The One You Feed - How to Find Your True Path with Paul Millerd
Episode Date: September 22, 2023In 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. In this episode, you’ll be able to: Acknowledge the necessity of stepping beyond pre-set boundaries to unmask your true potential Get comfortable with the unknowns while progressing in life’s journey Identify the impact of connecting your work with your deepest passions and beliefs Learn to interrogate societal expectations in order to prioritze to your own values and passions Get acquainted the process of self-realization for living a life that embodies who you truly are. To learn more, click here!See omnystudio.com/listener for privacy information.
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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 thinkers 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.
I'm Jason Alexander.
And I'm Peter Tilden. And together, our mission on the Really Know Really podcast
is to get the true answers to life's baffling questions like
why the bathroom door doesn't go all the way to the floor,
what's in the museum of failure, and does your dog truly love you?
We have the answer.
Go to reallyknowreally.com
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The Really Know Really podcast.
Follow us on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts.
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 new 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 and 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 I read the book. I'm really glad I did. So we're going to 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 her grandchild. And they say, in life, there are two wolves inside of
us that are always at battle. One is a good wolf, which represents things like kindness and bravery
and love. And the other is a bad wolf, which represents things like kindness and bravery and love. And the other is 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
in 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 a 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-20s 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 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 remarkable man.
I didn't know you interviewed him. I'm definitely listening to that right after this.
Yeah.
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 discover the phrase, the pathless path,
you're not meant to know what it means. But for me,
I had the opposite reaction. 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 release 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 are 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, in 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, you know, which is there's a
gate you pass through, but it doesn't exist. I mean, there's no thing that's blocking the gate.
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 context, I grew up, my parents didn't go to college.
They were very much on the default path.
And I write in 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 U.S. 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, McKinsey 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 stay till eight or nine.
And what I realized eventually is a lot of people in these worlds, their whole identity is work.
And by work, they identify 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 here.
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 school is 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 memetic 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 call it 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. He's like, you'll learn. Once you're in the real world, you'll figure out. 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. 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.
Yeah.
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 at a top business school.
You can't just introspect fully there.
You got to get a job.
You're going into debt.
I was like 70 grand in debt at 27 years old.
So 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 ask me, was it hard to 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 a hypothetical, you may not even be able
to put yourself in the mindset that this question would even make sense. But you're a son to a 10
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,
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 than 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.
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 24 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 24, 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'd 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 $500 to $1,000 a month in Asia.
a thousand dollars a month in Asia, really just like, I was sacrificing. Like I wouldn't even like eat food out. It was crazy. 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 into ambition? Then
you try to find the middle ground and you're always searching for the right path. I think the mistake with a lot of legible paths, paths that we can see, oh, I'm going to
become a data scientist, then a manager, then 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 sales person 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 defined yourself as a software salesperson,
you wouldn't be hosting a podcast.
Right, right.
And you probably kept going deeper with the 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 40. 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? I'm Jenny Gay.
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experiences, and feelings we often keep to ourselves are the very ones that are most
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My path to where I'm at today was certainly, it was a middle way path between staying in what was secure and made a lot of money. I mean, 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.
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, to doing this podcast and the,
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 is 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.
I did not cash in.
I am not somebody that got to 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 2017, salaries just started going up like 20, 30% a year. It was
crazy. I didn't get any of that. I lowered my salary down to like 25, 32, 40 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 are 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.
Yes. And feeling bad about that, being 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, right?
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.
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 fancy 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.
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 Ubers
and Lyfts 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 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 going to make money? What am
I going to 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,
more, more, more, more, 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 going to 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 going to 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.
Yeah.
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 $6,000 a month and I had like $50,000 in savings. And like month one,
month two, I'm like, oh crap, like I'm going to run out of money.
Yeah. month two, I'm like, oh crap, like I'm going to 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 Allbirds.
So I just walked around New York City and tried to spot people wearing Allbirds.
First day, I couldn't really find that many people.
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 Allbirds?
Right. And then I think I got 40 people to answer my four question survey. And I was like, I don't know if I could find 100.
They're like, 40 is good. But it was my first experience of, oh, you just made yourself feel
more uncomfortable than you did in the entire 10 years of your safe knowledge work job. Right.
in the entire 10 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 $1,000 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. 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.
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, 100% 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 hung over 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 a 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 I put in 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.
Yeah.
The thing that tips the scales over and over, and you can identify this in 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 like 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.
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 peace. 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, qigong, all these practices. There are different practices which let you
participate in the world in a different way. And John Verveke 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 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. Go 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 I think we all wrestle with in lots of different aspects of life, which goes back to the classic ser 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, well, 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 like being on my current path.
that's underlying some of this.
That's why I like 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 10 years,
it was very predictable. I did the same
kind of work on the same times of most days of the week for 10 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.
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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 anywhere, 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, OK, 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,
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, I 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 10 years of my sort of software career, I was doing consulting work for
very 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-2 from them does not mean they're going to keep paying me forever.
Their generation, it does.
100%.
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 Filer 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 that 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 going to 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 10 motivated by. If you're working for yourself, suddenly, if you try to
get me to do stuff I'm actually two out of 10 excited by, it will never get done. Yeah. So
it sharpens your focus to say, okay, I need to search for stuff that's at least eight out of 10
excited by. And that's why it was very easy for me to to search for stuff that's at least eight out of 10 excited by.
And that's why it was very easy for me to write a book because that was like a 10 out of 10. I was
like pumped, powering through that. And that's beautiful, right? And it ties back to what Bruce
Fahler 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 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, having 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 80% 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 400 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?
2022, January.
Okay. I thought it was a little bit earlier than 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. 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 enough.
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 ought 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 on taking care of my daughter's needs.
Right.
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.
Right.
And just trusting that I'll pay attention to that.
Yeah, 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 information 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,
I should write more for like a year. After a year, if you're not writing,
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' 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, right?
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.
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 10 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.
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 in 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, forget it, I'm just gonna 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 10 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 as somebody that takes these questions seriously, it tells me,
oh, I'm in the right place. 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.
What are you gonna do?
You gotta just struggle through life and suffer
and do these stupid things
because money is important and employment's 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. We'll have 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 gift 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. 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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