The Pathless Path: How To Recreate Your Life And Career In 2023 - Paul Millerd
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By the way, in case you haven't heard, my brand new book, Feel Good Productivity, is now out. It is available everywhere books are sold. And it's actually hit the New York Times and also the Sunday Times bestseller list. So thank you to everyone who's already got a copy of the book. If you've read the book already, I would love a review on Amazon. And if you haven't yet checked it out, you may like to check it out. It's available in physical format and also ebook and also audiobook everywhere books are sold.

What would happen over and over again is people would tell me things and I'd be like, have you shared this with anyone? Well, I've said like a little to my spouse, but like I can't talk about this with anyone. So I was like, oh wow, what I'm writing about is like this hidden knowledge that nobody feels they can talk about publicly.

Paul has written a fantastic book called The Pathless Path, of which I have about 10 copies here in the office because I give copies to anyone who is struggling to figure out what they want to do with their lives. I went out for a motorcycle ride. The ideas just came to me and I just broke down in tears. I realized it had like everything to do with my parents. They didn't go to college. They had to do the default path. And I realized what they gave me was the freedom to dream. It matters to like dream, do brave things. I really think this matters and I think I can help people with this stuff.

and I'm just gonna say it. Paul has a super interesting background. He used to work in a traditional field in management consulting, but then he quit his job to kind of wander this pathless path. And he writes a lot around how do we think of what a career means? As soon as I left my job, I sort of dealt with this jolt of reality of like this increased freedom and space in my life. And then in 2020, the whole world sort of like showed up, like asking these deep questions about work. And

my readership just like exploded. The old formulas of what led to career and like life success and fulfillment and stuff like, you know, just get a job and work your way up at the company and get the company car and all that kind of stuff. That's not really the formula that works anymore. I think Paul's ways of thinking about this are incredibly inspiring. So if you've ever thought you're not really sure what you want to do with your life, if you've ever had doubts about are you really in the right sort of career? I really hope you'll get a lot of value from this conversation. So Paul, welcome. Welcome to the show. Thank you so much for coming on. How are you doing?

I am excited to be back talking with you. I think we talked almost like two years ago at this point the first time. So excited to dive in and catch up on both our journeys. Yeah, that would be sick. So I've been every time I have a bit of a crisis in my life trying to figure out what I want to do, I always think of you and I always think of your writing and your book and your newsletter. So it's all just like, I mean, you're sort of my...

I don't know, my life path, pathless path guru, even though I'm sure you don't intend to be as such. I would love to get started with, if you can just, how did, essentially, like, how did we get here? How did you and I ended up talking like this? How did you end up developing this, I guess, career that you've landed into?

Yeah. So we'll have to dive into what we're talking about when we say words like career. But my path, grew up in a small town in Connecticut, sort of always did good in school, stumbled into all these really impressive career options in college, tried to break into them, ended up breaking into strategy consulting for like nine years. Loved my time working in that industry, but sort of

Ended up feeling more and more stuck the longer I spent on that path and really just desired to escape. So I saved not that large amount of money and enough to kind of buy freedom for a year. Wanted to run away from work. And on that journey, which has been five years at this point, sort of discovered I didn't want to escape work.

I wanted to have a different relationship with work. I basically wanted like things I could connect to, work that brought me alive, things that energized me. But it was really a slow stumbling awakening to that. And a lot of my writing was about that. I think that was some of the writing you connected with. And increasingly in 2020, a lot of the world started paying attention to what I was writing about.

um before that i was kind of i didn't really know if what i was writing about was connecting with people but in 2020 just so many people started showing up and reaching out and starting uh talking to me so that's a that's a pretty cool journey of you know starting out with a very very traditional career i guess and then deciding to break away from it and and do your thing um i can't so for for a podcast like this it's like there's

I think there's sort of two ways to go about it. One way is where I essentially act as an interviewer and ask you your story because I know that... I imagine most people listening to this are not familiar with your story. But I feel like because I'm already familiar with it, that bit is less interesting to me. And I just want to dive in. I think that's a path. Just sort of diving into...

the things that I am currently struggling with. And I would just love to get your take on it to be my personal therapist for this. How does that sound? Let's do it. I mean, this is the deep dive, right? So I love going deeper anyway. My story's out there. People can find it. They can get the surface level stuff. And I think the more interesting thing is that when we look at what other people do, we tend to look at the surface level stuff.

Um, and I was, I was writing about this this week and I sort of referenced you in a post that I was writing about, which is like just observing you, you seem to have found some sort of mode in which you're able to show up in your life doing work you actually like doing. Um, and we can dive into whether that is still true or not and to what degree. Um, but when people look at you, they probably look at like metrics, right? Metrics, dollar amounts, all these things. But

What I'm sort of talking about in a relationship with work is like that stuff is secondary. And convincing people that that is secondary is actually hard to do in today's world because so much of the world is oriented around the idea that like these metrics, these sort of goals, these titles are what matters. If that's secondary, then what is primary, I guess? I think what I'm trying to say with work is that...

If we're just sort of showing up and accepting what society tells us, I call this like the default path. The default path is what most people around us are doing. This is the story we grow up with in our culture that says you are successful if you do these things. Get a job, go to school, get good grades, start a family, right? And for most people, that works pretty well. But increasingly, large amounts of people, one, either can't make that work,

or end up on that path and something is just totally off. Now I think part of the nature of work and it becoming abstracted, we're not using our hands, we're not literally connecting to what we're doing anymore. People are just not as satisfied with their work. They're also taking these ideas like meaningful work and trying to fit it into a job container.

And they're not quite getting what they want. And so there's this sort of confusion and people don't really know what to do with that feeling. And I think those feelings are really human ones of like wanting to matter, wanting to be useful, wanting to feel connected to the world, to people around us, to ourselves. Um, and that those are the things I'm arguing I think are worth finding. Um,

But they're non-trivial to find and might require blowing up your life and doing things that don't look like success on paper. Yeah, I think that's where this gets kind of tricky because, you know, just like you, I've had a very kind of traditional education, went into a job that was by all kind of external metrics and stuff like a prestigious and useful and good for society thing to do.

And in a way, when I decided to leave medicine to become a, you know, YouTuber, for God's sake, that, you know, there was a huge part of me that was like, is this, is this really legit? Like, um, am I, am I making the right decision? Like, will I essentially become a, an outcast or a pariah in society? Because I have gone for this. I've, I've chosen to leave something as noble, a profession as medicine, which saves lives for the sake of making silly videos on the internet. Um,

And so I think that's part of it. It's like the, what will society think of me? But I think also, like, I've had a bunch of conversations with people since I announced my decision to leave medicine and stuff. People now stop emailing me having career crises that, oh, I'm in this job and the job pays well, but it's not the thing I really want to do. How do you think about it in terms of, like, we all need money to survive, right? Like, so there is a baseline level of money that we need to get in our jobs, right?

And the legible alternative careers of these days actually become a creator has become a lot more legible than it used to be back in the day. Become a creator is one of the things where there's basically zero guarantee of making any money at all, at least for the first while, especially if someone's a complete beginner to it. So how do you tackle that thing of I need money to survive, my job gives me money, but it's not the thing that I really want to do?

I think the thing to do is sort of unpair the stories, the shoulds. We all have these like shoulds. I should do this. I should do that. And like really what I'm urging people to do is like actually reconnect with what how they're feeling. It sounds so easy, but even with like the creator path becoming more legible, more and more people are coming to me and saying, oh, I think I want to quit my job and do my own thing.

But then they'll list out a bunch of like concerns and issues they'll have. And I'll have to be like, no, like based on the people I know who are thriving in this path, you are not those people. So what do you mean? I think in the sense, I think in the sense that like they aren't like valuing the freedom

of being on your own high enough. They aren't valuing. They'll come to me with like, oh, what if I can't make money? What if I don't have predictable income? And it's like, you're not yet valuing the upsides of such a path. Like, whereas a lot of the people I talk to, they're not coming to me for should I quit or not? Or how do I manage all these fears? They're coming to me and saying like, okay, I'm definitely leaving. Okay.

Can you give me like five pieces of information to like help me improve how I'm doing this? Right. And that's a certain personality type that is like craves freedom, needs autonomy over the how they're working, like really wants to like go on an adventure and do their own thing. And those are the people that are going to like thrive and make it. Whereas there's this meme now of like,

I want to quit my job and do my own thing or become a creator because people are seeing you can make money and gain status in it, though the status is probably questionable at the beginning. And then they'll say, well, like, oh, I don't know if I'll be able to like pay my mortgage. And like, I'm really concerned that like this isn't like a wise thing to do. It's like those aren't actually things that like the people like desperately committed to this path are thinking or saying.

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I mean, surely that's not what you're saying. It sounds like what you're saying is you need to have the sort of personality that is desperately committed to the path of freedom and autonomy and doing your own thing. And if you have concerns about money and mortgage and stuff, then you're not the right person to be pursuing this? Or is there more nuance there? I think that should raise a red flag, right? Okay. Financial security is your primary concern, right?

Like probably doing your own thing and having freedom is also not your primary concern. Right. So it's really just checking in with like what you value. Now, you may still be somebody that wants to do their own thing and go on that path. But it's really figuring out like, OK, how can I just test this?

And that's where like the biggest thing I've realized is I don't think most people should quit their jobs. What I think most people should aspire to get in their life is like a one to three month break from worker mode. Okay. So worker mode is kind of like when you're hyper scheduled, you're doing stuff constantly, you're moving towards stuff, you're working for other people, or you're just kind of in like an overscheduled reality. Right. Yeah.

And getting that space in your life to sort of sit back and say, like, okay, what am I doing with my life? What am I actually afraid of? What do I really value? How does it feel to be out of worker mode? Do I feel really terrible in this mode? Okay, maybe my job has some hidden benefits and, like, upsides and things I do value that it wasn't visible to me before. So I think, like, what is really happening is, like, these default scripts are so powerful in society today.

that even the people that are thriving on that path don't really understand like why they're thriving on that path. So what I want people to do really is like reflect more and say like, okay, what do I value? What are the costs I'm paying? And what path makes sense given those things?

Ah, okay. That's nice. Okay. So step one, figure out what you value. Step two, figure out, I guess, how much that costs in terms of time, money, freedom, et cetera, like all of the things that it costs. And step three, is that a price worth paying? Yeah. So for you, I mean, we, we talked, I think a year ago before you were leaving medicine and I mean, you, it sounded like your mother cares.

let you or a doctor, right? And that is a big thing for a lot of people. Like the number one question I ask people is like, will the people closest to you and your family judge you for making this decision? And if so, like, is that a cost you're willing to pay, right? And I imagine like you sort of ran that calculus and said, okay, something matters to me on this YouTube path. And

I think like even at the beginning, you're downplaying it a little. I think you're inspiring a lot of people. You're creating jobs for people. You're giving people permission to create and do things that are new and interesting. I mean, you're still dealing with the challenge of like leaving that path. No, not really anymore. I think when I, yeah, when we last spoke, I think it was on your podcast, I was still like, I'm not really sure about it. I'm kind of half in, half out.

But when I made the decision that, yep, it makes perfect sense to leave, at that point, it felt like I had a lot of clarity and realized it was really, I think what was holding me back was feeling like, oh, to be honest, I could always go back to medicine if I want to.

And in a way, it was always an option. And in a way, it kind of still is an option. But it took Lewis Hose on School of Greatness podcast to prod me to be like, are you saying that if you were desperate for money, you would actually go back and do medicine? To which my response was no, like I can... Probably better ways to earn money. Yeah, there are far easier and more, for me, more interesting ways to earn money. And for me, what I realized is that

you know, if I chart my life back from the age of like 11 onwards, the thing that I was doing in my spare time, the thing that I was doing for free was sitting on a computer programming and making websites and trying to build cool stuff. And that was the thing I was thinking about in the shower. That was the thing I was doing at university while supposedly doing a medical degree. The main path was never the thing that brought me genuine joy other than when I was teaching other medical students. And so if I...

in this hypothetical worst case scenario where I lost absolutely everything. And I remember you saying when you were on mine and my brother's podcast that, hey, if you lost everything and you're broken homeless, come over, stay at my place and I'll feed and clothe you for a few months. And I was just like, that's in a way, hearing you say that, which just sort of pointed out to me the absurdity of the thing that I was actually worried about that like, am I really worried about being broken homeless and alone and no one will love me forever?

And it's like, until I confronted that idea and realized that that's that worst case scenario is actually not is a not that feasible and be I can recover from it because of friends, family network and stuff. Then it was more okay to be like, you know what, even if in the worst case scenario, I lost everything, I probably still wouldn't go back to medicine. And it was that that click in my mind that yeah, I'm fully out of this now.

And that really gave me the peace to be like, you know what? This is fine. This is great. YouTube channel dies in the next five years. Great. No worries. I'll start a tech startup. I'll learn how to code again. I'll program in Web3 Solidity or whatever the thing is there. I'll continue to write. I'll continue to teach. And I trust my skills in being able to make money off of the back of those things almost by default, which means they don't rely. It doesn't rely on medicine to be the thing that I'm doing to make money.

Yeah, I wrote about this in my book. It almost sounds like you had a similar path to me. I grew up playing on computers, building websites, screwing around, earning money on random things online, selling things on eBay, participating in these online simulation NBA leagues. And then when I graduated college, the tech economy was booming and I went and joined strategy consulting and made PowerPoint slides.

And like in my day job, I was still like reading tech blogs and like still screwing around with websites and writing online. And I just wasn't paying attention to it. So I think it's a good thing that these paths are becoming more legible. But for me, it was like I sort of had this moment a couple of years into my journey. I was like writing, doing things online. It was like, oh, wait, I'm doing exactly what I was doing as a kid. Yeah.

It just took me 15 years to remember this is the things that energized me and I liked. Yeah.

Yeah. Do you ever... Okay, so I often hear from people... Okay, hang on. I'm just going to zoom out a bit. Yeah. So we're talking step one, figure out what you value. Step two, figure out how much it costs. And step three, make it happen. And so right now, I guess we're talking about step one. One way of figuring out what you value is thinking about what are the things you were doing as a kid? What were the things that genuinely brought you joy? What are the things you do outside of the day job that you would do for free? What are the things you're thinking about in the shower? One, I have...

I've spoken to a few people who say that, you know, when it comes to this idea of essentially follow your passion and figure out what your passion is that, I don't know, I don't really know what I'm passionate about. I go home and I watch Netflix and I scroll Instagram and occasionally I'll post a photo on Instagram, but like, I don't really have any clear passions beyond that. Like, I don't know, how can I figure out? And, you know, I've got my day job as a management consultant, for example, or a strategy consultant. But beyond that, I get home from work at like midnight. I have to wake up for work at 7 a.m. the next day.

I don't, you know, I kind of want to play the guitar, but like I've never picked up a guitar because I work is just too busy. Do you ever get sort of questions from from from people like that? How would you go about, I guess, giving advice or giving suggestions to people in that position? I can I mean, I can share my story. That was me.

And the reason I did not leave my path sooner is because I didn't have any imagination for what other possible paths or lives I could take. I was mostly surrounded by people like me doing things exactly like I was, who are also not cultivating an imagination of different possible lives.

So I think what I would say, like basically what I say to people now is like different states are possible. There's a state possible where you can be so energized and like discovering ideas and learning new things and reconnecting with that childhood joy. Like that state is possible. I think it is possible for most people. Now, knowing that state is possible means

How can you raise the urgency in your life to like go find it? Now, I don't perfectly know how to find it, but there are a number of things that can help you find it. Like certain things like health crises will force you there. Yeah.

I don't advise those, right? Losses of people in your life can do that for you. I think like the combo of a health crisis and losing my grandfather really like shook me and made me reflect on like what mattered. But still it only planted the seeds that I didn't fully explore even until I left my job. And I think a couple things, two of the most powerful experiences for me, one was

After seven months of freelancing, I decided I would not look for any work and I would not do any work that I wasn't like fully drawn to do. And I just sort of woke up. I wandered around Boston. I was like writing. I launched my podcast at the time. I wasn't trying to make money because like I didn't know how to make money in the creator economy at that point. It wasn't called the creator economy. And like I just like it felt right. Like, yeah.

I was just like, something feels right. I don't know what this is, but I need to follow this. And I had this sense that I had to protect like the writing, the things I was doing. And like making money was like, I'd figure out ways to do that. But like I had to protect that time and the autonomy and freedom to do those things. So that kind of committed me to the uncertain path. And then the second thing was really just traveling.

And moving abroad to Asia, I had started freelancing again, but moved to Asia and like couldn't find remote freelancing gigs. Like I just like was failing. So I didn't have anything to do. Also, it was a lower cost of living. And I sort of just like showed up and did the same thing. And again, like I started writing again. And like I started to slowly realize writing is,

Writing seems really important. And I reflect it back and it's like, oh, wow, I've been writing like every year of my life in some form. So in 2018, I just decided like, right, I need to pay attention. Like if writing disappears in my life, something has gone wrong. So that is the state I need to come back to. Need to protect that at all costs. Now, how I've made money has varied in so many different ways over the past five years. But like the writing has never disappeared.

Yeah, so it sounds like part of the figuring out of what you value is finding the space to take a break away from the, I guess, rat race of continuing to be in work mode.

And in a way, figuring out like almost realizing what you naturally want to spend your time doing. Yeah. And maybe for you, that sort of naturally just took over your life. Like you're already doing those things. Like I think spending 10 years in the corporate world sort of numbed my creativity and imagination. In a way, maybe if you start thinking about these things earlier and younger, it doesn't affect you as much.

But a lot of the past five years have just been a sort of unlearning of like certain cynical modes being like, I don't know, a little too passive, a little too powerless and like realizing, oh, I can show up and do things I want to do. What do you mean? So in the sense that, I mean, when you're in the corporate world, even if you're like in an impressive position, you're still constantly asking for permission and you're constantly being told, no, you can't do things.

hey, this cool new tool, we should try this. You can't just like update a website at a company. Like I can do that now. I can just like update a website and come up with a new service that I'm offering people and just do it in an hour. That's like a six month to two year process at a company sometimes. Yeah.

So like going from that state of possibility, which is like very little possibility, you start just like giving up ideas of what's possible to like having to be on your own and self-employed and starting to like, okay, how do I regenerate that? Like creativity, energy, like possibility for life. And I think this is why I love following people like you. I sort of just like,

I see people like you and other creators come up with ideas like, oh, wow, that's really interesting. I never thought of that. I could do something like that in a different way in my own unique way.

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Often, I find, kind of through conversations with people, that another thing that holds them back is, so for example, a close friend of mine is a highly paid strategy consultant, and she's been toying with the idea of quitting the job. But one thing that's been holding her back is the idea that, oh, currently, in my high-paying job as a strategy consultant, I am making X amount of money, which is like, I don't know, high six figures or something like that, or low six figures.

And therefore, in order for me to quit my job, I need to make sure I can make the same amount of money doing something else. And it's like, oh, but I can't make the same amount of money doing something else because it's like, how the hell do you make six figures a year doing your own thing? Therefore, I couldn't possibly quit my job because I need that

that money to be able to 10 years from now, send kids to private school or like, you know, I want to, I want to save money. I want to get on the property ladder. And therefore I kind of have to stay in this job because of them, because of the golden handcuffs in a, in a way. Yeah. How, how do you, how do you approach that? That's, that's the cost part. I've never matched my salary when I left five years ago. This is the first year, maybe I will come close, but I don't know. And then it's uncertain after that. So like,

This is like, what costs are you willing to pay? For me, I was willing to pay enormous costs because I had sort of discovered this path is not a winning strategy for life for me. I was so certain after 10 years on that path that like if I spent five more years in that path, I would definitely become less of a person I was proud of.

And that was so incredibly costly to me that like replacing my salary was like, this is trivial. Like this is my life. And I think...

I mean, the thing that seeded that for me was five years before quitting my job, like a health crisis. I was out of work and I had sort of lost my identity. I was just sitting around and like I desperately wanted my identity back. And I went through this reflection exercise of like what would happen if I couldn't work again? And it was like, oh, I'd be OK.

Like I'd have my family, I'd have people to take me in. That's why I make the offer to you and the offer still stands. I'll take you in if you go a few months without salary. But

Yeah, it's, I was willing to give it up. So like, this is why I share my income too. Like my income, the first five years, like if I look after tax, it was like 45 because I was freelancing, then like 30, then 25. And then I think last year it was like 55. Okay. $55,000 a year. Okay. US. Yeah. Um, so I've started a strategy consulting job is very low.

Yeah. And I was making, I think my final year, it was probably about 170, 180 US a year. And when I left, I had about 50 grand in savings. So I sort of said, okay, I can live for a year on 50 grand of savings. I need a year just to like,

figure out what I want to do with my life. Like my service level plan was like, I want to be a freelance consultant. But I sort of discovered quickly like, oh, this is just recreating my previous life, but like slightly less work. But in that space, the less work, I was able to get enough like breathing room that I was like, oh, I wonder what would happen to my life.

What are the possibilities if I like keep following this uncertain journey? So like this is the equation I talk about in my book. Like it sort of flips once you add this sense of wonder or possibility to an uncertain discomfort. Uncertain discomfort is terrifying. Yeah, that's pretty scary. But if you pair it with wonder, like, ooh, what might also happen? Then you can sort of immunize yourself for a certain period of time.

And I mean, this is when I start reading like people like David White or Rebecca Solnit and like people that are like giving me courage to like follow these uncertain journeys. This is when you need poetry and literature and like all these people that are like trust the flow of the universe. Like you need that stuff because like you have no idea what you're doing. And then when you're

doing it at the beginning, you, I also like people would ask me, what are you doing? And so like, I would feel the need to be like, I know exactly what I'm doing. Here's my, I had no idea what I was doing. And I was terrified. Now you like, every time somebody asked me, it would scare me. So yeah, you sort of have to have this surface level story, but at the same time, just this deep sense of like, okay, there's a direction. I'm going to follow it.

But I may also be wrong. Like that's the deepest humility in the world. Like I may be wrong. And I think that's the best way to follow any path. Yeah, no, that's nice. Yeah, I think I think it was when I added in the component of wonder that I still suddenly started to feel okay with the decision to leave medicine and pursue this uncertain path.

Because, and with medicine and with most traditional careers, there is a level of certainty you get. You know that, okay, if I stick at this for long enough, I will get the promotion, I will apply for specialty training in X number of years, then it will take eight years to become a consultant, and then dot, dot, dot, dot, dot, and then I'll die. But with

the uncertain path it's like uh right right now i mean i don't really know what i'm doing my youtube channel is kind of going well or maybe it's not maybe my podcast is doing well or maybe my side little software business is doing well or maybe i have nothing at all i have no side hustles and i just know i've got enough savings and enough of a family and friends safety net to be able to spend a year experimenting and then i know that if that experiment fails and i ended up end up needing to go back to a job great i'll just get another job but

But if the experiment succeeds, I guess kind of the upside of that is that I have figured out a way to live my life that is more in line with the person that I want to be. And for me, it was in there was a lot of a lot of fear around this uncertainty. But when I added the component of, yeah, you know, it would be interesting. It would be kind of interesting to see. I'm sure I'll be able to figure something out. And even if not, worst case scenario, I've got family that I can I can lean on to kind of help help prop me up.

That made it feel much more okay. And even now, even with like all of the traditional metrics of success on the YouTube channel and the business and everything, I still feel the sense of like five years from now, I have absolutely no idea what I'm going to be doing. But it's like sort of embracing that with a sense of excitement, curiosity, adventure, which I managed to do about half the time. The other half of the time, it still feels really scary. And I think, oh my God, I don't know what I'm going to be doing five years from now.

Well, yeah. And I think that's the part a lot of people don't talk about on these paths. And I think people probably miss when they look at people they deem successful, right? They're mapping their idea of success onto you. Now, like I see some of the success you're doing, but I also know for sure you're in the same point as me of like, you have no idea. We have no idea what's going to be happening in five years. Yeah.

As opposed to being in a more traditional career path. But I think one of the benefits of an uncertain path is it forces a constant grappling with the uncertainty. Like, one of the things I didn't realize on my previous path was that no one ever asks you, why are you doing this?

Oh, like no, no one deeply asked me, why, why are you working as a strategy consultant? Why would you pursue this path? It was so obvious, right? Because like, everyone thinks it's impressive. And like, everyone knows you make like good money.

Then as soon as I quit, people are like, what are you doing? How could you give up this job? What's your plan? Don't you want a family? Don't you want a house? Don't you worry about this? And like, you start to realize everyone has these fears. And then you realize, oh crap, I have them too. And now I have to face them. So like,

I think what I've learned to do over the journey over the last five years is you sort of are able to take these massive ambiguous like fear of death, fear of being loved, fear of not belonging and like break it down into like mini daily existential crises. So now like I can kind of like in a mindful way, like I see the like fear of uncertainty coming up and I'm like,

I see you. I see you. All right. Money insecurity, fear of going broke. Been here before. All right. We can deal with you. Gotten through this before. Gone through stretches of not making money for a couple months. We'll be fine. But it's still there. I don't know if it ever goes away. I was tweeting the other day about like, you know, what it feels like to hit 3 million subscribers and kind of how it's a sort of metrics or a double edged sword. And you linked me to this article by Paul Jarvis about finding your enough point.

And that was a good article. I was like, it's always nice when you post what you're thinking on Twitter and someone responds with the absolute perfect advice that you need to hear. This idea of figuring out what is enough is something that I continue to grapple with in the sense that

You know, I'm in a very privileged position now where it's like, oh, the business is growing and growing and growing. And it's like, now I need to decide how much do I want to continue to stress out in terms of, you know, numbers going up.

But another part of me is also like, I need to make sure the numbers continue going up because I need to have a safety net of 10 million in stocks and shares and crypto and real estate. And crypto is a bit volatile anyway. So I need to make sure that I have at least enough money to be able to 4% return, make at least 100K a year off of just the investment returns. And it's like the point of enough. I haven't really figured it out, figured out what it is, but it keeps...

a very high number right now and it keeps on getting bigger and bigger as the business grows. And I know that that kind of thinking left unchecked or like not examined is just like generally very unhelpful and not a way to live a happy life. I wonder if you can share your perspective on how do you figure out what is enough for you and at what point you can stop pursuing more in the sense of money and fame and numbers and ambition and promotions and all of those traditional metrics of success.

Yeah. So I think this goes with another default script. The default like drive in our world is more. It's always going to be more. So unless you're explicitly defining an alternative to more, it is more. Right. And I think that is good to sort of acknowledge because, I mean, you have employees now. So like unless you're telling them we're not

trying to make as much money as possible. That is the assumption in like a business and a job things, right? So you could probably do interesting things. I mean, like Paul Jarvis defined, okay, I'm not hiring employees ever. That is a constraint he created. That doesn't limit the amount of income he can earn, but it does limit it to a certain degree.

Yeah, and then I think what you can do is like just I attempted to write my own definition. I can read mine. I wrote it in the book. Yeah, what is yours? I defined it in the book. So I basically just decided like Jarvis's like I should just define what enough is and like write out my definition. So let's see. Bringing up my Kindle highlights from the book as well. Yeah, get the...

branding. So enough is knowing that no amount of money in my bank account will ever satisfy my deepest fears. It's knowing that I have enough friends that would gladly open their door and share a meal if I was ever in need. It's the feeling that I've been able to spend my time over an extended stretch of time working on projects that are meaningful to me, helping people with a spirit of generosity and having enough space and time in my life to stay energized to keep doing this over the long term.

Enough is seeing a clear opportunity that will increase my earnings in the short term, but knowing that saying no might open me up to things that could be even more valuable in ways that are hard to understand. Enough is knowing that the clothes, fancy meal, or latest gadget will not make me happier, but also that buying such things won't mean that I'm going to end up broke. Enough is having meaningful conversations with people that inspire me, people that I love, or people that support me. Nice.

How often do you return to that definition? Like, how is it? Does it help you in kind of day to day life? Yeah, I think by writing these things, I think by doing a lot of my writing, it's a sort of ongoing reminder to myself that I'm trying to live a sort of principled life. And

I think by writing about these things, a lot of what I'm trying to do is just hold myself accountable. Like I'm saying these things matter, like putting generosity over making my own money. Okay, how do I actually do that? Am I bullshitting on that? Like how am I actually doing that? And then also not being too stuck to these stories I tell about myself because

And like trying to do things just to like virtue signal. Like I want to do things that are really aligned with like how I'm wired. I love helping people. I love like connecting with people. I love helping random people on the internet and like navigate their paths. I love these things. And like, that's why I've kept doing them.

Um, but I don't want to be like unnecessarily tied to like, oh, I have to do these things because I'm writing about it. Um, so it's just constant reflection and trying to be honest with what I really care about.

Just a quick note from one of our sponsors and we'll get right back to the episode. And this episode is very kindly brought to you by Skillshare. If you haven't heard by now, Skillshare is one of the world's leading platforms for online classes for online education. They've got thousands and thousands of classes on all sorts of topics from business, entrepreneurship, lifestyle design, cooking, interior design, loads of stuff. And very excitingly, I've actually been teaching on Skillshare since 2019 and I've got 13 classes on Skillshare. Yes, 13 classes.

and you can access all of them completely free of charge by going to skillshare.com forward slash deep dive and that link will give you a free one month trial to skillshare during which you can watch any and all of my classes one class you might be interested in is my youtube for beginners class if you've ever thought about starting a youtube channel this is the class for you i'll take you step by step across like three four hours something like that through all of the steps you need to take to make your first two videos on youtube how to do the channel art how to think

of a name, all of that fun stuff. And loads of people have taken that class and said that that class was so good that they would have literally paid hundreds of dollars for it, but you get it completely for free on Skillshare by going to skillshare.com/deepdive. After your trial's over, you can choose to continue the subscription if you like, and you can access the thousands of classes Skillshare has from other teachers

including people that I know, people I'm friends with like Thomas Frank and Nathaniel Drew. But yeah, the main reason to check out Skillshare, of course, is that you want to check out my classes if you want to learn about productivity and video editing and YouTubing and even cooking. So head over to Skillshare.com forward slash deep dive. And thank you so much Skillshare for sponsoring this episode. One thing I wanted to ask you about is kind of this idea of following energy versus following money. And I wonder if you can elaborate on what you mean by that.

There's a lot of people that are very hyper analytical. We grew up in a world that clearly values money and it's very easy to understand like things that turn into money. I think the mistake is over indexing on that and just not paying attention to like what the actual energy of like what you're doing is. And like, I think people can get trapped in like local minimum and

where they're optimizing around like something that produces money and possibly even miss out on sort of those unknown opportunities that can emerge from just giving yourself time to explore other things or saying no to those things, right? Yeah. I imagine early on in doing YouTube videos, you sort of noticed, oh, I like this. Like in some ways, like you can't actually make it

to where you are now without actually being energized by what you were doing. Yeah, absolutely. Especially at the early stage. Yeah. So I think this advice is like super important at the early stage where like people think the issue, especially like if they want to follow a creator path is like, I need to make money as soon as possible. I think a lot of times that will short circuit this exploratory mode and like sort of finding paths where you can ride that energy wave.

such that like people can't actually make it to that second phase where they can commit to that path. So there's a lot of different ways you can do this, right? You can do like, all right, I'm going to do a 30 day challenge where like I call it ship, quit and learn. Ship 30 posts, 30 videos, 30 something, even do like seven. Do it small enough that you know you can do it. Design it to quit.

But like in the process of doing it, notice, oh, do I like this? Do I want to do more? Do I find myself trying to learn more things? If you're like resenting doing the post on like the fourth day, like you need to pay attention to that. You'll never make it to 100. I love that. That's sick. Riding the energy wave. Yeah, this is like basically the concept of my whole book. It's about like how the secret to effortless and sustainable productivity is to figure out what energizes you and

go towards that. And if you're having to do stuff like your day job that doesn't energize you, then there is a way that you can approach it to an extent that makes it more of an energy source and less of an energy drain. And I think that's why for me, like making YouTube videos, doing these podcasts, the stuff I've done has almost never felt like a chore. There are still, you know, there are times when it does where it's like, oh,

Sponsor deadline. We should probably get a video tomorrow. But those are very, very few. And broadly, I feel enormously energized by doing this.

videos and stuff. And that's great. And it's just such a competitive advantage as well, in the sense that if someone else is trying to be a YouTuber because they want to make money, but I'm doing it because I genuinely enjoy it and it energizes me, it's like, I am way more likely to keep going than the other person that is not going to see any kind of momentum on the money front for a while. Yeah. Like, I mean, I see a lot of people start newsletters and stuff, and I sort of know I'll probably make it to like a thousand issues of my newsletter. Yeah.

Like I've tapped into something and so I can play a slower and stupider game in some ways. Like I don't need to worry about monetizing or scaling or growing it or being super successful because that's sort of taking care of itself. And like as long as I protect the energy that like is naturally going there anyway, I'm going to keep doing it. So then in some ways, ambition is

And how much money or like how successful you want to be is really a question of like speed and time. So it's like and I think I've started to like rethink ambition over the past couple of years as I've like gotten more of a footing on my path. It's like, OK, I can be ambition ambitious just over like a longer stretch of time.

I don't need to crush it in three months, but like I can sort of have a sensible plan to like take the three to five year plan. And like because doing it at that speed will be a little more fun for me. Yeah.

I was listening to a good Cal Newport chatting to Tim Ferriss on Tim Ferriss' podcast where they were talking about the idea of slow productivity. Where it's like you're optimizing for creating meaningful output across a 10-year time horizon rather than a 10-day time horizon or a 10-week time horizon. And that just means that if I was thinking about can I make cool stuff in the world in a way that I enjoy and that is helpful to other people, that energizes me,

but I'm doing it over the next five to 10 years, then it means that I probably spend more time deep working on my book, for example, rather than feeling the need to every single week bang out another two YouTube videos, because that's all very sort of short-term productivity. Whereas the more longer term tends to be the thing that's, oh, but potentially the thing that is tends to be a little bit more needle moving. But also, I guess it just depends on what you enjoy. There are some people that love the high octaneness of

putting out content every week or even every day or even multiple times a day. And there are others of us that would rather kind of take it a bit slow. And as long as we're doing the things that we enjoy, we're being, we're feeling energized by them. And I guess they're useful to other people in some way, then that's a, that's a reasonable path as well. I think in the last year, I've sort of realized I'm on a path that's really aligned with what I value. So I

I don't pay much of a cost for like worrying that other people see my path as low status. I'm like, whatever. I also am not too worried about like not making tons of money. I just like don't have much material aspirations, nor does my wife. So yeah.

And I highly value the like creative connection and that creative mode. Like it's so valuable to me. It gives my life so much energy and like just keeps me going like at such a deep level. So yeah,

I can sort of look around and like see people panicking about money, like starting on this path is like, I'll probably still be doing this in like 20 years. Yeah. And the way the Internet's going, like you can sort of just bet on like, OK, you'll probably be OK because like this is just an expanding space and like you'll figure out some stuff. You'll slowly get better, maybe a slower rate than other people, but you'll be fine. Yeah.

Yeah, no, I like that. Okay, so coming back to our sort of anchoring three-part framework of like step one, figure out what you value. Step two, figure out how much it costs. And step three, figure out if you're willing to make that trade.

So we then figure out what you value. We talked about like the shower test or the free time test. What do you find yourself drawn to in your free time? I love this idea of yours of like ship, learn, quit. Is that it? Ship, learn, quit? Try something out. Ship, quit, learn. That's the one. Sort of try something out. Thinking like, oh, maybe I want to be some kind of YouTuber. Okay, cool. Try making videos for four weeks, once a week and see how you feel. Learn.

learn from that. And the more of these experiments you run on yourself, the more of a barometer you get for what are the things that I value? And one way of doing that is to figure out, did this thing give me energy? Did I feel almost effortlessly incentivized to continue? Or did it feel like a chore? And I guess if I think of people I know who say that they don't really have any hobbies and they don't really know what they value, they tend to have done very few experiments of this kind.

They'll have ideas in their head of like, Oh, maybe it would be cool to do X, Y, Z, but then they won't, they won't try it out because, and you know, this is, I guess the kind of the way we're taught is that like, it has to be perfect. Yeah. It has to be perfect. And it has to be long-term. It has to be sustainable. It's like, Oh,

oh, maybe I want to be a YouTuber, but I can't imagine what that looks like for the next 10 years. It's like, don't worry about the next 10 years. I should take this advice myself. Don't worry about the next 10 years. Just try it for now. Try it for a little bit and see if it energizes you. And if it does, then that gives you a decent data point that that is something that you potentially value. So other than what do you find yourself doing in your spare time and run experiments and see what vibes with you, do you have any other strategies for helping people figure out what they actually value?

in life? I guess that's a big question. Yeah. I mean, what, what you value, I think reflecting, asking the hard questions, we all know the hard questions we need to ask. Um, it's just really sitting down and like grappling with our answers. Sometimes we don't like our own answers. We hide from them. I think in terms of like finding things you actually want to do,

What I've found is that if you give people enough free time, and this is why I think like finding a way to take a one month sabbatical in your life is so vital to like reclaiming the energy in your life. Like people will just start doing stuff. In like 99% of cases of people I talk to, they start to, oh, wow, I literally forgot I liked playing this instrument as a kid. And I just started doing it.

And like you hear these stories over and over again. Oh, I started volunteering at a local garden. I was just like walking around my neighborhood and I like remembered I like engaging in my local community. So it's like we all have this. Like, I don't think this is a hard thing to do. I think the thing that's hard is we often have things that outcompete or zap our energy.

And the thing that's worth noting is like this is why it's so important just to like get reps of experiments. Like this is why I love helping people to like just start stuff, do 100 tweets, do five posts, do five YouTube videos, like even just do one.

Just to realize you can do stuff in the world. We don't need permission anymore. We have more freedom to do more things than like any time before. It's such an amazing time to be alive. And then these things compound. Like I see even you, like I feel like you're launching and trying new things like all the time.

And that's, that makes so much sense because you realize like the more experiments you do, like you constantly want to like keep learning and like keep finding those new spaces, those new ideas, those new avenues, those new energy slipstreams. Yeah. Yeah. And I guess as we, as we run the experiments, like if it, whether it's in my personal life or as a, as a team in the business where, um,

We're getting really useful data points from them. We ran an experiment thinking, oh, we should totally start a whole new YouTube channel, the Part-Time Creator Academy, teaching people how to be creators. Then we tried it, planned it out, did the whole thing, bashed out. We had seven videos filmed and ready to go.

And it would, you know, just the feeling of the project was so energy draining. Like, oh, this is such a heavy lift. We don't have the capacity to do this. If we wanted to do this thing, it would require us to hire an extra probably five people or cut some other projects and

In the end, we decided, you know what, let's take the loss on this. It was an experiment. We tried it out. It didn't work. The idea is still good. Someone could totally take that idea and run with it, but it's not something we want to do right now. And then we pivoted from that into thinking, what if we just did it as a newsletter and a Twitter account instead? It's like, oh, all of a sudden, it's like that feels like all of the weight has been lifted off because now that's a thing that other people in the team can write and can

can take ownership of rather than me having to be on camera at all times. So that was great. So now we've built this thing and we were like, okay, cool. Let's connect it to the course. And now that's sparked the opportunity to potentially collab with other creators and create courses for them because that's fun. And we're all about sharing ideas. And it's like doing an experiment.

And just sort of doing it quickly and realizing, okay, what is the data? What is the learning we've gotten from this experiment? And even if lots of time and money has gone into it, you know, that sunk cost fallacy, it's way better to quit a thing early or quit a thing when you know it's not right than it is to worry, oh, but we spent like six months preparing for this already.

And so I think that attitude of experimentation applied to life in general. You know, like I've been saying for the last couple of years, I really want to travel the world and do the digital nomad thing. The appropriate response there and the advice I would give to someone else is, well, just try it out for two weeks.

see what happens. And so right now I'm in Wales, we're on this four day team retreat. We're still making the podcast happen. The internet's a bit sketch. It's cut out a couple of times, but oh, well, it's working. The setup looks good. No one's going to complain about quality issues because the camera's sick. This is great. I'm currently looking on over, over these like ridiculous fields that like some cows and sheep and stuff. And this is so nice. And so what I should do is probably experiment with, okay, my hypothesis is that I think I would enjoy the digital nomad lifestyle. Great. Let's experiment. Let's try it out for two weeks. Let's

Let's see what happens. Cool. I enjoyed that. All right. That's good. That's good data points. Let's now try it out for a month. Let's now try it out for three. Whereas I think the thing that's holding me back on that front is thinking that, oh, in order for me to experience the digital nomad lifestyle, I need to wait for the conditions to be perfect. I need to wait for the conditions to be perfect.

I need to have a whole year where I have nothing to do and no responsibilities. And then I can get a one-way ticket to Bali or something like that. And that's just such a dumb way of looking at it. And it's only now saying this out loud that I realized that that's subconsciously how I've been approaching it because I haven't been consciously thinking about what is the smallest unit of experimentation that I could apply to gather data about this hypothesis that maybe I would enjoy this kind of lifestyle.

Yeah, and I think this is a key point, which is like you're starting with like a story of like a script of like what a digital nomad should be. When like what you're really trying to test is like, would it be cool to work in a different location than my home base? Yeah, that's it. Yeah. Right. And I think where people get into a lot of trouble on traditional paths or other things is like when they're trying to be something, right?

Rather than like literally just be themselves. Be something rather than be themselves. Okay. Like trying to be a creator. Yeah. Like Ram Dass talks about this idea of like the, this space suit, like you go on earth and you wear this space suit of like this person that's you. And you're sort of performing all these roles. And like really the human experience is remembering that like you aren't that space suit. You're just like,

this human body and like you're just living in the present moment. So what, how, how does that apply to like,

work, right? We're like, people don't want to leave their jobs because like, I am a consultant that makes this amount of money. And like, I need to be that kind of person that makes this amount of money. Right. When it's like, the real question to ask is like, are you feeling this fire in your soul that is telling you there is possibility and wonder to be found in the world? And like, how long are you going to not listen to that voice?

in service of like continuing to maintain this beingness of that role and identity. Yeah. Yeah. No, absolutely. Like even the, the digital nomad stuff, I sort of stumbled upon it by accident. I took a one month trip to Asia and I landed a freelance project right before I left because I,

Somebody reached out and I said like not available. They're like, we like your background. Can you please help us? So I was like, all right, I'll do it 10 hours a week from Asia for like double what I normally charge. And they're like, fine.

I'm like, oh, wow. So I like fully funded my trip. And then I found myself in Bali. This is the first year of self-employment. I was staying at a $20 a night surfer hostel overlooking like surfers with my friend. And like I walked down the rock ledge to a cafe and I'm like overlooking the ocean doing work, paying like way more than $20 an hour, right?

And I'm just like, oh, wow. I never even thought about the possibility of doing this. Yeah. And I sort of had this like, what else like haven't I imagined? And that sort of just expanded my imagination. And on that trip, I decided I'm going to move back to Asia and like figure it out. Yeah. And I really didn't have a plan. And like, I really was almost like crippled by the questions that summer from my family. Yeah.

like the people are asking what's your plan like you don't have any money like you're gonna run out of money what are you gonna do for health care are you gonna move there forever and like it was just a experiment i was gonna do it for three months like i didn't have a plan i didn't know if i would like not have work um but a month into my trip like it sort of changed my life and met my now wife um and that sort of changed everything um

Yeah, that's, yeah, this is definitely something I need to be, I want to be and will be more mindful of just this attitude of experimentation. Like, I was, I was good at it, though. Yeah, no, I think I'm good at it. I think I'm good at it at work. I think I'm less good at it in my personal life.

I was re-listening to an interview I did with Noah Kagan back in the day when I was doing live streams on the YouTube channel, because we released that as an episode on the Deep Dive, as an in-between-isode. And one thing he said, he was like, hey, you know, I've always been interested in the idea of living in a van. So I just rented a van and I'm going to live in it for three weeks.

And I was just, I was listening to that, like now, two years later, after the interview, thinking, damn, that's such a good attitude. It's like, I've also kind of been watching the van life videos on YouTube and thinking, huh, I wonder what it would be like to live in a van. And I've just not taken the step to be like, I could just rent a van for a week and see what happens.

And I've just been caught up in the default script of, oh, I guess I'm living in London now. I guess I have a studio and an office. Therefore, I guess every day I have to go to work. And like on the weekends, I guess I go home and see my family.

But I could do all that from a van just to see what it's like living in a van. Why not? And I was kind of like thinking, thinking to myself, like that exact thought process that you had. It's like, damn, what other things have I just thought of that? Oh, it would be cool to do X and just not done the extra step of, all right, how do I try this out for a few days or for a week or for a couple of weeks? Or just like, how do I turn this into an experiment? And let's see what happens. I do wonder if in certain cities, like I was living in Boston and New York,

for a long time and in London, if there's just this sort of like gravitational pull that like narrows out that imagination, like I think moving to Asia for me sort of gave me this distance from my default culture that new ideas started seeping in in interesting ways.

so i and maybe whales can do that for you yeah maybe just like thinking looking at the hills and thinking you know what yeah you're looking out at like a vastness right yeah i'll turn the camera around so the people on the podcast can see it if you're listening to this on the thing it's like it's just insane i'm currently sitting on a snooker table and there's this like enormous i mean i don't think it's going to focus because the lighting's all off but

It's just this enormous, like vast expanse of hills and trees and stuff. And it's just really cool. It's a good, good place to, yeah, to, to be here for a little reset. And the other thing is that even then it doesn't, I think it's, it's, it's easy to get too precious about this stuff that, oh yeah, I need to go out into nature so that I can think about my life. But like,

But like for me, if I had just spent a set of five minute timer and just be like, for the next five minutes, I'm just going to brainstorm cool shit that I can do for a week at a time. I would have come up with living in a van. I feel like that would just be cool. And it's just, I've never had the thought that I'll, let me just spend five minutes thinking about this. And then of course, yeah, I can do all this cool stuff. And five minutes is not that much time, but I guess it's so easy to get into, again, this default thing of life going on where you just don't genuinely don't stop to think.

huh, let me just ask myself a question. You know, what am I procrastinating from? What's something cool I could do? What's something that I would be glad I did 10 years from now? Like these sorts of prompts, I think are really helpful in just forcing yourself to just get outside of the mode of like the mode of life where you're following the script that you've always followed and just actually thinking a little bit outside the box to use that phrase. I think it's very hard. I think...

Even on my path, I sort of got in a routine of like living this sort of simpler existence and doing the same things over and over again. And like, I'm constantly amazed that like, I'm like, oh, I should have thought of this idea earlier. Like recently I've decided to lean back into my podcast and I sort of came up with the idea of like, oh, what if I like sought out a sponsor? And like, I just put that in my newsletter and then somebody reached out and said, we'll sponsor you.

And I was like, oh, I could have like came up with this two years ago. Oh, yeah. I was thinking of sponsoring you as well. I saw your page. I was like, oh, we should totally sponsor that podcast. Yeah. And it's yeah, it's just constant challenge. And I think this is something if you are going to be on an uncertain path, like

This is a challenge and something you need to have a plan for. Like, how do I continue to experiment? How do I continue to come up with new ideas? And like, if you don't like doing those things, like you probably shouldn't follow an unconventional path. One of the benefits of like having a job and a more stable career is like a lot of that thinking is sort of just baked into the path for you. Now, I would still advise you to like figure out like if you really value some of the benefits you're getting, um,

But you there's just less to worry about and sort of like constantly refreshing your life and injecting new things into your path. Have you gotten any mileage out of those sorts of long term thinking type exercises of like, imagine yourself in your deathbed and like, what would people say at your funeral? That kind of stuff. Do you ever think about that? I think so. A book that has really stuck with me is Two Sides with Maury. It talks about this guy at the end of his life.

I quote it towards the end of my book too. He's in his late 70s. He's dying of Lou Gehrig's disease. And it's doubly interesting because the writer Mitch Albom is at the peak of his work career. And he sort of realizes that, oh, this is my professor. He's dying. I lost touch with him for 15 years because I got carried away in my career. How am I going to reorient my life? So it's a really powerful book because...

It talks about this guy, Maury, who's fully alive and engaged with life at the end of his life. So I think a lot about role models in terms of like how they're showing up in their life. So I really admire like older creative men.

Like people like Maury, his story. I look up to people like Seth Godin. I think he's like in his 60s now. He probably doesn't want us like saying that, but he's still connected, energized, like seems fully alive with like what he's doing. I really admire people like Jim O'Shaughnessy, who's like still injecting this playful curiosity at his age. And like that's kind of like my aim in terms of a state I want to arrive at later in life.

So I don't think the way to get there is to like play the like, okay, I need to play the retirement game of like maxing out of like aiming at a target retirement number. Like, can that help? Sure. Like, I don't want to be broke when I'm older, but it's like, I need to sort of like have an intuition that I'm like headed towards that state. Um,

And this is what made it so easy to walk away from my previous path. I just, I wasn't on a path to get there. I was on a path to show up like a lot of the men I was surrounded by who are like cynical, overweight, slightly disillusioned, good bank accounts, but like, I don't know, some of them had been like divorced, disconnected from their kids. Like, I don't want any of that. Okay, so we spent a bunch of time figuring out this whole values question. Like what are the step one of the kind of...

breaking away from the default path. Step two, we talked about figuring out the cost of this. And we touched a little on the money side of things, but I wonder if you can elaborate on this. How do we genuinely figure out what it costs to take one of these non-traditional, more uncertain paths?

Yeah, so the financial costs are obvious, right? You're trading like certain income for uncertain income. And most people worry enough about money that they are hyper focused on this cost. The other costs you need to be aware of are what other people think of you. And this is a really important one, especially the people close in your life.

Do not be surprised if you take an unconventional path that you will receive less support than you expect because you will be feeling more uncertain about your path, which means you will crave like affirmation and appreciation from others more. And you will notice that the lack of active encouragement from others feels like you're not being supported. And that can be really hard.

for people early on a path and figuring out like how you're going to deal with that. And this is why I think one of the most important things and a real reason to share ideas in public and write about your journey is to like find the others, like finding other people you can literally just be around and you don't have to have the conversation of like, why are you doing this? Don't you worry about X? It's like,

No, we can just sort of like both exist in our uncertainty for like not knowing what we're doing and like connect on that vulnerability. It's a big reason why I'm in Austin. Like there's just a lot of people doing these weird internet online creator paths. And like people in your audience or my audience might look at us and say, wow, impressive people. But like we're kind of low status in the normie world still.

Like, if I try to talk about what I do in, like, fancier circles, people are like, what are you talking about? Why would you do any of this? Yeah. So you sort of need...

those connections of like people who do understand you and, and want to actively encourage you. This is why like, I've really tried to lean into like actively encouraging and supporting people across all different levels doing these paths. Cause like, I want to keep people in the game because like I need friends. Yeah. Yeah.

Can we zoom in to the money point a little bit? Because I think there's something there around the fear of the perceived cost in terms of money being different to the actual cost in terms of money. Yeah, my relationship with money changed dramatically from being employed to being self-employed. I went from making...

high income that was increasing throughout my career pretty steadily to making no income for the first three months after quitting my job. And I sort of like had this bold hunch, like I figured out, but like I totally underestimated how terrible it would feel to not make money. Especially I was living in New York spending like $5,000 a month. It felt so painful.

to like start to see my savings go down. I felt terrible. I felt like an idiot. And I sort of realized like, oh, this was there the entire time. It was just like, I never had to stare it in the face.

when I quit my job. So like I drastically took action in both directions. One was to like lower my cost of living. And I quickly like started dropping things out of my life and almost bearing like no cost. Like I just stopped going out to restaurants. I started cooking at home. I started eating much cheaper. And I'm like, what was I doing for the last several years? Like I'm not less happy by giving up any of that. But that was like a decent amount of money I was spending.

And like, even I thought like, I like kind of needed those things, right? That was like part of what made me happy and like, totally not true. I didn't value it. And then lowered my cost. And then the other side of that is like, I think one thing people underestimate when they go without income is like how motivated they will be. I was ready to like do any kind of work for any kind of money at the beginning of my journey. Like,

Like I held signs in New York, like walking around, like trying to find people for a survey. Like I got hired for a gig to like do research for this private equity firm. And I was just like walking around, like holding up this sign, trying to find people with wearing a certain type of shoe. And it was like, I don't care. I'll do, I'll do anything to make money at this point, make the pain go away. But like leaning into that to like realize, Oh, you can ride this wave of energy at the beginning. And,

I think that eventually like mellows out a little. So like what I say at the beginning is like lean into your money insecurity and like just go hard and try to earn money in a number of different ways in your first six months. But like eventually you do need to shift into a mode where like you're making money in a way that's connected with yourself. And that's where this like deeper stuff comes in.

But then I sort of got stuck in this like minimize spend mode, especially after moving to Asia. I was like tracking expenses, like minimizing spend. And I was short circuiting my creativity. I created a course at one point and I remember going into a store looking at these webcams

And like I like there's like $100 camera and there was like a $40 camera and I just like toiled. I ended up buying the $40 camera and like looking back, this is so silly. I should have just bought like the $100 camera. It would have like raised my ambitions a little. And like I was just like short circuiting my energy by like worrying too much about money. So I was playing accountant and I write this in the book like I was playing accountant

rather than like living my life. So I sort of just decided like, I don't want to be spending my day tracking my spending and counting my dollars. Like I was using a spending app, got my spending to under a thousand dollars a month. Like it was still pretty happy, but like I was playing accountant. I wasn't actually like living my life. And that was when I started like leaning back into like the creating stuff, like sharing on Twitter a little more, like writing a little more publicly and like being a little bolder.

And digging out of that, like even the other day, like I was thinking about relaunching my podcast and doing an in-person one. And I was like, you know what? Like I'm wasting zero time. I'm buying the best equipment. I bought like a $260 cam link. I bought a share mic. And I was like, you know, I'm not playing accountant. I'm just like going to commit, go all in. And like, I think this is a better bet. So I'm still learning to like play with money. Yeah.

And investing in myself has been really hard for me to do because I went into it with like, I need to break even. I can't like spend more than I make. I don't want to see my savings go down. Whereas like now I'm five years in and I'm like, I'm giving myself these pep talks. I'm like, Paul, you've sort of found your footing. You wrote a book about like being confident on your path.

Like, okay, you can be a little bolder. You're not going to turn into this hustle bro. Like, I don't think there's any chance I'm going to turn into a like hustle productivity bro. I'm not going to start like money maxing. Like, I'm going to be okay. I can like be 30% bolder and like still be myself. Yeah. Yeah. Yeah.

Can we talk about the book a little bit? So how did you just write a book? Yeah, we got to talk about your journey too. Oh yeah, we can do that. But like, yeah, let's do yours first. Yeah, how did you just write a book?

So mine was very emergent. Like I said at the beginning, I was writing about this stuff from as soon as I left my job. I sort of dealt with this jolt of reality of like this increased freedom and space in my life. And like, what does this all mean? Like, why was it so hard to leave my path? Why was it so weird feeling when I became self-employed? So writing about that and then just consistently committing to that after moving to Asia was

And then in 2020, the whole world sort of like showed up, like asking these deep questions about work. And my readership just like exploded. And I started just having more and more conversations with people. I had these weekly curiosity conversations and I actually just like recently paused them. But I had 383 of these over the last five years about people's relationship with work.

And what would happen over and over again is people would tell me things. And I'd be like, have you shared this with anyone? It's like, well, I've said like a little to my spouse, but like I can't talk about this with anyone. So I was like, oh, wow. What I'm writing about is like this hidden knowledge that nobody feels like they can talk about publicly. Like I'm just going to like lean into this right more. And then at the end of the year, like I had like three or four people that said to me, Paul, you have this like

broad range of ideas. Like, where do I start? Like, can you just write a book? And it had an interesting trade-off at the time. Tiago Forte was running a bootcamp with Billy Brose around like, okay, how to take your course to the next level. And I had this consulting skills course that was like really crushing it in 2020 because of remote work. And I had a clear path. Like it was like, okay, if I double down on that and go all in on this this year, I'm

I could probably make a lot more money. And I asked myself, like, what would I do if I made more money? He was like, oh, I would use that to get more free time to write. I was like, oh, why don't I just write? I'm in Taiwan for the year. My cost of living is lower. I'm really drawn to like write about this stuff. And I just committed to write the book. Early on, I thought it would be just like I'll package some essays.

from my newsletter and just ship it. And then in the first three months, I really realized, wow, this is a deeper like just self-reflection exercise of like figuring out what this is all meant to me. And I knew there was something deeper to say. And I just sort of committed to

the book and I sort of had this sense of like I know I can end up somewhere and I'll know when I'm heading towards that and I know I can get there um so I spent 13 months writing it and that was kind of the main priority for the entire year and yeah it was a magical experience actually um

The introduction, when I write about like why this stuff matters to me, didn't come to me until like my final weeks in Taiwan. And I was feeling so frustrated. I went out for a motorcycle ride and like the ideas just came to me and I just broke down in tears. And I realized it had like everything to do with my parents and like they didn't go to college. They had to do the default path and they felt like they sacrificed so much so that like I could succeed.

And I realized like what they gave me was like the freedom to dream. And I, for the first time, this was like October. So seven, eight months ago, like finally felt like I can say this as a human, like it matters to like dream, to like do brave things, to like create. And yeah. And I think these things are important. And before that,

I didn't have the courage to say that stuff. I always couched my stuff or like qualified it. I was like, you know what? Like I really think this matters and I think I can help people with this stuff and I'm just going to say it. And so it was a really powerful experience for me. And I imagine you're going through something similar. Like it's been really cool to watch your journey too, because I feel like it's allowed you to understand your own journey better too. Yeah.

Yeah, yeah, the journey of writing a book is interesting. A lot of, like, windy turns along the way, but I'm very happy with the direction that it's currently going. And the plan is today, tomorrow, and the day after, bang out a first draft of one of the chapters each day. Nice. So we'll see what happens there. Yeah, I was just kind of thinking, as you were saying that, that, like, your path is almost...

Like it's weird when it comes to the creator economy and kind of making a living, doing what you love on the side and all that stuff, that a lot of people's paths seem to follow the same general trajectory of I started making stuff that I liked. In your case, I started writing about this job stuff and this career stuff. Yeah.

And I did that a bunch of times and I realized I liked doing it and that it energized me. So I kept on continuing to do it. And then along the way, people started to find out about it. And then what you did was you had your calendar link where for free, anyone could just book a call with you and you would just talk to them completely for free on the internet for like 383 times. So through that, you're speaking to people about this thing that you really care about, this thing that energizes you. And then the next step is you're like, all right, cool.

this is interesting let's write a book about it and then you go and write a book about it and self-publish the book and it's like now your newsletter you know if you wanted to get more and more lucrative sponsors on it you could probably easily do that like there's all these options that you now have for making money out of this thing because you've now done it to the point where you were just following your curiosity you've you know built an audience now and and it's just like

You know, when people ask, oh, how do I quit my job to become a creator? That's literally the method. It's like step one. Yeah. Experiment with lots of things. Figure out the one that energizes you. Do that repeatedly. At some point, you can quit your job if you've got enough of a financial safety net, etc., etc.,

And then just keep on doing that repeatedly. More people will find you. And then you will just figure out opportunities along the way, whether it's a book, whether it's a course, whether it's sponsorships, whether it's consulting gigs, whether it's corporate speaking for a hundred grand for an hour of speaking, like there will, there will be stuff that comes up by virtue of the fact that you are showing up there in the world and you're

providing value, I guess, in inverted commas, but in a way that energizes you in a way that feels somewhat effortless for you. Like even if you weren't making money, you would probably continue doing the writing thing. And so it's about finding, finding, finding that thing. Like what is that thing for, for people listening, if they're interested in, for example, quitting their job or like doing the creative thing or doing the business thing.

And like, I think it's the same with startup founders, like the startup founders that exit, what do they do? They tend to take a few months off and then they just start another company because they just love it in theory. Or maybe they're just chasing more and more. But like, you know, mostly the people I've spoken to genuinely just enjoy building companies and like, oh, great. Now I can start a new app.

And I think what we're all trying to do is just get to that state where we can be showing up and doing the things that genuinely intrinsically motivate us, which as a side effect happen to make enough money to sustain our lifestyle. I think that's spot on. I think the opportunity and upshot of doing your own thing is that you can lower the percentage of things you're doing that you sort of resent or like you feel like you're sacrificing, right? In a job, you may just have like too many things

And this was my case. Like I was just doing too many things that I thought were silly, pointless, or just like grueling to power through. And like, I still do some of those things. It's just less. So it means there's more space for that creativity and curiosity to stay alive. And that is really important to me. And if it's important to you, it's possible. And I think this is kind of what I was trying to get at and don't find a niche.

Like find a mode of being in which you can show up. And like, if you can find that, I think like ambition is really just like how fast you want to go at that point or like how much like leverage you want to implement into your life. I tend to like to go slower. I find like super scale or super large ambition pretty scary. And maybe that will change over time.

But I have the mode. So I have this like deep faith that like I'm going to be OK. And I also just like my life. And but to someone looking at my life on a spreadsheet and trying to like do the math of like how life should be lived, they'd be like, how is this going to work? How are we going to afford a house? Like I can't afford a house right now.

It's fine, though, because that's not what I'm valuing right now. And I feel really good about my life. And I don't feel like I'm failing. Do you feel like if and when you have kids that your attitude towards this sort of stuff will change? I think so. We want to have kids soon. And I assume my perspective on a lot of things will change in ways I can't predict yet. However, I think it will just...

force me to be more like committed to like the things I'm doing. I think I've like, we've already started to think and talk about kids. So like, I do want to be a parent. And like a lot of what I've been doing on this path has been preparing myself to be a parent because I want to be a present engaged and alive parent. And that is just really important for me. So like this kind of life gives me the highest odds of doing that. Yeah. Yeah.

But this is also why I've been like leaning into like, okay, maybe I should like try to like monetize some of the things I'm doing. Because I also realized like when I do have kids, I am going to feel more responsible and that's just going to make me braver at this point probably. And also people are going to want to root for me to succeed too. So like there's going to be benefits too. People sort of look at these things like what about kids? Like,

What they're doing is like mapping their fears onto me. I already have those fears. I have all the fears. On an uncertain path, you grapple with the fears every day. But I can make choices and I feel really good about having ownership of the degrees of freedom I have. And after five years, I do see paths to make money. So like if that was my prime aim, I have confidence I probably could do it at this point.

Or I'll just apply for a job on your team. Yeah, absolutely. You're welcome anytime. Paul, this has been absolutely fantastic. Thank you so much for coming on the podcast. Where can people learn more about you?

So my newsletter, boundless.substack.com or website, think-boundless.com. A lot of the ideas we talked about are better put in my book, The Pathless Path. Check it out. Pretty active on Twitter too. Love hearing from people's stories. So definitely reach out.

Amazing. And yeah, just wanted to say a massive thank you to you as well for like all of the stuff that you've written in the book and in the newsletter and on Twitter as well. And in podcasts that has continued to inspire me over the last couple of years as I've gone on to more of this non-traditional, more uncertain path than the very traditional one that I was on. And yeah, anyone listening to this, if you are considering...

breaking away from, say breaking away, from a traditional path and you would like some advice on how to pursue an uncertain one, yeah, check out all of Paul's stuff. I was just looking through my Kindle highlights on your book and they're just absolutely enormous. And yeah, at some point I've been thinking, oh, I need to get around to actually turning your book into a book club video for my channel. There's just the incredible, like, copious amount of highlights I have for it. I'm just like, damn, okay, this is going to be like a whole, like, week-long project to just try and parse all this stuff, figure out what are the bits that most resonated with me. Because...

I find that when I'm reading a book and I'm just enjoying all of it, it's just highlight, highlight, highlight, highlight. And I'm like, oh, damn, I highlighted like 80% of this book. Damn, that's kind of annoying. I need to go back through and progressively summarize the highlights as some people would recommend. Awesome. Well, continue to be inspired by your journey too. Keep going, man. Thanks very much.

everyone thanks for tuning in and we'll catch you later bye bye all right so that's it for this week's episode of deep dive thank you so much for watching or listening all the links and resources that we mentioned in the podcast are going to be linked down in the video description or in the show notes depending on where you're watching or listening to this if you're listening to this on a podcast platform then do please leave us a review on the itunes store it really helps other people discover the podcast or if you're watching this in full hd or 4k on youtube then you can leave a comment down below and ask any questions or any insights or any thoughts about the episode that

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