Redefining success, money, and belonging | Paul Millerd (The Pathless Path)

Transcription for the video titled "Redefining success, money, and belonging | Paul Millerd (The Pathless Path)".


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Intro (00:00)

Take three hours during a workday, has to be during a workday, block off your schedule, and sneak out. People can pull this off. Go for a walk without a destination or do something from your childhood that you used to do all the time. Did you used to play basketball? Did you used to paint? Did you used to play an instrument? And just pay attention. What is emerging? Do you feel bad for sneaking out of work? Where does that bad feeling come from? What does that mean about your definition of work and what work means to you? A lot of people have never really thought about, like, why do you work? People say money. Okay, that's fine. But like, what else? Like, why? Are you trying to be a good person? Do you see a good person as somebody that works every day? Maybe. These are a lot of scripts people grow up with. You're really just creating the space to get in touch with like, how do I actually feel about work? How do I get to know myself more? Are there things that I've lost touch with that really bring me alive? Today, my guest is Paul Millard. Paul is the author of "The Pathless Path, Imagining a New Story for Work and Life." His book is getting a lot. Paul is the author of "The Pathless Path, Imagining a New Story for Work and Life." His book is getting a lot of traction within the tech community because it explores a different way of living, essentially breaking free of the default path for your work and your life that we all basically start on. What Paul describes in his book is almost exactly the path I took to figure out this very weird and wonderful work that I do now with a newsletter and podcast. And because of that, I think this is an important conversation to have, because it may inspire you to explore a different path in your own life. In our conversation, Paul explains what the pathless path is, how to go about exploring your own pathless path, how to address fears we all have around money and prestige and safety that keep us on the default path, plus tons of stories and examples and very tactical advice for thinking about exploring a new direction in your own life. With that, I bring you Paul Millard after a short word from our sponsors. This episode is brought to you by Sanity. Your website is the heart of your growth engine. For that engine to drive big results, you need to be able to move super fast, ship new content, experiment, learn, and iterate. But most content management systems just aren't built for this. Your content teams wrestle with rigid interfaces as they build new pages. You spend endless time copying and pasting across pages and recreating content for other channels and applications. 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That's This episode is brought to you by Maui Nui Venison, a mission-based food company bringing the healthiest red meat on the planet directly to your door. I actually joined Maui Nui Venison earlier this year after hearing their ad on the Tim Ferriss podcast, and I'm excited to be spreading the message further. Not only does this company provide the most nutrient-dense and protein-dense red meat available, their operation produces the only stress-free, 100% wild-harvested red meat on the market. That is the only one of its kind in the world, actively managing Maui's invasive axis deer populations, helping to restore balance to vulnerable ecosystems, food systems, and communities in Hawaii. Also, it is seriously delicious, not at all gamey, and easy to cook. My wife and I made stew and steaks and all kinds of grilled goodies with the meat. We also feel great about it as a protein from an ethical standpoint. I highly recommend trying their all-natural venison jerky sticks for an optimal protein snack as well as a wide variety of fresh cuts all available in their online butcher shop. There are limited memberships available but you can sign up and get 20% off your first order at That's Paul, thank you so much for being here. Welcome to the podcast. Excited to be here, Lenny. I am more excited to have you on. You published a book called "The Pathless Path," which I have right here.

Discussion On The Pathless Path

The Pathless Path (04:44)

The last I heard, you've sold over 40,000 copies of a book called The Pathless Path, which I have right here. I know that puts it in the top 1% of books sold, possibly in the top 0.1% of books sold. It's an absurdly high number for books sold. People don't really know this. And especially for a self-published book, it's a huge success. I thought it would be good to start with a concept that you call the default path. What is the default path? Yeah, I think the default path is different for everyone and slightly different in every different culture.

The Pathless Path concept (05:11)

It's really the story in your head about what you should do. And most of us have some sort of script that we're living out. This is especially powerful when we're in our late teens and early 20s, right? We're trying to execute a script. And it can be different in every country. Like in the US, it's sort of like go to college, get good grades, get a good job, make a good salary, buy a house, get married, have a family, things like that. And when it comes to work, the default path is to get a job and work continuously for all of adulthood. And when you opt out of the default path, there aren't really offerings. Like people have a hard time even contemplating it. Like you'll trigger insecurities in other people by just existing outside the frame of the default path. And it's the default path in their head of their conception of how the world should work and does work, right? And so a lot of what I explore is what is life beyond the default path? And what are the stories we can use to 1) at minimum feel better about what we're doing? And 2) what are the stories we can adopt to thrive? I imagine many people listening to this are feeling like no way I'm on the default path. I'm doing so many interesting things. I'm doing what I want. But they probably still are on this default path. What are some signs that might tell you that you actually still are on this path? And there's such a new direction you could explore that you haven't explored? Yeah, I think there's nothing wrong with the default path. The difference I would make is, are you sort of conscious about what you're actually doing? What are the costs of your game? What are the trade-offs? What sort of implicit contracts are you creating with yourself? A lot of times when people quit their jobs, they forget to fire the manager in their head, right? They don't realize they can take the afternoon off to spend it with their kids. They've created this implicit contract that Monday through Friday, eight to 10 hours a week, you have to work, right? And that may work for people, but are you actually opting into that? Or are you just sort of accepting the default? I think it's a really important point. It's totally fine to stay on this default path. Like it's not for everyone to try something totally different. Can you talk a little bit about just how to think about the benefits of that and the trade-offs of, okay, this is great. I'm going to stay where I am. It's interesting. I did not think my book would resonate with people that were firmly in sort of the traditional work role, full-time jobs, big companies, things like that. But I've had many people reach out that say, "wow, this this sort of loosened the tightness between my identity and my work reality and loosened it up a little bit." And "I'm able to play with it a little more." I had one friend. He said, "From your book, I made a list of the four priorities. Right now, I'm getting three of them." And it's helped me become more aware that, "oh, I'm actually getting these three things that I prioritize. I'm missing the fourth. I'm probably going to have to make a change two years from now. Maybe another role because I do want to lean into that fourth thing." I think it's really just about like remixing your path. My hot take is that we're all on a pathless path. Like you were at Airbnb, every two years you were there was a different company. Absolutely true.

Right. And so we're constantly needing to reinvent and reevaluate. And I think thinking of our lives as this smooth trajectory up this corporate ascent sort of limits the possibilities of our own life. So just acknowledging that we are being disrupted, we all have personal lives where we have relationship challenges, health challenges, external shocks, inflation, things like this that are changing our reality all the time. Things like this that are changing our reality all the time. And it sort of sucks that there aren't these comfortable middle-class jobs that are growing and abundant. They're shrinking. David Autor, an economist from MIT, has pretty good research on this. And it's just making people a little more unsettled. It sucks. But this is the reality we're living in, especially places like the US becoming super tech-heavy. And how do you navigate that? It's hard. Everyone's struggling with their relationship to work. So let's actually talk about the pathless path. You've been kind of touching on various ways of thinking about it. What's the simplest way of thinking about this concept of the pathless path? You've been kind of touching on various ways of thinking about it. What's the simplest way of thinking about this concept of the pathless path? I really shied away from trying to define it super clearly, right? I think I have this passage at the beginning of the book that it's like the pathless path is basically a shift away from the default. It's a shift away from not knowing what you're doing as a problem to be solved toward an embrace of discomfort, and uncertainty. And it's sort of a personal journey of shifting away from operating around scarcity towards operating from a sense of abundance, having faith that things might be okay, right? And this, on a path like yours, this is a necessary condition. You have no idea what comes next because nobody has been on the Lenny path before. True. Right. And a lot of us are in this situation. Now, if you're an accountant at an accounting firm in your early 20s, maybe there is a track and you can sort of plan it and it's pretty legible. But even still, I would argue that developing a relationship with uncertainty, not knowing what's happening, experimenting a little more, it's all of these things in one. And it's sort of my attempt to come up with a better narrative around work. And it's sort of my attempt to come up with a better narrative around work. And it's been pretty cool because a lot of people are embracing this and now using the term like, oh, I'm on my pathless path. Right. And it allows people to sort of name it and gives them comfort. I've had people email me that have been on a path for seven years. And they're like, this is the first time I actually felt okay about my path. Because a lot of what my book is, is an exploration of like, why does it feel so weird to do your own thing? Why does it actually feel shameful to leave a full-time job, which is an aberration in the history of the world. I imagine a big question everyone's mind right now is this sounds amazing. I would love to just do the work I love and break out of this path. How do I do that?

Key Ideas of the Book to Give Yourself (12:15)

And I want to talk about that. But before we do that, what are some examples of pathless paths people have ended up doing? Just to make it a little more real, like here's what you may end up, here's what people have ended up doing with their life. Yeah, so I think it ranges from a short sabbatical to someone like you or me who are sort of on this path and committed to this creator path, and things like that. There's a huge component of the creator economy. Not the creator economy from a VC perspective of all these start-ups that are going to save creators, but creators that are actually betting on themselves, finding some deeper satisfaction, a better relationship with work, and committing to it. But it also encompasses people that are independent freelancers that have a stable path, more predictable income than like creator economy stuff. And it also includes people that are jumping from job to job. I also have examples of people that are older. I talked to a lot of people in their 50s. They've solved their financial problems, but they've lost that sense of aliveness and they're looking to re-inject that. And they need maps of how to approach that, how to think about that, what are the models, things like that. So yeah, it's a nice way to claim everyone's path. But yeah, I think the shared ethic is really a sense of possibility and opportunity and optimism. So just to kind of list out some of these. And I think what's interesting is there's no end to this. It's an endless path to continue discovering. There's actually this quote that I wrote down here that I'll read that I think is a really nice way of thinking about this pathless path: "The goal is not to find a job, make money, build a business, or achieve any other metric; it's to actively and consciously search for the work that you want to keep doing." The big shift there, the big shift for me, actually, when I left my job, I wanted to run away. I wanted to escape work. I wanted to not work. And I just, I more or less accomplished that, like I basically lowered my cost of living in Asia to about 1000 per month. But then I started developing this relationship with writing and creating and all these things I actually really enjoyed. And I wasn't doing them to be famous or grow a following. I was just, I just really liked them, and I liked doing it in public because I was meeting others that were engaging on these ideas.

Design Around Liking Work (14:45)

So the big aha for me was, "Oh, you can design around liking work." The hidden assumption I had around work for the first 32 or 33 years of my life was, work sucks. You have to figure out how to tolerate it, right? And within that frame, try to do your best to enjoy some of it. But ultimately, it's a trade-off of your time. You have to suffer through it. A lot of it is going to suck, and you have to put up with that. Now, I think I'm very protective of what I do and don't do. This is why it was very easy for me to say no to Penguin. I didn't want to write a second book for them. I want to write a second book the way I did, which was a super fun process. Writing a book was one of the most fun things I've ever done in my life. And so, I sort of think about protecting that. And yeah, a lot of people are looking for meaning through work in a job-shaped container. And I think that's just really hard to find. You can find it for short bursts, but maybe after seven or 10 years, it's just not doing it anymore. But maybe after seven or 10 years, it's just not doing it anymore. So let's talk about how to go about finding your pathless path and create the space and opportunity to do this. Because again, a lot of people listening are like, "I have bills to pay. I've got kids to take care of."

Find a Pathless Path (16:17)

I have a home. I have a mortgage. I can't just go on a sabbatical, explore, travel and find a here. I'm going to start a newsletter.

Suddenly (16:24)

Go on a sabbatical, explore, travel, and find solace. I'm going to start a newsletter. So, what have you found are ways to enable this exploration without risking everything? A three-month sabbatical is much more attainable than people think. Companies are desperate to keep people and are much more open to things like this these days. And the way I frame it is, if you're assuming you're going to work continuously in adulthood, that's about 500 months. Try to find three months of that where you can create space and reconnect with yourself, explore things, just see what emerges, see how you feel. I think this is so vital for people in their 30s or 40s who have worked for 10 years, just to reconnect with themselves. And three months in a total of 500 months, like people accomplish much more impressive things than that, like saving for their dream home. That is such a powerful thing people aim for that they make it happen, right? Even people who don't have a ton are able to make that happen because it is such an important priority.

Sabbatical (17:32)

And for me, I think creating this space was more important than owning a house or getting married. It was the most important thing for me. And I actually quoted your piece. I pulled up the quote and said, "Lenny Richitsky took a sabbatical after a long career in product management, thought he would return to work. But by the end of the break, it was crystal clear to me that I was ready to move on to a new adventure." And then you said, "Several weeks into your sabbatical, you stopped checking your email. My heart was no longer in the work. I didn't yet know what I wanted to do next, but I knew it was time to shake things up." Right. And you probably weren't in that state when you were still at Airbnb. That's right. I was super into the work. And I think the way I thought about it is the Kool-Aid kind of exited my bloodstream and taking that time off created kind of separation. And then I started thinking, "Man, is this really what I want to be doing?" And that visceral feeling of getting excited about the work disappeared, which was crazy and scary. Yeah. And so you have smart listeners and smart people who are great at excuses. So they'll say, "Oh, I can't do it because of this, this, this, this, this." I always think these things are much more possible if they really are the main priority. So what I tell people is fine. Don't take a sabbatical. Take an afternoon. Take three hours during a workday. Has to be during a workday. Block off your schedule. Sneak out. People can pull this off. Go for a walk without a destination. Or do something from your childhood that you used to do all the time. Did you used to play basketball? Did you used to paint? Did you used to play an instrument? Do one of those two things, even better if you do both. And just pay attention. It's a sort of form of like work mindfulness. What is emerging? Do you feel bad for sneaking out of work? Where does that bad feeling come from? What does that mean about your definition of work and what work means to you? A lot of people have never really thought about why do you work. People say money. Okay, that's fine. But like, what else?

Why Do You Work (19:41)

Like, why? Why do you work? Are you trying to be a good person? Do you see a good person as somebody that works every day? Maybe. These are a lot of scripts people grow up with, right? Or like people that don't have a full-time job. Are they bad people? And so you're really just creating the space to get in touch with like, how do I actually feel about work? How do I get to know myself more? Are there things that I've lost touch with that really bring me alive? It's interesting how much of what you describe, like we didn't know each other before we met for this podcast episode, but so much of what you say is exactly what happened in my path. I took three months off, exactly. I took a sabbatical. I started poking around, exploring, doing a little writing. It basically led to what I do now, which is a crazy thing I never imagined in my wildest dreams. And so, clearly this works. Yeah. And I think people will say, "Oh, you can do that because you work at Airbnb." Or, "Oh, you can do that because you..." I've talked to hundreds of people. So what I did before the pandemic for years was I opened up my calendar every Wednesday. And I said, "Anyone that wants to talk to me about work can talk to me about work." So at this point, I've probably talked to 500 plus people about their relationship to work. And yeah, the reason that's not surprising about what happened to you is it happens to like almost everyone. The sabbatical is almost the... It has like a 99.9% approval rating. I talked to one, I talked to one person, she was like, "I took a sabbatical. I stayed at home, my husband was still working for two months. I couldn't wait to go back to work." I was like, "Cool, you're the first person I met that didn't get anything out of a sabbatical." David Pérez de Lozano, That's hilarious. I haven't met that person. Okay, so your advice is try to take a sabbatical and you're also encouraging people to... You can actually probably do this at some point, but maybe takes a bit of time to set people up for the fact that you're going to do this. Maybe you need to work at the company for a while, but in your 30s or 40s, it sounds like try to find time to take three months; in this three months important. Is that what you find like that large of a block of time? I've found it takes like six to eight weeks just to unwind, yeah, that's exactly what I found. I think for me there was like the initial unwinding after six to eight weeks and then like a deeper unwinding after probably like two to three years where you... you start to trust yourself a little more, if you stay on the uncertain path that is, but yeah, David Gaworski. If founders are listening to this and feeling like, "Shit, why would I give people sabbaticals, they're gonna leave start their own companies find some other default, other other pathless path, I want them on my default path." Is there anything you could say to a founder thinking about offering sabbatical?

What about the startup founder running things? (22:28)

I would say if that's their reaction, it sounds like they have an insecurity around work. So, I would interrogate that first. What is the implicit story they have about how much people are supposed to work and such? I don't know if it's a good employer strategy. I think a decent amount of people would leave. Like I know at Intel, I have friends that have done the sabbatical at Intel. You get like six weeks after seven years, maybe after seven years, they're a bit burnt out and don't have enough time in those six weeks to unwind. But, getting creative, especially now that remote work is so much more common about these opportunities to let people become the people they want to be. People leave companies because they don't see a path to be the person they want to be. Okay, so you take a sabbatical or you take an afternoon or you take a walk. You talked about being mindful for what comes up. What are you feeling about work? What is the thing you want to do? Do you want to go play basketball? Do you want to go draw? What else do you encourage people to do to try to discover a potential new path? I think meeting others. So, an exercise I'll have people do if they're curious about this. And for the most part, I don't want to convert people that like what they're doing in traditional jobs, but a lot of people are curious. And I say, have a path expert conversation, reach out to somebody sort of like a podcast that's ahead of you on a similar path, and just send them a message and say, hey, really thoughtful message. Say, hey, you're on a path a few years ahead of me. I'm really curious about this. I don't have people in my life that have done things like this. Can I just pick your brain? If we can't jump on a call, can I send you a list of questions? Most people will agree to that, especially the latter if they're a writer because writing just enables them to come up with new ideas. So, I'll always agree to do the written questions. I don't do the open calendar anymore. Now that I have a daughter, she wins my time over random strangers booking. But if people want to send me questions, I'll always answer them in text form. And again, this path doesn't have to lead to creator, artist, writer, person. It could lead to starting a new business. It could possibly lead to a new career, like a shift in careers. Is there anything else, again, of just like where this could lead to people? So, they're like, oh, wow, that's interesting.

Isak (25:21)

Somebody sent me an article today about this guy. I think he was a performing artist. He became a therapist. I forget his name. But yeah, I think just the possibilities for reinventing yourself and taking different paths, working online, working flexibly, it's way more possible than 25 years ago. It's also going to continue to be more possible. Like all the tools and technology to enable these kinds of lives are just getting better and easier. And like, especially this week, like ChatGPT just released their new GPTs. I was playing with that today. This episode is brought to you by Wix Studio. Your agency has just landed a dream client. You already have big ideas for the website, but do you have the tools to bring your ambitious vision to life? Let me tell you about Wix Studio, the new platform that lets agencies deliver exceptional client sites with maximum efficiency. How? First, let's talk about advanced design capabilities. With Wix Studio, you can build unique layouts with a revolutionary grid experience and watch as elements scale proportionally by default. No-code animations add sparks of delight, while adding custom CSS gives total design control. Bring ambitious client projects to life with any industry with a fully integrated suite of business solutions, from e-commerce to events, bookings, and more. And extend the capabilities even further with hundreds of APIs and integrations. You know what else? The workflows just make sense. There's the built-in AI tools, the on-canvas collaborating, a centralized workspace, the reuse of assets across sites, the seamless client handover, and that's not all. Find out more at I'm curious if it's in your case, I make significantly more doing what I do now. I try not to talk about the income of this stuff, but it's significantly more than I made at Airbnb as a very senior product leader. And I feel like that often happens. You discover a way to do something you love and also make a lot more money. I think it's easier to make money in a sustainable long-term way doing stuff you actually like doing.

Making money (27:45)

That sounds so simple, but it actually would have been really hard for me to stay on my previous path. Now, in my case, it was not until my fifth year that I came close to the salary I left. For the first three years, I really optimized for exploration, creativity, just like getting to know myself again. I made 50 grand the first year because I was freelancing. Then I made like 30 grand, 24 grand, and then 30 grand. So I was really optimizing for getting to know myself. I dramatically lowered my cost of living. And that is one path. To know myself, I dramatically lowered my cost of living. And that is one path. But this year, I'll make more than I ever made. And that is mind-blowing to me because every single day of this year has been absolutely delightful. I've spent abundant time with my wife and my daughter. And yeah, it's so crazy. Now, if I had stayed on my previous path, I'd be making a lot more than I make now. But that path was not viable for me for like becoming like I could I'd be so frustrated right now if I had to go back to work, like an eight-month-old, like I know you have a four-month-old wait till eight months old. They're so fun to hang out with. What other tips and tricks do you have for people to create this space where they can continue living and, you know, paying the rent while exploring and wandering and exploring these things? Is it cut down on expenses? Is there anything else that one can do? I've talked to so many people at this point. I've seen all sorts of things. I've seen people move abroad. I've seen families with kids and a mortgage sell their house and decide to live in an RV. I've seen people dip into their retirement. I've seen people apply for grants and get those. I've seen people apply for loans. A big move that a lot of people do is turn their current job into a contract job, which a lot of employers are a lot more open than people would think. Because a contractor is very easy to fire. You can fire a contractor in a day. So if the company is struggling, boom, you're gone. And so there is more risk. But if you're sort of known in the company, it can actually be a somewhat stable path to create more space in your life. You say, "Hey, I want to work three days a week. I want to be a contractor. Here's exactly what I want to do. Are you open to this?" And as soon as you're a contractor, they can't tell you where to work. Right. You can develop a relationship and they can ask you to work in a certain place, but they don't have control over where you work. A trick that I found really useful, actually, for helping me feel comfortable about taking time off. I ended up taking six months off and then it ended up being a year off because I kept trying to figure out what is the thing I wanted to do. The way that I felt good about that is I set a budget of here's the runway that I'm going to give myself. Like here's how much it's going to cost to do this for six months. Here's the runway I'm going to give myself. I'm just going to burn through this money just with the bet that it'll lead to something interesting. And that made me and my wife also just feel like, "OK, we were going to lose all that money probably."

Naming what youre spending money on (31:08)

But the bet is, it's going to lead to something really great. Yeah, I love this. I think this is something I've been thinking about a lot lately, and I've actually been trying to write something around this, which is that naming what you're spending money on or coming up with agreements like that, you're sort of like saying, "this is money I'm investing in my life MBA," right? Because if somebody says, "I'm going to Stanford Business School," generally you'll receive positive praise. "Oh, that's awesome." But what they're really doing is not working for two years and spending $150,000 to $200,000 and not earning a salary. And then to me, it was really interesting to look back at my path. Now, the first three years of my path, I broke even. But compared to being in business school, people thought business school was way better of a path for me. People were judgmental of my path, critical of my path, insulted me, projected their insecurities on me. "How could you do this? This is so crazy. What's your plan?" So coming up with these reframes is super powerful. One powerful one that worked for me was consider it a gift from your former self, right? So on the consulting path, I did like it for a while, but at the end, I didn't like it. I was sort of just grinding through, going through the motions. I was good at it. But I really didn't want to be doing it if I had a choice. And so I earned a decent income doing it. So would I like to gift that to my future self to be happier? Yeah. So now that I'm in the present, receive that gift and be like, "oh, thank you, former self, for working that job." It's interesting. I could also flip it from the other way. Have your future self returning to, hey, here's some money to spend to help become who I've become. Yeah, exactly. So I imagine not everyone ends up on a beautiful, amazing new life. They go down this route, they spend a bunch of money, and then they're like, "God damn, I don't have anything to show for it."

The alternative wonders (33:24)

I've spent all this cash. Imagine there are stories of that. Is there anything you could share about those stories and how to maybe either avoid them or be okay with them? I think there are surprisingly few stories of that. I think that is people's fear of what might happen. What I've seen in reality, as soon as people are without an income or without a job, they spring into action. We're far more creative than we give ourselves credit for, right? Like having a child, we have no idea what we're doing when they come out. But it makes perfect sense that you're going to figure everything out because you have to, you have no choice, right? And so the ingenuity and creativity of people as soon as they sort of bet on themselves and go off into the wilderness is far more than people expect. And it also has to do with regrets. People do not regret the things they do. They regret the things they didn't do, right? And the reason for this is if you've made a mistake, you can actually take action to correct it. But if you didn't do the thing that you're regretting, there's nothing you can do except do the thing. It reminds me of a quote that you have in your book that I have here. The secret to doing good research, and I think it's related to this, of finding a new path, a pathless path, is always to be a little underemployed. You waste years by not being able to waste hours. Yeah, and I wonder if you found this too. Yeah, and I wonder if you found this too. Sometimes the best way for me to write is to go for a walk or to take a couple of days off and just sort of like reset. Like creative work can't be forced a lot of the time. And increasingly, a lot of work is creative work, right? Your work at Airbnb was ultimately creative work. You're creating new products and offerings in a whole new conception of an industry, right? You're making stuff up, right? A lot of times, I think people get fried in these companies because they're not actually given the schedules and the support systems around what actually enables creativity.

Creative work cant be forced (35:35)

Yeah, absolutely. Although, I find with writing, there's the benefit of the opposite of "I'm just going to sit here and write and I'm not going to give myself a chance to go walk around. I'm just going to keep writing, even if it's terrible, because it'll maybe lead to something." Yeah, and even that, a lot of times what ends up on the page surprises you. Right. So, you do need a certain sense of openness to let that emerge. So, kind of along the same lines, another important concept that you talk about in your book for finding this pathless path is just this idea that it's not ever like this all or nothing, "I'm just going to leap into this new thing." It's kind of the way you put it is, "people quit jobs after years of awakening and safely testing changes, kind of eliminating risks along the way." So, years before I left, and I'm curious if you had a similar experience, I was starting to read personal development books. I was reading Tim Ferriss. I was doing these small experiments like coaching on the side, helping people with resumes, volunteering, and helping people with careers. And so, I was writing too. I was writing for fun on Quora with no goals. And all these things make perfect sense now. And even looking back further, I was always tinkering on the internet, and all these things fit my story perfectly now.

Identify Shiftable Paradigms (37:13)

But I didn't know why I was doing them at the time. But each one sort of gave me the confidence to be like, okay, I don't love my day job, but all these random things I'm doing on the side, like writing an article and posting it on Medium and LinkedIn, and the people I'm meeting, this is really interesting and energizing. I'm going to pay attention to that energy. Something is there. And when I quit my job, I didn't really have a plan for how to deal with that. But I had experienced enough of this positive energy, I was like, I want to chase that. I want to go after that. That's exactly what I found. So let me, I'll tell my story briefly on this. Some advice I got when I went on my sabbatical that ended up being incredibly powerful is essentially what you just said, which is when you're doing stuff during some period of time off, pay really close attention to what gives you energy after you do the thing. Like say you have a call, did that give you energy or did that sap you of energy? Do you feel like more energized or do you feel like, oh, I'm tired now? So it's like after calls you make, after things you do with friends, after some kind of hobby you're trying to do, after you write some stuff, just pay really close attention to do what energizes you and saps your energy. And then my whole strategy was just do more of the things that energize me and do less of the things that de-energize me. So in my case, I thought I'd want to do some advising or consulting. I found after every advising call I was de-energized. I just like, no, I do not enjoy this as much as I thought. But after writing and putting a piece out, I was like, wow, this is really cool. Even though writing is very hard and there's a lot of de-energizing moments. Oh, broadly is like, wow, this is cool. People seem to really value this. I started doing that more. I thought I wanted to start a company, but that kept sucking me of energy as I was working on ideas. So that alone was really powerful. And it sounds like really simple advice, but that kept sucking me of energy as I was working on ideas. So that alone was really, really powerful. And it's like, sounds like really simple advice, but it's really effective. It's hard too. I think the pull to create a company when you leave a big tech company is so powerful. Yeah. And you're, what you're saying is sort of crazy. You're saying, oh, I just feel good writing. I'm going to follow that. Yeah, it was not a popular path amongst my friends and family. And I think the root of that is you're triggering insecurities in them. You're doing something they weren't allowed to do at your age. The thing I found really helpful there, some another friend gave me this advice. Just tell people you're tinkering. When they ask you, what are you working on? I'm just tinkering. I'm tinkering with some writing. Because that something about that word makes it sound like okay, cool. It's delightful. And cool tinker way. I feel like that did not work with my parents. But yeah, trying different things. I think I always tell people you need a boomer-compatible story for what you're up to, as just like, just give them something, just say, oh, I'm an entrepreneur or I'm a business owner.

Facing Fears (40:07)

That totally resonates. I would be excited about that. If I was a boomer. In the book, you also talk about taming fears. So we talked about a few of these things. And just the power of taming some of these fears that you have. There's success, the fear of not being successful, of money, of belonging, of loneliness, and of health. Can you just talk about either all of those or any of those or just why it's important to tame those fears and then how one goes about taming these fears? Yeah. So a big source of inspiration around this is Tim Ferriss' fear setting. And he basically forces you to write down what are your fears? How could you mitigate these? But more powerfully, the second part is, and you're framing them around action. And so he reframes like, what is the cost of inaction? And that was really powerful for me. And it sort of exposed like a lot of the costs in the current state of what I was doing, right? And so actually, I want to thank you. It's funny, you messaged me right as I was listening to a podcast. You were on, I think it was the one with David Perel. Yeah, I slid into your DMs. But I was listening to your podcast and you were talking about hiring a community manager. And this is actually something I've done in the past few weeks. And I think I was scared to commit to the community because I didn't want to create a job for myself. And one thing I realized is that I'm scared of creating a job for myself. But I sort of reframed the cost of inaction. Like, what's the cost of inaction is, like, if I don't actually hire someone, I'm going to drain all my creative energy. And that's like an existential risk to this path. Right. And so that's one example of I'm always thinking about these things. And that enabled me to take very quick action on that. But I think it was helpful to hear from you. You were like, I'm not a community manager. And this is a big aha for me because I launched my community at the beginning of this year. I suck at community management. I'm like not good at it, but I found somebody that actually was good at it. And I was like, oh, there are people that like this and are good at it. So that's one thing. I think more broadly though, is some fears don't disappear. So that's a very like specific project-based fear. Existential fears around health though, is some fears don't disappear. So that's a very like specific project-based fear.

Importance of Selfcare (42:43)

Existential fears around health, death, importance, and money don't really go away. I think the great thing about this path for me, is that you can't pretend like they don't exist.

Open Discussion On Lessons Learned

Painful Awakening (42:54)

They sort of just punch you in the face. You'll wake up one day and you'll have an existential breakdown, like, what the heck am I doing? Is this sustainable? This is so silly. Am I going to run out of money? Next year, are my book sales going to tank? And so the longer I've been on this path, those big worries turn into these small little daily things that pop up. And I'll sort of have a conversation with my fear. And I'll say, "Oh, we're worrying about money today. Okay, I see you. Yeah, that's real. Yeah, I don't know if we can solve that. But yeah, six and a half years. Let's keep going. Let's see if it works." Yeah, that's the thing that makes me feel better. Every time something like that comes up is like it's worked this long, probably gonna work for a lot longer. There's this concept of Lindy of just the time something is going to last is usually as long as it's already lasted. And so that always makes me feel better. Like the main thing I think about is just am I going to run out of stuff with a newsletter to write about? And it's been four years now, like that's probably gonna keep going for at least four more years. David Pérez, it's very important to like dance with your fears and really get in with them.

Not making money (44:16)

If I'm afraid of not making money, right? Like, it's very reasonable that book sales will fall, and so I don't know if we can sustain our lifestyle. I'm like, what I have set up two, three years down the road. But taking that fear and saying, okay, I'm going to solve that and make that fear go away by getting a job is like off the table. So I have no choice but to like, actually just be like, yeah, that fear is going to be here. It's going to be part of my life. And we're going to have to just deal with it. Along those lines, is there a path you took that was a big failure or didn't work out something that you thought was going to be a big opportunity and wasn't? The first 10 years of my career, I just kept jumping from job to job. I think I was looking for my current path in job-shaped containers, and I couldn't find it. And I just so desperate to like find a really good situation. And there were all sorts of circumstances like bosses who hired me kept quitting immediately after I would join layoffs, all sorts of random things that happened that were very weird. And yeah, I just sort of like kept searching. So I've been comfortable with trying things and starting new things and experimenting for a long time. And so one frame I have, I call it ship, quit and learn, which is what is the quickest way I can ship something designed to quit. But as soon as I ship it, I learned about what to do next. And so this is how I started my podcast. I just said, I'm going to do five episodes. I stole this from Tim Ferriss as well. I'm going to do five episodes. I stole this from Tim Ferriss as well. I'm going to do five episodes, I'm going to see how it feels. And this is one of these things super energizing. I love how I feel after podcast conversations.

Quit and learn (46:09)

I'm going to keep doing it. I wasn't aiming for success. But it was like, I know I can keep doing the podcast in my newsletter because I had that experience, that feeling from it. But there are things I've tried that I'm like, yeah, not again. A couple of consulting and advisory types of things early on in my path, I was like, "Whoa, I need to build in protectors such that I don't take a gig like this again." I connect to something you said earlier, which I super resonate with, which is you want to avoid creating jobs for yourself that you don't enjoy.

All these things (46:42)

With this path, there are so many things you could be doing and so many pulls that often, like, oh, for me, it's like writing a book is always this thing that's out there. Actually starting a podcast with one of these for a long time, like I don't want to start a podcast. Life is good. I got this awesome newsletter. Things are going great. Why would I want more work? Eventually, I crumbled and I did it. And here we are. And I'm happy I did. But there are all these other things that are always like, I should do these things. But I think it's really important to pay attention to what do you not enjoy and don't do that. Like it's easy to create bad jobs for yourself. A really clear example that is finding a niche that you don't enjoy spending time on, like in this life of writing about something you don't actually care about or podcasting about something you don't care about you just created a job for yourself you hate why would you do that and so it comes back to paying attention to what gives you energy. Yeah, I've created a percent of my days I cannot work so I don't do meetings. I don't really have employees or anything like that. I have contractors, but I hire contractors for very specific roles, and I create systems such that we can do it asynchronously, and of course, I'll have conversations with them if they want to jump on a call. But I optimize for like people that want asynchronous and work on those specific things. So I'm just very conscious of that. I think one challenge I have now is I've created so many things that I'm doing a few things really well and then sort of ignoring a lot of them. So I actually feel like I'm in this evolution right now of like trying to figure out what comes next. So we haven't even talked about this, but I started this business, Strategy U, early on in my path because I wanted to productize my consulting. And one of the consulting projects I loved early on was training people on consulting skills. I did a training program for a consulting firm in Boston. And I was like, oh, I could turn this into an online course. And that has slowly built and evolved. And I do workshops now with companies. And that made most of my money for the first from years two to five when I started moving away from just like project-based consulting. And so the game I was playing was make money from that. Like don't focus on it too much, spend minimal time, don't try to maximize for success. Create a self-paced course because I'm not interested in making more money in a cohort-based course because I just don't want to spend the time. And then use all the abundant time to write and explore, create podcasts, spend time with my wife, and do all the non-work experiments, see how I feel and write about it. Now I'm making money from the work I love, which is very weird. I'm going to make I'll hit soon about $200,000 made for my book, which is like mind-blowing. This is I published a book completely on my terms about what I love, and love the process of it. It's so crazy. And so now I'm building a community around that. That's really fun. I'm doing the podcast. I have some sponsors around that. And so like that's sort of taking over. I still have this strategy, though. So now I'm trying to figure out how to like unwind some of these things. I'm actually exploring trying to find somebody that might want to start their own pathless path, like a strategy consultant that wants to leave that world that like wants to be an operator on this business. So if you're listening, I've recently come to terms with like, this might be the path forward. But yeah, it's a constant journey of protecting your time, creating that space, going down projects you want to execute, but then stepping back and like, okay, I have all this maintenance I'm doing. How do I outsource this, eliminate it, restart, recreate? And I think this path is really just a commitment to constant reinvention, which is really, really hard. And you shouldn't do it unless you get some satisfaction out of like personal reflection and that journey. For someone that may want to help you with that program, what's the best way to reach out to you if they're just like, oh shit, this is a cool opportunity? Yeah, Twitter, or I'm very easy to find my emails all over the place. But yeah, we'll link to it in the show notes too. Just a couple more questions. I feel like one criticism of this path is, is there anyone left to actually do work at companies and build things and scale if everyone ends up being on this pathless path, creating content, starting their own companies, do you have any thoughts on just that side of things? I don't buy that because I've met most people and most people are like, hell no, when they hear about my life.

Most people would hate my life (51:42)

I think it's an interesting critique. I also think there's a more secular trend of "gigification" of work. All the growth in the economy from 2005 to 2015 in the labor market came from alternative work arrangements. So if you search David Deming's work on this, it's pretty compelling. Right now, we don't really count non-traditional work that well. So it's really hard to get good data on this. But even the way companies are treating their internal talent, it's much more project-based. People are shifting around, moving to different roles a lot quicker. I think that's going to continue. So you could make an argument that people will actually be able to slot into companies more easily in the future. Right now, companies underexploit the creator economy and the freelance economy because they're so tied to "you have to hire somebody through a full-time job." So I think there's sort of two sides to that; it's like one, most people would hate my life.

Becoming not gigafied (52:47)

And too, like the world is becoming more gigafied, so it could go back the other way actually. I really like that advice. Paul, is there anything else you want to leave listeners with to maybe start down this pathless path or any other piece of advice before we get to our very exciting lightning round? I think the key thing is that doesn't get talked about enough is it might be hard and it might suck, but it might be worth it. And I think that's a hard reframe for people because people will say like, well, I'm worried about not knowing what I'll do or not making money and all these things. And it's like, yeah, I felt like shit after quitting my job. But man, I am so glad I did it because it enabled me to now know that I don't have regrets about trying this and figuring it out.

Choosing The Right Path And Life Lessons

Finding the right path (53:44)

And a lot of people who do go back to their jobs are so much happier because they know I tested that. I found my boundaries. I need more stability. It's not this like "quit your job and get rich" pitch. It's very much like if you're somebody who has a sense that there's something more, there probably is. And it might be worth exploring. What's the next step you recommend someone take to start exploring this pathless path? What's something they could do today or tomorrow? Oh, read my book. Perfect. So I'm very committed to creating resources for people around this. My podcast is all conversations with people on an unconventional path and the inner game of work. And I don't talk about tactics and outcomes as much as really just like, how does it feel? How did you deal with that? Things like that. And so I do that in my newsletter, my podcast, etc. But yeah, just find people who are on interesting paths and ask them about their lives. One interesting thing I've had happen to me over the past few years is I've just met a much wider diversity of people. Like, I'm friends with people who work at restaurants and work part-time and work weird schedules and work nine months of the year and take three months off. And now it just feels so much more normal, what I'm doing. Because before all I knew was full-time workers because I was working all the time. That's all you're surrounded by. So yeah, try to find the weirdos. Awesome. And for folks who want to check out your book, should I just Google the pathless path? I just moved over everything last month.

Almost recommendations (55:34)

Okay, great. And then we'll link to all of these things in the show notes. With that, Paul, we reached our very exciting lightning round. Are you ready? I am ready. What are two or three books that you've recommended most to other people? Yeah, one is called The Great Work of Your Life. Sounds like a cheesy title, but that's actually a good resource for people who want to hear about people from history over the past several hundred years, different eras of people that really designed their life around work. It was really interesting, and it was a great book. A second book I'd recommend is Luke Burgess's book "Wanting." That was another great personal story/deep dive into a nerdy topic. That's like my favorite kind of book. That's the book I wrote, which was like personal memoir plus nerdy deep dive. And Luke Burgess's is really good too, more from a tech perspective because he went down the startup path as well. But that's a great book. That was my favorite read of the year. What is a favorite recent movie or TV show?

Pauls favorite movie/TV show (56:47)

I struggled to answer this because I don't watch much TV. I did watch the Anthony Bourdain documentary. That was excellent. That, like, talks about a pathless path and the ups and downs and the struggles and the dark side of it. Man, that person was bringing forth what is inside of him and grappling with his demons at the same time.

Pauls favorite interview question (57:14)

That was a powerful story worth watching. Do you have a favorite interview question that you like to ask when you interview, say, contractors, or anyone else you work with or hire? I'm always curious about what makes you come alive. I want to work with people who are alive, connected, and inspired. So the two people I'm working with right now: one's a podcast producer in Poland, but he's doing a bunch of other stuff around video and he's super energized; used to be a lawyer, reinventing himself. The other person is also a former finance person in India, and she's two years into the self-employment journey. She's writing and exploring all these ideas. So yeah, I'm always looking for that energy first and skills second. Is there a favorite product you've recently discovered that you love?

Pauls favorite product (58:03)

I really love the Nuna travel stroller. It's super convenient for traveling. We don't have the travel stroller, but we have the Nuna car. Yeah, we have that one too. It fits. So we've brought that around the world. That's been super convenient. And then more on the tech side, I just got into the eSIM game. That was amazing. And then, like, ChatGPT, I just created my own GPT to do podcast show notes automatically for me. It took me an hour to train it, and it is incredible. That's amazing. That's awesome. I don't know if folks know, but there's a site that uses all of my podcast transcripts and newsletter to have a little bot that you could ask questions to. That's working actually shockingly well. We're going to try using the new GPT thing that they just launched. We can kind of train our own GPT. And that'll be fun. And actually, a podcast listener reached out to me and offered to help build this thing. So that's a huge success story from this podcast. Next question, two more questions.

Pauls life motto (59:13)

Do you have a favorite life motto that you find yourself sharing with friends and finding really useful in work or in life? Mine is "One coming alive over getting ahead." That's something I keep coming back to. I'm inherently skeptical of chasing achievement, and I use this motto to remind myself that it is about personal energy versus extrinsic outcomes. From my own life experience, I am convinced that extrinsic outcomes aren't going to do a ton for me. Sure, I need to make enough money, but when I'm in extended states of feeling alive and connected to everything I'm doing in my life, that's it. I basically repeated this mantra to myself right before rejecting the book deal.

Remarks And Recommendations

Advice (01:00:01)

It was like, I did not feel good in the conversation with the people. They talked down to me. They told me that, like, I probably wouldn't succeed. And it was like coming alive or getting ahead. I don't need their prestige. Final question. You've been podcasting, I think, for six years. What's your best piece of advice for someone who wants to start podcasting, has maybe already been doing podcasting like myself, or being successful, or anything along those lines? Yeah, I think if you want a podcast to make money, it's probably not something you should get into. Like, even if you have an audience, it's probably not the best way. I think if you have a massive audience, it can work, but it takes a really long time. Like, a podcast is the ultimate long game. So you need to find some intrinsic connection to what you're actually doing. If you don't love the conversations or the format you're doing, like, don't do it. But yeah, I would recommend more people start podcasts. I'm against the New York Times' saying there are too many podcasts, but I take the opposing view. I don't think there are that many podcasts. If you ask people in their personal life, out of tech bubbles, how many people in your life have a podcast? Now in Austin, a lot of people have podcasts. But yeah, most people don't have a podcast.

Keep practicing, newsletters, podcasts (01:01:29)

Even if you do something like interview your parents, or anything, like it's such a cool, creative thing, it's free. It's free, and you can send it to everyone in the world. Podcasts and newsletters are incredible innovations. Let it rip. You had to get permission to do these things 10, 15 years ago. It's so great to be alive in today's world. I feel like when people say there's too many newsletters, too many podcasts, my answer is always there's always room for better newsletters and better podcasts. If you can deliver more useful, valuable, interesting stuff, people are going to pay attention. The bar just keeps rising is the challenge. Yeah, it's also like do it for the sake of itself. Do it for the creative act. The creative act can be super meaningful in and of itself. I've lost money in my podcast over the lifetime of it. Love it. I don't care. I'm going to keep doing it. And also the best stuff often comes from just doing it for yourself and then realizing that wow other people might find this interesting. Yeah, I didn't start getting podcast feedback until the last two years when it started growing a lot more. I was sort of just doing it into the void. Speaking of that, Paul, we've been on our own pathless path.

Where to find Paul (01:02:46)

I feel like we're going to send a number of folks on their pathless path. Two final questions: Where can folks find you online if they want to reach out and learn more about what you're sharing and your journey, and how can listeners be useful to you? Paul Yacoubian: Yeah. So I've been compiling a lot of my more recent stuff under, which will link you to my podcast, newsletter, community, and book. I'm always willing to gift my book to anyone in the world who wants it, just email me. I'll even send you a printed copy if you don't have the money to do it, and I'm always happy to send bulk orders to people who want to gift it and do book clubs or things like that. I'm happy to send it at the author rate, which is about $4 per book. And yeah, what help? I think, yeah, I am starting to explore the potential of selling my strategy business or finding like an owner-operator who might want to get some sort of profit-sharing or something like that. It'd be interesting if there are former consultants who might be interested in something like that. I don't know. I'm so bad at asking for help. I think if you want to share my book, that would be cool because it is pretty neat to make money doing something from something I'm really proud of.


Closing (01:04:00)

Go buy "The Pathless Path," available at all online bookstores, I imagine. Paul, thank you so much for being here. Amazing. Keep going on your path too. I'm really inspired by how you're approaching your path and sharing your reflections too. I appreciate that. Bye-bye, everyone. Adios. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at See you in the next episode.

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