226: Paul Millerd — Walking The Pathless Path

wonderful mind expanding read for me. I think it's a great metaphor, like the whole book and every concept in it. And it's likely one that my audience of founders and creators who are listening and people who are generally are just ready to go on their own journey, are ready to learn about. So please tell me, enlighten me and the listeners, what is the pathless path?

this 10 years ago. That's also me. Like, I wish I had this. And I think it's my own sense making of what is life look like not centered around work. And sort of my accidental stumbling into, oh, there's a different mode of life you can exist in, in which you actually like your work that will make everything else seem silly and nudge you to want to build your whole life around that. And that's sort of what I discovered throughout my journey. And it's still pretty, not, I mean, it's still not a

widely held view of the world. And it's just like, wow, I feel like I have this secret knowledge. Other people are telling me the same thing. I need to get it out there into the world. And that's what I did with the book.

it, right? Because I've been trying to fight narratives that other people try to instill in me for most of my adult life. And now that I see this in a cohesive unit as the book, it feels like yes, this is exactly what I've been doing. I'm glad there's another one. There's something that you wrote in the book that I really enjoyed, it's like find the others as one of the kind of the tenants of going on that path, right? Generally, you present the idea as the default path that everybody is

supposed to take. And there's the pathless path that people take because they have chosen not to go with the default route. And in the default route, everything is kind of predetermined and people tell you where to go. You know where you need to go because you have these goals already set for you. And if you take a path that is less like this, going at it alone becomes complicated, right? It's not as easy as follow the career ladder that somebody else is laid out for

you. So how do you find the others? How did you do this? Like you definitely you made the choice at some point to quit and get into this nomadic lifestyle that you had at some point in your life. How did you find the others? Did you look for them? Or did they just come to you?

paths. I didn't have the imagination because I didn't see people around me and say, oh, there's somebody like me doing something different. And I could be like that. Eventually, I just got so fed up and I left. And I felt really alone. Like I couldn't communicate what I was going through. It was like, people are like, aren't you worried about income? That's all my default path friends would say. And it's like, yes, of course. But I'm more afraid of having to go back and get a job.

And I sort like I think in my first year I struggled but I started sharing more. I was actually living out what I was claiming to care about instead of complaining about my boss or company and I started attracting people. It was very slow at first. 2017 was a much harder time to find the others. Now, it's way easier with communities like indie hackers, Nomad list, Twitter, especially. But it was hard back then. I met some

people at a conference in New York. One thing led to another and one of those first people I met actually led to the naming of my book. So it sort of speaks to the serendipity of how these things happen. Somebody I met at a conference said, you have to meet this guy, Steven Mosley and he had been doing a podcast for years about an unconventional path called Unstackable. This is

like 10 years ago. I met him. Not only did he eventually take over my lease in Boston as I moved to Asia, he said you have to go to World Domination Summit. This is where the unconventional people are. I went there. I made like three or four great friends. One of them was Johnny Miller. And Jonny Miller, the second day after I met him, he walks up to me and he goes here, you have to read this book. It was David Whyte's The Tree Marriages. And in that book was the phrase, the

pathless path. And David Whyte writes about this pathless path is like, you're not supposed to know what this phrase means. But it sort of takes over everything and becomes an explanation. And that phrase, then when I met my wife later, was the phrase we kind of gravitated to together to sort of describe our shared journey. So it's kind of funny how these things happen. But without finding the others, none of this happens. And none of it

is fun along the way. I would have just been like building a business. But really, I've wanted to build a life and that's what my book is really about.

ones, are quite powerful. I think for me, when I went to MicroConf, the first couple of months after we sold our business back in 2019, I didn't expect this to be a like a pivotal point in my life. And it's not even that MicroConf was a conference. It was way out of where I was. I was a software engineer building a software business. MicroConf is exactly

for those people. But what I learned there was like standing on stage and telling people my experience, sharing what I know, helping other people find their way, that's something I enjoy. Because I didn't know that about me before. I didn't know that I wanted to write. I didn't know that I wanted to, you know, speak and teach. But just getting the opportunity, being invited onstage to give like an attendee talk wasn't even scheduled, right? If the idea was, oh, yeah, sure. Talk about

what you just did. And I did and I liked it. And ever since then, that's what I've been doing. And I met people that just like you said, that have increased just the whole the potential that I have in the world by just exposing me to other ideas and other concepts. It's funny that that is something that I can resonate with, with my own experience. It's really nice. It's nice to see that if you just choose to act, like the impetus of action just pushes you forward to explore these

things much more. I really like that.

was changing things up. I was only changing jobs in the same career narrative and trajectory of my life, which was really freaking boring and dumb and not aligned with what I actually cared about. And eventually, over time you become cynical and disconnected from what you care about. So I think what happened at those series of conferences, it was multiple conferences is that I got rid of that heavy weight over me. And I would just show up and say, I quit my job. I'm freelancing, a.ka. I don't

really know what I'm doing. But the magic of that was for the first time I met people not based on how much money I was making or what status rung I was in. I was meeting people on shared vulnerability, right? And this is the magic of meeting other people on unconventional paths is you can bond over your shared, not knowing what the hell you're doing this. And that leads to some really powerful friendships. And what I found is

basically I've bootstrapped a life. And because of that the people around me, they inspire me to keep going bet on myself, believe in myself to write books, like models like you. You've written multiple books. It's like, oh, if Arvid could do it, I could do it, right? And it's so arbitrary but it's so

just see you for the first time and see that it's possible. I think you're right about this, like in your book, even at a very early stage, when you were still, like full time consulting, like a business consultant, you started seeing a part time consultants like freelance consultants that just came in for particular projects and then left again, who sometimes worked for half a year and then went half a year and traveled or, you know, worked a couple of days a week and did

other things as a side project. And I think just being exposed to this, sometimes can just change the way you think about work. I really, really appreciated that about how you wrote about your own journey. It was very clear that you just you leveled up your enlightenment about what it means to make an impact in the world, right? You had all these goals that somebody else set for you because you were surrounded by people who were following the regular default track. And then

you just saw other people who had different goals. And all of a sudden, it became obvious that oh, you don't have to follow that singular set of goals. You can have your own goals. It's really nice. And I think the phrase that I want to talk to you about because I found it quite the thought of it invigorating in terms of what we currently are experiencing in the world of entrepreneurship. You call people who go on the default path, hoop jumpers, like people who jump through hoops

that, you know, are set out for them to jump through. And I was wondering because you know as bootstrappers, we are a small indie community and we don't really have much media representation. Most media representation around our field is VC funded businesses. It's like the big I need to be a massively funded entrepreneur to be an entrepreneur. And that to me sounds again, like hoop jumping, like you need to get the credibility that an investor gives you. Are we chasing the

wrong dreams? Or more or less is the media attention, just another hoop jumpers and that makes us also want to jump these hoops? What's your perspective on this?

story did not pass the boomers sniff test. Like people were like, what do you mean? What's your plan? You know, but if I had said I'm starting a company, they probably would have been like, oh, yeah, that's a thing people should do, right? Just because it is out there. It's a known thing, maybe less so on the east coast, where I'm from in the US and more on the west coast. But yeah, that's the thing people do. And there's a

legible path. You raise money then you raise more money. Then you hire a team, you scale, you go big, you exit, and then you have your existential crisis and then eventually reach out to us and ask what the hell am I doing? But, yeah, it's a legible path. And I think I didn't write about this in the book, but I call these hustle traps. And the core issue people are trying to solve is that I feel like I need to do something. I need to be

special. I am a worker in the world. And where I come at it in my book is starting from the assumption that we are in fact not workers. There are some people that are possessed with other worldly effort and like enthusiasm toward extrinsic goals. Most people are not those people. I suspect you and me are not those people. We don't have that, right? We can only do things we're actually interested and excited by, right? So the mistake is taking other people's goals for your own. That's what

I call a hustle trap, right? You actually need to start from within. And the problem with that is to go within in today's world, which many people have not done early in their life, it's been undermined by school and jobs, is that it usually involves a season of wandering and non doing. It involves getting lost to a degree, trying random things, taking time off. And that does not fit the story in people's head about what you're supposed to be doing in life, which is essentially

working all throughout adulthood, right? So you need to go within and figure out what actually fires you up. If starting a company is the path for you, fantastic, but don't do it in a very, like short sighted way. I see a lot of people quit their jobs thinking they want to start a startup, but then they have a taste of space and looseness and lightness in their life. And they're like, ah, not for me.

was the not at leisure part. So you can be at leisure. That was the general idea for most of humanity's life, that you work as much as you need to be able to not have to work, which has been completely perverted. And now even the word leisure has a negative connotation as if you are avoiding work, which is this glorious thing to do. So what is the difference for you between non work leisure and I guess laziness? That would be like the most negative version of that that I could find. Are they the

same? Or do they differ?

sloth, right? So I think when people are talking about laziness, it's really a byproduct of building your life around too much doing, right? You've lost connection to what matters with you internally. Whereas, like leisure is a whole nother axis. Like leisure can be passive, that contemplative mode. Maybe you don't do anything actively for weeks or leisure can be the active mode. I find writing to be incredibly leisurely. It's delightful. I love it. And when I don't feel

like doing it, I just don't do it. And I feel connected. I feel energized while I'm doing it and it doesn't feel hard. It's not hard effort wise. It's hard in like a skill wise. It's like, oh, it's gonna take me a lifetime to get good at this. But it is not hard in terms of like aligning with my natural flow of life.

that did everything. So you could live a life of you know, of optionality, of choice, of not being like forced into anything. But you say your dad worked like 10-12 hours a day for 47 years in the same company just to empower you to do what you're doing. Did he have a choice? Or are there people like him out there that should have the choice but don't?

suffer. And that doesn't perfectly make sense. Like we're not trying to pass on suffering, right? And the challenge, too, is like, my father was working in manufacturing, building stuff, working on the factory floor and he actually liked it. The problem is, too many people in today's world are actually suffering doing absolutely meaningless work, producing reports that don't need to be re produced for bosses that are totally unsure why they're doing what they're doing, but they're

just going along with it, right? And a lot of people I call this like self gaslighting is like, don't you think it's wrong to like actually pursue your own path? And it's like, that's kind of weird. Like, if you have the possibility to potentially show up in the world in a larger and more loving way, like, why not do it?

default path, you're a good egg. And the moment you go and you go off the beaten path, you're a bad egg. And you consider yourself one because you think other people think that of you. But in a way, you are way more selfless by being out there and empowering and helping people than the people who climb the corporate ladder. Why do we still perceive it so obviously, wrongly, in the society?

work, there are more paths and possibilities, right? And from what I've seen, people that are betting on themselves working on their own, I'm talking like indie consultants, solopreneurs, self employed, they're owning all the downside of their path reputationally and financially and that typically makes them more vulnerable. And from what I've seen, even though many of them have less money, much more generous. And I don't know if

there's a self selection thing with that. But I sense it has something to do with the vulnerability of being on a weird path. And so yeah, I think, for me, I was incredibly selfish on the default path because really, I couldn't come up with a point other than I would make more money and that would make some parts of my life easier, right? But I'm honestly a nicer person now. I think I'm more generous. I think I've grown much more in the last six years than I did in the first

ten after graduating. And for me, it's been just a beautiful opening of my life and to meet other people like you who are embracing that open spirit motivates me even further.

know because you could make more but you're not. You are choosing to do something else, but still in our community, indie hackers, creators, like MRR figures and graphs that go up into the right. They are all super important still, but it's still what we project outwards. Like even in our solopreneur community, we kind of act like we're these huge businesses on

the growth trajectory to wherever, you know. It's so weird how we use these default path mental models and kind of try to cram them into our unique own pathless path like life that we have. Does that mean that it's a continuum? Or does it just mean that we are kind of looking at the wrong side of things?

And if you look at that, like nobody is like, I want that

just makes people unhappy. Because, like, they'll look at my recent income be like, well, you can say this because of this. And it's like, well just go back. Like you can read all my newsletters.

way, right? Like, had they read the book?

the money will inspire them, that's so cool. Because making a money from a book is pretty amazing. Like other stuff can get super scammy like people can hack together a course and put together something pretty scammy. You can't fake your way through writing a book. money on. Like that's the one thing where I'm most excited to make money is because I know other books are gonna be written because of it and I can't wait to read them.

altogether. That is one of the best things that I think ever happened to me is to see that I actually gave somebody, it's like what you said, you have this wonderful phrase in the book where you talks about permission. You just have a line in there, I give you permission to do whatever you want. I paraphrase, but you kind of say if you need permission, I give you permission. And sometimes people just need this. They just need this little push of you know, you can write. Like you

literally write every day when you're on social media. You don't consider it writing, but it is writing. You're trying to teach people something, right? Might just as well consolidate that into a blog post or a newsletter or a book. So do it, you can. So I allow you to do this. I love that part of the book because I hope that this particular part just kindles this little reframing in people's minds. And sometimes that's all you need.

know something or like I have some special abilities. It's like, no, I just stupidly did something I enjoyed for years, didn't expect anything from it. And now I'm having some serendipity and luck. I have no idea how to do that. Like I couldn't have come up with a strategy. And that's why my book has no how tos. There's like some high level challenges at the end. But there's no how tos because the truth is the only path is your path.

And that's the last chapter in your book like these eight or nine steps, just one of them is reflect like, obviously, right? That is something very basic. But if you forget to actively think about where you are and where you want to go, if you just follow whatever other people give you, well, then you'll never find your own way. So they are actionable steps. But there are unspecific enough for people to find their own

version of it. I really like that. And what I absolutely like about your writing is you write about writing, which is always great. It's always great when people write and then write about how they learn to write or how they found writing. And for you, it was related to your health issues that you had at a certain point, right? It was kind of cathartic. You were

dealing with pain. You were dealing with struggle and you wrote your way out of it and you have this Quora post, example where you wrote a lengthy Quora post a reply to somebody's question about these health issues. And you notice that the responses coming in where people were like, extremely happy that you gave them the opportunity to learn from your experience. You were empowering others by writing. That is something that I really appreciate, like, how important is writing to you?

life, the prime of my 20s. I'm more or less lost two years to a day to day suffering of physical issues and the mental challenge that went with that. And yeah, but I didn't notice at the time that a reading maybe could be something that's part of my life. It was always just like, yeah, I'll do it here and there. And then it snuck up on me over the next three years when I returned to work. I wrote on the side and it was where the flood of energy and sensemaking of what was happening to me was

going and yeah, it's such an amazing thing. I mean, so many people have fallen in love with writing. And when you do it, there's really no choice. Like you have to write. And for me writing is easy because like spending time with my daughter writing was only thing I felt like I had to do. And I just missed it. I don't have a complete life unless I'm writing. I don't think all the other work, ah I'm fine. I don't

need to do it. I rather go break broke and be riding in the middle of nowhere at a beautiful mountain or something.

think you want and what you think you need. We could unravel this. That alone was a wonderful way of expressing burnout because it exactly describes what I went through. But it was the end of an era for me because we were selling this business and I was mid burnout. And I started writing. I needed some cathartic way out of this. I was like, constantly under stress, permanently anxious, the only technical person in the business who could deal with whatever may come and we had 1000s of

customers. So there was always something going on. I had a lot of, you know, I was overwhelmed. And I was mid burnout, close to burnout. I still don't know, I never really diagnosed it. But I was there. And I wrote this 10,000 word piece, the first thing I ever wrote because English is my second language. And I never really wrote much in terms of articles or anything, but I just started writing about, I think, like mental health issues for bootstrap CTOs. I think that was the

title. And I just pulled out everything, like every single thing that I felt went onto the page and then never published it. Like because we were mid selling the business. I'm not going to publish an article about how hard it is to run a business while you're trying to negotiate a good price. That doesn't make sense. But what it helped me was to crystallize my thinking and I think that's what writing is, in its purest essence is intentional thought. It's not thought that just

happens. It's thought crystallized into a shape, we can retrieve it and mold it and shape it, right? That's what writing is, which is also why I will never give up writing. It's going to be just like you, the last thing that I give up. I will join you at that pond or that mountain that you're hanging out doing. I'm just going to co write stuff together because that will be like that is why I live is because I can

do this at this point. And later, a couple of months after we sold, I revisited this article and I thought I quite enjoyed this not just for the catharsis that it gave me. But because I solve a couple problems while writing the article. I thought about a couple of scalability solutions, how to deal with certain, you know, customer service problems and automations that all came to me while writing and I thought

oh, I'm gonna keep doing this. This is fun, started my blog, started writing, started newsletter, wrote a couple books. That's where my journey came from, from a mental health issue that I wrote my way out of just wanted to share that with you because it feels like you very similarly found writing to be the catalyst for a journey of teaching, which is kind of cool. Just wanted to share this.

absolute success. Why? Because in the final months of writing it, I sort of like broke down in tears and like, I've connected a few pieces in the book and pulled some pieces together, wrote the introduction. And it was just like an enormous release of tension and realizing, like how scared I was to really admit that this shit matters, like being like living a life where you do what you claim to care about. It matters.

And I was so scared to say that. I had all these voices adults I grew up around who would cynically say oh, you're just naive. You got to work, buddy. Like I had all these voices in my head and I was small and I was scared. And what the book enabled me to do is actually show up in my own life and not be afraid of what people would say, like I was living as if it mattered, but I was small and scared, right?

then it's scary. It is a scary thing. Yeah, that's kind of why am I mentioning this year because you kind of have to find out. I think that's your Oprah quote there. You have to find out who you are and then do it with purpose, right? The idea that

They were raised in the German Democratic Republic and to them finding a job and not talking about what you're doing because otherwise people might get jealous, that was the epitome of a good life. And that was what they instilled in their kids and what their kids instilled in their kids, which is me. So I had to do a lot of unlearning when I became an adult, of the things that were taught to me as this is how you live a stable,

safe and good life. And then finding out that I'm actually a different person that will openly share a lot of things that my grandmother, she already passed away. But she would pass away again, if she knew how much I share about my life. That's kind of how I feel. She would probably like it still because I could explain it to her and she would see the resonance that I'm getting. But that would freak her out. Like whenever we talked

about money. And we rarely talked about money in my family, it was like never ever mentioned what you have because somebody else might take it because that was the system that they came up on, right? And unlearning this, whew, quite the challenge and probably a challenge for many people today who come from, like, you know, like, multi generational immigrant families that come from a different culture and that kind of stuff.

natural way. For our generation, living out your parents' idea of how the world works is the normal route, right? Because our world is so safe. When the world isn't safe, you're an idiot not to adapt. When the world is safe, if you don't adapt, you're likely going to please your parents and make them feel comfortable. It's been surprising to me how many people get uncomfortable just based on my life choices even if I'm not talking about it. They'll unprompted bring up like, don't

you think like people should work in a job? And it's like, I didn't say anything. What are you talking about? I think people should do what's best for their life.

not live that life. Yeah, I love what you wrote about with the boomer generation and like the how the life that they're leading is the anomaly. I think that's what you just said too, right? We're

And then there's these weird 50 years or so, where everything is great. And we consider this to be the new normal. I'm quite frightened for the financial systems of the future because I think the systems we have right now are built on our expectation that this great phase is going to keep on growing and going to establish itself forever.

Yeah, and this is the weird thing about like, saying, people are privileged to take an unconventional path because when you take an unconventional path, you pretty much always face criticism, lack of lack of support from family members, you lose friendships. And it can be pretty shitty. And this comes back to what we were talking about at the beginning, which is that this is why finding the others is so

important. And this is why I share my work. And I'm out there in public because it's a generous act to share your work because you might let the others find you, right? And

your essence. It's incredible what happens around a person that's found that. And at a deeper level, when you're around someone that's really in their essence, really in their mission, you can feel it in them. There's something about their life, that you look at it and feel yourself lean forward in your chair and you feel like you can just feel the depth of it and it starts to wake you up to what's possible. I think that's it. That's everything, like live true to the track of your own life.

only thing you could fathom changing, right? That reminds me so strongly of the overton window that we have in society, like the things that we are allowed to discuss, right? There's stuff that was taboo on the left and taboo on the right and everything in the middle. You're allowed to talk about it and you're allowed to discuss it and criticize it. But anything beyond it, beyond those barriers to the side, that's off limits. And I think there is a mental overton window for how we live

our life. And we talk about a lot like, oh, career progress and I'm gonna go to work in that firm. And then I'm going to find that job. I'm going to go to this school to get these kinds of degrees. And you have a lot of choice and a lot of option and people min max all these little things. But just in that really narrow frame, what you do and what you found is a way to

expand the window. And I think that is incredibly powerful. And I'm extremely grateful that you're sharing this with me today, obviously, but in the book and in your newsletter, in your work. I want more people to be exposed to this, which is why I'm talking to you, which is why I'm highlighting your work wherever I can. And I want people to find their own way so I can learn from them. So that's kind of my selfless approach to

sharing. I think that's one of the last things you say in the book as well as like, yeah, I'm doing this not just out of the goodness of my heart, although there is so much generosity, but it's also something that gets back to you. There's reciprocity in this. There's an actual relationship between the people that are on the journey and that, to me is sharing in public, building in public, teaching in public. That gives you this reciprocity where you get something out of it

eventually, it's the long game. It's the infinite game that you play. And sorry, you can probably tell I'm excited by this because I feel this is something that just if more people even just consider it for little, that will massively impact their life. So yeah, thank you so much for being here today. I cannot express how much I enjoy this conversation with you.

can't promise you'll make money from it. But you'll find a different relationship to self in the world in which you might go places you can't even imagine.