49] Paul: Yeah, this is the whole thing for me. I have so much fun.

[01:46:55] Kris Abdelmessih: That's, this is life.

[01:46:56] Paul: That is life. Yeah. Like me and my wife have already probably lived in 15 to 20 different places. That's more, more places than most people will live in their life. But what we're learning is so crazy. Like we're getting down to the details, like, Okay, do we want like a, a window with outside sun in our bedroom and at what angle?

Okay, do we like a desk out there? Do we like a desk in our bedroom, a desk in the living area? Do we like a separate kitchen? All these minor things we get to like tweak and experiment with. It's pretty cool. And you end up knowing exactly what you need and don't need.

[01:47:37] Kris Abdelmessih: The, Yeah, it's, it's, uh, I do think the other side of that will end up being feeling looser about that a little bit, just because like, yeah, sometimes, sometimes I'm just kind of like, if things are kind of held together, I'm like, great, we're doing great. Like, like, yeah.

[01:47:57] Paul: And I think I sense that having more resilience is going to be a lot very helpful when I have kids. And I guarantee I'm going to want to ratchet down the randomness of my life path when I have kids because I want to absorb the randomness of a child. Yeah.

[01:48:21] Kris Abdelmessih: And you, I mean, and you, you, you will, I mean, it's actually, it's a great, the way you think about it is a great, um, It's actually really funny. I'll tell you, I'll tell you this. You, you are going— you're— I feel this way. You're— you are going to learn more from your kids than they're going to learn from you.

[01:48:43] Paul: Yeah.

[01:48:44] Kris Abdelmessih: Oh yeah, yeah. It's like they are going to change you in like a, like a very— like, because, um, because you're listening. Yeah. So it's kind of pretty cool. Yeah, you're listening, so you're going to hear them.