What's After BigLaw & Consulting? - Allie Canton & Paul Millerd On Reinvention, Parenting on The Pathless Path & as Parent

[01:39] Paul: Without further ado, here it is.

[01:42] Allie Canton: Welcome back to Practically On Purpose. Today's conversation is one that I have been looking forward to for a long time. My guest is Paul Millerd, author of The Pathless Path. Paul's writing found me during a time of burnout and questioning. I had just almost given notice at my last job and I ended up staying there 6 more months, but Paul's writing really helped me realize that there was another way of doing things and that it was possible to choose meaning over status. In our conversation, we talk about what it really looks like to step off of the default path.

Why The Pathless Path isn't a playbook, but more of a compass. We also dig into Paul's Ship, Quit, and Learn framework, his family's experiments with nomadic living, and what he's discovered about work, money, and meaning since he published the book. With the new hardcover edition of The Pathless Path coming out soon, we thought that this would be the perfect moment to revisit what it looks like to live life as an experiment rather than a blueprint. All right. So Paul, first off, I just wanna say it's such a joy and honor to, to have you on the show. I think we talked about this a little bit before, but your writing was exactly what I needed when I was struggling with burnout and a sense of purposelessness.

And as I was getting ready for the podcast, I was looking back and I was like, when did I find out about Paul Millerd? Like how, like where did he come from?

[03:14] Paul: And I still can't figure this out either. So please enlighten me.

[03:17] Allie Canton: So what I have figured out is that I I got my first copy of your newsletter about a week after I had a conversation with my boss to quit my job and actually recommitted and ended up staying there for 6 more months. So I was obviously quite lost at the time, wrestling with what to do with that feeling of being lost. And somehow the universe brought your writing into my world and I think it really helped me start realizing that there's other people out there who have made this— it's not an impossible choice, but at the time it feels impossible. At the time it feels like idiotic, really, just to leave this like shiny gold star-filled life for a sense of like, I don't know. So I just wanted to say thank you because your writing helped give me a lot of courage to know that there are other people out there making these choices, living life differently in a way that's authentic to them.

And I know that you're a beacon of that for so many, so many other people. So thank you for being yourself, being authentic, even when it's messy. I think we're gonna get into, um, some to like modern manifestations of that, but also for bringing people together.

[04:36] Paul: No, I actually really appreciate, I love hearing from readers who read my stuff and resonate with it because I was you at one point. And I was pretty lonely when I quit my job back in 2017. I was sort of desperate to find people and a big theme of my path has always just been, I wanna share everything along the way because like I wanna plant poles for like former me to latch onto. And I also thought it was like so funny too, like I wasn't that successful. Out of the gate. I, I've had some success now and like way more people are paying attention, but for like 5 years, I didn't really do any, any better than breaking even.

And I don't think I crossed $50 grand a year until I was 5 years in. Wow. And so people would always be like, I don't get this Paul guy. He's talking about doing things he loves, but he doesn't seem to have a plan or have any, any way of making money.

[05:39] Allie Canton: Um, or people just assume that you're making a bunch of money. Cause I think that people who aren't yet in this like creator journey—

[05:46] Paul: well, I was posting, I was posting my incomes, so people were reading my newsletter knew.

[05:51] Allie Canton: Yeah.

[05:52] Paul: But yeah, they do. I have had a few people in Chiang Mai run into me now and like they think I'm like famous.

[05:59] Allie Canton: Yeah.

[06:01] Paul: And I've made a lot of money one year for my book. But every other year, money from writing wouldn't have supported my cost of living.

[06:09] Allie Canton: Mm-hmm.

[06:10] Paul: And so like, I'm still, I still have the experience of like still trying to hack a living and like, I have no idea what I'm doing. And they're like, oh my God, you know everything. Like you got everything figured out. And it's like, no, you're the guru. Yeah. People, uh, I've had many people email me and be like, I feel like I'm doing— I had one person email me and was like, I feel like I'm doing The Pathless Path wrong.

I was like, there's good news. There's good news and there's bad news. Good news is you can't do it wrong. The bad news is that you have to do it on your own.

[06:42] Allie Canton: Yeah. Yeah. Like I can't give you— it wouldn't be the Pathless Path if there were like an exact playbook, right? Of like step by step by step by step by step.

[06:51] Paul: Yeah. There's plenty of books for those people. Go read Atomic Habits and a thousand other books that have been trying to be Atomic Habits for years.

[06:59] Allie Canton: Yeah. Yeah, but that is not The Pathless Path.

[07:01] Paul: No, I can barely keep any habits. I can mostly drink coffee every morning, but I have a really nice streak of like eating mango most days here in Thailand.

[07:11] Allie Canton: That's great. Yeah.

[07:12] Paul: But besides like seeing my— hanging out, like spending quality time with my daughter every day, like I, I don't have any sustainable habits.

[07:20] Allie Canton: Wait, so I want, you know, for people who don't know, first of all, like what is The Pathless Path? So when people say I'm doing it wrong, like what is it?

[07:29] Paul: My favorite quote from the book, which I have not memorized, I probably should memorize it, but this really came to me as I was finishing the book and I'm trying to figure out like, what is it? Like I wrote this very, like a month before I finished, probably 2 months before I finished the book, I realized that I had a book that was a little too vague, so I needed to add a little like definition. I needed to take a stand to understand what The Pathless Path was to me and The reason I couldn't do it until the end is because I didn't really know what I was trying to achieve or write until the end. And so The Pathless Path is an alternative to the default path. It is an embrace of uncertainty and discomfort. It's a call to adventure in a world that tells us to conform.

It's also a gentle reminder to laugh when things feel out of control and trusting that an uncertain future is not a problem to be solved. So that's my best definition. Now you can't really create a framework around that. But I think to the people I want to reach, The Pathless Path is a phrase that helps you take like a deep breath and you're like, oh, okay. I'm not insane.

[08:40] Allie Canton: Yes. Yeah. I mean, as you're describing it, right, as you're sharing that excerpt from the book, to me, it's very, it's like a very somatic sense. It's almost like a heart sense, which to me is cool because I think that for your readers or for people who are first encountering their work, who are gravitating towards it, like they, I can just speak for myself. It's like, I was miserable. I was completely miserable.

Like that was what, that was the feeling that was pervading my body. I was miserable. I was lost. I felt like I wasn't having fun in life and just hearing that excerpt, it is almost like a, that feeling is a north star in and of itself. And I really think it is a beacon, you know, kind of like a north star too of like, oh, I can reorient towards that. And, you know, I am my own compass of like, am I feeling more that way or am I feeling more in the misery place?

Not that it's all like rainbows and butterflies as you're figuring things out, but it does give you a little bit of a sense of, is this good or is this not good?

[09:50] Paul: Yeah, it's, it's something to keep coming back to. I mean, I've been on this path for more than 8 years now. I keep getting like, you can say unmourned, get stuck trying. It's often in the trying mode of like, I, I need a plan now. Like I think for the last, for the last 2 years before I moved back to Asia, like it was very, it was starting to get really stressed about income. And the reason was like my income was basically going down, but I had to go back to all the principles and writings I had committed to.

Okay. Consider money from my past self a gift. A gift from my former self to my current self. Okay. Now I can relax a little, keep spending time with my daughter. Okay.

Well, how am I actually spending my time? Oh, I'm actually not working toward trying to make money. So I should just admit to myself that I actually wanna spend all my time with my daughter.

[10:39] Allie Canton: Right.

[10:39] Paul: And just even more fully embrace that, even if it's uncomfortable. And, and that's like, in that discomfort is me aiming at my number one priority. And it's also just interesting to me. It's like, what will happen? If I don't worry about money, because like no one that obsesses about success and money ever tries that. They never try that.

They just try to recreate another job making money for themselves or do their own thing trying to make a lot of money. And so from the beginning, it's always just been super interesting. What if you don't try to make money? Now that doesn't mean your money problem goes away. It means you sort of have to find your principles. You have to find work that matters to you.

You have to find sort of the things you can commit to. Otherwise you are really lost and unmoored.

[11:28] Allie Canton: Yeah. So there's two things that are coming up from that. One is I think that there's a famous David Foster Wallace quote that was basically like, whatever you're obsessed on, whatever you're focused on, like that is your God. So if it's money, like that's going to be the thing that rules you, but If you're in a moment where you're actually looking to step into a life of greater purpose, but all you can think about is the money, like you're going to be stuck because you're sort of serving two masters in, in that world. The other thing that I really like about what you said, and this is something that you wrote about in the book as well, is that when you're in business school and then getting like sucked into the allure of consulting world, that No one ever asked you, why are you doing this? And that really, that really hit me too.

[12:19] Paul: And now everyone asks me that all the time.

[12:21] Allie Canton: So why are, why are you doing this?

[12:23] Paul: It feels right. Like, I think that's like, it's, that question doesn't bother me because it's like, I don't know, it just sort of feels right. That's a simple answer, but there's a lot under that, I think. It's the 8 years of practicing a new approach to life. It's, I'm able to live in the present and I'm not stuck in the future trying to escape my present. I don't have any goals.

Like I was telling you, I just want to keep doing what I'm doing. And so, yeah, I don't feel defensive though. And if I, somebody had asked me that really intensely and they were like, Paul, like, Really, like maybe in grad school, if a friend sat me down like, Paul, you're reading books all the time. You're skipping classes. You're not even trying to get jobs in consulting. What the hell are you doing here?

And I don't know, it would've been nice to have been slapped across the face once by somebody because I think I was always scared to, I don't even know if that's true. I was really good at like going after like legible goals. Like breaking into consulting, I was so driven to like prove myself. I was so insanely curious. All I did was read with my time. I just wanted to work on ideas.

Like I was just like so convinced I would do well in consulting. And I was right about that. Like I was such a good fit for consulting. I really loved it and did well in it early on. But I was so driven by like people who just like, no, you went to the wrong school. Like people like you can't do this.

You have to go to a good grad school before you go to it. And I was like, screw this. Like I'm just going to keep hammering over and over. But the problem was like after that first job at McKinsey and then grad school, both of which I did enjoy, I had like no plan. I was like bullshitting, like in my entrance to business school, I was like, oh, I want to lead a global operations team. Cause I was joining the global operations dual degree program.

[14:23] Allie Canton: Yeah. It's what you had to say to get in. Yeah.

[14:26] Paul: Yeah. And everyone has to say certain things in interviews, but there was no, like, my heart wasn't moving toward that. Like, it was like I was running out of steam a little more and more every year. And so that gradual loss of interest was really hard to notice.

[14:41] Allie Canton: And, and I think also when we're in these, in like elite educational environments, people just supply the goals for us. And, and I don't know, for myself, I feel like, and they're cool goals. Yeah, they're cool. And it's like fancy people or like cool events or travel, whatever it involves. You know, it's almost like wonderful problems to have, but I just remember for myself in law school, like I got so caught up in all like the groupthink around it. Like I remember, you know, at the end of my first year, everyone's like, well, are you going to try to write onto law review?

And I was like, well, I don't really want to be on law review. Like that's not actually how I want to spend my time, but it's all of a sudden every, everyone is doing that or everyone is interviewing.

[15:27] Paul: Obama did law review. What are you doing?

[15:29] Allie Canton: Yeah, exactly. Yeah. What have you done with your life?

[15:33] Paul: Yeah. Interesting enough, like I sort of rejected the groupthink reflexively. I always have. But the problem with that is I didn't have another channel to move toward. I wasn't like, this groupthink is wrong. It was like, the groupthink is wrong and I'm gonna put in less effort than other people, but then like eventually go after all the same goals.

Like it was actually really embarrassing in grad school. I applied to McKinsey and they rejected me after working there. It was so embarrassing. Um, I was walking on Cambridge Ave in Boston, yeah, in the, um, Beacon Hill, and the partner called me. He's like, yeah, we just like, we couldn't understand like why you want to come back. Uh, it wasn't like a clear case and He was right.

I didn't talk to anyone the entire time I was in grad school about coming back. I didn't make a clear case. I didn't stay in touch with people to try and support my case. I didn't really like put the effort in.

[16:36] Allie Canton: Yeah. You didn't play the game.

[16:38] Paul: And when I left, like, I didn't think I'd go back. It was just, I didn't have an idea by the time it came to apply. And after that, I really just became desperate to get a replacement job. And so I talked myself into this other job. And another thing I experienced is I kept getting recruited by these people I was really inspired by and they'd quit before I started. So that happened with two successive jobs.

And then I, in my consulting jobs, I think I had like 15 different managers over like 7 years.

[17:09] Allie Canton: Wow.

[17:09] Paul: And so it was just over and over again. I could never find like the right fit. I could never find like a slipstream that like made sense and an aim I wanted to go to every— it was always just like changing and in turmoil. But now like on this path, it's like, I just want to keep going. This is awesome. This is so, this is so great.

And like, that is the thing in my body. I think you're sensing from the quote as well. And it really is a somatic experience.

[17:35] Allie Canton: Yeah. I'm sure people would be curious. I actually get this question all the time of So what does pathlessness actually look like in practice? So like today's Tuesday, we're recording, like what does a random Tuesday look like for you?

[17:50] Paul: Woke up at 7:20. My daughter woke up about 5 minutes later.

[17:54] Allie Canton: So you had a lot of time for your morning routine?

[17:57] Paul: Yeah. I don't like wake up early. I just wake up when I wake up. I try to get as much sleep as possible and then hung out with her in the morning. She's really fun to hang out with in the morning. She helps me make coffee, which is really fun.

Yeah. And we hung out for a bit. My wife's dad is living with us in Chiang Mai for the last 3 months, which is a really cool experience. It's kind of a dream of ours to like travel with her family and live in different places. And so he's helping us and like, she, my daughter like loves him so much. So as soon as like he's up and about, like she's like, daddy, goodbye, daddy, come to work, come to work.

Gongzuo is work. And so then I go to the coworking center. I got there around like 9:15 and then they had like a yoga class at 9:30. I took yoga class, 9:30, 10:30 to 12, I did some editing for a zine I'm creating as part of like my Pathless community. Then I had lunch with my wife, uh, and we're talking about her book publishing. I then came back, edited and wrote some more for like an hour.

And then there was a tea time. At the coworking office too, from 3 to 4. And I basically just like sat around and hung out. I sort of always opt for like social over work. It's sort of one of these principles of like, at the end of my life, I'll probably just like remember the times I'm like randomly hanging out with people over working. And so my revealed preference is just not to work very much.

So I worked like 3 hours, hung out for 3 hours, and then came back Wandered around with my daughter for a couple hours. We went to a restaurant, we got some mango sticky rice and coconut ice cream and went to another restaurant and back here, did like a whole night routine with her and then, uh, talking to you.

[19:47] Allie Canton: Wow.

[19:48] Paul: But that every day is so different and I think I optimize around different days. I've written a post, Paul Millerd Week in the Life too. If you Google that, you'll find another one.

[19:57] Allie Canton: Awesome. But yeah, people can check that out and just see. So it's really quite varied. Both the content of each day, but then even day to day. Yeah.

[20:06] Paul: Yeah. And it's been extremely different. The first 2 years of my daughter's life, I was spending a lot more time with her cuz we didn't really have as much help, but we sort of chose that as like our, our path. And then over the last 6 months, 7 months, it's been pretty wild. I mean, we're moving around Austin waiting for my wife's citizenship appointment. In the US and then we spent a month in Oaxaca.

We came back, then we went to Taiwan for a month. We went to Koh Samui for a month and now we're in Chiang Mai for 4 months.

[20:38] Allie Canton: That's great. And is that on the, on the community chat, one of the things we talked about a bit was like this traveling village idea. Is that part of this or can you talk a little bit more about, about that?

[20:51] Paul: Yeah, so I love to live out questions. So the question is like, what does a life look like? With kids given location-independent parents, right? So we don't have to go to an office. What does life look like? And we, we happen to like, like living in different places.

And so this is part of a year of exploration and we're just sort of hoping like answers emerge, relationships emerge, and like aims emerge out of this, but we don't really know what the plan is. So we're going back to Taiwan for a few months, then we're participating in this family village of 20 families. It's called Traveling Village. Travelingvillage.com. It started about this Danish guy and we're gonna spend January to the end of May with 20 families in Hualien, Taiwan, Hoi An, Vietnam, and Busan, Korea.

[21:39] Allie Canton: Wow.

[21:40] Paul: And it's all like self-organized. So it's very fun experiment. We're really excited to kind of like meet the other parents. We've already started like connecting with the parents. We have calls and so there's a lot leading up to it. It's pretty fun.

And then like, I think one open question for me is like, I love mentoring. I love teaching. I love to think about like, what does it look like for me to get involved in that in the future? And it's just an open question that I plan to sit with for the next few years. And it's sorta, that's sorta how I guide my aims and interests too. It's like, what am I actually curious about now?

[22:13] Allie Canton: Yeah. So I'd be curious for the traveling village. I imagine that the other families are all location independent, I'd be curious where are folks in their Pathless journey, just from the people that you've met with?

[22:27] Paul: It's a range. I think there's like longtime travelers. There's one family that's been traveling with their daughter who's now 11 for like 9 years. And they've like figured out how to make remote work. There's younger families that like haven't quite figured it out, but are gonna do like a semester traveling. Like you can, if you're in like Europe or the US, you can like rent near home and it's probably cheaper to live in Asia.

And then yeah, I think some people are figuring it out. This is also like a forcing mechanism for some families. I think there's a whole range and there's a whole range of kids too, right? Different responsibilities at different ages. Some people have 15-year-olds, some people have 2-year-olds like us, some people have 4 kids, some people have 1 kid. So it's going to be really interesting.

I have just as many questions as you.

[23:17] Allie Canton: Yeah, I was about to, I'm like, oh, so what is education? Cause this is something I've shared with you. Like I am curious about doing something like this with my family at some point, you know, my daughter's 8 months old. My son is 5 years old, but I know a family in my town that spent, I think it was a whole school year traveling around Europe. The father was writing a book and needed to do research in different places. And they said, like, let's just bring the kids.

I think that they were like 10 and 12 at the time. So I have questions like, oh, what does education look like? And people even within that village, right, probably have different educational priorities. Maybe some are coming out of a structured environment, some are like explicitly unschooling, and then there's like a whole range in between that. I'd be curious to hear just like how has the community talked about that to the extent that they have.

[24:06] Paul: Yeah, so my wife and I have been nomadic on and off for the last 7 years, and we always knew we wanted kids. So everywhere we went, we always met people with kids and we'd like talk to them and interview them. And the thing you realize is there's 100 different flavors of living abroad with kids. You have like expats working for big companies on massive pay packages, putting their kids in the most expensive elite schools in like random countries. You also have people who like are like ideologically opposed to like public school and just the whole system, like the whole financial, like crazy Bitcoin people who are like, everything's broken.

[24:43] Allie Canton: I have family members like that. Shout out.

[24:47] Paul: Yeah. And they want to like reinvent everything. And oftentimes I, it seems like they're just trying to reinvent the default path with like their buddies. There's the people that want their kids to be like entrepreneur bosses at like 7 years old. Honestly, we're like, we're like both deeply curious and like wanna explore curiosity with our kids and wanna give them a lot of opportunities to learn and are like non-ideological. We're still very open.

I think we're like very grounded, but weird and curious and open-minded.

[25:20] Allie Canton: Which is perfect. Right. It's like you're not gonna spin out, but like you're willing to go explore and see what, like see what causes and conditions present themselves. To you and what you want to do with that.

[25:31] Paul: I think I approach so much as an engineer too, and it's like, you can just think of these things at first principles. Like, what are we trying to do here? Everyone starts with the question of like, what is, what are you going to do for school? Well, school is not an aim. Education, however, is timeless and like a human desire. Like, we will go out, we'll go to incredible lengths to learn things.

And explore our curiosity. For hundreds of years, people who dared to write and share their ideas with the world would go to incredible lengths to do so.

[26:04] Allie Canton: Yeah.

[26:04] Paul: And so that's very human and innate. So I start with the question of like, how do we foster education for someone coming alive in today's age? And starting with the assumption of like, everything I think now is probably like wrong. Right. Everyone's always trying to like correct the mistakes of their parents or like what they think is wrong with the current state of the world. But like, we're not even gonna be able to predict the challenges they're gonna face like 15 to 20 years from now.

And so I'm very glad I'm raising a, raising kids now, like after we've started to figure out some of the like phone and social media stuff. Like, so I'm not really worried about like phones and technology cuz like we're gonna develop immune responses and learn how to deal with these. But yeah, there'll probably be new challenges and I think it's really just about keeping that spark alive in your kids.

[26:59] Allie Canton: Yeah. Yeah. Like fostering their natural curiosity and supplying experiences that help meet that.

[27:06] Paul: Yeah. And I think like we do have backgrounds to lean back on. That's real. And like, I have to acknowledge that. But also it's not the credentials that give you strength. It's, it's the ability to like do things in the world and like understanding how the world works.

So that's what I can support my kids with. And that's like the most powerful stuff.

[27:29] Allie Canton: Yes, it really is just getting things done. And then also like your curiosity and your willingness to just try new things. Like I have realized very quickly, I've been only podcasting for about 3 months at this point, but I already have multiple people coming to me and they're like, oh my God, you started a podcast. What is that like? How do I— and I'm like, oh, I've developed a little bit of skillset here. Definitely it'll be refined over time, but you know, I think it's very cool how quickly just by doing things, we start to develop experience and expertise.

And this is kind of a, I guess, unintended transition to something I wanted to talk about from your book, which is like your ship quit. And learn framework. And I don't know, it's like, was the just do thing, it was just do things maybe before just do things. It was tiny experiments before that too. I was wondering if maybe you could talk a little bit about that and yeah, what that looks like.

[28:29] Paul: Yeah. So, ship, quit, and learn is an idea of mine that never quite took off, but like certain people just love this idea. Like, honestly, it's not that many people, but like the people who find this idea, who want it, like love it. This guy, Andrew Kappel, who I've gotten friends with, he texts me. I think I put Ship, Quit, and Learn in Good Work, right? Or did I put it in Pathless Path too?

Yeah.

[28:54] Allie Canton: In Pathless Path too. Mm-hmm.

[28:55] Paul: Yeah. So he's texting me about this probably like every 3 months. I'm applying Ship, Quit, and Learn. And so it's really funny, but it was a really simple principle. It's how I started my podcast actually. And I've always just like, I just find the playbook so boring.

I worked in strategy consulting, creating playbooks and best practices for 9 years. This stuff is so boring. It never leads anywhere interesting. And so at the time I was launching my podcast in 2017, there were playbooks, right? The playbook was, well, you gotta record 5 episodes first and then you send it to a ton of friends and then you get like a bunch of accounts and then you download it all on the first day and it gets on the new New and Noteworthy section of iTunes. Nobody even knows what this is anymore.

[29:38] Allie Canton: Yeah, I don't even know.

[29:40] Paul: But, and then it'd be like, well, why? That's how you do a launch. And you're like, well, that's dumb. I don't like that. And so I just want to start a podcast. And so I just recorded me speaking into a mic and the idea was I'm going to reach out to 5 people I've been really excited to talk to, and then I'm going to quit the podcast after that.

That was the goal, like ship it, like, so record the first episode, ship it. I'm gonna do the 5 interviews. I'm gonna like publish 'em as they are recorded and then reassess. I just recorded another episode of my podcast, uh, last Thursday. So that is, I dunno, what, 6 and a half years later?

[30:20] Allie Canton: Yeah.

[30:22] Paul: So I'm still going, it's like on and off. Uh, it's never been a big, like, driver of like income or anything, but there are people that like absolutely love it and it's just been a great way to talk to people.

[30:34] Allie Canton: Yeah.

[30:34] Paul: Like I've been saying no to podcasts for a long time, but your writing's awesome. You're, we've chatted before. It's really interesting. It's like, oh, this is gonna be a really good conversation. So you were asking me before we started, when can, when can I ship the episode to optimize for your goals? I'm like, well, I don't have any goals.

You should just do what feels right for you. And the reason is this conversation is an end in itself. I'm spending my time how I wanna spend it.

[31:01] Allie Canton: Mm-hmm.

[31:01] Paul: This is, I love this. This is so fun. And I, I have ideas and like stirs my brain up. This is how I wanna spend my life.

[31:08] Allie Canton: I love this. Yeah. Yeah. And that's how I, I feel like that's what, again, like not to fluff you, but your writing really sh— it's like, oh, you can just have fun. I actually have. A post that I've had in the hopper for a bit, and you had a note on Substack.

Just, it was like, you can just have fun. Like, that is an, a valid choice for how to approach your work. And it's like, on the one hand, it sounds very flip, but for me, that's actually a very ra— like, that's a radical reframe, especially as a lawyer where you're like, oh, I'm grinding, I'm miserable. It's like, the more miserable that I am, It's almost like the more important the work is that I'm doing, the more impactful or something that it is, the more valuable that it is. So I think it's like, it's very cool. I would like want people to just hear if they take one thing away from this podcast of like, you can just have fun with like how you spend your time.

And I think that you're a, you're a model of, and you can have a family and do, because that's the biggest pushback that I get that people are like, well, this isn't realistic, especially if you have have kids, but I don't think that's real. It depends on what your priorities are. Like, what is the rest of your life look like?

[32:24] Paul: There's so much in that statement, right? There's so much you can't do this if you have kids. You can't live the upper middle class premium life in the US if you want to purely explore your curiosity and your curiosity is not writing about finance or starting a company. My interest was writing, and so there was a certain level of sadness with that. At the beginning it's like, yeah, this is the thing. This is not gonna be easy to like reclaim any sort of my former life, but I'm having the time of my life already.

I'm just gonna see where this goes. And yeah, that it's just like, it's really what you want.

[33:02] Allie Canton: Mm-hmm.

[33:03] Paul: Right. I like to put, like in the US it's not even fashionable to like buy used cars anymore. Everyone just buys a new car. It's like you don't have to do that in a new car. You're like $40,000 car you're buying. That's a year of travel.

You can live anywhere in the world on 40 grand, especially in Asia. But you don't want that, right? When you're choosing to own the home or buy the nice car or send your kids to private school, you're choosing you don't want other things. The only reason that sounds weird is 'cause like those things are, have become the norm. And so I don't own a home. I don't own a car.

I don't own any nice stuff. The nicest thing I own is this, my iPhone, and that's like a business expense.

[33:47] Allie Canton: Mm-hmm.

[33:48] Paul: But yeah, it's, uh, it's doable. And then like a hidden side of this is like a lot, a lot of people are just like, well, my partner would never let me do this. Me and my wife are nuts. We're like so committed to like, we want to live the full expression of our lives. And unfortunately the full expression of our lives for us is like creative paths. My wife's been working on her writing for years and has struggled to make money.

She's putting out her first book this year. For the last 2 years, I've been supporting her by watching our daughter, and she's been probably working the majority of the days. Joy of my life to take care of my daughter, but we definitely sacrificed earnings to do that, and we don't know if it will pay off, but the goal is not maximizing our financial potential. It's living out our principles, which like creative work is super valuable. It's above paid work in our, our like family hierarchy.

[34:41] Allie Canton: And did you and your wife ever have, before you got married or while you were dating, like an explicit sit down where you're like, these are priorities of what we want to optimize for?

[34:52] Paul: Yeah, I think early on we were pretty aligned on like the work thing. We met on Tinder. My Tinder bio was like, I'm trying to build a life not centered around work. I'm spending my days. Yeah. I'm spending my days writing, exploring my curiosity and contemplating like what matters.

So it was because I had just left New York the year before and I kept attracting the wrong people who would like see my job and like want the upper middle class life. And I'd be like, what if we blew up our lives and just wandered?

[35:25] Allie Canton: And they're like, this guy's nuts.

[35:28] Paul: And so when I met my wife and she's like, well, he's just like doing what he says. And like, I want to like quit my job too and like go after things I care about. So we were very aligned on that early on. We also did this thing called the LifeBook.

[35:43] Allie Canton: Hmm.

[35:43] Paul: I heard about it on the podcast, but we didn't do it through the formal program. They have like 12 parts of life and we went through the question is like, what do you want? What are you willing to give up to get it? Why does this matter to you? Like simple, like simple but deep questions like that. We spent an afternoon in Bali, like 6 hours.

My wife doesn't like contemplating or discussing that long, but I was like, we have to do this before we moved back to Taipei and moved in together. But yeah, going through those categories of like, what do we want in work, family, generosity, taking care of our parents, kids, family, all these things and I mean, there's, there are obviously some very clear differences. We grew up in two very different countries, two very different cultures, but I think those clashes and differences were interesting to us. It was like, it was always like, how can we write our own story? That's the combo of these. And that's really the only way out of like marrying someone from another country.

Otherwise you just end up picking one or the other cultures and just like sticking to it.

[36:48] Allie Canton: Yeah, yeah. I, I see this in my own family. My brother's wife is from China, and it's like a very act— because it's like they're— the ways that they were raised were just so different. And I think that they're trying a little bit to create their own blended, but it feels a lot like, okay, just choosing. It's like, all right, well, she's the mom and she's putting in all the work, and she's like, okay, this is kind of how we're gonna do it. And my brother's like, okay, well, I love you and I love how you turned out, so like Seems like a good enough model.

[37:18] Paul: Yeah. And does that work for them?

[37:20] Allie Canton: I think it's working for them, though there's moments for the rest of our family, right, where we're not Chinese and some of their choices are really hard for us to understand. So like, that's been a lot of the dynamic of my brother really serving as translator to say like, we are doing this thing that you guys don't get, but yeah, you know, this is what her culture is.

[37:41] Paul: Yeah, it's very interesting. Like, Angie's parents are, are doing so much for us and they're just offering more and more. They're offering money and time and resources. And like, it's really hard for me at first accepting this. I'm like, oh my God, like they're doing too much for us. And just like, I kept needing to clarify.

They're like, no, this has been our dream. This is part of our life. This is what we value. This is helping us. Like, and so yeah, I, I feel guilty. Like, I'm like, are they doing too much?

Am I?

[38:13] Allie Canton: Like, are you a bad son-in-law if not? Yeah.

[38:17] Paul: Yeah. And they're like so eager to support us and it's so, I just feel so lucky I'm able to tap into that. And yeah, there's also like, there's nice things the other way. Like I think with American individuality, like you have a lot of freedom to like live your own life. The hard part about that is you have to figure it out all on your own.

[38:38] Allie Canton: Mm-hmm.

[38:39] Paul: But you can pursue this crazy path that I'm on. And so even though it probably makes my mom uncomfortable, she's supportive because it's like, yeah, of course you're supposed to like go do your thing, follow your, your path and things like that. So yeah, it's, it's all these different things and over time it's, it's very beautiful to like discover many cultures.

[39:02] Allie Canton: Well, it's funny as you're saying that I'm reminded of It is very American as well. It's like life, liberty, and the pursuit of happiness is like in right in there in our founding docs. And yet, at least for— I won't say everyone, but for some people, we have just really narrowed our sense of like, well, what is happiness? Like, what are the prerequisites of happy? It's like you got the car, you got the house, you got the kids in a good school, they go to camp, you know, whatever. It is.

It's interesting how much we've like shrunk it down, even though the grounding principle is like so much broader and so much more individualized, individualistic, I guess.

[39:42] Paul: So I call this my accidental meaning hypothesis. I didn't go into depth in this in The Pathless Path because it was a little too, a little too hard to track. But basically I think what happened, especially in the US, is like The US just had economic tailwinds behind it since World War II. Incredible luck to be like basically the center of the financial universe still. Like basically we get to like grow and have higher wages because people want to buy our treasury bills. That's why we have a trade deficit and like why it's probably good for Americans, but we don't, we won't go down that rabbit hole.

[40:21] Allie Canton: That'll be another episode.

[40:22] Paul: The trade deficit. Yeah, the US economy from like 1950 to 1980 grew like 4 to 5% a year, which is massive. 4 to 5% a year is not double 2 to 3% a year. It is exponentially more because it compounds more and more and more every year. And so more and more people moved into the middle class and into the upper class. And so we now have, multiple generations where like basically the formula for like getting ahead was like getting a job and remaining employed.

And this is still true as much as people want to talk about how hard it is to be in America. Like it's honestly the best labor economy in the world. Like it is basically true that if you find a job in a decent company and just stay employed, you're going to be doing pretty well. The problem is as part of that life, we, this emergent, like suburban middle-class ideal of like the home, the home, the cars, the stuff, the job, it became this package that was like passed down multiple generations. And I think what happened is people started ascribing meaning to like the objects rather than giving any credit to like the underlying economic engine. And so the goal became not like find something you care about and work hard at it and like work hard throughout your career.

It became like get the job and the house and the cars and the family and the meaning will come. The problem with aiming at the stuff and the job is like the economic engine doesn't give a two dams about how anyone wants to set up their life, how they're feeling. And so that engine, that game, like the default path works as long as everyone else thinks that the path works, right? It's a common knowledge thing, right? If everyone knows that everyone knows the game is working, then it's fine. If enough people start questioning the game and don't think it's working, everyone knows that everyone else knows that they're kind of just playing along.

It starts to fall apart really fast. And so I think that's more or less happened in the 20, last 20 years, probably since the great financial crisis.

[42:36] Allie Canton: Yeah.

[42:37] Paul: And we just haven't talked about it yet. I think one piece of evidence is like seeing how crazy my book has done. Like it didn't even promote promote it or do a book launch and it still took off.

[42:47] Allie Canton: Yeah. And you self-published it, you know, it's like it, you didn't have that whole industry behind you.

[42:53] Paul: Yeah. The engine, the economic engine, the, um, yeah. And I think people were just desperate to talk about this stuff. It's like, what the hell is going on with work? Right. Like we both played the game and we're like, what the hell is going on?

Like the craziest thing is like, I wanted to just care about ideas and like do hard work and do good work. And that was, I deemed that impossible on my path. I realized that I would have to do stuff I didn't care about. I had to have to pretend to care about certain people and certain things, and I had to play a game. And it's like, this is crazy. We're spending our best, we're sending our best and brightest off to like do the silliest stuff they have to pretend to care about while they all are secretly wishing there was a different path.

And so, I also call this like the inspiration deficit, right?

[43:44] Allie Canton: Yeah.

[43:44] Paul: There's this latent desire for like challenge, inspiration, hard work, and this is basically what I've created for myself. Like the book was a challenging project, but like, man, it's just, it's just so crazy. Yeah. It's so, you know, it's like people could take my book and be like, all right, Paul made me talk about this, but it's his fault. I'm not the one bringing it up.

[44:05] Allie Canton: Yeah. This wasn't my idea. It's not my fault that like private equity roll-ups don't get me excited to like get out of bed. It's, it's all Paul's fault.

[44:14] Paul: So private equity recently, they've started giving equity ownership to all employees of the companies they take over, which is really interesting.

[44:23] Allie Canton: And so that is interesting.

[44:25] Paul: This is part of the problem I have with like, this is a tangent, but like critiques on capitalism are so silly because like capitalism is just us and it's an evolving system. It's like the only system that keeps evolving. And it can get better. And so like a lot of jobs have gotten better, but yeah.

[44:43] Allie Canton: But we just don't think about it.

[44:45] Paul: But yeah, the, the problem with like private equity is they do lay off massive amounts of people and it is for financial leverage. And a lot of the capital goes to people in New York. And I've seen houses of people that worked in private equity and it's, it's like, holy shit, this is crazy. And I could have had that too. I went to a Bain Capital recruiting event and that was a path that I saw in front of me and like, consulting was more interesting to me, but it was like very clear, like looking back, like I could have went down that path too.

[45:16] Allie Canton: Very easily, right? Like it's almost, I don't know, the river kind of coming from MIT Sloan, it's like that's where the river naturally pulls you to. You just, the Charles takes you there and it takes you to the big law jobs. And I guess now it takes you to the big tech companies too.

[45:32] Paul: Yeah. Yeah. And, but another problem, I think, I think it's gotten even more challenging now to care about work and to find work you actually care about is increasingly like an insane thing to do because the economy has turned into like a secure the bag economy. Like grab, like secure your jackpot as soon as possible by any means possible. And it's, there's so much cynicism like in the job market, in the job world, like, and I was probably part of this though. I wasn't always aiming at, I kept applying for jobs that paid less than I paid and then be like, offered me a job like for equal salary 'cause they thought I wouldn't accept the jobs.

But all the job hopping is 'cause people wanna make more money. Yeah. People wanna just get more and more and more. And I knew it was time to leave when I was in New York making $150,000 a year and I was like, I feel like I have enough money to like try stuff or like at least take a couple years off. And people would be like, you're crazy. You can't live on low six figures.

I'm like, what are you talking about? I could raise a full family on this. I could figure it out.

[46:41] Allie Canton: Yeah.

[46:41] Paul: People were just so disconnected and it's crazy.

[46:45] Allie Canton: Yeah. They had, well, they had one narrow version, right?

[46:48] Paul: Law's even crazier. Like you graduate and they give you like the nine-year salary.

[46:53] Allie Canton: Oh yeah. You know, exactly. Yeah. Yeah. And it's like, don't just don't get fired. And the thing is except for in around 2008, 2009, it's really hard to get fired from law.

[47:04] Paul: Yeah, because they need you.

[47:06] Allie Canton: Well, no, they— even if they don't need you, I saw this in the firm where it was like, we're slow, and there's a bunch of people who I kept being like, oh, they're definitely gonna get fired. They're still there. They're like partners now. And I'm like, this is crazy, because lawyers are also really risk-averse about like firing other lawyers.

[47:23] Paul: And then lawyers in accountants They don't want to try anything.

[47:26] Allie Canton: Yeah. They don't want to try anything. They don't want to try anything, but I know it's, it's totally insane anyway. Yeah. Much love to all my lawyers out there. Yeah.

[47:36] Paul: I, buy my book, lawyers. You guys have so much money. Like all the people I know who stayed in big law, they, they're so wealthy, but like most of them are like, oh, I don't know what I'd do with my life.

[47:47] Allie Canton: They're miserable.

[47:49] Paul: I've thought about offering a service for like multimillionaire big tech and lawyers to like Okay. You can pay me $35,000 and you just get to spend a week with me. You can ask me questions and spend a week with me and I'll help your nervous system relax.

[48:04] Allie Canton: All right, Paul, we got to talk more about that. I will, I will do this with you. We could go somewhere wonderful for a week, get all of our miserable lawyer tech friends there.

[48:14] Paul: But that's the problem. I don't want to hang out with miserable lawyers. Like, like my favorite people are like My favorite, you do like half and half, like my favorite people now are like the people I'll meet. They're like, I had $2,000 saved up, so I was like, screw it. Time to like quit my job and explore. They're just like wired to like experiment and like they have to try other stuff.

And I think I was always this person deep down. I was just scared to admit it. But yeah, I don't wanna change anyone's mind. It's too hard. And like, I'm certainly not going to convince a lawyer who has like hundreds of reasons ready to go.

[48:53] Allie Canton: No, I'm thinking more about the lawyers who are feeling kind of like what I felt like this deep sense of dissatisfaction, curiosity about a different way, but it's almost like the Pathless Path experience.

[49:05] Paul: I've been thinking about events for a long time, but I don't do it. That tells me I don't really want it that bad. I think I would really enjoy it. It'd be really fun. For me. I love doing stuff like that, but I just don't want to organize it.

[49:18] Allie Canton: Yeah.

[49:19] Paul: But yeah, I'd be happy to explore something like that with you. Leave a comment if you're still listening, leave a comment. And I feel like you're way better at planning than I could be.

[49:32] Allie Canton: Yes, we could totally, we'll talk more about this. We could totally plan something like this. So before we, before we record, you mentioned that you're going through sort of your own, I don't know, rebirth, uh, entering into a phase. Yeah. What is that?

[49:49] Paul: Every day is pathless.

[49:51] Allie Canton: That's the joy, right? When every day is pathless, every day is new, a new life, a new adventure. But like, what's real now?

[49:58] Paul: I think the last 2 years were all about leaning into fatherhood, and I think through many slow days, I really softened into this new version of myself. And I think for one, I really confirmed again that like, Okay, I need writing. Writing in my life is very important. It's very life-giving to me, and so I need to keep creating time with that. I also do have ambitions that are aligned with that. I do want to help people on these paths.

I feel a duty to help people. So many people have bought the book and like, I feel like I don't have enough stuff to help them, but I do want to create in that direction. I love the people that are my readers. And so the problem is like, the choices are just like, do a full-time work and like, see my daughter from like 6 to 7 every night, and I just don't want that life. So my life is going to continue to be around working less. I need to partner with people.

I need to figure out how to do that. I'm worthless to work with. We had some exchanges about you helping me with something and like, I just don't even respond. And this keeps happening. This is a cycle over and over again. And it's just part of it is like, I love my life and like, I have enough.

For now and I feel really good. And so like, I'm not motivated to like do more for like money. Like it's just like so, so unmotivating after like a break-even point. It really is like the $70,000 point, like from Kahneman's study. And so I'm still figuring that out. I have a lot to develop.

I think I have some fear of success of doing more. I always meet people that are like, oh my God, you could do so much. And I'm like, Why? I don't know. It also like doesn't feel that possible. I think because I'm constrained by my own like work hours and work habits, which is generally just not working that much.

[51:50] Allie Canton: Yeah. Yeah. Unless it doesn't feel like work, right?

[51:53] Paul: Like that's the thing, like finishing a book feels totally obvious and I know I'll write several more books, but for other people writing a book is insane. Really challenging, but it's like, that's so fun and exciting for me to think about that. I know I'll do it.

[52:11] Allie Canton: Yeah. For you, it's like, it's not work, right? Like it's fun to actually write the book, even though it's like time where you're applying your effort in this concrete way.

[52:20] Paul: Yeah. I call it good hard versus bad hard. Bad hard is like the grinding all the hustle bros are always trying to convince us we really need to do. We need to like maximize our potential. I don't want to maximize my potential. Maybe if it includes like being a good father, but even then, like I'm going to just drop the ball in aspects of my life at various points.

And so I just want to be a normal human with flaws, but I do want like hard challenging things in my life. And that's where like writing seems to be a continuing edge I can push. Like, man, writing never ends being hard.

[52:55] Allie Canton: Yeah. Well, it's funny though. I don't know. Writing feels hard, but then there's also these moments where it's like, it's just flowing through.

[53:03] Paul: Those are magical. What I mean is like, there's always like, I think with a book, there's always like an aim. I'm aiming at this final feeling. My books are very somatic. It has to be a feeling throughout and toward the end. And it's like, I don't know how to get there, but it's, it's there.

And some days I'm just like rewriting a paragraph for hours and it finally clicks and then you just keep going through. Some days it flows, some days it doesn't. But yeah, it's so fun. I, I love it so much, but it can, it can be very challenging.

[53:38] Allie Canton: Yeah. And that's real too, right? Like I think that sometimes when people think about, oh, I'm gonna embark on this creator journey or whatever, it's like, I'm just gonna be having fun all the time and it's just going to be easy. And it's kind of like in contrast to where we started, like The Pathless Path as a somatic feeling, but even, you know, within that feeling, it's a life. There's challenges that arise too.

[53:59] Paul: Yeah. I think that it's always a straw man, cuz I do think you can feel good most of the time, but I don't think you can, like, I think people portray that as like, oh, it's gonna be constant fun and pleasure and joy. And it's like fireworks. But like that, that's just like fake anyway. No one wants to feel like that all the time. Like the ups and downs of life are what gives life It's beauty.

And so I do think it is far more possible than people think to not feel bad while working. And so that doesn't mean aiming at trying to just have fun or be like super passionate, but if I feel like I'm grinding or working towards something I don't care about, or it's like really hard and I'm like, it's not a priority for me, I just stop it. I just don't do it. And so I just sort of do, like, I don't have a schedule most days. I just do whatever randomly pops into my head. The downside of that is like, maybe I do need to rethink this approach to like actually achieve like some of the, the direction I'd like to move.

But I do think you can mostly spend your days in work mode without feeling bad. And that's pretty radical for most people.

[55:12] Allie Canton: Yeah.

[55:12] Paul: But that's what my second book is about.

[55:14] Allie Canton: Good Work. Yeah. Well, Paul, I think that's actually like the perfect place to end of like, you don't have to feel bad about work. You can feel lit up in terms of how you spend, spend your days and contribute. And for listeners out there, if Paul's ideas resonate, he has a new hardcover edition of The Pathless Path coming out in fall of 2025. Um, yeah, I think it's going to launch around November, December.

[55:43] Paul: It's going to be the most beautiful book. You'll own that you've ever seen. It might be. It is beautiful. At least for Americans, we don't have many beautiful books, but like places like Europe, they still sell like beautiful books in bookstores. Yeah.

The goal is to take a ton of money from my royalties I earned and create something that's beautiful and inspiring for me. And it seems just really fun to create something so extravagant and beautiful and delightful and I don't know what's gonna happen. I invested, it's probably gonna be about $60,000 to $70,000 of my own money in this project. It's kind of a crazy experiment. It's not a, it's more like a medium experiment rather than Ann Lor's tiny experiment. And we're gonna see what happens.

Like, I really want to take a bold stand for like doing work on your own terms in ways that matter to you. And this is my bet. Yeah, that's, I, I don't know how I'm gonna launch it, when timeline, how I'm gonna do it. What's— I still need to think through that.

[56:39] Allie Canton: All right.

[56:39] Paul: Well, pathlesspath.com is where you can find most of my stuff on that, or pmillerd.com.

[56:44] Allie Canton: Amazing. And then people can also find you if they want to follow along generally on Substack and anywhere, just search Paul Millerd.

[56:52] Paul: I'm the only one on the internet.

[56:53] Allie Canton: You're the only one. Amazing. And then people, I just want to take a moment also for The Pathless Path community. So there are a lot of other people who are feeling this way. You always say find the others and it's helpful. Started to collect some of them together.

Can you just say a word about the community?

[57:13] Paul: I always forget to promote the community. People always yell at me. They're like, you need to tell people about this.

[57:18] Allie Canton: Yes.

[57:20] Paul: Yeah. pathlesspath.com/membership. I should probably come up with better— like if you have ideas of how I should better promote this, Yeah, it's about 500 people now. We started a WhatsApp group, which has been pretty active. We have monthly hangouts and still experimenting, thinking about a global meetup day this fall. So that could be really fun too.

[57:43] Allie Canton: Yeah, that would be super fun. I'm in the community.

[57:45] Paul: It's a one-time fee. Uh, you can pay either $75 or $150, whatever feels right. Or if you honestly don't have the funds and really need financial help, just email me. I'll take care of you.

[57:56] Allie Canton: That's very generous of you. What I was gonna say is, is really cool about the group is the way that people support each other. You know, there was someone who is doing a coaching certification and there's this amazing moment of like they need to do a certain number of sessions and there's a lot of people in the community who also could probably benefit from coaching support. And I, I think it's very cool as well how you consistently promote people within the community. I'd say about a third of the self-promotion posts in the WhatsApp group seem to be you promoting other people.

[58:28] Paul: 'Cause people don't do it. And so like, I've gotten over all my shame of posting and sharing ideas in public, so I'll just let it rip. Like I'm gonna brag about people.

[58:39] Allie Canton: I think, I think that's beautiful. It's beautiful. Well, Paul, thank you so much for joining. This was such a joy. Yeah. And I'm really excited to see your ongoing experiments and where, where they might lead.

[58:52] Paul: Cool. I appreciate this combo. It was very generative and Great. I loved it.

[58:57] Allie Canton: Thank you.

[58:57] Paul: And people should follow your stuff too. I'm happy to put this episode on my podcast feed as well, if you want.

[59:04] Allie Canton: Oh, that would be amazing.

[59:04] Paul: Introduce people to your podcast.

[59:07] Allie Canton: Oh, thank you. Yeah. So I'm over at Practically On Purpose on Substack and I write about same topics like helping high achieving folks step into greater meaning and purpose. I'm also a meditation teacher and a Reiki master. So I write about some spiritual weirdo stuff too, if you're into that.