Walking the Pathless Path with Author Paul Millerd
Paul Millerd is an independent writer, creator, and consultant. He has been self-employed for almost five years after spending many years working in consulting. He recently published a book, The Pathless Path, about his experiments with designing his life and improving his relationship with work.
Paul joins Chris Sparks to ask the dangerous question: What if we threw out the default scripts of success and carved our own path? How would our relationship with work transform?
This is a conversation about living in alignment with our values and doing meaningful work towards a meaningful life.
See above for video, and below for audio, resources mentioned, and conversation transcript.
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Topics:
(01:56) What is "the pathless path”?
(14:36) A collaborative path
(27:03) Overcoming career fears
(48:22) Signs of progress on the pathless path
(53:34) Finding trust in yourself
(01:07:32) Letting go of default scripts
Conversation Transcript:
Note: transcript slightly edited for clarity.
Chris (00:05): Welcome to Forcing Function Hour, a conversation series exploring the boundaries of peak performance. Join me, Chris Sparks, as I interview elite performers to reveal principles, systems, and strategies for achieving a competitive edge in business. If you are an executive or investor ready to take yourself to the next level, download my workbook at experimentwithoutlimits.com. For all episodes and show notes go to forcingfunctionhour.com.
It is my pleasure to introduce Paul Millerd. Paul Millerd, author of The Pathless Path, is an independent writer, freelancer, coach, and digital creator. Paul spent several years working in strategy consulting before deciding to walk away and embrace a pathless path. I've been really enjoying my conversations with Paul recently about our relationship with work. Can we make it more healthy, and how can we be thriving, more meaningful, fulfilled human beings? We all subscribe to default scripts of success, whether we realize it or not. We often choose our career paths based on prestige, and we can often end up selling our happiness and freedom for money. Paul asked this dangerous question: what if we threw out these default scripts? What if we carved our own path?
So, this is going to be a conversation about this. About making our own path, so that perhaps we can live more in alignment with our values, both that we get in touch with what's more important to us, and that our lives are a reflection of that. So with that in mind, let's join Paul to explore making our work and life more meaningful. Thanks for joining me, Paul, really excited.
Paul (01:52): I'm excited to be here, Chris. I loved that intro. I'm pumped for the convo now, too.
Chris (01:56): Good, good. So, let's hop into the book. The Pathless Path. What does "the pathless path" mean to you?
Paul (02:05): "The pathless path" was a phrase that was first introduced to me in a book. It was handed to me by a friend at a conference I went to in 2018, my friend Johnny Miller. We had this really powerful conversation. We had been on similar paths, both about a year into a new journey, and the next day he just walks up to me and hands me this book. He goes, "You need to read this." It was David Whyte's The Three Marriages, and in that book, I found a number of things. One was just a different language for thinking about work, and another was this phrase of "the pathless path." Now, I think it's a Buddhist phrase that's been used in many different areas, but it was something that instantly resonated with what I was experiencing. I was feeling a bit lost, but also had this deeper sense of I was heading in some sort of sensible direction. So I think this phrase really helped me make sense, and as I write in the book it was kind of a release for me, where I was able to for the first time kind of soften into this journey about a year and a little more of leaving the corporate world and being self-employed.
Chris (03:14): So it put what you were doing into a context that made sense to you. Maybe it gave you a little bit of permission to continue to walk it.
Paul (03:23): Yeah. And the first year of self-employment, I more or less quit without much of a plan. I was really seeking to just escape work. I had done some experiments and creative things on the side and had tapped into this energy to kind of explore, have a little more adventure in my life. And I had enough of that, and then this really bad experience in one of my final jobs where I just wanted to run away. And in that first year, I totally underestimated how weird and different it would feel. I didn't desire to become like an entrepreneur, I really was just trying to reinvent myself. I didn't really know what I was going to do.
And I experienced all these things, and now people don't really know what you're doing. They ask all the time, "Why are you doing this?" Whereas when I was in consulting, nobody asked me a single time, "Why are you doing this?" It was just so obvious, and I had fit into models of success, that I hadn't even thought to ask those questions myself. So being self-employed, feeling a bit lost, feeling like I needed to prove, like, what I was doing made sense. And I didn't really have many friends in that first year, taking alternative paths. That's changed a lot now, but Johnny was really one of those first friends too, where the things I was telling him—he was like, "Oh, yeah, me too." And I didn't need to kind of defend myself, and there was just kind of a softening into that too. So the phrase combined with meeting him really was the start of meeting a lot of different people and really leaning more into embracing this unknown journey.
Chris (05:09): Do you find that helping to put it in this context of a possibility was a really big shift for you? It seems like, you know, reading your story that many of the choices you've made were the obvious ones, where once you decided that you wanted to do something with prestige or do something that allowed you to work with leaders or even just what your friends and peers thought was worth doing, that for a long time it felt like maybe your decisions were made for you. When did that start to shift for you?
Paul (05:48): Yeah. So I think I grew up with a very narrow conception of what life paths and success look like. Most people around me had full-time job sort of lives, middle-class families, all structured in pretty much the first way. So my first exposure to different opportunities and paths was really in college, and getting exposed to these elite paths was new and exciting for me. So I think there's always been this draw towards paths beyond what I thought was possible. So when I was first introduced to strategy consulting, for example, that was far beyond what I knew was possible. And that made me wanna go after it. I think after a while—It took me forever to realize that what I was really after was like this broader search for possibility. And it took me a while to realize that that was something I was searching for. I think in my first couple of years I was just trying to find my footing in my self-employment path and try to just get some distance and kind of recover from being so hardwired into a certain way of thinking about work in my life.
And it wasn't until I think I had moved abroad about a year and a half after starting my path, I arrived in Taipei. I would cut costs to try and extend my runway forever. And I realized I'm just playing a cost-cutting game and trying to extend the runway forever. That wasn't exciting for me, and it was when I shifted to, "Okay, I'm not gonna try and cut costs, I might make investments in myself, spend money on things that make my life better." I started opening up more and more to possibility.
So when I was quitting my job, it was—I definitely had enough of a crack of, "Oh, there is something out there worth finding," but it wasn't until even a couple years later that I really stepped into that and started owning that possibility space. And now it's so exciting. But this is like five years in, and it took me a while to get here.
Chris (07:48): Talk to me about the "inner ring." There's this desire to be on the inside. You mentioned, when you got to school, the concept of these elite circles, and presumably only knowing that that was a possibility but having access to it through consulting—Why do you think this desire is so alluring, and perhaps why it can lead us astray?
Paul (08:13): So, I didn't discover this idea until later. I was reading this essay from the 1940s, and I was fascinated reading it. It put words to something I had fully experienced in college when I found out about consulting. People told me, "Oh, they only hire from elite schools." Like, Harvard, Yale, top public schools like Virginia. And the reaction is like, "I'm good enough, I could be part of that, why can't I do this?" And I started networking, reaching out to me, people tell me, "Paul, you can't do that, you didn't go to the right schools." That just made me want it more.
I think everyone's probably experienced this at some point in their life. They've either been left out from a sport or people tell them they can't do things because of certain things. Like I think especially like young men when you hear that, you want to fight, you want to prove yourself, you want to feel special. And I think that really drove me. But as soon as I broke in, I really kind of fumbled around 'cause I didn't have that drive to go anywhere anymore. I had kind of solved that, whereas a lot of people around me hadn't fully solved that, they wanted to go further. They wanted to be a senior executive, they wanted to be a partner, they wanted to be at a level in an organization where they're going to like Davos and things like that. All that stuff was like, I don't know. I don't really care about that stuff.
So yeah, it's also this trap on paths we're on, too. Right? We're on these solo-preneur paths, and it can be very easy to think, "Oh, I wanna be like that person," but that's probably one of the biggest traps of all, because the only way you're going to succeed on these paths we're on is to make it our own journey.
Chris (10:00): Yeah. We all wanna be the rock stars but we don't wanna go on tour in the crappy van for a few years, or all the things it takes to reach it. We just want the final outcome. And it seems like a lot of times just to prove that we can do it, whether we're proving someone wrong from our past or just proving it to ourselves. I know that it's a realization that a lot of the things that I've done in my life were in fact just trying to prove things to other people, almost a performance piece. You mentioned that the façade started to fall away when you didn't see that next thing you needed to prove to yourself, you didn't have that next one. One that comes to mind for me when I became disillusioned with the corporate path, I was interning at Nationwide, and I had the opportunity to work on a project with the CMO. I was that annoying ambitious kid who wanted to be CMO of a Fortune 500 by age thirty. And I was like, "Great, I have thirty minutes of this guy's time, I'm gonna pick his brain, and he's gonna tell me the secret to being in his seat twenty years earlier."
And I realized pretty early on in the conversation—I mean, not saying this needs to be the case, but you know, he worked very long hours and was on his third divorce, didn't see his kids, obviously stressed and was starting to age prematurely because of that, didn't feel like he was finding a lot of fulfillment but, you know, was sort of trapped by continuing to just climb the ladder. And it made me realize, like, "Well, I can reach this place, but is that really what I want?" And that's kind of the most dangerous thing, it feels like, is that we realize we can achieve a lot if we really put our minds to it, but if we don't pause to think, "Hey, is this actually what I want," we can find ourselves in a very privileged, prestigious position that wasn't actually what we were bargaining for.
So, when did this narrative start to shift for you, where on the outside all of your friends were saying, "Man, Paul is so successful, look at what he's doing," on the inside you're probably feeling some of this dissonance?
Paul (12:06): Yeah. Early in my career, especially in consulting, I loved it. Like in most jobs, you're getting promoted, you're learning a lot, you're growing, you're progressing, you have this feeling of growth. Right? And then I went to business school, I started working after, and then I think it was really the three or four years before I left my job, like, I was making more than I thought I needed, I was happy, but everything around me was like, "Well, you should care about this, you need to go for this position, you need to be progressing." And I didn't care about a lot of that stuff. I didn't want to succeed by impressing some senior executives. I really liked just doing the work, and I've more or less just created a path now where I get to just work on stuff directly. I don't have to manage stuff. I don't have to present to other people.
And a powerful thing was my last job. I was doing consulting to boards, and one of the things we did, I did about ten to fifteen CEO succession projects, and I kind of had a similar realization to you. I was working with these CEOs of Fortune 500 companies, and it was pretty obvious what made them successful, or reach those positions. It was the most important game in their life. I talked to one guy who was about to be named the CEO of an insurance company. We interviewed him, we did like a three hour interview, and he told us. He said, "At twenty-five years old I decided I wanted to be CEO." He said, "I realized that if I worked in six different functions, three different geographies, and moved jobs every two years and always made sure I had mentors supporting me that I could do it." So he was like, "That's exactly what I did." And then he walked us through his career, and that's exactly what he did.
And to me that just didn't seem—It was like, "Yeah, I get it. I have no interest in—We're not wired the same." So it was so obvious, like, at the time my path was running out. But the biggest challenge that kept me from taking an alternative path is I had no conception of any other possible life. All my friends were working full-time jobs, everyone in my family was working full-time jobs. The only idea I had was to become a freelance version of what I was doing, which is what I did in the first six months after leaving my job.
Chris (14:36): The story I always loved to share, because I certainly was very much on the default path—When I tell people about my poker career now, they're always like, "Wait, it took you how long to become a professional poker player, and you were making how much?" And just the concept that, hey, I can play a game for a living and this is something that I can do, it never even crossed my mind as a possibility until I actually was in Brazil and I found a group of other players kind of hunched over their laptops in the lobby. You have, you know, waves crashing on the shore of Copacabana Beach in the background. I'm like, first I'm like, "What the heck are these guys doing hunched over their laptops? They should be on the beach. You're in Brazil." Then I realized, "Wait, this is just another day for these guys." Like, well, I mean I look like that, I could probably do that too.
But until you encounter the others you don't know it as a possibility. And you mention your relationships, this starting to have more calls, getting more involved in a community. How do you find the others? How do you turn this into a collaborative path so that you're not walking it alone?
Paul (15:50): Yeah. I joke that my first friend was Seth Godin. Because I had just read his books and followed his path and he seemed like a man later in life that was still fully energized and alive. So I was terrible at finding the others. I first sought them out in conferences. I would reach out to people on LinkedIn, that was the major social platform I was using in 2015 to 2017. Now, I mean, through a podcast, Twitter, newsletters, it's so easy to find other people. And one thing I always suggest people do is have a path-pro conversation. And this has been really eye-opening for people. And I just tell people, "Pick somebody ahead of you on an interesting path and just reach out to them and say 'can I interview you? If not, can I send you a few questions to think about?'"
And it's something I wish I had done more of earlier, to kind of sample and get ideas from different people's paths. But it can be game-changing to realize, one, these people are also still looking for friends, and, two, they can just tell you all the mistakes they stumbled upon and all the lessons they learned, all the things they wish. And best case, you just make friends with these people.
Chris (17:11): What role did values play into your decision to walk a different path? If I remember, you had this list of things, priorities that you were evaluating yourself on. Like, one was an adventure. And you're like, "Man, I don't feel all that adventurous." Like, how did this play into your decision to change course?
Paul (17:32): Yeah. In business school I wrote this letter of what I thought leadership was, and I listed out these nine principles of things I thought mattered to me. And I always had it in the back of my head, like I had this really bold vision of what I wanted my career to be, and I wanted to kind of be this person that was light, led with humor, really cared about people, mentored people, didn't take work too seriously. And slowly that just became less and less true. Like, who I wanted to be was not lined up with what the environment was allowing me to be or who I was showing up as. And so I decided to evaluate myself against these nine principles.
So I've literally created a scoring metric of rating myself against these, and I came up really low on a bunch of them. I wasn't being humorous at work, I wasn't injecting that into work, I wasn't learning new things that I cared about, I just wasn't being my best self. And over time I just had to stare at myself in the mirror and say, "I'm sick of this, I need to take action." And part of that just made me realize that like, those reflection exercises can be so powerful, just as a way to check in and call BS on yourself. And I think this is something you've done incredibly well, too.
It's funny. Your list of values is something I've independently landed on as well. Like, I created this values exercise, and it's a way for me to force-rank things. And I've constantly done this. I do this probably a few times a year now of just saying, "What do I claim to care about? How do I reflect on how I've been spending my time?" And then call myself out on my BS. If I claim to care about generosity, what am I actually doing about that? Am I actually embracing that in my life? If not, what's the mismatch? Either—Two options. I either don't really care about that, or I do and I need to do a better job of it.
Chris (19:47): It's so powerful. Yeah. We've come across the same technique because we need some—It's like a systematic way to call yourself out. And reflection just seems to me to be the speed limit on growth, personal or professional. You have to be willing to look, to think about what is going on. People think of cognitive dissonance in a bad way, right? It's a way of justifying your own behavior. But I almost think of these values exercises as ways to generate this dissonance. As you describe, once you say that something is important to you, you can't help but become aware of how your life is or isn't a reflection of that. And as you said, you have one or two options. Either—Hey, you said generosity. Either, "I value being a generous person and I need to take steps in my life so that it's more in alignment with that, take more generous actions," or, "I'm not a generous person." Which is also okay, by the way. There's no right answer in terms of values. But whatever you decide to value the most, that should be a wake up call, a trigger, a cognitive canary, whatever you want to call it, for, "Perhaps I need to be taking some steps in a direction so that my life is a reflection of this."
So once you had identified these values, you created this dissonance and said, "Okay, maybe I need to—I'm not being humorous at work, I'm not having fun." What were the steps that you started to take? You mentioned kind of experimenting, to move in this direction, to put some of these values to the test?
Paul (21:34): Yeah. It's hard. I think for me I had a hunch that leaving my job was going to be a key help in just me having a life I wanted to live and design around. So the first thing I did was experiment around work. So I started doing all these side experiments, I started writing a little more publicly, I created an online course about resumés, I did a career coaching experiment, I did a group coaching experiment, I got paid to do some speaking gigs. And I was doing this all on the side. And everything I did was intended to basically inject a little serendipity into my life. Like, I knew how everything would go if I just devoted all of my energy to my job. I was probably just going to get promoted and have more job opportunities doing the same thing. None of that excited me.
So I designed experiments to basically try things out but that I could quit them afterwards. So what's the smallest thing I can do such that I might learn something new about what to do next. And the only goal was to learn what to do next, or to reflect on how I felt in those experiments. Early on, most of those experiments made me feel incredibly uncomfortable. And our default reaction is to run away from that discomfort. But for me, it was this sense that—Okay. Every time I do this, it's really uncomfortable, but it's also really exciting and interesting at the same time. And I just learned to trust that the discomfort was a direction to follow, and that is what gave me the confidence to quit my job without much of a plan. It just told me, "I'm just gonna try and keep doing more experiments to become uncomfortable, and in that I might figure something out." So it was really just having faith more than anything else. Like, I had no proof that what I was gonna do was gonna work or on what terms or where I was gonna be headed.
Chris (23:48): Really powerful, and I think there's a couple principles there that are really worth expanding upon. You know, first think about like failure modes with something like this, something that I often see is you know, before I change course, you know, maybe change careers or roles, I need to have this perfect plan in place, I need to save up a certain amount, I need to know exactly what I'm going to do, I need to have all of this validation, and putting a lot of pressure on an individual experiment, feeling like this experiment needs to work out because you've put so much of your identity into it, and the acknowledge that you have that many of these experiments won't necessarily lead to amazing outcomes, but that they'll bring learning and that they'll better inform the shape that this path could take. So making those experiments really small and gentle and not turning them into huge pivots feels like a really important one and being open to whatever occurs. Right?
It's like, a good strategy for life in general is not being too results-oriented. Like, if you have a failure it's not that you are a failure or even that you've failed, that you've just had some unexpected results. That's always like the key experimental mindset that I like to talk about.
Paul (25:15): Yeah. When I left my previous path I had a sense that I didn't want to create another job for myself. I mean, when you talk about goals I think you're talking about something much deeper, but I think a lot of people get distracted by the idea of goals. And it's very easy to just gravitate to other people's goals. Right? When I was doing a career coaching experiment, it would be very easy for me to adopt the idea that my goal is to build a career coaching business. Right? But my goal was much deeper. Basically, to experiment and find information that might lead me in a more interesting direction. And I kinda knew that if I just build a career coaching business, I would just be creating another trap for myself. So it's really having enough wisdom to know that you're searching for something much deeper. I think the level of my goals has shifted from surface-level goals to make money or prove myself to basically this infinite game of, "How can I design a life that I want to keep living?" And then everything is geared around kind of checking in with that all the time.
And this is really fun for me. I think this is something people miss when they think about leaving their job or being self-employed or doing their own thing. I love thinking about this all the time. So this is a lot more fun for me to be uncertain than it is for other people. People will say, "Don't you worry about not making money or having uncertain things." It's like, yes, I worry about that all the time, but the puzzle of figuring that out and designing experiments and trying new things is super fun for me.
Chris (27:03): Yeah. The way that you put it that I really loved is as an equation, is, you know, "Can your wonder put you over the hump that the risk of movement is less than the risk of not movement?" Because otherwise it's very easy to generate excuses that keep you into place which sound very plausible. And again, coming in knowing that it's going to be uncomfortable helps to inoculate yourself against that. Something that I often see when someone leaves a full-time role, right, they talk about, "Well, what I really want is more autonomy and freedom and when I'm working full-time at a company I'm in meetings all day and I have to do what I'm told, I can't generate my own assignments," and all of a sudden there's no one asking them for anything and they can wake up and do whatever they want, and feeling a little bit lost without that structure. It's like, "Wait, I can do anything I want. Oh." It's like Kevin in "Home Alone," right? "What do I do now?" And both this impulse to try to recreate that structure that they were running away from, but trying to use this as an opportunity, that in the discomfort there can be a lot of wisdom, is to just feel—What do you feel pulled towards, and trying something small in that direction and trying to double down.
You mentioned some of these fears. So, "What if it doesn't work out?" "What if I can't make money?" When you were talking to someone about their career, even just friends now, how do you help them both acknowledge these fears, right, they're good reasons to not move, but to help to work with them, to help to overcome those fears?
Paul (28:54): One of the things I've realized is there's a wide range of personalities and desires and interests and individual psychologies. I'm sure you've realized this too in coaching people, like, what people are seeking and what they're after is a huge range. A lot of the people that are reaching out to me are not the people that are deeply afraid of the uncertainty. Right? A lot of the people that reach out to me are already onboard with, "Hey, I'm already on this uncertain path, I just wanna like trade ideas and pick your brain and kind of bounce things around." That's like seventy to eighty percent of the people that talk to me. So then the kind of people that have really strong reactions, that will come at me with, "What about this? What about that?" To me, it's like, "You may not actually be somebody that wants to take my path." And a lot of those conversations are me trying to help them reframe what they really want. Like, they may think they want my path or they want to create their own work or they want to take an entrepreneurial path, but they may just be buying into some story that is helping them solve something else that they're struggling with. Right?
I have an unreasonable need for freedom and autonomy over my life. Like, I'm on the far spectrum of that. And combine that with an interest in screwing around with technology, and I get a kick out of designing experiments and stepping into the uncertainty. This path is awesome for me. Right? So it always comes back to, "What are you actually designing for?" Most people's fears are pretty consistent, though. We all have fears and yearnings for what we want. We have a fear of health challenges, we have a fear of not knowing what we're going to do. We have a fear of not being good enough, we have a fear of failing. Those things are consistent. It's really how do those match with the environment you create for yourself to either cope or deal with those fears.
Chris (30:59): Yeah. It's so brilliant. It feels like many fears are protectionist. They justify the status quo and allow ourselves to sleep well at night in our current situation, that it couldn't be any different. So it's useful to pick them apart. And I like the questions that say, "Hey, like, well what if I could wave a magic wand and you didn't have to worry about that anymore? It was solved? Like, what would you do?" And those are always interesting because sometimes it brings up that actually wasn't the fear that was holding them in place. It brings up something else. It's like, "Well, then I need to figure out this," or, "Actually, I wasn't really worried about that, I was worried about this." And sometimes it's, well, I still don't want to move. So maybe that wasn't the reason at all.
So I think what you've kind of uncovered is that it's easy to fall into a metaverse of this—meta-version of this. "Metaverse." Sorry. Oedipal. A meta-version of this, where we see someone who we think is walking a non-traditional path and be like, "Oh, well I'm not on the right path, maybe that's the path and I want to do what that person is doing." And I think what we're kind of both saying is it's this ongoing lifetime process of trying to tap into what we value, what we find most meaningful, and trying to bring elements of that into our daily life. And it doesn't necessarily mean making a big shift, but having this vision that we can work towards.
What are ways that you've seen someone to kind of include some of these elements in their current situation, right? Maybe they're not looking to make a big jump right now, how can they start to put some of these pieces in place?
Paul (32:49): Yeah. So, touching on the fear thing first, and I'll definitely answer that, but the fear thing—I think the default path, and what I consider the default path, is kind of the socially accepted path in adult life. In the US, in many countries, it looks like a full-time job for a company with a steady salary. And that path works incredibly well for people, and compared to a hundred years ago it is just an incredible innovation. These jobs deliver basically stable, great lives for so many people around the world. I think what those paths do is cause people to mis-price their fears, however. They put enormous weight on the fear of not having that situation. And I think like what Tim Ferriss's fear-setting exercise did for me is basically make me accurately price the fear of stagnation in my current state. And now on my current path, I constantly have a fear of kind of like creating a job, creating stagnancy, creating this state where I'm not growing, not evolving, not learning, because what I've found is when I'm pushing myself beyond my limits, when I'm learning, when I'm growing, when I'm challenged and uncomfortable, I love that. And it makes my life meaningful.
So, connecting that to your question, what can you learn or how can you inject that into your life, I think one is just starting with that and realizing there might be some value in looking at my path differently and saying, "Sure, there's bad things that could happen from an uncertain path, but there might also be costs to my current path of not experimenting enough." So, I mean, a couple things that I tell people to do is just create space in their life. And a lot of people want to leave their job. I think what most people want is actually just a month away from their job and their responsibilities and being in that like non-stop worker mode.
And this can work even for solo-preneurs, too. Like, I know you've lived in other countries. Living in another country can be the ultimate hack for this, whether you can do it with remote work or taking an unpaid leave. Just getting in that different state. If you're in a country like Mexico, or Taiwan, where I spend a lot of time, you can't actually show up how you're wired to show up in the US. It's not an option, because everything is so different enough that you're going to have to orient in different ways and be uncomfortable. So yeah, I mean, travel is the biggest hack. Health crises are great for reimagining your path, but I don't recommend those.
Chris (35:38): I mean, you talked in the book that that was a major motivator for you. That, you know, health challenges were making it very difficult just to show up every day, and if there was a different way of being, it would be something that would work with where you're already at. Maybe talk to that. I think just the acknowledgement that there's no straight path, that it has lots of these ups and downs—Like, how did your health act as this existential opening for you?
Paul (36:10): Yeah. So I went to a great business school, and worked at a company like McKinsey, so like, in the top of the world. Graduating, about to make like six figures doing consulting, like every opportunity ahead of me that I thought I wanted when I was younger and in college and had just been exposed to these worlds. A couple weeks into that job I start feeling sick, and like my health just starts slowly deteriorating. There's nothing I can do. And suddenly I have to take a leave of absence. And I was out of work for a good four to five months. And that really just made me question everything. Literally just sitting in bed and thinking about everything. And I wanted so desperately just to be back to normal. Like, I just wanted to restart my career. And I was obsessing over just getting back. Back to normal, back to normal. And it wasn't until I released that script that I was like, "Maybe there's no back to normal. I don't know if I'll ever recover." And it took me another year to really recover and find confidence in just showing up in the world again every day.
And in that, I changed. And I saw my own vulnerability and fragility, and it was awful. Like, I wouldn't advise anyone going through it, but it also made me just loosen my grip on my "successful person" identity. It's like, "Yeah, that's great, but what am I really doing here? Do I really care that much about helping somebody increase profit by ten percent?" It's like a good container, it gives me status, people think I'm successful, it gives me money, but I don't know. It doesn't seem all that important.
Chris (38:05): Yeah. We build all of these behaviors, all of these beliefs, by accretion over time, and if we never have this restart, this hard reset, we're never forced to reckon with, "Hey, are these all still serving us, given where we are?" So it can be useful—I like the investment analogy. Rather than thinking about the positions you're already invested in, imagine you sold everything. Like, what would you buy back into? If you wouldn't buy back into it, you probably shouldn't be holding it now. Right? If you wouldn't start it again if you could do everything, maybe you shouldn't be doing it right now.
So some of those experiences that you mention, like, travel, sabbatical, having a challenge of some sort that forces a change, it disrupts this reference point of normal. That one of the—Let's say the, you have these things that could be a feature or a bug in terms of human iOS, and one of those is our ability to normalize everything. Well, one of the ways that this can be a bug is that we become blind, that something that feels normal to us because we've gotten used to it maybe doesn't need to be normal, or even shouldn't be normal. So it's like getting out of your current bubble, your current situation, to be able to view it from the outside and say, "Hey. Like, what do I want to pick back up that I've put down," or, "Given I don't need to do any of this, what calls to me?"
So I think that is a very valuable part of the process, and that's part of like the role that I like to play as a coach, both 'cause it's useful and it's also kind of fun for me, is to just disrupt this reference point of what our assumptions are, what we take for granted, and pick that apart. "Well, what if this thing you assumed to be true wasn't? What if this thing that you're always doing, you didn't do that anymore. What would you do otherwise?" Even just starting to ask those questions brings up interesting things.
You're smiling. I wanna hear what's on your mind.
Paul (40:12): Well, I love that analogy. I'm just applying it to my own path, and it was like—I wish I had had a conversation with you ten years ago. Like, if I think of my career as like a growth stock, right, the first five years were thrilling. I was probably growing at like twenty-five percent a year. And it would be crazy to, like, sell. I don't know if stock is the right analogy, but like the growth rates just stagnated, or maybe even were shrinking in my final few years. But it's like a company, it's like, "Well, they're still profitable. Like maybe they'll turn it around." Like, you're just holding. I should have just sold earlier. Like I was so attached, it was a sunk cost. I should have just taken my gains earlier and moved on. But it took me so hard to kind of move on from that 'cause psychologically it's crazy to walk away from a guaranteed, like, cash flow. Basically.
And I tell people, I've kind of reinvented myself. I don't really have status in the old world I came from, still. Like, I think probably most people think what I'm doing is silly. I haven't equaled the earnings of what I have in my past life. But man, I'm having so much fun.
Chris (41:36): That brings up two interesting questions. I'll let you pick. One, like, how do you care less about status these days? Right? It feels like a lot of what drives this default path is the prestige. And the second question is, what have you learned about these identity transitions? You know, becoming a different person in order to walk the different path?
Paul (41:59): I never really cared that much about status. And it was just me realizing that. I was in an environment that was optimized for status and money and success, and it's just hard to give that up when you give it up. And when I gave it up, I, I don't know. I've just been very comfortable not caring what others think of my path.
Now, that doesn't mean it's easy. It's very hard when you've punctured an idea of other people's perception of you. Especially your parents, right? I wrote about my parents in the book. And for them, I went from part of their success story, right—the great American dream is not actually just succeeding on your own, it's sending your kids to college and having them succeed. Right? And then I just walk away from all that. Like, my parents didn't go to college, they didn't have the options I did, and to them, they just can't understand. "How could you make so much money and want to walk away from that?" And I think it basically took them about five years to see what I was up to. I think it took me writing a book. They were like, "Oh my god, you're an author now, this is so amazing." And like I'm getting all these heartwarming messages from my family, now.
That's probably the hardest part. Like, do we care about what our friends think? Maybe a little. A lot of what it comes down to is like our parents and loved ones. And I've been lucky, I met my partner Angie on my path, and she sees building a life around creativity and connection and a life around that as very valuable. So neither of us are willing to compromise things. Like, for some people owning a home is very important, right, and for us right now financially that wouldn't make sense, given what we're willing to trade-off or not. So finding a partner along the way has been game-changing too, because none of this is crazy to each other.
Chris (44:03): That brings up so much for me. I mean, I always like to ask someone, you know, "Do you think you're playing the right game?" And in a lot of worlds it's the, "What's the thing that's going to bring you status within this community?" So first, even just realizing that you're playing the game, and asking yourself, "Hey, is this the game that I want to play?" Sometimes you can put up with it, and you can play it if the outcome is desired. But you know, going in eyes wide open and deciding, "Hey, is this really what I want? Is this the game that I want to play?"
You talk about this notion of compromise. I think compromise is—I like to try to flip this language on its head. Like, compromise is usually considered a good thing, but I find that a lot of compromise, especially when it comes to values, breeds resentment. And you see this in someone who maybe they start to feel this dissonance, that their life isn't in alignment with where they want to be and they feel like they're having to compromise on values to satisfy someone else, whether it's their boss or their corporate culture or their partner or their friends who they're surrounded by. And that this compromise is unsustainable. So not only that the right environment people included can really reinforce these shifts, but also that the wrong environment can—The values aren't going to change. They're still going to be there, festering, they'll just come out in more surprising ways.
Paul (45:35): And that's what happened to me. I think there was a deep resentment and sort of self-loathing in the final years of my path. And it wasn't obvious to me at the time, but now it is, and I was just so frustrated that I couldn't fully be myself. And I think the exciting thing about my journey is I've managed to design a life around being the person I'm proud to show up as. And part of my journey, too, is having the confidence to actually say that. I felt ashamed to say that. Like, I had all these scripts I had to untangle in my head. Like, I think one big one for a lot of people is that work is supposed to be suffering. Like, we suffer such that we can make money to take care of you. Right? A lot of people grew up with this. And I don't know if I believe it, in the fullest scale of it. Right? It's—You need to add that into, "Okay, what am I actually willing to trade off to get certain things I want?"
And I think one thing I've realized is based on who I am and what I'm capable of, I'm not the kind of person that is like full out going after goals. Or financial goals, or metrics. That's not the best version of myself. Some people are wired like that, right? There are people thriving that are also crushing it against traditional metrics. My metrics are different, and they're a little illegible to the world. And it ties into what you're saying. Like, I think—Like, I still want status. I want to be appreciated by other people, that's important for me. And it's just I want to be appreciated by people like you doing stuff like this. Like, other people on independent paths who get a kick out of what I'm writing about.
And I think that's the opportunity of our world today. There's these mega-values like money, status, and success. Everyone knows these exist. You can't pretend like they don't exist. But now there's all these niche communities where you can get a micro-micro-status. Like, I think inspiring for me was somebody like Khe Hy early on in my journey. He's just being generous and being nice? What? This is possible? And he's getting status from this? I want to give him status. Like, status is just attention. And I think that was a powerful unlock for me, realizing, "Oh, I can just define my own prestige. It might not be legible to my parents or peers." But in my email inbox, people are like, "This is amazing. This is so helpful. I'm so grateful." That's enough for me. I love that.
Chris (48:22): You bring up this concept of legibility, and that a lot of aspects of progress on the default path are legible to others. The salary, the promotion, the brand name that you're working for, who you're working with, the school that you go to, the car that you drive, this type of stuff. And getting off script requires getting away from these well-trod legible metrics of success, and part of the discomfort seems to be not knowing if what you are doing is working. Right? If you are making progress. So how do you know if you are making progress when you're walking the pathless path? Do goals still play a role? Like, what sort of signs are you looking for to know to keep doubling down?
Paul (49:18): So I'd love for you to challenge me on this, too, if I'm deluding myself, but I think the longer I've been on this path, and like the mix of like activities, intentions, things I work on, things I say "no" to, the more practiced I've gotten that, the more confident I've gotten that like I can just more or less show up without specific outcome goals, and shifting more to like process goals.
So, one of my goals is, "Write most days." It's light, and it aligns with me. I know if I create the space I'll write, 'cause I actually just freaking love it. I don't need to force it. So I try to come up with mantras like that, and just make them happen. And I've noticed that these things just happen. I don't really have outcome goals. But I've become more open to it. I've realized that I'm not gonna burn myself out now. I have my footing on this new path where I actually could be more ambitious, so I'm very open to it in the next few years.
Chris (50:23): Yeah. I like the gentle approach, and it's easy to think about the shadow side, where the outcome goal gets confused for the reason you're doing it in the first place, right? The goal itself is really just a milestone, a yardstick, and I like to think of a good goal is just a way for me to tell, it's like, are the things I'm doing on a regular basis leading me to where I want to go? And I think to get back to what you said earlier, it becomes a form of somewhat more objective reflection. So something, like a goal of like "write most days," you know, the books wouldn't recommend that. The books are like, "Hey, it's easier to write every day than most days, because if you let in a little bit of wiggle room then you know, that small leak can sink your whole ship. What do most days look like? What are the days that are acceptable to, or not?" But the gentleness that is introduced, I imagine, by your regularly reflecting not only on, "How often am I writing? How is the writing going? When am I enjoying it? What's working?," but also coming back to, it's like, "Do I want to be writing most days?"
All of those are kind of the necessary pieces of turning a goal from something that can become a leash into more of an opportunity, a guiding star.
Paul (51:50): Yeah. I mean, I've published hundreds of things without any writing goals. So I know I'll do it. Like, this is something I'm going to do. Even if I didn't have the "write most days," it will happen, so I can kind of trust that and move on from my goals. I almost think there's this phase one, like a forcing mechanism. And I actually did a challenge for myself in 2015, where I did a Quora post every morning when I started work. And that was a very outcome-based goal. And I did that for a hundred days. And I think after that I kinda kick-started something, where it's like this phase two, and this is what I talk about, the real work of your life, is—Okay. How do you design the environment now, such that it will enable this thing you've already kick-started to start? Right? Starting everything is hard and painful, but once you get to a certain point, I think people can confuse the goal for what they're really doing, and they might actually even get more interesting work if they step back from their rigid goals. Right?
So, for me, a big breakthrough happened when I stopped writing for a month. I just stopped, 'cause I was stuck and I didn't know and I said to myself, "You know what, I think if I just stop writing I'll figure it out." And it worked, because I basically just spent a month wandering, taking notes on walks, and like the ideas emerged. They came. But they needed to happen on their own.
Chris (53:29): I'm just getting this sense of trust, where—
Paul (53:33): Yeah, yeah.
Chris (53:34): —part of this trust is built up over evidence you've accumulated over time, but I imagine it extends to things where you don't have years of evidence or hundreds of articles to fall back on. How do you find that you're able to just have this sense of faith, this trust in yourself?
Paul (53:54): I don't know. I've always sort of had it. I think I have faith in the world. I love people, and I just think people are amazing and they inspire me, and I've had this optimism about the world my whole life. I think part of what's enabled me to thrive on my path is re-tapping into that from my childhood. I kinda lost it and became a bit cynical. So I think, like, I see people and I just think they're capable of stuff and get excited about them doing things. And I've been able to channel that into myself, too. And I just don't get caught up when things don't work. Most of the things I've done have not worked.
Chris (54:40): Do you think in the sense that success, however it's broadly defined, comes down to getting many shots on goal, not only to figure out what works but to figure out what you want to work?
Paul (54:54): Yeah, for sure. I think—So, I didn't have goals for my book launch. Right? I loved writing the book, and I just wanted to write it. However, I'm not naïve or ignorant to what's happening in the world. Like, I have been talking to hundreds of people for the past few years. I've had people responding to my stuff, I've been doing tweet threads around the same topics for years, I've been reading tons of books. And I realized that, "Oh, the way I'm thinking about this really is different. Nobody in the media is talking about this in this frame. This is different, it's resonating with people, people are telling me to write a book." So I had a hunch, like, if I wrote a book that it would find at least like micro-success. At least in my corner of the world. So I'm both equally surprised that my book sold a thousand copies in the first like thirty-five days, and not surprised, because I was still gearing things towards what would work while still staying true to my own path.
I have a hard time explaining this, because it really does come down to a deep trust that if you do things well, put your heart into it, give it your all, like things might work out sometimes.
Chris (56:16): It's these mindsets. I always feel a little bit guilty for talking about the frames with which we view things, but it really has this big compounding impact, and one frame that I found really powerful is around inverting regret. You know, I think especially when it comes to making a change, there's lots of fear of regret. Like, "What if I choose the wrong path? What if I make a mistake?" You know, "What if I have this public failure, or I didn't want this thing?" All these ways that I regret making this choice. And this fear of regret causes delay on making a choice or making moves that could inform that choice. And with any decision, the decision to stay, to maintain the null hypothesis, is a decision. Right?
We have a status quo bias for a reason, where we're generally geared to keep normalizing, keep doing what we're doing, but the need to try things in order to validate these assumptions that we're carrying around—Oh, man. I'm trying to figure out where I'm heading with this. But what strikes me is that the life that doesn't have regret is a life where you've tried your best. That you keep doing things to the best of your ability, and trust that the outcomes, you know, book sales, number in bank account, the size of your business or the impact that you're able to have in just your daily life, a lot of that takes care of itself if you try your best.
So I like that framing. And it comes back to, "Hey, what can I do so that I've done all I can?" And then not be attached to what comes out of it.
Paul (58:18): Yeah. Maybe there's a rebel spirit in me, too, like wanting to prove that a path not optimizing around money is possible, and that you can be really happy on it. I think I always just saw so many people so convinced money was the most important thing in life, and they weren't happy, and they weren't thriving. So like, money certainly doesn't hurt, and I think money when you're entrepreneurial as well can be a lot more rewarding. But I also meet many people who have solved their money problem and then they're reaching out to me like, "What am I supposed to do with my life and time?" So it's like I kinda wanted to shortcut that whole thing like make money first and then do what I wanna do and design my life. The big question is, "What if I just do those things now?" Like, I read about Tuesdays With Morrie, and Morrie has this exceptional life at the end of his life. It's a full life. And what if I just try to embrace those principles now? That sounds so crazy to people, but to me, it sounds like a really cool question to explore.
Chris (59:30): Yeah. The issue with the statement, of you know, "Money can buy happiness," is not that it's false. A lot of things that we can do to accumulate income will bring forms of happiness. It's that we get a really poor exchange rate along the way. All of this narrative of delayed gratification, of, "When I do this and then I do this and I accomplish this, then I can be happy." And naturally, that continually recedes into the horizon and we keep adding all these extra steps in order to deserve the thing that we want after all. And instead, what's the most direct path, is, "Are there ways to incorporate happiness or meaning or connection, whatever it is that you value, into your experience right now with which you're already doing, where presumably the opportunities are right there in front of you, if only you're looking for them?"
Paul (01:00:25): Yeah. One of the things this journey has done for me is totally refactor how I think about money. And when I was in New York making a decent salary, I was basically just anchoring to what people around me were spending money on. Like, a lot of fancy dinners out at restaurants and stuff. And I don't think that was really bringing a ton of value, but I wasn't thinking creatively in like other ways to spend money. Right? Like I was just taking default vacations and basically spending what other people were spending. And even my rent, I was like very conscious, "You can't spend more than this, 'cause other people don't spend that." Now I've actually had experiences of—I mean, this past year, or now I'm living in Austin, I'm making much less than I was making—I'm probably making about half of what I was five years ago, and I'm spending more on rent, and I don't feel uncomfortable about that at all, because I made a choice to opt-in to living in a certain part of the town where I could kinda like ride bike, walk around, have access to like, street tacos, and I know that's gonna make me very happy.
So it's like, okay. That's the cost. That's gonna make me happy. I really value that money I'm spending. And I'm not trying to like play accountant with my life or like, "Okay, here's how much I spend, I'm trying to minimize this and save money here." And I'm much freer, which doesn't really make sense, 'cause I don't have as much confidence in the ability to earn higher and higher incomes, but I'm opting in to choices a lot more freely now.
Chris (01:02:12): It strikes me that a lot of this accounting comes from a scarcity mindset, where all of this could be gone at any time, and that would be completely catastrophic, and you know, trying to differentiate the catastrophic from the merely inconvenient.
Paul (01:02:32): Well, maybe you experienced this while playing poker. I think making a thousand dollars as a freelancer was worth like a hundred thousand dollars as a full-time employee, because I actually made it happen, and if I did it once I could probably do it again. And that was so hidden to me, that I had these fears that were just latent. And I could never solve them by earning more and more money in a full-time job. But by literally just going and betting on myself and trying to land freelance projects and then pulling it off, even if it was like less money, it was like, "Wow. I'm capable of things." And that was so powerful for me. So I think that's my looseness with money now, too, is, "Okay, if I need to make money I could probably go figure it out." And I've done it in fifteen, twenty different ways.
Chris (01:03:26): There's a lot of strength to this self-confidence, and yeah. I've experienced it in my own wanderings through this pathless path as well, where any time that I'm offering a course or putting out a book or launching a podcast, it's all these old, you know, traumas and fears come up around, like, "Am I just fooling myself? Am I gonna be able to pull it off? Everyone's doing the same thing. Is any of what I'm doing really all that valuable?" All that sort of stuff. And then I do it, and every time it's, "Oh, wow, that actually was pretty good." And it doesn't mean it doesn't come up again the next time, but at least I have that fallback. It's like, "Well, I've been here before, I've felt all these things before, all those other times it turned out okay. Seems like based off of the evidence, this is probably going to turn out okay." Doesn't mean I'm not gonna try, doesn't mean I'm not gonna try to prepare and plan, but just going into it with this, like, "Hey, it's probably also going to go okay as well."
Paul (01:04:31): Yeah. That's what I always say about these kinds of paths. It might suck, but it might also be worth it.
Chris (01:04:38): All right. So you mentioned yourself ten years ago. If you were able to send a note to Paul in 2012, what would you write on that note?
Paul (01:04:52): I always really struggle with these questions. I've listened to you ask a couple other people on here, and I just get scared messing with the history of time. I think it would just be, "Keep going." Oh my god, it would be so, like, “Man. There's so much excitement ahead.” I don't even know what I would say. I would really just say, "Keep going."
Chris (01:05:16): And if you read that, I'm gonna have to pull on that. If you read that, Paul, in 2012, you got a note from the future that said, "Keep going," what's your reaction to that?
Paul (01:05:26): I think that I would like to trust my gut. But I wouldn't know what it would mean. I think it would excite me, I think it would invoke a certain sense of wonder. I think I've always had this pull towards the unknown of adventure, of trying things I don't know if I can do yet. And it took me a while to realize that maybe a very defined success path is not the best container for that.
Chris (01:05:55): Yeah. It also reminds me that the best way to trust your intuition is to trust it, that if you don't trust it you can't calibrate, so just trusting in the long run it'll work out even if it doesn't in the short run.
Paul (01:06:08): Yeah, and it's hard. I think what we're both talking about is really getting to know yourself. This is the oldest game in town that everyone who's written something in history has talked about. And the challenge with this is you might not like the results of what you find, because what you might find is that how you're actually wired or how you're inclined may not best be suited for an easy path to like success, respect, financial success. Right? The kind of things that if you can get them will make your life easier and win you love and approval and respect.
I think part of my path has been learning to say, "Oh, this is actually you, Paul. That past, like, you were really forcing yourself into that path. You couldn't have gone longer. Other people may think you could have gone longer, but like, that chapter's over. And there's a new chapter, and learning to just trust who you are and try to be more and more of that person and show up in the world, no matter the costs of what that means, is—It's like really hard, but I think over and over again I think people that do it do find a lot of meaning and happiness.
Chris (01:07:32): So to that end, if I were listening to this, and maybe I'm becoming more aware of ways that I'm following one of these default scripts, what advice would you have for me today?
Paul (01:07:48): I think one is just become aware of 'em. I think two is to try to inject some sort of serendipity or adventure into your life. I tell people to just go to another town without a plan and just wander. Try to connect with somebody outside your comfort zone. Read a book about somebody that's taken a different path. And just see where that little seed of inspiration takes you. I don't think everyone should quit their job. I'm increasingly thinking most people should take at least one month's sabbatical before they turn forty. But yeah, that would be my recommendation.
Chris (01:08:32): That's a softer version. I don't know if I told you this, when I was in my, let's say, "more annoying" state, people asked me what my purpose was, I told them I wanted to get a hundred people to quit their job. Not that quitting your job is a good thing, but if someone is on the fence that they should probably do it. But I like this softer version of, "Everyone should take a sabbatical." That's one of those things that have zero chance of regret.
Paul (01:08:57): Well, some people aren't wired to take this path. Or aren't there yet. Right? There's a lot to work through to have the comfort with uncertainty. And I think, like, yeah. I mean, my partner Angie is trying to figure out if this kind of path is for her. She's not so sure. For me, it's like, hell yes. And it's been pretty clear from like six months on to now. But for others—yeah. I'm not sure. Yeah, I went through that rebel phase of thinking this is the one true path, and then you kind of soften and realize there are different paths for everyone.
Chris (01:09:35): Any final words? Any places that you'd love to send people to? This book, Pathless Path, I've gone through a couple times already, so thanks for sharing it with me. It was—I mean, it not only brought up a lot of understanding and self-compassion for past choices, it really brought some current reflection to situations. So I highly recommend it. You have a fantastic blog, think-boundless.com. Lots of great articles on exploring the philosophy of living a life worth living, and having work that brings fulfillment. Anything else you'd wanna share or send people?
Paul (01:10:18): Yeah. And that's cool to hear. I mean, I wrote the book to kind of be a friendly companion to people on an uncertain path and just have somebody there, "Oh, I'm not alone. There are other people struggling with these questions." And, yeah. The book is, The Pathless Path. I'm happy to gift it to anyone. If people don't have a book budget right now, just email me. Always happy to talk to people about these ideas too.
Chris (01:10:44): Cool. We'll drop all those links in the show notes. Paul, this was a blast. Thank you so much for this conversation today. I have no words. It's been very inspirational.
Paul (01:10:55): Thanks, Chris. Yeah, I wanna ask you a bunch of questions, so I'm gonna have to ask you in my podcast, to go deep into your journey. There is a lot to learn there as well.
Chris (01:11:06): Public accountability. It is done.
Tasha (01:11:08): Thank you for listening to the Forcing Function Hour. At Forcing Function, we teach performance architecture. We work with a select group of twelve executives and investors to teach them how to multiply their output, perform at their peak, and design a life of freedom and purpose. Make sure to subscribe to Forcing Function Hour for more great episodes, or go to forcingfunctionhour.com to sign up for our newsletter so you can join us live.