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

Paul Millerd: 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 use to play basketball? Did you use to paint? Did you use 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, why do you work? People say money. Okay, that’s fine. But what else? 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 this space to get in touch with, 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?

The Interview Begins

Lenny: Today my guest is Paul Millerd. 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 the 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 Millerd after a short word from our sponsors.

Forward-thinking companies like Figma, Amplitude, Loom, Riot Games, Linear, and more use sanity to build content growth engines that scale, drive innovation, and accelerate customer acquisition. With Sanity, your team can dream bigger and move faster.

As the most powerful headless CMS on the market, you can tailor editorial workflows to match your business. Reuse content seamlessly across any pager channel and bring your ideas to market without developer friction. Sanity makes life better for your whole team. It’s fast for developers to build with, intuitive for content managers, and it integrates seamlessly with the rest of your tech stack. Get started with Sanity’s generous free plan. And as a Lenny’s Podcast listener, you can get a boosted plan with double the monthly usage. Head over to sanity.io/lenny to get started for free. That’s sanity.io/lenny.

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 mauinuivenison.com/lenny. That’s mauinuivenison.com/lenny.

Paul, thank you so much for being here. Welcome to the podcast.

What Is the Default Path?

Paul Millerd: Excited to be here Lenny.

Consciously Choosing the Default Path

Lenny: I’m more excited to have you on. You published a book called The Pathless Path, which I have right here. Last I heard you’ve sold over 40,000 copies of this book, which I know 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.

And I thought it would be good to start with a concept that you call the default path. What is the default path?

Paul Millerd: Yeah, I think the default path is different for everyone and slightly different in every different culture. 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 twenties, right? We’re trying to execute a script.

And it can be different in every country. 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 get a job and work continuously for all of adulthood.

And when you opt out of the default path, there aren’t really offerings. People have a hard time even contemplating it. 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?

So a lot of what I explore is what is life beyond the default path, and what are the stories we can use to one, at minimum, feel better about what we’re doing? And two, what are the stories we can adopt to thrive?

The End of Job Security

Lenny: 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?

What Is the Pathless Path?

Paul Millerd: Yeah, I think there’s nothing wrong with the default path. The difference I would make is, are you conscious about what you’re actually doing? What are the costs of your game? What are the trade-offs? What are the 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. 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. And that may work for people, but are you actually opting into that, or are you just sort of accepting the default?

Many Faces of the Pathless Path

Lenny: I think it’s a really important point. It’s totally fine to stay on this default path. 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”?

Designing Life Around Work You Love

Paul Millerd: It’s interesting. I did not think my book would resonate with people that were firmly in the traditional work role. Full-time jobs, big companies, things like that. But I’ve had many people reach out that say, “Wow, 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 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 remixing your path. My hot take is that we’re all on a pathless path. You were at Airbnb. Airbnb, every two years were there was a different company.

Finding Your Pathless Path

Lenny: Absolutely true.

Paul Millerd: 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.

And it sort of sucks that there aren’t these comfortable middle class jobs that are growing and abundant. They’re shrinking. David Autor, a 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.

The Power of Time Off

Lenny: 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?

Paul Millerd: I really shied away from trying to define it super clearly. 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 uncomfort, 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. And 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.

Advice for Founders

Lenny: True.

Connecting to Explore New Paths

Paul Millerd: Right? And a lot of us are in this situation. Now if you’re an accountant at an accounting firm in your early twenties, 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 been pretty cool, because a lot of people are embracing this and now using the term like, “I’m on my pathless path.” 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, 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.

Making Money Doing What You Love

Lenny: 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?” And I want to talk about that. But before we do that, what are some examples of pathless paths people have ended up doing? Something just to make it a little more real of, here’s what people have ended up doing with their life.

Paul Millerd: So I think it ranges from a short sabbatical. And 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 their creator economy. Not the creator economy from a VC perspective of all these startups 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 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 talk to a lot of people in their fifties. 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 pretty big umbrella. It’s a nice way to claim everyone’s path, but I think the shared ethic is really a sense of possibility, and opportunity, and optimism.

Creating Financial Space

Lenny: So just to kind of list out some of these end, 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.”

Exploration as a Gift

Paul Millerd: 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 more or less accomplished that. I basically lowered my cost of living in Asia to about 1,000 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 just really liked them and I liked doing it in public, because I was meeting others that were engaging on these ideas.

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, 33 years of my life was work sucks. You have to figure out how to tolerate it.

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 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 them.

And 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.

Real Stories of Leaving Corporate

Lenny: 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 got kids to take care of. I got a home, I got a mortgage. I can’t just go on a sabbatical, explore, travel, and find here I’m going to start a newsletter.” So what have you found are ways to enable this exploration without risking everything?

Paul Millerd: 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 thirties or forties who’ve worked for 10 years just to reconnect with themselves.

And three months in a total of 500 months, 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. Even people that don’t have a ton are able to make that happen, because it is such an important priority. And for me, I think creating this space was more important than owning a house, getting married. It was the most important thing for me.

And I actually quoted your piece. I pulled up the quote. It said, “Lenny Rachitsky 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.” And you probably weren’t in that state when you were still at Airbnb.

Leisure and Creativity

Lenny: 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 kind of created 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.

Paul Millerd: Yeah. And so you have smart listeners, and smart people are great at excuses. So they’ll say, “I can’t do it because of 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 use to play basketball? Did you use to paint? Did you use 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 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 what else? 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. Or people that don’t have a full-time job, are they bad people?

And so you’re really just creating this space to get in touch with, 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?

Small Steps Instead of All In

Lenny: It’s interesting how much of what you described, 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. And basically led to what I do now, which is a crazy thing I never imagined in my wildest dreams. And so clearly this works.

Making Peace With Fear

Paul Millerd: Yeah, and I think people will say, “You can do that because you worked 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 the reason that’s not surprising about what happened to you is it happens to almost everyone. The sabbatical almost has a 99.9% approval rating.

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.”

Embracing Detours and Mistakes

Lenny: That’s hilarious. I haven’t met that person. 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 it 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 thirties or forties, it sounds like try to find time to take three months. And is three months important? Is that what you find, that large of a block of time?

Cultivating Ease in Life

Paul Millerd: I’ve found it takes six to eight weeks just to unwind.

Lenny: Yeah, that’s exactly what I found.

Knowing When to Quit Projects

Paul Millerd: I think for me, there was the initial unwinding after six to eight weeks, and then a deeper unwinding after probably two to three years, where you start to trust yourself a little more, if you stay on the uncertain path that is. But yeah.

Lenny: If founders are listening to this and feeling like, “Shit, why would I give people sabbaticals? They’re going to leave, start their own companies, find some other catalyst path. I want them on my default path.” Is there anything you could say to a founder thinking about offering sabbatical?

The Gig Economy and the Majority

Paul Millerd: 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?

Yeah, I don’t know if it’s a good employer strategy. I think a decent amount of people would leave. I know Intel, I have friends that have done the sabbatical at Intel. You get six weeks after seven years. Maybe after seven years, they’re a bit burnt out that they don’t have enough time in those six weeks to unwind.

But I think 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.

Lenny: Okay, so you take a sabbatical, or you take an afternoon, or you take a walk. You talked about be mindful for what comes up. What are you feeling about work? What is a 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?

Reframing What Is Worth Risking

Paul Millerd: I think meeting others. So in 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 and like 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, 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 stranger’s booking. But if people want to send me questions, I’ll always answer them in text form.

Lenny: And again, this path doesn’t have to lead to creator, artist, writer person. It could lead to starting a new business. It could probably lead to a new career. It could shift in careers. Is there anything else, again, of just where this could lead to people so they’re like, “Oh, wow, that’s interesting.”

More Book Recommendations

Paul Millerd: 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 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. All the tools and technology to enable these kinds of lives are just getting better and easier. And especially this week, ChatGPT just released their new GPT. I was playing with that today and I’m like, “Oh my gosh.”

Favorite Recent Movies and Shows

Lenny:

First, let’s talk about advanced design capabilities. With Wix Studio, you can build unique layouts with a revolutionary grid experience, and watches elements scale proportionally by default. No-code animations at 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 wix.com/studio.

I think when people might hear some of these professions like, “Maybe I’ll become a therapist, maybe I’ll become an online writer person. Maybe I’ll start a business.” It may feel like that assumes you’ll make less money doing these things. But in my case, and 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.

Paul Millerd: I think it’s easier to make money in a sustainable, long-term way doing stuff you actually like doing. That sounds so simple, but it actually would’ve 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 getting to know myself again. I made 50 grand the first year, because I was freelancing. Then I made 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.

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 it’s so crazy.

Now, if I had stayed in my previous path, I’d be making a lot more than I make now. But that path was not viable for me for becoming… I’d be so frustrated right now if I had to go back to work. An eight-month-old, I know you have a four-month-old. Wait till eight months old. They’re so fun to hang out with.

My Favorite Interview Question

Lenny: I can’t wait. You talked about this lower spend, lower expense life. What other tips and tricks do you have for people to create this space where they can continue living and 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?

Paul Millerd: 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’s very easy to fire. You can fire a contractor in a day. So if the company’s struggling, boom, you’re gone, right?

And so there is more risk, but if you’re 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. 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.

Favorite Recent Discoveries

Lenny: 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. 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, okay, we were going to lose all that money probably, but the bet is it’s going to lead to something really great.

My Life Motto

Paul Millerd: 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 saying, “This is money I’m investing in my life MBA.” 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 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 in 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. 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 choice. And so I earned a decent income doing it. So would I gift that to my future self to be happier? Yeah. So now that I’m in the present, receive that gift and be like, “Thank you former self for working that job.”

Advice for Podcasters

Lenny: It’s interesting. I could also flip it from the other way of your future self is returning to, “Hey, here’s some money to spend to help become who I’ve become.”

Paul Millerd: Yeah, exactly.

Wrapping Up the Conversation

Lenny: 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. I’ve spent all this cash.” Imagine there are stories of that. Is there anything you could share around those stories and how to maybe either avoid them or be okay with them?

Paul Millerd: 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 spur into action. People, we’re far more creative than we give ourselves credit for. 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. And so the ingenuity and creativity of people as soon as they 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. 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.

Lenny: And 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.

Paul Millerd: Yeah. And I wonder if you’ve found this too. Sometimes, the best way for me to write is to go for a walk, or to take a couple days off and just sort of reset. Creative work can’t be forced a lot of time.

And increasingly, a lot of work is creative work. Your work at Airbnb was ultimately creative work. You’re creating new products and offerings, in a whole new conception of an industry. You’re making stuff up. 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.

Lenny: Yeah, absolutely. Although I find with writing also, 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.”

Paul Millerd: Yeah. And even that though, 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.

Lenny: 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 this, the way you put it is people quit jobs after years of awakening and safely testing changes, kind of eliminating risks along the way.

Paul Millerd: 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 their resumes, volunteering, 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.

But I didn’t know why I was doing them at the time. But each one 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.”

Lenny: That’s exactly what I found. So 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. Say you have a call. Did that give you energy or did that sap you of energy? Do you feel more energized or you feel like, “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 what energizes you, what saps you 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 was 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’s very hard and there’s a lot of de-energized moments, broadly it’s like, “Wow, this is cool. People seem to really value this.” So 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, really powerful. And it sounds like really simple advice, but it’s really [inaudible 00:39:10].

Paul Millerd: It’s hard too. I think the pull to create a company when you leave a big tech company is so powerful. And what you’re saying is sort of crazy. You’re saying, “I just feel good writing. I’m going to follow that.”

Lenny: It’s not a popular path amongst my friends and family.

Paul Millerd: 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.

Lenny: The thing I found really helpful there, 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 something about that word makes it sound like, “Okay, cool, it’s delightful and cool. Tinker wave.”

Paul Millerd: I feel like that did not work with my parents. But yeah, trying different things. I always tell people you need a boomer compatible story for what you’re up to, as just give them something. Just say, “I’m an entrepreneur,” or, “I’m a business owner.”

Lenny: That totally resonates. I’d 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, just why it’s important to tame those fears, and then how one goes about taming these fears?

Paul Millerd: 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, what is the cost of inaction? And that was really powerful for me, and it sort of exposed a lot of the costs in the current state of what I was doing.

And so actually, I want to thank you. It’s funny, you messaged me as I was listening to a podcast you were on. I think it was the one with David Perell.

Lenny: Yeah, I slid into your DMs.

Paul Millerd: 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’ve realized is that I’m scared of creating a job for myself, but I sort of reframed the cost of inaction. What’s the cost of inaction is if I don’t actually hire someone, I’m going to drain all my creative energy, and that’s an existential risk to this path. 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 not good at it, but I found somebody that actually was good at it and I was like, “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 specific project-based fear.

Existential fears around health, death, importance, money, they 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. They sort of just punch you in the face. You’ll wake up one day and you’ll have an existential breakdown of, “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, “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, it’s worked this long. It’s probably going to work for a lot longer. There’s this concept of [inaudible 00:43:56], of the time something is going to last is usually as long as it’s already lasted. And so that always makes me feel better. The main thing I think about, is am I going to run out of stuff with a newsletter to write about? And it’s been four years now. I’m like, “Nah, it’s probably going to keep going for at least four more years.”

It’s very important to dance with your fears and really get in with them. If I’m afraid of not making money, it’s very reasonable that book sales will fall. And so I don’t know if we can sustain our lifestyle on 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 off the table. So I have no choice but to actually just be like, “Yeah, that fear’s going to be here. It’s going to be part of my life, and we’re going to have to just deal with it.”

Lenny: 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?

Paul Millerd: 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 was just so desperate to 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 I just sort of kept searching.

Lenny: 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 learn about what to do next?

Paul Millerd: 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’m going to see how it feels. And this is one of these things, super energizing. I love how I feel after podcast conversations. I’m going to keep doing it. I wasn’t aiming at success, but it was like, “I know I can keep doing the podcast and my newsletter.” I had that experience, that feeling from it, but there are things I’ve tried that I’m like, “Yeah, not again.” A couple consulting and advisory type things early on in my path, it was like, “Whoa, I need to build in protectors such that I don’t take a gig like this again.”

Lenny: 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 with this path. There’s so many things you could be doing and so many pulls that often, 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, “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’s 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. It’s easy to create bad jobs for yourself.

A really clear example of that is finding a niche that you don’t enjoy, spending time on 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.

Paul Millerd: So I’ve created a lot of slack in my life. So I’d say 95% 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 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 trying to figure out what comes next.

So we haven’t even talked about this, but I started this business strategy 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, “Ooh, 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 from years two to five when I started moving away from project-based consulting.

And so the game I was playing was make money from that, don’t focus on it too much, spend minimal time, don’t try to maximize for success. Create a self-paced course, because I am 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 mind-blowing. I published a book completely on my terms about what I love and loved the process of it. It’s so crazy.

Lenny: That’s amazing.

Paul Millerd: 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 that’s sort of taking over. I still have this StrategyU though.

So now I’m trying to figure out how to 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 wants to be an operator on this business. So if you’re listening, I’ve recently come to terms with 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 personal reflection and that journey.

Lenny: 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”?

Paul Millerd: Yeah, Twitter, paul@strategyu.co, or I’m very easy to find. My email is all over the place. But yeah.

Lenny: 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 that side of things?

Paul Millerd: I don’t buy that, because I’ve met most people and most people are like, “Hell no,” when they hear about my life.

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. And 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 under exploit 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 two sides to that, is one, most people would hate my life. And two, the world is becoming more giggified. So it could go back the other way actually.

Lenny: 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 very exciting lightning round?

Paul Millerd: I think the key thing 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, “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 after quitting my job.

But man, I’m 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. And a lot of people that 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 quit your job and get rich pitch. It’s very much like if you’re somebody that has a sense that there’s something more, there probably is, and it might be worth exploring.

Lenny: What’s the next step you recommend someone take to start exploring this pathless path? What’s something they could do today or tomorrow or in the next-

Paul Millerd: Read my book.

Lenny: Perfect.

Paul Millerd: So I’m very committed to creating resources for people around this. My podcast is all conversations of people on an unconventional path, and sort of the inner game of work. And I don’t talk about tactics and outcomes as much as really just, how does it feel? How’d you deal with that? Things like that. And so I do that in my newsletter, my podcast, etc. But just find people that are on interesting pasts 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 more wider diversity of people. I’m friends with people that 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. I was working all the time, and that’s all you’re surrounded by. So yeah, try to find the weirdos.

Lenny: Awesome. And for folks that want to check out your book, should I just Google The Pathless Path?

Paul Millerd: Pathlesspath.com. I just moved over everything last month.

Lenny: Okay, great. And then we’ll link to all of these things in the show notes. With that Paul, we’ve reached our very exciting lightning round. Are you ready?

Paul Millerd: I am ready.

Lenny: What are two or three books that you’ve recommended most to other people?

Paul Millerd: Yeah, one is called The Great Work of Your Life. Sounds like a cheesy title, but that’s actually a good resource for people that want to hear about people from history. Over the past several hundred years, different eras of people that really did design their life around work. It was really interesting, and that was a great book.

A second book I’d recommend, I actually really like Luke Burgis’ book Wanting. That was another great personal story/deep dive into a nerdy topic. That’s my favorite kind of book. That’s the kind of book I wrote, which was personal memoir plus nerdy deep dive. And Luke Burgis’ is really good too, more from a tech perspective, because he went down the startup path as well. Tut that’s a great book. That was my favorite read of the year.

Lenny: What is a favorite recent movie or TV show?

Paul Millerd: I struggle to answer this, because I’m not watching much TV. I did watch the Anthony Bourdain documentary. That was excellent. Talk 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. That was a powerful story worth watching.

Lenny: 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?

Paul Millerd: I’m always curious about, what makes you come alive? I want to work with people that are alive, and 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 this self-employment journey. She’s writing and exploring all these ideas. So yeah, I’m always looking for that energy first and skills second.

Lenny: Is there a favorite product you’ve recently discovered that you love?

Paul Millerd: I really love the Nuna travel stroller. Super convenient for traveling.

Lenny: We don’t have the travel stroller, but we have the Nuna car seat.

Paul Millerd: Yeah, 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 ChatGPT, I just created my own GPT to do podcast show notes automatically for me today. Took me an hour to train it, and it is incredible, so that’s amazing.

Lenny: That’s awesome. I don’t know if folks know, but there’s a lennybot.com 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, where you can kind of train your 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. Do you have a favorite life motto that you find yourself coming back to, sharing with friends, finding really useful in work or in life?

Paul Millerd: One, coming alive over getting ahead. That’s something I keep coming back to. I’m default skeptical of chasing achievement, and I use this to remind myself that it is about that personal energy versus extrinsic outcomes.

I’m very convinced from my own life experience that the 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. And I basically repeated this mantra to myself right before rejecting the book deal. It was like I did not feel good in the conversation with the people. They talked down to me, they told me that I probably wouldn’t succeed, and it was like coming alive over getting ahead. Don’t need their prestige.

Lenny: Final question. You’ve been podcasting, I think, for six years. What’s your best piece of advice for someone that wants to start podcasting, has maybe already been doing podcasting like myself, or being successful or anything along those lines?

Paul Millerd: Yeah. I think if you want to podcast to make money, it’s probably not something you should get into. 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. 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, don’t do it.

But yeah, I would recommend more people start podcasts. I’m against… The New York Times says there’s too many podcasts, but I take the opposing view. I don’t think there’s 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. Even if you do something like interview your parents or anything, 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.

Lenny: I feel like when people say there’s too much of say 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.

Paul Millerd: 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.

Lenny: And also, the best stuff often comes from just doing it for yourself and then realizing, “Wow, other people might find this interesting.”

Paul Millerd: 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.

Lenny: Speaking of that, Paul, we’ve been on our own pathless path. 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 in your journey, and how can listeners be useful to you?

Paul Millerd: Yeah, so I’ve been compiling a lot of my more recent stuff under pathlesspath.com, that will link you to my podcast, newsletter, community, and book. And 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 that want to gift it and do book clubs or things like that. And happy to send it at the author rate, which is about $4 per book.

And yeah, I am starting to explore the potential of selling my StrategyU business or finding 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 that 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.

Lenny: Go buy The Pathless Path, available all online bookstores, I imagine. Paul, thank you so much for being here.

Paul Millerd: Amazing. Keep going on your path too. I’m really inspired by how you’re approaching your path and sharing your reflections too.

Lenny: I appreciate that. Bye everyone.

Paul Millerd: Adios.

Lenny: 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 lennyspodcast.com. See you in the next episode.

Glossary

Reformatted by reformat_english.py