Matt Yao Interviews Me

[00:58] Paul: Today I am talking with Matt Yao. He's actually going to be interviewing me. I met Matt, I think the first time through a phone call. He basically sent me a message over Twitter saying, hey, I read your book. I am reorienting my life, thinking about quitting. And we had a call, super curious.

I followed his journey. He's been writing a ton about taking sabbaticals, rethinking work, and his journey finding what I like to call good work. And yeah, he just read my second book. We met up in SF as well, and he wanted to interview me, so I figured it'd be fun to dive in and also chat about this with him.

[01:39] Matt Yao Interviews Me: Yeah, thanks Paul. Thanks for having me again, and I'm really excited to have this conversation. Good Work and anything else that emerges. And really, I just view this as a way for me to pepper you with all the questions that I have about what you've written about and also just the impact that you've had on me in my life and also now in my career as well. Maybe we just start off with how things have been so far with launching Good Work and what's been emerging. You know, the thing with books is they're kind of a one-and-done project.

At least in terms of the book itself. So I'm really curious what's been going on since.

[02:18] Paul: Yeah. So in the book I write about my relationship with the work after having a kid, and I think it's something I had to completely reorient, not my relationship to the work, but how it fits into my life. And after I put the book out, I've basically just stopped writing a lot. I think I really had to lock into this. Very disciplined of writing at least 3 days a week. And then especially toward the end of the book, letting the book take over basically like every free moment of my life.

And so I think I was a little, I think I needed more rest than I thought at first after pushing the book. So I've mostly just been taking it easy. I think 2025 is really when I'm gonna start probably writing a third book. What I found through writing the second book was that yes, I actually do love this. It's awesome. I love how it shapes my relationship to work and just helps me focus and go deep and do the things I love.

But yeah, it's been fun promoting the book. My approach is basically I'm going to promote it over like 3 to 5 years slowly and see what emerges over time.

[03:29] Matt Yao Interviews Me: Awesome. I, I'm sure we'll go into more specifics and deeper, but One thing I wanna just start off with is big picture. How do you define work? Because you define it in a very different way than the conventional American views it. And so just right outta the gate, I think it's important to lay out on the table how you define work because it's certainly not what most of us might think it is.

[03:57] Paul: Yeah, I think, I don't even know if most people have a definition of work. I think they've sort of absorbed a very surface level idea idea of work that is pretty shallow. I would say it's more like work is something you have to do, something really basic like that, or work is what you get paid for. And I think those definitions are fine. There's nothing wrong with those definitions, but they sort of ignore two things. They ignore one, all these things that can't be paid for, but might still be worthwhile doing.

And two, all the kinds of work that don't fit into like formal employment and paycheck work, right? I think your journey over the past couple of years, you've done a lot of stuff. And I think many people encounter this when they become self-employed. Like, what is work? Is your newsletter work? Is it or not?

Like, is it? It's enjoyable, but it might also lead to opportunities that you actually do want to get paid for down the road. And so my simplest definition is work is things worth doing. Which sounds really silly, but when you think about it, it like, that's really what life's about is like trying to pack in as many things worth doing that you won't regret, that feels satisfying, that delivers some value to yourself or the world over time.

[05:19] Matt Yao Interviews Me: Yeah. If work is what's worth doing, how do you reconcile that with other words that people associate with what's worth doing, like hobbies, passions, or Is there just a lot of overlap?

[05:31] Paul: Yeah, I, I think I just try to get to the essence of these things. There's so much bullshit out there in terms of like how people are thinking of work. And I think a lot of it comes from a very cynical or a naive place. So the cynical is, well, you don't have any choice. You gotta work. So what are you supposed to do?

It's not like I can stop it. It's interesting because these scripts are very strong and I've heard that from people I know, know who have like millions in the bank and they'll be like, yeah, I hate what I'm doing. It's terrible, but you gotta work, right? It's like, well, the math is a little weird there. Maybe not, or maybe not spending as many hours doing these things you also claim to dislike. And then the second is this, like, I think it's a reaction to our world, which is that formal work and formal employment and successful work where you make a lot of money is so central in our conception of work.

And so the naive reaction to that is like, okay, let's make this even more special. Right? And so you've— everyone's seen this ikigai diagram, right? Where like, do what you love, impact the world, make a lot of money. And I forget what the fourth one is, but the combination of those three things to me is like actually a really terrible starting point for searching for things worth doing because it, it just narrows the imagination to basically formal employment or a very narrow type of entrepreneurship, right? And I think it's this wishful thinking of like, Okay, here's how like everyone seems to be working and living.

I wish this framework could map onto that so I don't have to make too many changes. And I think mostly I don't write for those people. I write for the people that are like, I actually do want to rethink and make those changes and maybe pay some costs to find something even better. And so that's sort of what I'm exploring. It's this ever-evolving open question. And I think even in the past year, like I'm thinking a lot about these things and I don't really know what work looks like in the age of AI.

[07:55] Matt Yao Interviews Me: Yeah. That's something I want to get to later. I also have a bit of a gripe with Ikigai because a little bit of a different gripe. It's that it's sort of framed as like this one-time sit down and think really hard and you'll find the intersection of these four circles. Whereas I view it as more of like a continuous process.

[08:15] Paul: Yeah. It's, it's always interesting because I mean, this comes from a Japanese word, which is reason for being. And I think that definition of like reason for being probably connects deeply with what I'm talking about in good work. But the Western imagination must fit these things into like very defined things. Like even the idea of like you need to have an impact. Like, I think it's a very sexy idea.

It's like, I want my work to impact a million people. You hear this from some people and I think there's a craving in that that can't actually be satisfied. And realizing this, I think, can lead to a certain devastation of like meaning, like meaningless or not mattering. But I think working through that and on the other side is this like, okay, if I'm not sure what an impact is going to be, I might as well do things I care about and really just try to like maintain that connection at a local level.

[09:14] Matt Yao Interviews Me: Yeah. The word impact is really interesting. I remember when I was first working in tech as a product manager, you know, fresh out of college, we would, we cared a lot about the impact that we had, like me and my peers who were all in the same cohort. So we were all 22, 23, and we would like look at the different teams and the different options and think about how many users we were touching and what sort of features we were building. Do you hear a static?

[09:41] Paul: No, that might be Angie vacuuming. It looks, I think we're live streaming.

[09:47] Matt Yao Interviews Me: What? Wait, on where?

[09:49] Paul: We are live streaming on my YouTube. Oh, we have questions in the live stream chat. Hello. Hello viewers. I think we should just, I think we leave it running. Sure.

I guess we're live streaming.

[10:04] Matt Yao Interviews Me: Okay.

[10:05] Paul: Yeah.

[10:05] Matt Yao Interviews Me: Cool.

[10:05] Paul: Keep going. I'll just, yeah.

[10:07] Matt Yao Interviews Me: Impact. Yeah. I was gonna say two things on impact. One is I definitely had this like external orientation towards impact. Thinking about like, oh, if I can touch a million users in some unquantifiable way of really how much of an impact do they feel from my work, then somehow that makes my work more valuable. And the other thing I was going to say on impact is I think we've both written about how if you look at like the largest companies and their mission statements, all of their mission statements are all more or less like, make a huge impact through your work.

And if it's just hilarious, if you look at it across Coca-Cola, Walmart, Meta, Google, all of these major companies at the core of it, they're trying to say the same mission statement of like, show up here and make a huge impact.

[10:58] Paul: Yeah. So Meta's now is build the future of human connection and the technology that makes it possible, right? The future of human connection. Right. And yeah, it's all these pictures of like people in public and hugging and dancing, but like, it's just this, like we're—

[11:20] Matt Yao Interviews Me: it's a lofty, it's a lofty—

[11:23] Paul: well, I think there is some truth to it. Right. And you almost need to tell yourself these positive narratives because I think one thing I realized, and I study a lot of organizational change and complexity, is there are a lot of unintended consequences of change at scale. Or decisions at scale. And you basically have to have a positive view of things if you are going to do things at scale, because at scale you will cause some level of destruction. Every change is going to have a ripple effect and have unintended negative effects that you can't predict.

That's just the nature of change in general.

[11:58] Matt Yao Interviews Me: Yeah.

[11:59] Paul: Yeah. Hold on. I'm going to ask if Angie will— should be good now.

[12:04] Matt Yao Interviews Me: So, you know what? We'll just came up for me is it definitely does feel like we're— well, I don't know if this is because I'm in a bubble or if you're in a bubble or if we're in the same bubble of good work and just, I don't know, whatever is going on on Twitter, but it does sort of feel like there's a zeitgeist, like a certain timing from a historical and like a labor trend perspective, even big things like remote work and AI, like you just mentioned. And As much as I've enjoyed your personal stories, I also really like when you take a look at the big picture. Even when you're like tweeting those, those charts of like percentage of people back in office, I always find them really interesting. So I'm curious, how do you fit good work into the history of labor? Paint that timeline of however, however far back you want to start, Industrial Revolution or 100 years ago.

Like, what is it about right now that makes good work a fit for the current times?

[13:04] Paul: Yeah, so I mean, I think my overarching takeaway is that work is always changing, right? I think this is something people can miss because I think the narratives a lot of us grew up with feel like so strong, and there was sort of like a period of stability in which like, okay, put your head down, get your education, transfer to a uni, to a company and like follow this path and you'd be taken care of, right? And that more or less worked. And that was the industrial era script. That's sort of like the final, the final like job-based existence in the industrial era. But toward the end of that, as we graduated into like more, more me than you, like I, my first job literally had a desktop computer.

And so I saw like the tail ends of this, but the internet has upended everything. And the internet is going to take anything with a transaction, and this will be accelerated by AI, and take the transaction costs to like near zero. So that's going to upend the economics of like everything, right? And so this is basically the same thing that happened with the Industrial Revolution, right? The Industrial Revolution, through mass production and factories, lowered transaction costs and increased the benefit to like gathering a bunch of people working through these factory-based processes, right? And then a lot of office work really followed that same model.

And so we're going through this shift where like firms, the like firm size like is shrinking. If you look at like revenue per employee, right? More people are employed for bigger companies from bigger companies, but those companies are making more money per, especially at the high end, like superstar companies. And then the superstar employees who were able to extract enormous amount of value. And so I think we're shifting more to this like probabilistic outcome of like more chaos and randomness and less and more variance in the labor economy. And I think this is just incredibly unsettling, right?

And so psychologically, like people need new stories. This is sort of like why I wrote my book, Imagining a New Story for Work and Life. That's the subtitle of The Pathless Path. It's my attempt at writing a story for myself that helps me make sense of all these changes. It does seem to have helped other people, right? The Pathless Path is a phrase that admits we don't know where we're going, but we want to be grounded and have some foundation in the present, right?

The path without a future path. Right. And so I think that's sort of like what we're facing. I think unlike many future of work thought leaders, I don't have a good, like, prediction of like where we're going. I just think it's going to get weirder and it's going to be different than we expect.

[16:00] Matt Yao Interviews Me: Yeah, that makes me think it definitely does seem like what you write about, it has an unexpected amount of inner stuff, like the importance of, like you said, in a world where it gets increasingly complex and chaotic and dynamic. Yeah, I'm thinking about like the term antifragile and even what complexity science would say is when the systems get more complex, then it's all about flexibility, slack, and being able to react as things change. And that all points to like what you talk about with inner ambition. And a lot of it seems to be like an inner quest, which is very different than I think from other types of Like the books that might get clumped with yours, which are more oriented around like looking outside for what you want to do.

[16:50] Paul: Yeah. And I just, I just apparently we're live on LinkedIn too.

[16:55] Matt Yao Interviews Me: Really? Is this like an automation that you set up or?

[16:59] Paul: No, I think I was playing with it and I think it just auto went to a bunch of steam. Let me see where we're, yeah, we're, we're going to LinkedIn and YouTube. Great. I'm just gonna update the captions. Talking good work with— this is, this is a Pathless Path podcast. Um, so this is on brand.

[17:20] Matt Yao Interviews Me: What were, what were you saying again about, um, yeah, it's less of a question, more of an observation that what you write about seems to be quite around like all these buzzwords, self-discovery, self-awareness.

[17:35] Paul: Personal development, the inner world, right? And I think this is really the bigger theme is we're shifting from like 99% focus on the extrinsic, right? What, what does my job say about me? What does the path say about my ability to be successful? What does my employment status say about me being a good member of society? Right?

All these things. Two, actually, we live in a more prosperous world now with more paths, more possibilities, more economic opportunity. This actually affords us more permission to not ignore the inner game, right? And so I think people are saying like, okay, if I am going to work, I might as well not sacrifice everything, right? And I think we just have this really intense legacy of this top-down industrial era where Like society was like marching to the beat of a drum, right? We had to be like ready to mobilize as societies and cultures and industries to like for the Cold War coming outta World War II.

But one, our economy is no longer like that. And two, people are waking up that you can actually feel good with work, right? And I think jobs in general are like way better than they were 40 years ago. And so people are experiencing this in their job and then they're just figuring, okay, there are actually other trade-offs I might want to make. And other paths like self-employment, underemployment, entrepreneurial paths become more possible because it's not about maximizing income or optimizing legibility on a path. Yeah.

[19:22] Matt Yao Interviews Me: The topic of work inevitably has a lot of association with money. And I actually look at you, look towards you as a, as like a, a role model when it comes to healthy relationship with money. I mean, I know you, you, you've told me before that you still think about money and you, you worry about money, but I think it's, it's like admirable how you remain so conv— like have such a strong sense of conviction in, in the path that you're on and knowing that it'll adapt and that like, you know, you have, you have a kid, like you're gonna be able to figure out. So just broadly on money, like what is— tell us about money and how that shows up in Good Work, the book.

[20:03] Paul: Yeah, I think this is like work and I shifted from having a very surface level relationship with money to one that is much more in-depth, real, and actually tested with my lived experience. Right. And so I think with work, if you've only worked in a full-time job, it's scary to work on your own because it's totally unknown. You don't actually know what's going to come. But once you spend a few years working on your own, it suddenly becomes normal to like find your own work, create your own work, charge for your own things and try stuff, right? And then any other kind of work seems kind of weird.

Same thing with money. I went through a radical shift, right? And so if you just have a monthly paycheck coming in or biweekly paycheck, cutting that off feels crazy, right? All of life has been about acquiring this paycheck up until 22 years old for me. And then for the next 10 years, I built my life around that steady paycheck and ideally to be seen as successful, that's rising paycheck, right? Quit my job, had no paycheck, savings start shrinking.

But the thing that happened is I became like, I was able to lean into my own agency. I was able to take actions and go try to make money. Right. And so I've made money in a bunch of different ways. One of my goals early on was to try and make money in a bunch of different ways explicitly. And so the more evidence and experience I had making money in different ways, the more confidence I had that I could kind of figure it out.

Right. And so along the way also, I stumbled upon this way of describing what I was doing called coast fire. Right. And so financially independent retire early is all about saving as much money as possible so you never have to work again. Right now, if you define work as something you don't want to do, that makes sense. But if you define work as something you can actually enjoy and gives your life meaning, that doesn't make any sense.

Right. And Coast FIRE says save enough money so you do have a safety net, some retirement savings that hopefully you're not going to touch. And then the entire goal is to basically work less than full grinding or sacrifice and focus on things you enjoy. And that's basically what I've been doing for 7 and a half years. And so for 7 and a half years, I've at least broken even every year. The first few, 4 years, I pretty much broke even, did not make much money.

I don't think I made more than $40,000 in my first 4 years. And but I didn't touch my retirement or investments. And so my net worth grew. Right. And so this is something that people just basically don't ever test. Like even, even people that are retired, like they see their wealth as a product of their earnings and hard work, when in reality, for a lot of retired people who have a lot of money, most of their wealth came from compounding earnings on investments, right?

They earned money from capital, not labor. Right. And so you can be smart with your finances and basically just spend less. I was never a big spender and so saved really aggressively for retirement and savings. And as soon as I had $50K in savings, I basically just like left and my mental goal was always keep the 50 even. That's sort of like my runway to pay for times when I don't— maybe don't make money and then don't ever touch the investments.

So that's the game I set up for myself. And for 7.5 years I've succeeded on that. And then especially in the past few years with some of the success of my book, I was able to even save even more. And so just watching this and having the experience over time, it's like, oh, I'll be okay. Right. But if my script was still like, I should maximize my potential or earnings based on my skills, I'm an utter and complete failure, right?

Utter failure. Yeah. Right. Compared to my business school classmates, I'm probably one of the least well-off people. Probably bottom 1%, right? Many of my, like, even college classmates or like peers who work in consulting, same thing.

And so that can be really intense. And so a lot of your relationship with money is about ego and letting go and actually like feeling through like, yeah, I do feel really dumb and stupid sometimes. but I just like sit with that emotion. The goal of my life is not to make those emotions go away. It's to actually try to fully lean into like the feeling of connection, presence, and aliveness that I really want.

[25:05] Matt Yao Interviews Me: Yeah, that, that I can relate. I remember being on sabbatical last year and I, I basically track my net worth once a month. That way I don't have to look at any of these apps ever, you know, throughout the month. And it was just this really disorienting feeling to see my net worth at times stay the same or even increase month over month while I continued to live off of savings. And then the other surprising thing was I had sort of budgeted going into my sabbatical conservatively like $5K a month or $6K a month. And then I, at times I spent like $1,000 a month.

And there was like no noticeable decrease in happiness or quality of life.

[25:44] Paul: Yeah, this, this happened to me too. My spending dropped dramatically after I quit my job. And I think this is something people just don't give themselves credit for, like their own agency to make changes in reaction to changing conditions. Right? If you're— if your income disappears and you're spending a lot of money, that will feel shitty. So you'll be like, okay, I have two choices here.

Let it rip and decelerate my savings as fast as possible, or just spend less. And the beauty of spending less is you can actually just notice how you feel. And I experienced the same thing and I was like, I'm fine. I'm happy. Life's pretty good. And I have like more free time.

And so it was like, I'm willing to fight to protect this free time. This free time is so valuable to me because that's the time I can figure out what I'm going to do next. I can tinker on stuff. I can try stuff. I can read, I can hang out, I can go for bike rides. And so yeah, over the second year of being self-employed, I went from about $6,000 in spending a month to $1,000 living in Asia.

And I was under $1,000 for probably like a year. And yeah, it was just really nice. And it also just showed me at 34 years old, I got my spending down to $1,000 a month and I felt like I was thriving. This is pretty good.

[27:05] Matt Yao Interviews Me: Yeah. You know, the topic of creativity, I feel like, is also central to good work. Like we just talked about money. I think creativity, I see as one of those sort of big bubbles of association with good work. It seems like you take a pretty explicit stance that good work is inherently, there has to be a sense of creativity or maybe a large amount of overlap. One thing I've noticed in my own experience and just people that I talk to is there's people in full-time jobs, there's like a lack of creativity and also a sense of pent-up creativity.

Like there's this yearning or this longing to be able to express themselves. What is, what is the role of creativity in finding good work?

[27:49] Paul: Yeah, I think the creative urge is human. I think I sort of define creativity broadly. I joke that a lot of people planning massive weddings really are trying to express their creativity. And for many adults, like a massive wedding is the, like only creative project of their early young adult lives. And so yeah, I think the desire to be creative is human. I think we're creative in many ways.

Like, we're creative in how we raise kids. We're creative in like how we figure out how to do things, like all the paperwork you still have to do in a modern world. We're creative in like how we write and reply to emails. We just don't see it as creativity. We see it as like creativity has to be big C creativity, which is you wrote a book and all these things. And a lot of people pair creativity with needing permission to do something.

And so it's really hard for them to see their own creativity because they assume, oh, I don't have permission, I can't do the thing. Right. Somebody asked me once, was like, how, who, like, who let you write a book? And I was like, me, me, I just did it. Right. But like, we're so trained to think we need permission to do this, to do the thing.

Right. And so with the internet, you can often just do the thing directly, like you have with your writing, like I have with my writing, but our model is built on this job-based reality where it's like, oh, I need to get a job as a journalist first before I can write in public. Yeah.

[29:30] Matt Yao Interviews Me: Permissionless creating.

[29:32] Paul: Right.

[29:32] Matt Yao Interviews Me: Yeah. I feel like we've both written a lot about sabbaticals. We've both gone on our own sabbaticals. I don't know if you, if you get this, but I've sort of gotten this. I feel like I sense it in the periphery too, of just people thinking that I'm like, I just shill the idea that everyone should take a sabbatical. And I, I think that we, neither of us actually, that's what we're, we're saying.

Maybe it's just a question around the role of sabbaticals and finding good work and how you draw that distinction, you know, holding the importance and the transformative nature of a sabbatical and saying that like everyone you know has had a really good experience while also, you know, not necessarily telling everyone to go do it.

[30:13] Paul: Yeah, I, I think it's a lot of people's fears. People don't like non-default ideas. Many people, right? All new ideas are heretical by nature, right? Because they're new ideas, right? And so they make people uncomfortable.

Like, I'm not actually trying to communicate to like the default path that loves their job and is crushing it on the default path. Like, I actually don't know why they're listening to me. They shouldn't, right? And all my stuff is like free on the internet competing with other free stuff on the internet. Like, you should go listen to Adam Grant or like Simon Sinek, like they're much better people for you to absorb if you love the default path, right? What I'm communicating for and what I'm investigating is for myself, and I'm sharing it with other people, what I find along the way, right?

And so the difference between somebody already on, already curious about taking different paths or a sabbatical is so vastly different than that other person. Right. You've probably had the same experience. They come to you and it's like, all right, I'm going to plan a sabbatical next year. I have 9 months. What should I know?

What should I think about? I'll absorb any book you recommend me. I'll read everything. I'll prepare. And so those people are the best. That's who I create and write and share for.

I am not trying to build a— this comes back to the impact question. I'm not trying to be a mainstream influencer. If I was, I would talk a lot more about how full-time jobs are the greatest thing in the world and how you can thrive at a big company, right? I might land speaking gigs for that, but I'm not actually interested in that, right? And so I think people are confused. I call this like mass media delusion, thinking that everything they see on a screen is like something that is communicating to everyone.

It's like, no, all I'm doing is planting curiosity triggers to find the others. This is the beauty of the internet, to like find small, beautiful, wonderful niches of like-hearted humans.

[32:23] Matt Yao Interviews Me: Yeah, I like that. Curiosity triggers. I've also found that when people come to me, they actually, they like start off the conversation. I'm guessing that this is the way for you is they start off the conversation and make it seem like they're just starting to contemplate leaving. And then as you talk to them, you realize that like, they've actually gotten pretty deep in their exploration. And it's almost like they're looking for permission from someone else to actually take the leap.

But also, the question I get most often is like, how are things right now? It's almost like a check just to make sure that I'm still like, sane and not crumbling.

[33:00] Paul: Yeah. And I mean, you've said before like, oh, Pathless Path helped me quit my job, but you were probably headed in that direction anyway, right?

[33:08] Matt Yao Interviews Me: Well, what's, yeah, what's interesting is like, I've definitely, I, it's probably written down somewhere where I was like, I think I've used the metaphor of the first domino was reading The Pathless Path. And so that set off, you know, more dominoes eventually.

[33:21] Paul: Why did you read it though?

[33:22] Matt Yao Interviews Me: Yeah, well, what's interesting is like, I think this is also when I started journaling, like I didn't have a set practice of journaling. But, um, so, so when I read The Pathless Path was February 2022, but there's at least one sporadic journal entry in 2021 where I was like already thinking about quitting my job without a job lined up. And I just used a lot more words than sabbatical, and it's because I didn't have the vocabulary. So it's exactly what you said. Like I, I even still view it in my memory as like that was the first domino. but I had the thought like a couple months prior.

[33:58] Paul: Yeah. And I think this goes more broadly to how people tell stories about their leaps. People will ask me all the time, what's the moment you knew you were going to leave your job? And if I'm truly honest, and I tried to talk about this in The Pathless Path, I don't actually know. Right. I think there are like hundreds of small little moments and awakenings.

Over 10, 15, 20 years, right? There were even glimmers of me sort of like not following the rules in high school and college, right? And looking back on those, it's like, oh, it's very obvious where I ended up. But in the midst of it, we're sort of incentivized to tell this very clean, clear story of a moment, right? And I think the idea of a moment is a myth. It's, it's neat, it's nice, and it would be cool if there was a moment, but often there's like the moment before the moment.

[34:52] Matt Yao Interviews Me: Yeah. Yeah. Do you know the, do you know, have you heard of the term slow hunch by Steven Johnson?

[34:56] Paul: No, I like that. That was perfect.

[34:59] Matt Yao Interviews Me: Have you heard of Steven Johnson, the, the author and the—

[35:01] Paul: Yeah. Yeah.

[35:02] Matt Yao Interviews Me: So he, I haven't even read the book, but yeah, I think it's a great term. Something about how innovation happens and he actually takes the view of how innovation happens at big companies. And there's like an, some example of like Toyota figuring out how to use their recycled tires or something. But the slow hunch is just his contrast to the, what we usually view as a, a moment, an insight, a flash of inspiration. And his book shows how in these organizations, the way they came to the most innovative ideas is actually this slow hunch. And it could, you know, I use, I, I say it could be like planting seeds and you don't, when you plant the seed, you don't know actually when it's gonna sprout or even What is actually gonna sprout, whether it's gonna be like a flower or a tree or whatever.

But it's like this constant tending. And I think I was more or less doing that where I would have this idea of like wanting to quit my job and then I would just revisit that idea month after month, or even sometime every day I would think about it. But just in having that view of like, it doesn't have to be this flash, there's other ways of of making decisions helped me like find a sense of relief.

[36:17] Paul: Yeah, it's a great phrase. Yeah. Yeah, it's perfect. Slow hunch. I like it.

[36:22] Matt Yao Interviews Me: Yeah. Something I wanna ask you about is being a father, being a dad, having a kid. I'm an aspirational dad. I hope to have a family one day. I'm curious, like pre-having a kid, What did your puzzle of work look like and how has it shaped, you know, after having a kid beyond the obvious of like less time and have to make maybe a little bit more money?

[36:51] Paul: Yeah, I think it's, yeah, I, I think it's mostly a time thing, right? And so I just have a lot less time. I think also the starting conditions of both me and my wife being self-employed. Leads us to more naturally lean into parenting. I think if we still were in like job world or full-time employment world, there's a very natural idea of like, well, you have to work, right? So you have to then organize daycare and help outside of your jobs.

We've leaned in the complete opposite direction. So I've sacrificed a lot of work time. And so that's been really hard for me because I went from, I could just work Whenever, like literally whenever, I never had a structure or schedule and any day was just sort of up for grabs to, okay, if I want to actually get stuff done and do the things I care about, I need to prioritize it and schedule it. And so to write my second book, I had to lock into this 3-day-a-week, 3-hour each of those days, no matter what pace and schedule. And when I did that, it was delightful, but it took me like a year to shift away from, I'll just work when it feels good. And so So I'm still adapting and adjusting.

And I think the thing with being a parent is it's always changing. My daughter's almost 21 months and every month has been different. Right. And yeah, still adjusting. And then we've just sort of decided over time to just watch our own daughter, which seems crazy, but like, I mean, most humans did this for most of the time on the planet. And so me and Angie are just bouncing back and forth watching her.

So Angie's been finishing the draft of her memoir she's writing right now. And so I've mostly just been like in dad mode and since publishing my book, which has been great. I think one of the challenges with this though is like there aren't many dads like prioritizing taking care of their kids during the week. And so it can be a bit lonely. I'm still trying to figure that out. But yeah, I don't think I'll regret this when I'm older and that's sort of the bet I'm making.

[39:07] Matt Yao Interviews Me: Yeah. I haven't heard any dad regret or parent for that matter, spending a lot of time or wishing they spent less time with their kids growing up. So that's cool to hear.

[39:18] Paul: Yeah, it's very, yeah, it's so rewarding. It's sort of like how I look at good work and I think being a parent is part of my good work depending on the day. But when I look back at like all the moments I would call good work, like writing my first book, writing my second book, it's like, oh man, I miss those times. In the moment though, it often can be frustrating or hard or challenging, right? But when you look back on those moments or extended periods of times, it's like, oh, that's really nice. And that's often the same reflection I get when I look back on the time I spend with my daughter, it's like, oh, it was really nice to spend a lot of time together over the summer.

[40:02] Matt Yao Interviews Me: Yeah. Because I think what you write about is all about, um, being open and knowing yourself and what you want and adapting. I'm curious, what in this moment do you see as like potential changes or adjustments that you make to, you know, improve your life or however you want to take it. Like, it sounds like being around other dads with young kids would help or something like that.

[40:27] Paul: Yeah, still figuring this out. I feel like I have a lot to learn as a parent. And yeah, I'm not sure what the right setup is. I think once your kid gets into like schools or daycare, which is something we'll probably explore soon, then you start meeting other parents, you get in more of a schedule and a rhythm. And so finding those others that are living in similar ways, I think is a really big priority for us. And Yeah, I just don't have good answers.

I think we're looking at potentially living abroad and things like that. But yeah, we're still very exploring and in learning mode, I would say. And I think that's just one big reflection about how me and my wife approach a lot of things is we treat everything as an experiment. We sort of say like, okay, we're living here now. What are we learning from this experience? What does it tell us about the life we want to live?

Right. Okay. We did this schedule and structure with our work and how we're hanging out with our daughter. Like, what are we learning from this? What, what should we tweak? What should we change?

And so that's very opposed to how most people live, which is like, once you have kids, like your life's set, you have to lock into this like script. And I think scripts are just a lot more adjustable than people think. They just have to fire the manager in their head first. Yeah.

[41:42] Matt Yao Interviews Me: Do you have like an actual, um, like how do you relate to the scripts that are, that you have? Like, is your own script even a script or do you call it something else where script is just a word that is society's conditioning?

[41:56] Paul: Yeah, I think script is a good like starting point. I definitely have scripts I'm running, right? Talk to curious, generous people, right? That's sort of a script I have running, which orients my time and attention. Like try to write. Consistently write over time.

That's like a script. And in my head, like those will lead to like good outcomes. Now, when I get evidence that those scripts are no longer true, I need to change. Right. And so one of my scripts before having a kid was talk to anyone who's curious about work. Right.

I can schedule for those people. Yeah, exactly. Now that is not my script. My script is I can't afford to talk to anyone at any time because I won't accomplish the things I want to accomplish and I'll be distracted from my family. And so, yeah, I think like rewriting those scripts and updating based on what's happening in your life is really important.

[42:56] Matt Yao Interviews Me: This topic of experimentation that you just brought up, I think is so key because it really flips things upside down from how we've been doing it where like we probably all learned about the scientific method in like 3rd grade or something, 4th grade maybe. And there's like this hypothesis where there's just this innate sense of curiosity and being open to what the experiment proves or disproves as it relates to the hypothesis. Yeah, exactly. Which I found to just be a very powerful frame to approach things. And I'm wondering for the people, you know, I'm just assuming that most people are probably still in full-time jobs that are reading Good Work or are in your audience. How do you, how would you advise them as it relates to experiments and what to look for as the first step?

[43:46] Paul: Yeah, I have this idea I call ship, quit, and learn. And so the idea is just to try stuff and basically the cheat code to like figuring out what you want to do in life is just trying a lot of stuff. And the problem is most people just stop trying stuff. They think their life is set at like 25 or 30 years old. And so it's really coming up with experiments. And I, I call it ship, quit, and learn, which is basically ship something as fast as possible, design it to quit, right?

So you're time bounding it. You're saying, I'm going to try this for a week or a month or something like that. And then the only goal is to learn something. Right? So ship it as fast as possible, design it to quit, and then the goal is to learn what to do next. Right?

And so since the default is shutting it down or moving it, moving away from it, it's relaxed. Like there's nothing to fear here. Right? And so I've run courses before where I have people do something like called an action challenge. Right? And the action challenge is This is ship something in a week, no matter what.

And you can do infinite things. You can host an event in your town. All that requires is setting up a landing page, right? A Luma page, a Mixoly page, a Partiful page, something like that. Just say, hey, I'm going to invite 6 people to a restaurant. We're going to talk about topic X.

People love this stuff, right? I'm going to host a cooking class for my friends. I'm going to publish one essay and send it to 3 people. I'm going to start a blog. So many things. You can do.

We all have these ideas like, oh, one day I'll do X. Move that out from the recesses of your brain and try to activate it as fast as possible. And so, yeah, that's the thing I keep coming back to is like, what can I try in a month or less? And so I've tried all sorts of stuff living in different countries. We've lived in multiple places for month-long stints and we always learn stuff. It's always interesting and it always reshapes how we're thinking about the future.

I've done so many experiments of my work. Most of the things I've done have flopped or failed, but along the way I've learned stuff. And so the more things you try that don't work, you learn, okay, what not to try, or that you actually enjoy or don't enjoy that task, and you can update. You can keep trying stuff. Yeah, I just love this approach to life. It's very fun.

Yeah.

[46:17] Matt Yao Interviews Me: It, uh, It reminds me of what you said the title of your next book might be, but I won't divulge.

[46:24] Paul: The, yeah, I mean, I've told people it's gonna be called Experiments in Living, but yeah, I'm probably gonna start working that in January.

[46:33] Matt Yao Interviews Me: Yeah. Nice. Final, final, it's not really a question, but I just remember when we were chatting in SF. You know, catching up and you told me that like you haven't been doing the podcast as much and you've been prioritizing time with family and then obviously you're sort of in the, well, I assume the promotional phase after putting out this good book. So a book on good work. So yeah, I'm wondering maybe you can just do your lightning pitch of Good Work that I've seen on Twitter, but in podcast form, because most of your podcast episodes are where you interview other people.

[47:09] Paul: Good Work. Yeah, I'm actually working on a video right now about this, which should be pretty fun. Some of the, some of the ideas from the book are, it's really like focusing on prioritizing a connection with what matters, right? And really defining like what is good work. It's talking about the entire journey to like getting lost, not mistaking a good job for good work. Uh, not working like too isolated or taking on too much suffering, like flowing with your emotions, having useful work scripts, right?

And then like how I've left money on the table. And it's an exploration of all that. And if you're somebody that has something you enjoy and wants to make it a bigger part of your life or senses there's something more to your work life, this book is probably for you.

[48:02] Matt Yao Interviews Me: Sweet. Actually, now I want to jump in and share my What I took away from it as a, as a reader. I think it's interesting. Something I've noticed in my, in my coaching as well is like, work is such a big part of our lives and often the inquiries that we have around work, money, meaning, it's like almost an entry point or a Trojan horse to talk about what it means to live a good life. So, you know, your, your book. Good Work is really a book about a good life, but I don't know, maybe if it was called Good Life, it just wouldn't, you know, it wouldn't attract the people that are stuck in jobs they don't like and they think that the solution is around changing a job or what happens in Silicon Valley where you kind of move diagonally.

You work 2 years at a company, you get, you move to a new company, get slightly more pay, and you're just kind of doing the same thing all over again. So to me, I appreciated how it, it really starts with framed around work, but it really touches on how to use work as a vessel for, for living a good life. And also the importance of, like, I think you do this really good job of, it's almost like a paradox where work is so entrenched in our lives and yet it's, it's, it's like, it's serious, but it also doesn't have to be.

[49:22] Paul: Right.

[49:23] Matt Yao Interviews Me: Crippling in seriousness. There's like this playfulness to it. There's this lightness to it. And it's, it's making me, it's making me question along, along other things that I've been thinking about recently of how can I continue my quest for good work? Like I think it's an ongoing set of inquiries that we ask ourselves and it's kind of like what Rilke said about living the questions.

[49:44] Paul: Yeah, exactly. Yeah. I, I love that. All my writing is basically just an excuse to find the others that want to ask the deeper questions about what is the good life. I think that's one of the most important questions. I wish more people asked, asked it.

And yeah, I think with work, it's, for me, my journey has been, um, I unconsciously was holding work up as extremely important in this, in the narrow sense of the traditional path in my past life. And now it's, I've sort of transcended it in this, like, I think work is actually very important, but not that serious. Like it isn't everything. It's like you actually should approach it with care and lightness. And through that you can find stuff you care about. And it's that caring that really matters.

And yeah, it's, it's cool to hear you took that away. Yeah.

[50:37] Matt Yao Interviews Me: Awesome. Uh, grateful for this conversation.

[50:41] Paul: We end our, uh, informal livestream.

[50:45] Matt Yao Interviews Me: Yeah. Well, do you, do you want to say where people can find the book or do you think it'll be pretty easy for people to find it?

[50:51] Paul: PaulMillerd.com/goodwork.

[50:54] Matt Yao Interviews Me: Thanks, Paul.