In this conversation, Paul Millerd explores the significance of aligning one’s career with personal values to be able to follow your own unique and true path. Paul shares how often people get stuck in jobs that don’t resonate with their true selves, leading to dissatisfaction and burnout. By understanding and prioritizing personal values over societal expectations or financial gains, individuals can guide their career paths towards fulfilling and meaningful work, thereby promoting greater satisfaction and well-being.
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The really hard to understand reality for many people is that a job container is probably not the right path for you. But if you are going to opt into that, you need to be fully aware of the trade offs you're making and understand what are the principles that really matter to you and how do you prioritize those principles given the path you're on or what you're choosing to enter into.
Welcome to the one you feed Throughout time, great tinkers have recognized the importance of the thoughts we have. Quotes like garbage in, garbage out, or you are what you think ring true. And yet for many of us, our thoughts don't strengthen or empower us. We tend toward negativity, self pity, jealousy, or fear. We see what we don't have instead of what we do. We think things that hold us back and dampen our spirit. But it's not just about thinking. Our actions matter. It takes conscious, consistent and creative effort to make a life worth living. This podcast is about how other people keep themselves moving in the right direction, how they feed their good wolf. Thanks for joining us. Our guest on this episode is Paul Millard, an independent writer freelancer, coach, and digital creator. He's written online for many years and has built a growing audience of curious humans from around the world. Paul spent several years working in strategy consulting before deciding to walk away and embrace a pathless path. Today, Paul and Eric discuss his book The Pathless Path, Imagining a news story for work and Life.
Hi, Paul, Welcome to the show.
Hey Eric, excited to be here.
Yeah, I'm excited to have you on. We're going to be discussing your book, The Pathless Path, Imagining a new story for work in Life. I came across you on Twitter, I think, and you're good friends with Johnny Miller, who was a guest on the show, and I just kind of kept seeing your stuff for a little while and I was like, I really want to talk to this guy. So on read the book. I'm really glad I did. So we're gonna be talking about it. But let's start like we always do with the parable. In the Parable, there's a grandparent who's talking with their grandchild and they say, in life there are two wolves inside of us that are always a battle. One is a good wolf, which represents things like kindness and bravery and love, and the other's a bad wolf, which represents things like greed and hatred and fear. And the grandchild stops think about it for a second and look up at their grandparent. They say, well, which one wins, And the grandparent says, the one you feed. So I'd like to start off by asking you what that parable means to you and your life and in the work that you do.
Yeah, I was reflecting on it before this call, and I've listened to a number of your interviews, and I love this framing. It's such a good jumping off point for a conversation. I think early in my life I didn't feed either of them. And I guess you could say I fed fear a little in the form of sort of just fitting in and going along with things. But I just didn't have the role models to be sort of an emotionally connected man in the world. And I think when I entered young adulthood, I sort of just drifted along, and I don't think I was hyper aware of what was driving me. I just kept making impulsive decisions, jumping from company to company, chasing the next impressive accomplishment. But I didn't have much self awareness of why I was doing that or what really mattered to me. And it wasn't until my mid twenties in which I started to actually get more in touch with those and then eventually leaving the corporate world. I think my journey has been a journey of really figuring out how to have a relationship with fear, love, bravery, courage, creativity, all those things, and I think, to me, that's really what life's all about.
That's a really interesting framing to say that you don't know that you were feeding either wolf, right, or you weren't conscious of which wolf you were feeding. You were kind of just feeding the wolf that was laid out in front of you as the next thing to do. You were accepting culture's values. And I don't mean culture broadly, although perhaps, but I also mean the culture that you were in, you know, which said here's the next thing you do. Right. In the book, you refer to it a lot as the default path. Right, It's just you kind of follow what's laid out in front of you. Let's talk for a minute about the title of the book, which is called The Pathless Path. What drove that and what does that mean to you?
Yeah, so I discovered the phrase in a David White book. Have you read any of David White.
I have, Yep. I've read him and he's been a guest on the show, and he's a remark man.
I didn't know you interviewed him. I'm definitely listening to that right after this.
Yeah.
So he's written about work, and I think his language helped me transcend an understanding I had of the world, which there's like prior to reading David White and after reading David White. Prior to reading David White, I just thought work was part of life. Right after reading David White, I had this whole new interpretation, which is like, Okay, there is like work to fit in and do what other people are doing, and then there's work. There's work that is deeply connected to who you are, what matters in the world, and something that can give you sustainable energy throughout life. And he talks about his own journey, and he talks about this phrase, the pathless path, and I remember it. The book actually came to me via a gift from another person you mentioned earlier, Johnny Miller. He handed me the book. He's like, you need this. This is a year after I quit my job. He's like, read this book. I was like, okay, read the book over the next couple of weeks, and this phrase the pathless path just jumps off the page and just like sort of took over my life. And he said something like, when you first discovered the phrase the pathless path, you're not meant to know what it means. But for me, I had the opposite reaction. And that's what he said. But to me, it was like, oh, this was such a release. It's like, I'm not supposed to know what I'm doing. I spent my whole life always trying to orchestrate the next step, and it was that orchestration of life that sucked the joy out of life, right, And it was really that that guided me over the next several years of contemplating what if I just released the tiller, what if I don't orchestrate and I just try to lean away from any active planning in life, which a lot of people at first glance so like, you can't just do that. Well, it turns out you can. You will still do things, you will react to things, You're going to react if you're in danger and need all these things. And what I discovered is that I got to know myself. I started feeding my good wolf and I think I started feeding the bad wolf at the same time, which was I started to get in touch with like, oh, I have passion for life, I care about things, and also I have these fears. I'm scared of going broke, what's that about. I'm scared of people not loving me? What's that about? And learning to kind of coexist with all that. And over the next few years, I didn't really think about writing a book, and then eventually a bunch of people just kept asking me, and I was like, Okay, I think I'm going to write a book. And that name was just so obvious to me. It had to be called the pathless path.
Yeah, it's such a Taoist Zen phrase. In Zen, we talk about the gateless gate, right, you know, which is there's a gate you passed through, but it doesn't exist. I mean, there's no thing that's blocking gate, the same as you. When I heard that phrase, I was like, that's such a great phrase. So you were kind of on what you would consider the pathless path now, but before that, let's talk about your life on what was kind of the default path. You know, give us a couple minute version of kind of what you did and where you were.
Yeah, So for contexts I grew up. My parents didn't go to college. They were very much on the default path. And I write my book, I think in previous generations there just weren't alternatives as there are now, right, and so they did well on the default path, and their goal was to make sure their kids have everything they need. We went to public schools. We didn't have a fancy upbringing, but we had enough, and we had love, and they just wanted us to go to college. And I think also part of that was, I think the expectation that the goal in the US is just to make a lot of money. I didn't realize there was that implicit expectation, but I followed that path. I was always good at school. So if you're good at school, the opportunities just eventually show up. You're good at school, you do good in tests, you get into the honors program at college. I went on a full scholarship to undergrad which was the only college I considered because I just did not want to go into debt. Went to University of Connecticut. Surrounded by all these high achievers. They're like, I'm going to go to Harvard Law School. I'm going to get into med school. I want to work for these impressive companies. And suddenly you start to figure out, Oh, there's like a ranking, right. I'm in the business school, and I'm realizing ge is the best company to work for. Everyone who gets hired there. People pay attention to those people. Oh wow, that person got this offer right, So you just start competing. It was not that hard for me to be good at these things. I just had to like figure out the steps and then execute. But by doing that for so long, I think I was short circuiting my own curiosity, my curiosity for life and all these other things. And at the same time, I would get in these companies and I wouldn't fully absorb the identity of like a high achiever. I'd always be slightly skeptical. I eventually broke into strategy consulting one of the top firms in the world, Mackinsey and Company, and I would work less than other people. I'd be like, why are you guys working so much? They said, we could go home at five or six, so why not? And everyone would say till eight or nine. And what I realized eventually is a lot of people in these worlds like their whole identity is work, right, and by work, it's they identified with a career narrative about their life, which is their life, and the whole point is to get to the next steps and keep going and build wealth and sort of live out what the previous generations did. I didn't really have that example though growing up, so I was always a bit lost. I never fully understood like the elite codes of talking and what people were angling about, how people had all these political opinions. I was always so confused, sort of an outsider in these worlds, and eventually, like, you just can't last in these worlds if you're not like of that source material. And I think my questions just eventually got to me. It's like, well, we're making enough, and everyone around me thinks we're broke. I don't understand what we're doing.
Yeah, well, I mean, so your default path was a very successful path in the traditional sense, and that you went to a really good school, you got a full scholarship, you were able to go work for some of the top companies in the world. Your career was off to a really strong and good start. You know, I think It's interesting you talk about prestige in the book and you just referenced it a little bit here, which is you start to realize there's a ranking, oh, going to Harvard Business schools better than going to Ohio State's business school. You know, going to McKinsey is better than going to I don't know, what's a lower tier consulting company. Right, So that there's all these rankings and that this prestige is you use a quote in the book, a powerful magnet that warps even your beliefs about what you enjoy. And I love that idea because what you're talking about is mimetic desire. Right. We had a guy on the show, Luke Burgess, who writes about this, which.
Is, yeah, I love Luke's book.
Yeah, you start to want what the people around you want, and it's a really interesting idea that we all do, which speaks to thinking about who you're around and what they want and whether you have these values. So you started to, as you said, question whether this was really the right fit for you, because you weren't all in in the same way that everybody else was, and you were sort of a as you called in the book, a hoop jumper, and yet there's something else going on inside of you. Tell me a little bit about the process of going from I'm on this path and I'm just jumping through hoops to going, huh, maybe this isn't the right place for me.
Yeah. So I always had those doubts. In my first internship, I read about this in the book. I'm looking around and seeing all these men not really doing anything, and I'm like, why are people doing this. I remember talking to one of my aunts or uncles and I was like, nobody seems to be really doing anything. It's like you'll learn once you're in the real world. You'll figure out, like you gotta just work, that's what you do. So I always had these questions. But it's more confusing for other people that I left than me, Like it makes so much sense that I left. It's just that I was good at the game that the vast majority of people think is the point of life. But I was good at a life that wasn't mine, and the only thing that kept me in it was my stunted self awareness. And I think the first thing that really opened me up was the loss of my grandfather. This was about a month before I started business school, and it really just broke me open. Like I started crying a lot more. I don't even know the last time I cried before that, But like I just became a lot more in touch with what I was actually feeling in life, and I started to introspect a little more. But at the same time, I was still a top business school. You can't just intros back fully there, Like you got to get a job, You're going into debt. I was like seventy grand in debt at twenty seven years old, so like I needed a job to pay that off. But over the next five years, there were all these tiny little moments of starting to write a little more, getting interested in coaching on the side, going on a personal development retreat, going on a solo travel trip up the California coast, and the spaciousness and wonder of life started to creep in. And once that happens slowly, it became very easy for me to walk away. Like people asked me, was it hard to watch walk away? Not really. I didn't feel like I had any move left, Like I felt hopeless for the future. I was surrounded by people that were cynically going through the motions I struggled to find role models, and wandering around without a plan seemed way better than that.
Yeah, yeah, I think it's really interesting. I'd love to ask you a question about life now because right now, and this is hypothetical, you may not even be able to put yourself in the mindset that this question would even make sense. But your son to a ten week old baby, and you know a lot of people who don't walk away from the default path even when it feels like it's not the right place to be. And I did this for years is because of what feel like responsibilities around children and family and things like that. Do you think it would have been harder for you today as a parent to walk away and make that decision then it was for you in a relatively sort of independent place in your life.
Yeah, of course. But I probably would have married the wrong person and been in the wrong life, so it would have been way more disastrous.
Yeah.
Yeah, Like I wouldn't have met and married my wife. She wouldn't be with me unless I was actually chasing what was true to me. Yeah, it's hard to answer, right, And part of what drove me is I did have a sense that I wanted kids in the future, and I wanted to build the kind of life so I could be present and have time flexibility. And I'm so rich right now because I have that time. Yeah, I don't have a return to work plan. I'm like fitting work in. I have two hours of stuff I'm doing today and the rest of the day I'm hanging with my daughter. It's awesome. I love it. And this is like the whole point. This is why I tried to get more time instead of more money.
Yeah, it's certainly a useful reframe, right. Like I was telling you before the call about my son who's twenty four, and I raised him largely at sort of the peak of trying to succeed in my career, Right, my path is different than yours. Instead of sort of blindly following the default path, I just blindly drove my life off a cliff, you know. And by the time I was twenty four, I was homeless and had a drug addiction, so things were not going well. So then I was sort of frantically trying to climb on some sort of path that felt like it was going, you know, somewhere, and I think I overcorrected. I went like, oh god, I've been way over here time to buy into all these ideals around career and responsibility and all that, and then it took me years to sort of find my way what for me felt like a middle ground of actually my own path. And so when my son was little, I was right in that thick of you know, trying to make up for lost time. You talked in the book about your father who always felt like he had to work harder because he didn't have a college degree. Like that was me. I was in these worlds where everybody had degrees and MBAs and all this other stuff and I had nothing, and so I was always like, I can outwork these people, but I missed time with him that I trade to have back today.
Yeah, it's hard, And I write something also in the book, the longer you're on the wrong path, the longer it takes to find the one that is the right path. Right. Yes, and it's taken me a really long time to find my footing on this path. This will be my sixth year in like two weeks, and only in the last year or two I feel like I have like my footing, but it's constantly going to shift. My first few years, I think I overcorrected in terms of like going full wandering vagabond, avoiding employment, not trying to make money. I was living on like five hundred and two one thousand dollars a month in Agia really just like I was sacrificing, Like I wouldn't even like eat food out. It was and I sort of stifled my own imagination for possibilities and creativity. But then you come back and you're like, Okay, do I lean more new ambition? Then you try to find the middle ground, and you're always searching for the right path.
Yeah.
I think the mistake with a lot of legible paths, paths that we can see, oh, I'm going to become a data scientist and a manager than a VP, is that it tricks you into that is the path that is right for you. And the really hard to understand reality for many people is that a job container is probably not the right path for you. But if you are going to opt into that, you need to be fully aware of the trade offs you're making and understand what are the principles that really matter to you and how do you prioritize those principles given the path you're on or what you're choosing to enter into.
Right, I sort of avoid binaries in general, and so I think there is a way to be on something that resembles a default path that is valuable and meaningful. I mean, the first years in my career I was in software startup companies and I loved that work. I was ambitious and there was a certain, you know, path there, but it was also very exciting and I loved it and I was challenged. And you know, throughout my whole career, even as I moved into consulting for big organizations, I always felt like I had a job that I liked, you know. In that like, I was like, I'm intellectually challenged and I'm around people. As I got older, I got more and more into meaning. And I think you can make meaning in any role. Right. We read books about, you know, janitors at hospitals who their meaning is making a beautiful and clean place for the patients, and they make meaning out of it. So I think we can make it anywhere. But it's at least for me easier to find it in certain places.
Yeah, and it all comes down to self awareness, right, Yeah, understanding those two wolves as you say it, and you could have said, I am a software salesperson, right, and then defined yourself as that. But I imagine that was not it. It was probably something around curiosity for people and connecting things, making things happen, and without knowing yourself. Like, if you define yourself as a software salesperson, you wouldn't be hosting a podcast right, right, And you probably kept going deeper with a curiosity, and then you get to this raw just curiosity for the world. No one starts a podcast to make money.
Not if you have an IQ above forty. No, you don't.
And so you figure out, oh, there's these things worth doing in the world, right, And then as you're hosting a podcast, you're paying a cost monetary cost, right, because you could be doing other things with your time, you could be selling software, right. But eventually you realize there's certain upsides to life, and in today's world, many people are blind to those upsides. So you have to pay the tax of other people not understanding what you're doing. And as long as you're okay with that, you can find a path in which you can thrive.
I think.
As women, as humans, really the world can trick us into believing we're doing life wrong, which keeps us small and separated, but we don't have to play along. Let's make a plan together, shall we.
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My path to where I'm at today was certainly was a middle way path between staying in what was secure and made a lot of money secure as much as anything is today, I mean that's an illusion, right, but more secure or doing the podcast where I mean, I did the podcast for four and a half years while I worked in a career, and after a couple of years, I started going, Okay, I know where I want to be. Now how do I get there?
Right?
How do I get from this job to doing this podcast and the work I do with people full time? And you know, I kind of made my way there, but there was a point where I had to go, Okay, like when you get to be my age as successful as you were at your age, Right, this idea of golden handcuffs is a real thing, you know, Like I had to make a decision at some point, like I'm walking away from a substantial amount of money in both the short term and the long term in order to do this now again, who knows, maybe next week I'll be Joe Rogan. Right. I think it's unlikely, But like you, I made a decision of meaning and purpose and loving what I do over money.
Yeah, I left right as my peak earning years were about to begin. Yeah, I did not cash in. I am not somebody that got too financial independence and walked away. I stupidly lit probably millions of dollars on fire. Like the economy went crazy too for the consulting world and strategy work, Like, starting in twenty seventeen, salaries just started going up like twenty thirty percent a year. It was crazy. I didn't get any of that. I lowered my salary down to like twenty five thirty two forty grand for the next three years. But they were the best years of my life. And the challenge is I think people think that you can escape the base reality, right, especially if you're in the US, if you want to live in the US, you can't escape the fact that most people see money as one of the most important things in the world. If you were going to make a decision to say money isn't the most important thing in our world, you need to figure out how you're going to manage that tension and feeling bad about that being in insulted by other people. Many people have said, don't you think you're wasting your degrees? It's a really interesting way of framing it, right, wasting your degrees, aka the whole point of life is to get credentials to trade in for money. I disagree. I think the point of life is not to maximize financial income, and the point of life for me is something I can't fully explain to you. I tried to explain it in writing a book, but it's a felt sense. It's a deeply felt sense. Yeah, I'm a little crazy for believing it at my age, and I'm just going to follow that feeling. And I ended up meeting a wife who sort of values the same things. And it's going to be harder for us to build a life because we don't have the payoffs that like all my former peers and coworkers have. They're all in million dollar houses, living in fans see neighborhoods with good schools and like putting their kids solidly in like private schools. Cannot afford that. We don't own a home. We rent. We don't own a car. We do this by design because we live like in a walkable area. We bike a lot of places, and we're comfortable using like oohers and lifts and stuff like that. But yeah, it's totally worth it because we're thriving. I get to write most days, I get to talk to people like you who are inspire me. My wife spends a lot of days painting and creating, and we both get to spend bountiful time with our daughter, which is like that's it. That is like the point for me.
Yep. So let's talk a little bit about the fear and uncomfortableness that comes with choosing this different path because it's real, right, and what can happen? And I've watched this sort of manifest in myself and had to sort of work on it, right, which is that you step off the default path to do this other thing. But the fear of holy crap, how am I going to make a living? How am I gonna make money? What am I gonna do? My son's in college. I got to pay for his car. I mean, all this stuff can drive me to turn my pathless path into I don't know what the word is, a hugely ambitious and stressful pathless path right where I box myself into a new corner by letting that anxiety drive me to do more and more and more and more and more and more. And that's something I've had to kind of work on going, all right, and I've gotten better at it, like you, it takes. It took me a few years to kind of get my foot in I think where I was like, okay, relax, you're gonna be okay, relax a little.
Yeah. A lot of people leave their jobs because they don't like their managers, but then they instantly hire a manager in their head to control their behavior.
Yes, who's a tyrant.
And one good thing about feeling like you're gonna run out of money and not making money, especially if you're raised in the US, You'll just start freaking out and try to make money. And a lot of people have not felt this. This is probably one of the most useful things that happened to me. I quit my job in New York. I think I should have thought more deeply about this, but I was spending about six thousand a month and I had like fifty thousand in savings, and like month one month too, I'm like, oh crap, Like I'm gonna run out of money, and I just started getting really aggressive. I'm like calling everyone, emailing everyone I know, applying for all these contract jobs, putting my thing on all these talent platforms to hire for consulting gigs. One of my first gigs was walking around New York City for this investment firm. They needed this last minute freelancer to do surveys of people wearing all birds. So I just walked around New York City and try to spot people wearing all birds. First day, I couldn't really find that many people. The second day, I'm like, all right, I need to figure out how to do this better. So I held up a sign in Union Square Park and said, does anyone own all birds? Right? And then I think I got forty people to answer my four question survey, and I was like, I don't know if I could find one hundred. They're like, I have forties. Good. But it was my first experience of oh, you just made yourself feel more uncomfortable than you did and in the entire ten years of your safe knowledge work job, right, you look like a fool holding a sign you're desperate for money and you only made like a thousand dollars doing this over a week. And then analyzing the data and all this, and yeah, it made me realize there's so many ways to make money. It's just that for knowledge workers, what they're really afraid of is can I make what I used to make? And I didn't really set out to replace my income replacing your income, I have no advice on how to do that. It took me until my fifth year to actually make a comparable amount to my last year of working. Yeah, and I don't know if I'll match it again. It could go down.
Yeah. I think that's a really good point about matching your income is a hard thing to do, you know. I think, like you did, it's a matter of looking at everything is trade offs in life, right, I mean, I think you said that earlier. I mean, everything has its trade offs, and we just have to find the ones that we're willing to live with. You talk in the book about this idea of many people on the default path will live with certain discomfort and then layer coping mechanisms on it rather than face uncertain discomfort. Talk to me a little bit about that, you know, knowing that you are uncomfortable and then finding ways to cope with it so that you can stay where you are.
Yeah, you probably have more knowledge about this than me. I think. With the addiction, if everyone around you is slightly uncomfortable and anxious, it becomes normal to feel slightly uncomfortable and anxious, right. And then if everyone's coping in similar ways, namely drinking a lot on weekends like me and all my friends. One hundred percent of my friends did then that's just life. Right. But now looking back, I don't drink anymore. And it's really weird to look back because I didn't have trouble drinking. I don't think I was addicted, but it sort of fell out of my life in a weird way in which I look back and say, oh, I did have a drinking problem. And when you say that, it triggers a lot of people, because a lot of people get defensive. Drinking in the US especially is one of these things that's just part of life for people, and to bring this up makes people feel really uncomfortable. But I think for a lot of young people, especially living in cities, binge drinking on the weekends is the bomb for the discomfort of the work week, right, And as long as everyone's doing it and it seems fun, you don't notice that it's a problem. But I wasted so many days being hungover and recovering from drinking and probably stifling my curiosity and actual passion for life.
Yeah.
I think this is a really interesting point, which is I mean, a lot of the work that I do, I would say, is about people increasing their healthy coping strategies, right, So I think we could probably all go, you know what, if you've got a life that's bad and you escape it by drinking or doing drugs or whatever your thing is, your addiction, that's very problematic. We would all go, well, you know what, there are much better ways to cope with that, right, And I think part of what we do here is help teach people those mechanisms. Part of what I occasionally am uncomfortable with and that I wonder about is the point that you're making that even healthy coping mechanism oftentimes is keeping you in a place that may not be the right place for you. And that's a fundamental question that I think a lot of people who are later in their career, who've been on the default path for a while, who are going, I'm not really comfortable here, or I'm not happy or I'm not fulfilled, and their question that they spend a lot of time on is do I just accept that this part of my life is this way and build everything else around it in a really meaningful and purposeful way, or do I sort of blow the whole thing up. I don't think there's easy answers, and I think depending on the person and the situation and all that those are both reasonable approaches, but it does get to there are other ways of coping with situations that maybe we shouldn't be coping with, even if we're doing it in a healthy way.
So to connect this to the previous point, I think the equation and I the book is certain discomfort from plus coping mechanism is better for many people than uncertain discomfort of blowing up your life and taking that new path.
YEA.
The thing that tips the scales over and over and you can identify this and the way people talk about the future is a sense of wonder and possibility. They say, Okay, I might blow up my life, but there might be something interesting worth finding. And Johnny Miller has been a huge influence on me. I've lived with him in three different countries and he's helped me think about this in terms of nervous system regulation and connecting with your body. And I think the thing to ask is how do I experience different states of being? Right, you're coping because you're in an uncomfortable state of being. But if you talk to enough people, you read history, you read poetry, you read literature, you start to discover there are states of being where people feel at and given that knowledge. We should all sort of be freaking out figuring out how to try to get there, and there are many ways to get there. I think sabbatical, taking one month disconnected from work can be very powerful for people. Breath work can be very powerful for people. I know a lot of people are experimenting with psychedelics. I haven't used those, Yoga, tai chi, chiekong, all these practices. There are different practices which let you participate in the world in a different way. And John Varvaki is really good around this. He talks about it in terms of participatory knowing right, how do we experience the world in a different state of being such that we can sort of come to a different state of knowing right? And in the West and in knowledge work jobs, hardcore career jobs, we're not at the participatory level. We're at the propositional level of like concepts, abstract ideas and all these things. So we're existing up here, but we're not down here. We're not in the heart, we're not in the body, we're not in a state of flow. We're not experiencing the magic of deep leisure of this connected contemplative state. Because if you've never experienced that you're going to just keep going on what you're doing. But the thing I love about podcasts is you have people in your ears telling you different things are possible. So if you're listening to this, like different states are possible ghos, see if you can find them, and you can find them in a weekend, you can find them after work. All you need is enough of a window to say, ooh, I want to follow that and see where it leads.
Yep, yep, totally. And the question underlying this is sort of this fundamental one that I think we all wrestle with in lots of different aspects of life, which goes back to the classic serenity prayer, right, like what situations do I need to excit and make the best of and that the way that I'm responding is an internal problem. The problem is in here, right, and what situations is legitimately the problem out there? And there are many situations where in certain cases that's very clear. Right. If you're in an abusive marriage, for example, it may not feel clear to you in the moment, but deeper knowing will lead to a clarity that says I'm clearly in the wrong spot. The answer is not to learn to tolerate my abuse better. The answer is to get out of here, right, So there are examples where you can go, oh, that's a little bit more obvious, but for most of us in life, this figuring that out is really sort of the challenge of you know, what does this situation call on for me? Do I need a whole new career and everything to be different, or are there ways of relating to the life that I have very differently that will cause me to be in a much greater state of peace and calm. And that's sort of the fundamental question that's underlying some of this.
That's why I liked being on my current path. My current path is not a path, and you probably experienced this as well. Every week is different, every month is different, every year has been different. So I've had all these mini lives in these last six years. Whereas I look at the previous ten years, it was very predictable. I did the same kind of work on the same times of most days of the week for ten years, around the same kind of people, thinking in the same way, showing up in the same way, coping in the same way. Now my life is just weirder, and there's more possibility for people to tap into this, Like I've challenged a lot of people do a freelance year. Do one year where you just go try to make money on your own. It's going to be scary, it's going to be hard, it's going to be uncomfortable. But you might discover that you have more courage than you thought. You might discover there's more people out there willing to help you than you thought. And you might discover you're curious about things you forgot about. Right And that's been the magic of this path is we touched on this before, but I still have fear, Like I'm really leaning into being a parent right now and I'm dropping the ball on a lot, and I'm just wondering, like, if I keep leaning into this, am I going to not make money? Am I going to not plant the seeds of the next thing that might take off. I've had four or five different things that have gone like up and down and dissipated, and I don't know, but I've been on this path long enough to say, Okay, I'm going to have a mini existential crisis every few weeks. But it's just there. It's always going to be there. The fear doesn't leave, right, And maybe this is the point of the parable is like you're always feeding the bad wolf, right, but you learn to just accept it. It's part of life. Fear is part of life totally, but is existing with that fear in a more relational way, more comfortable way, more like, oh yeah, yeah, you're afraid for the future. But the other side of that fear is love. Right, You're afraid for that future because you love the people in your life. You desire to show up with your full self. And it's all related, I.
Think, depending on our makeup, we all live with different degrees of fear. You can be in the default path and be terrified, right, I mean, so fear can come from any but there is when you're on sort of this pathless path, there is more opportunity because uncertainty is not a state that we naturally do well in. And I agree with you. What I think I've gotten better at doing is just going Okay, there's the twinge of fear going on over there. I can't make it go away, but I'm also not going to react to it. I'm going to respond to it and hopefully a wise way, but I'm not going to allow it to sort of jerk my chain, and it's just funny over. I don't know, maybe it's been four or five years now that you know, since I left my software world. I mean the first year. I mean I remember it as clear as day. I don't know, it was maybe nine months into it, and all of a sudden, the coaching work that I've been relying on just hit a dry patch, and I was like, well, that's it. I'm doomed. You know, everybody who wants to work with me has already done it. You know, they've heard the podcast. They don't want to do it anymore. And you know, now when any part of the business sort of quote unquote dries up a little bit, I'm like, that happens, let's move this way. I don't freak out. In the same way. I've just gotten better at handling the uncertainty.
Yeah, uncertainty is not a problem to be solved, and I think the great delusion of the modern world is that we can solve uncertainty. Paycheck life sort of promises you that a steady paycheck solves uncertainty, but all it does is enter you into a vast conspiracy with all the other people with a paycheck to not mention it right, and then working on your own it just punches you in the face and eventually you're like, oh, we're dancing with uncertainty, right, This whole path is just about dancing with uncertainty, and it's just an ongoing dance. You can't leave the dance, and it just keeps going. But eventually you start to see, oh, there's some fun in it.
Totally. I mean, the last ten years of my sort of software career, I was doing consulting work for very long large organizations on really big, complex software development projects, and the whole time, my mother and my father, to some degree but not to the same extent, just kept saying, well, why don't you get a job there, right, Like it's so uncertain being a consultant, Like, just get a job. And I was like, Mom, I don't think you quite understand, Like getting a W two from them does not mean they're going to keep paying.
Me forever their generation it does.
And you know, for me, I just was like, you know what, the fact that this is like a six month consulting gig at a time that just sort of keeps going on some level for me was like Okay, I have to sort of keep my skills sharp, right, I have to stay connected in this world. And to me that was the better hedge against uncertainty was my own ability, my own confidence in myself to say, Okay, if this thing doesn't work, there are other things that will, you know, And so I just think that that certainty question is different for everybody. I interviewed a guy recently. Have you seen a recent book by a guy named Bruce Feiler called The Search?
I haven't seen Search, but I read Life is in the Transitions right here.
Okay, well, he's got a new book that you would be fascinated by because it's sort of life is in the Transitions for work specific.
Oh wow, it's my wheelhouse.
It's totally your wheelhouse. He basically goes through and he comes to a lot of the conclusions that you do. I mean, one of them is this fundamental idea though you think there's a path, but you're not on a path, Like life isn't certain enough. The world isn't certain enough that your path is assured. You know, there are some that are better trod than others, right that we can sort of see. But if you really understand the nature of the world. You realize that your path is unfolding as you go and there's gonna be things in that path that you just don't expect.
Yeah, I love this so much and it ties to what you're doing. Right. One of the features of being a consultant it's hard for people to understand is that you can't delude yourself about what you're doing because you need to opt in and take responsibility for your path right.
Right.
If you're in a job, it's such a subtle shift, but people just start talking themselves into like, well, this is what I do. Right. And there's a motivation question. If you're working as a contractor, they can't tell you to do anything technically, of course they can. But when you're working for a job, there's just stuff you have to do, so you can do stuff you're like, actually two out of ten motivated by. If you're working for yourself, suddenly, if you try to get me to do stuff I'm actually two out of ten excited by, it will never get done. Yeah, So it's sharp your focus to say, Okay, I need to search for stuff that's at least eight out of ten excited by. And that's why it was very easy for me to write a book because that was like a ten out of ten. I was like pumped, powering through that. And that's beautiful, right, And it ties back to what Bruce Faylor writes about is life is just disruptions, one after another. Life Is in the Transitions is such a good book because it brings alive so many stories. It's like this person thought they had a path and like boom, disruption, disruption, disruption, disruption. It's yeah, basically constant in everyone's life. And I looked at my life and it's like, oh, I wasn't on a steady path. I had a health crisis, I lost my grandfather, I moved cities, I moved companies five times. Just constant disruptions.
Yeah.
Yeah, you should check out his new book. You'll absolutely love it. If you like Life Is in the Transitions. And I know, given your love of exploring this different way of thinking about work, read these two books in somewhat close proximity.
Right.
What Bruce does is interview hundreds and hundreds of people and sort of compile that data and put it together, and after doing so, he arrives at the same place that eighty percent of your book is at. Also like, it's just a different way into what are very similar conclusions about the way things are in today's reality.
Yeah, it's just I think with my book, I just don't like those books where they interview a lot of people. I just want to hear like people's personal stories. So I just trusted my intuition, and mine's fueled by I had probably four hundred conversations with random strangers on the Internet. I've injected a lot of the lessons from them, and it was very an emergent book from those conversations, which spiked during COVID. Suddenly everyone was like, oh, wait, what are we doing?
Yep? When did your book come out?
Two thousand and twenty two January?
Okay, I thought it was a little bit early that. So let's talk about a couple other ideas here. Talk to me about the idea of the ought to self versus the ideal self.
Yeah. This was Davidovich, the psychologist at Cornell. I think it's this idea, like we think leaving the default path, for example, leaving your job is just going to destroy your life. That is how our brain works. We imagine all terrible things because we're scared. That's our fear talking right, But they argue that our ought to self is so powerful that we're still going to take care of our responsibilities and obligations, Like I'm scared of leaving my job because what about taking care of my family? Well, in that statement, I'm scared of taking care of my family. You're actually going to take care of your family, like you will figure it out because it matters to you, right, And we don't pay attention or trust this ought to self. I'm not and we sort of neglect our ideal self. And this is for many people the whole point of life. Becoming the person you want to be, right, That drives a large percentage of people. And if you neglect that, pursuit the aspiration to become your ideal self really just growth. There doesn't even have to be anything to aim at, just growing evolving as a person. If we neglect that, we're going to have regrets. So the takeaway is trust your aught to self. And this is why I don't really stress with having kids. It actually I think will make it easier because there's no way in hell I'm going to drop the ball and taking care of my daughter's needs. Maybe I'll skimp on some of my needs, like I'll drop the ball on my needs, not buy new clothes or whatever to keep my path going and protect my creative work. But I won't do that with my daughter and just trusting that I'll pay attention to that.
Yep, that ought to and ideal self is a really interesting idea because on one hand, you know, we hear this idea ought to self and we think that's a bad thing, right, Like that whole phrase, like you know, if you're saying the word should, you know, don't should on yourself, as if the word should is always a bad thing. I mean sometimes it is. Sometimes it's taking on values and ideas from other people that aren't your own. But sometimes it's just a simple shorthand for what matters to me right and ought to is the same thing. Like it could be bad. It could be me neglecting and only taking on the values of others, but it could be my inner self saying here is what you ought to do to be the person you want to be, So it's not all bad. And also that ideal self, it's having both of those things being in some sort of balance.
Also, it's all about self awareness, right. If you think something matters to you and you're living in concordance with that. If somebody gave you advice or more in about how to do that better, you would never get offended. You would just figure out how to integrate it into your life. Right, Instead of we have these ideas sometimes of what we should be doing. I should be writing more. I never say such things. It's like, I'm either writing more or I'm not. Like there's probably a reason for one of those or the other. Typically we're doing as much as we can.
Let me dig into that a little bit further though, right, because, at least in my case, I find situations where in order to be the person I want to be, I'm having to push myself sometimes to do things that I'm like, well, I don't really feel like doing that. So the word should comes into it again. It may not be the right word, But I'm wondering how you think about that if you're writing or not writing, but part of you is like, I really I want to finish this book. I mean, how do you think about that question? You know, to be the person you really want to be, are there situations where you're having to sort of push yourself in directions that you don't feel like at the.
Moment, yeah, I think this is something I need to think about more. I don't know if I have the best answer to it. Now people come to me for advice on how to create stuff online, and I think what I'm talking about is a narrow case of somebody has been saying, oh, I should write more for like a year. After a year, if you're not writing, like your sense of what you should be doing is not the problem. It's a problem of something else, your environment or how you're designing your life right. And that really just gets to thinking differently about, Okay, what are the pieces in the environment I need to change to actually get what I want right? And Tim Ferriss's fear exercise has been great for me, which is what are the risks in taking this action? How could you mitigate those risks? And then flipping it and saying what are the risks of inaction? So what are the risks that you're pricing into your day to day existence? And then I don't know, this is like a really interesting question because I think this is something I wrote about in my book, which is I can't really pinpoint like a moment. You know how everyone asks when's the moment you knew. I don't know if there was a moment, rather than like I was just on an emergent path, right, yeah, And it's really a felt sense. Right. So then the question is how do you just know when you're not on the right path? And that I think might be everything, which is just figure out when you're on the wrong path and just keep shaking things up. The answer might literally just be do random stuff on your drive home, take a different route, go take a walk without a destination, Go play an instrument if you've never played an instrument, I don't know. Just do random stuff that might shake things up for you. And this is the hard thing because a lot of people want playbooks, they want how to but the truth is there are no how tos to find your own true path.
Amen to that. That is a very very true statement. I think that we can listen to podcasts, we can read great books, we can get great ideas, and those are all very useful things. And learning from others and having teachers and all that and mentors has been incredibly important for me. And at the end of the day, I had to find my path because I am not someone else.
I am me and my own.
Set of causes and conditions that make up who I am. My path is going to be a little bit different, and that's why this sort of ten easy steps for X, I'm always like, well, okay, that's probably not Like I don't think anything is easy, and we all might need prompting in different directions depending on who you are. That's the other piece of like one size fits all advice is it's like, well, maybe for some people that's the right thing, but for other people the exact opposite might be the right thing.
Yeah, it's so hard in today's world. I think I have a certain psychology which was not able to thrive on the default path, and that's meant I had to leave that and it's made life harder. Like the truth is, my current path is harder. It takes more reflection, it takes more introspection. It's frustrating sometimes, but it's also I know in terms of just the day to day wonder, the joy I have for life, the sense of creativity, the contentedness. It's a lot better for me, and it's going to continue to be hard. Kids don't make it easier, they make it harder, But also the payoffs are much bigger. Too, to finding the right path and which not only can I thrive? Can my wife thrive? And my child thrive? But that's the lifelong question, and I love trying to figure it out. And I've just found over and over again that thinking about this and trying to find the right path is worth it.
Yeah, you've come back to the phrase. You've used it multiple times in this conversation, which is self awareness, right, And I think the important thing, at least for me, is in the willingness to continue to ask the questions now. Like you, I feel like I have a psychology makeup and a life conditioning makeup that makes it almost impossible for me not to. You know, if I could just shut it off and be like I forget it, I'm just going to coast here for a while, I think I would do more of it. Maybe I don't know, I just am not wired up that way. But I do think that a meaningful life comes from asking a lot what is a meaningful life?
To me?
And am I doing it? Like not every ten years on some you know retreat, but regularly again and again and again. You know what matters? Am I living that way?
That?
To me is how a meaningful life is created. And I think that's a big part of what your book says to me at the end of it is, you know, ask these questions and be willing to look at the hard answers.
Yeah. It's all about noticing for me and paying deep attention to how I'm living my life week to week, month to month, year to year. Yeah, this conversation right now, me talking with you is somebody that takes these questions seriously. It tells me, Oh, I'm in the right place.
Yeah.
Ten years ago, I was surrounded by people who mocked me for asking deeper questions. Oh, that's ridiculous. You have to work. That's a stupid question. Deep cynicism, and I was surrounded by that, And it's scary looking back, because I almost convinced myself that cynicism was the right orientation toward life. Ah, what are you going to do? You got to just struggle through life and suffer and do these stupid things because money is important and employment is important. I'm glad I just kept asking questions.
Yeah, I'm glad you did too. And I think that is a perfect place for us to wrap up. Paul, Thank you so much for coming on the show. Of links in the show notes to your website where people can get your book and all the ways to find you.
Yeah, and I'm always happy to give the book to people. It's such a joy to connect with people who are asking these questions like you. So I appreciate what you're doing and this was a beautiful conversation. So thank you.
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