This video is a case study about how to quit your job without a plan where Paul Millard who is the author of The Pathless Path and the wonderful book Good Work. Paul and I are charting both of our respective paths towards moving off of the default path where we had lots of titles and credentials on our resume more towards the path where you're sort of figuring things out as you go along. But in theory, you're happier and more fulfilled and more joyful because of it. And so when Paul came over to visit Hong Kong, we sat down for a lengthy conversation about this and sort of broke it down into a 10-step road map. So, if you are currently on a high prestige path where society thinks you're successful, but maybe you're feeling like it's not as fulfilling as it once was, but you don't necessarily have a plan, then hopefully this conversation will have some value for you. Step number one, win the prestige game. So, the conversation between me and Paul started out exploring this idea of prestige and how prestige is often the north star that when you don't really know what to do with your life, if you're like us, you tend to gravitate towards whatever gives you the most prestige points in the prestige game. >> What sort of jobs did you do and how much money were you roughly earning? >> I've done many different jobs. So, in college, I did three different internships and I was making pretty good money as an engineer in undergrad. But every summer, I decided I don't want to stay at this company. I need to try something new the next summer. I was always trying to move towards something more impressive, right? I got sucked into prestige because prestige is a really useful outcome and salary high salaries too if you don't know what you want to do, right? And you're restless. Early on, I worked in finance in my first job at GE. That lasted about 12 months. The whole time I was desperate to escape and try to break into consulting cuz that's what I where I really wanted to go. I went to consulting. Um, I was making similar salary at consulting. I worked at Mckenzie. I was only making 50 grand a year. Uh, went to grad school for two years. I did an MBA and masters in systems engineering at MIT. >> Nice. It's quite high prestige. >> Yeah. So, I don't even really talk about this anymore, but yeah, I basically dominated prestige bingo. >> Nice. >> For 10 years. >> Okay. McKenzie, Boston Consulting Group, uh MIT, MIT MBA and engineering, worked for GE in one of their top leadership development programs. And at the end of it, I just absolutely lost. And the weird thing is now being on this path, 8 and 1/2 years in, I have no idea what I'm going to be doing 6 months from now. But I am lost in that way, but I feel totally grounded and at home in myself. Now, when I first discovered Paul's work and when I first read the pathless path, this was part of the journey that actually really vied with me, right? Because I've read some books from people that are like professional vagabons, right, where they've never, you know, they don't graduate high school, they've never been to university, they've never held a real job. And then those people are like, "Oh, you should totally like travel the world and do your own thing." But like I could never take it seriously because they'd sort of opted out of the default path way earlier than I did. And so I couldn't really relate to them. But when I first discovered Paul's stuff and I realized that, oh, he too had fancy logos and like credentials on his resume and then decided to give all of that up to pursue the pathless path, I was like, "Oh, that's much more interesting and relatable to someone like myself." >> You're doing the things that a lot of people in our audience think that they aspire to. Mackenzie, BCG, like MIT times 2, you know, all of that kind of stuff. >> I was good at it, too. And so, this is the crazy thing. All I had to do was basically just keep showing up and doing it. and I would become a millionaire. I could have the upper middle class comfy life doing whatever I wanted and it was all laid out for me there. There was really no downsides on the default path in terms of career opportunity, right? And I actually have estimated what did I actually give up if I had just coasted and like market salaries with like maybe normal or even conservative promotions. I think I probably gave up about a million dollars in income over the last eight and a half years. I don't really feel anything when I hear that, oh, I left all this money on the table because what I got back was a life I actually wanted to live. >> And this is the thing on the previous path. I had all these things you're supposed to want, but I didn't want any of it. Now, as we go through the video, I'm going to be offering you some tentative uh homework suggestions uh if you're serious about potentially leaving the default path and maybe stepping onto the pathless path where you're sort of doing your own thing. And so, your homework from step one is to write down what version of the prestige game have you been playing in your life so far and what version of the prestige game are you continuing to lean towards when it comes to figuring out what to do with your life. So then once you've done very well at playing the prestige game, step number two is to spot the misalignment. work was the stuff that slowly sucked away all my energy and passion in life by the age of 32. And so when I quit, I really just wanted to run away. I wanted to minimize that thing and what it had done to me for years. >> I want to double click on this. Uh in what way did work slowly suck away your your passion by 32? >> I was sort of uh on this journey of what I call following the default path. The default path is basically what you might consider what most people are doing and how they're orienting work and the role of it in their lives. Early on, I loved work. I got a lot out of it. I was learning a ton and then I think slowly over 10 years there was sort of an inversion of the learnings gradually decreased and the pay was increasing and so the intellectualization of work made sense. So oh you should just stay makes sense your career trajectory is looking good but I was constantly restless. I was leaving jobs after 12 months, after two years, after 14 months, after 15 months, after two years. I never stayed in a job. I'd just get restless as soon as 6 to 9 months would hit. And every iteration of that kind of left me at a lower point. And so by the end I did this self assessment sort of analyzing these goals I had came up with in grad school and had to look in the mirror and be like you're not doing well against your own values. You sort of lost your way. >> What were the goals that you came up with in grad school? >> Don't take yourself too seriously. Don't become too narrowly obsessed about money. Don't uh lose your sense of humor. And so as I was doing this 5 years after grad school, about nine years into my career, I was grumpy. I was showing up to work sort of feeling like I was in a battle with my boss. I needed to like fight for a promotion. I felt undervalued. I was pushing for a raise and promotion and just like I don't want to show up as this person. >> So with whatever you're doing now, you're probably following some sense of direction that you had a few years ago when you decided to do this thing that you're doing now. So I think what's worth doing at this point is to identify what were the things that you claimed were important to you let's say 3 years ago or 5 years ago. So with whatever you're doing now, is it moving you towards the person you thought you wanted to become or is it moving you away from the person you thought you wanted to become? In Paul's case, it was very much a moving away from it. He didn't want to be the guy who was like a corporate drone who had the energy and vitality sucked out of him. And yet, you know, 10 years into his career, he ended up being that corporate drone with all of the energy and vitality sucked out of him. And so then he had the sort of realization and then moved on to step number three which is to face the shame. And here we talk about the private shame that you sometimes feel about the fact that you hate the work that you do. Now, since he started to write about this stuff, Paul has actually had conversations with at this point probably thousands of people around the world who are in the same position that I sort of was, that Paul was, that maybe you might be, where, you know, you secretly hate some aspect of your work and maybe even a lot of aspect of your work, but like it's it's a little unfashionable if it feels a little shameful to actually talk about it out loud. >> I remember this conversation really early. This guy is telling me all about these challenges. He's really struggling. Verbal abuse at work, in pain, like totally lost, wants to blow up his life, has some money to do it. I say, "Have you talked to your spouse about this?" No. After this call, I'm like, "Okay, this person on the internet won't talk to his spouse about this, but he's talking to me, internet stranger, who's never met before." And so, I really felt, and I had a bunch of these conversations where people said, "I don't tell my friends about this. I don't tell my spouse about this. I don't tell my parents about this. And so it sort of felt like I had this secret knowledge through these conversations. >> And what sort of stuff are people saying in these conversations? Like what's the this that they're not telling people about? >> Just that they don't like their work. This this seems crazy, right? That people wouldn't talk about this, but I think the pandemic blew the door open a little in terms of making it more allowed to have these conversations. People feel an immense amount of shame about their relationship to work. >> Tell me more. What do you mean? >> Work is how people determine whether they're a good person in the world. >> What do you mean? >> Right. So, in my first book, I write about this idea called a bad egg. Right. This is an idea from Ben Hunt. He talks about the idea of an industrially necessary egg. And so, the industrially necessary egg is the egg that needs to be clean. It needs to be fit in the carton such that it can be stacked and shipped, right? It has to be a certain way. It has to be defined and uh standardized. Similarly, we're we're products of the economy too. Many of us are in the industrially necessary job, right? The jobs fit because they fit into the economy and generate value in a very specific way. Now, when you don't fit in that, you feel bad. when you leave the industrially necessary job, you are a bad egg. >> And so I'm sure even you face this, right? I think this is something people get wrong is they'll look at someone like you and say, "Oh, you quit your job. You had all this YouTube income. It's easy for you." I can guarantee that you got criticized by people and probably people close to you in your life, right? This is because you're making them feel uncomfortable. Why don't you just fit in? Do it like us. Do it in the appropriate way. >> So with me, I had this shame around leaving medicine for for a long time, probably for years after I made the decision to leave being a doctor. This shame around am I a bad person for leaving medicine. Now, in my mind, I thought this made sense, right? Because medicine, you know, being a doctor is one of those things that's like, you know, explicitly supposedly good for society. But surely if you're like a lawyer, corporate lawyer or a management consultant or a hedge fund guy or an investment banker or whatever, surely you wouldn't feel that same thing, right? Because it's not really in the same category as like saving someone's life. But having spoken to loads of people in those kind of jobs, those sorts of people also feel this shame around leaving that path. And it's this idea of am I a bad person? Not because I'm quitting a job that results in like lives being saved, but like am I a bad person for kind of not creating economic value? like there's there's this like weird connection that we have between the work that we do and being a good productive member of society or something and it's like an an assumption baked into that that we very rarely think to question. So you said that um there are a lot of feelings of shame that people get at like I don't like my work. I wonder if we can just sort of double click on that. Can you tell me more about like what sort of thoughts and feelings people are describing to you? Feelings that you might have had yourself around this thing of like oh I kind of kind of hate my job. >> Yeah. So I think a good way to separate it is guilt and shame. Guilt is I feel bad for not doing something right. And so if I'm away too long from home and not helping out with my daughter, I might feel guilt. But on the other side of guilt is like responsibility. Some guilt might be good, right? Shame on the other hand is I'm a bad person. And so after I quit my job, I felt like I was a bad person. like I had really done something wrong. It was incredibly painful. And I realized over time I was soaking up a lot of the insecurity of the people around me, right? They would say, "What's your plan? You can't just quit. You you need to make money. Like you need to have a job, right?" And so I internalized a lot of that. It was really hard in that first year. And a lot of my writing is sort of permission to myself to feel better about what I was doing. I grew up in a family where many people had built lives around full-time employment, right? Doing something like your own path was extremely risky. And there's this silent agreement of just do it like us. Don't make us question the underlying uh assumptions in what we're doing and how we do it. >> At this point, I would like to tell you about the ultimate productivity hack, which if you're not using, you're really missing out. And that is using voice dictation rather than typing. And that is where Whisper Flow comes in, who are very kindly sponsoring this video. Whisper Flow is blazingly fast, amazingly high quality voicetoext. And so on basically any device that you use, like your phone or your browser or your computer or whatever, Whisper Flow acts as a sort of keyboard replacement. Like you just hit the dictate button, you speak into it, and then like within a couple of milliseconds, it just transcribes everything that you've said and automatically inserts it into wherever your cursor is. So for example, in my case, I use this a lot when I'm talking to AI tools on my phone or on the computer. Yeah, you could use the dictation that's sort of built into the AI tools, but it's not very good. And it's like if you use voice mode, it's kind of annoying because like you got to wait for them to respond and then if there's background noise, it's like they struggle to respond. But with Whisper Flow, I just hit the dictate button and it like immediately transcribes everything I've said. I can just have a scan through, make sure it is what I actually want it to be, and then send it to the AI tool, which then responds back. And so this has saved me so much time cuz even though I type really fast, I speak faster than I type, which is true of basically everyone in the world. Worthflow is also better than the standard dictation built into your phone or your computer because a it actually works and b you can also define its own vocabulary and so it'll remember things like the names of your products or the names of your business or the names of your co-workers or your family and stuff and it will do the appropriate capitalization and you can even change the settings so that if you're for example in WhatsApp you might not type with capitalization and so you can set a profile that's more casual that uses less punctuation and stuff when you're on WhatsApp compared to when you're on email in which case you might want to use slightly more like capitalization and punctuation and all that kind of stuff. All of that stuff is built in by default and is really really helpful. These days I use dictation for absolutely everything I do on the computer. I get actively annoyed when I have I'm having to, you know, like a freaking caveman type fingers on a keyboard. And so if you are not yet using voice dictation to drastically speed up your workflow and your productivity, you are really missing out. And if you'd like to try it out, you can get 1 month completely free of Whisperflow Pro and that will be linked down in the video description. You should totally check it out and I promise you won't look back. Yeah, to your point about sort of criticism, I found that uh over the years I've spoken to a lot of friends who are still in medicine and sometime and I'll I'll sometime sometimes ask them to be like, you know, they'll say, "Oh, you know, I met someone the other day and they ask they found I went to Cambridge, like, oh, you know, Ali Abdal." Be like, I be I'd say to them, you know, I'm curious like I'm sure people don't talk about this very much, but like what's the sentiment around the name Ali Abdal in like the medical field? And they'll be like, "Oh yeah, I'd say maybe half the people I speak to are like fanboys and the other half really hate you." And I'll be like, "Oh, that's interesting." Well, it's easier to hate you than sort of absorb the message that there are more possibilities for them than anything else, right? And so, from a survival standpoint, it's easier to just internalize the message that, okay, the only option is full-time employment. One of the weird things for me after quitting my job was realizing I had not considered self-employment as a viable path until about 6 months before I quit. I had just been surrounded by everyone who is succeeding and achieving and making good money in full-time jobs and my family like that. And I hadn't considered other options. >> People would just self gaslight themselves. >> Nice. What do you mean? >> They would say, "Well, like my boss is manipulating me. He's kind of a psychopath, very aggressive. Um, embarrasses me in front of my teammates, but you you know, like I have a good job. like I shouldn't complain and it's like whoa whoa not healthy like you you can actually complain about that and you can actually just say yeah that kind of sucks but people are just very willing to dismiss sort of low-grade suffering at work just because it's a default script. Now when I speak to people about this this idea of like lowgrade suffering um often the story that keeps people uh in a job for way longer than they should be in that job is this idea of ah I should be grateful I should be grateful to at least have a job. There's all sorts of people that don't have a job. The economy is so tough, you know, etc., etc. We just sort of take it for granted almost that work is supposed to have this level of suffering attached to it and we often don't view it as a reason enough to make a change in our lives. And this idea of shame that we're talking about in this step, uh, is going to come back later on when we talk to Paul about how conversations with his friends, his family, his co-workers, all of that kind of stuff, like this this idea of the shame you feel at potentially quitting your job or actually quitting your job is a thread that goes through a lot of people's journeys on this pathless path. Interlude, are you actually wired for this? Now, before we continue with the rest of the steps in this journey, it is worth flagging that, you know, this idea of living life on the pathless path is not necessarily for everyone. There is a certain kind of person, probably you, definitely me, that sort of eventually has to make it work, has to go do their own thing, has to carve their own path. And those people will eventually just sort of keep like by brute force or experiments, keep trying stuff, end up moving in that direction. I think increasingly the idea of quitting and doing your own thing has become a lot more popular. or there's YouTubers with millions of followers promoting these ideas and it's a good thing because I think it is more possible than people think. And so there's a couple ways I would challenge people to think about this. Do a pro bono freelance assignment before you leave. Right? And so this is something I actually did and was pretty shocking for me even though I was an employed consultant for 9 years. I did a pro bono consulting project for a small startup in Boston and I realized two things. One, there was a lot more to learn doing this on my own and that was interesting and exciting. And two, wow, I was pretty good at this even though it was kind of scary. How do I know if I'm intrinsically interested in this pathless path entrepreneurship do my own thing thing or because it's now sort of sexier than it once was where everyone in the dog seems to be starting a lifestyle business or doing becoming self-employed or doing becoming a freelancer doing their own thing. How do I know I'm not I'm not just sort of mimtting myself into thinking that I want to do my own thing when in reality I actually love full-time employment. A lot of people are hypnotized by stories of quitting your job and doing your own thing. These have become supercharged since the pandemic. More and more people are selling courses, sell writing books, promising the journey of succeeding when you do your own thing. I actually love what you're doing in terms of just make $1,000, right? A really simple thing. And so that's really what I would focus on instead is try things before quitting or notice things in your life that might translate. Can I make money on my own? Can I do a project on my own? What do I do when I have free time? Am I drawn to do creative stuff, network with people, connect with people, start things, host things? 3 years before I quit, I started doing all these things. It naturally happened. And I think when I quit, I had the confidence in knowing I could show up in a certain way. I didn't have confidence I could make money or that I could make it work at all. But I saw myself volunteering to do stuff. I've saw myself doing a coaching business before I quit my job. I made money in a bunch of different ways. Not a lot of money. I did a online course on resumeumés before I quit. And so I had all this like proof of energy, but not proof of making it. So, I like this question of like proof of energy rather than necessarily proof of success. If you're thinking of maybe living life on the pathless path, if you look at your life to this point, do you have some evidence that you can give to yourself about how you've done experiments with stuff over the years? You know, people I know who've thrived on the pathless path are the people who I know started random side hustles when they were in school or decided to start a blog or a random YouTube channel or start posting on Instagram or like start like, I don't know, knitting as a hobby or something even though it was uncool and no one was really doing it when they were when they were teenagers. like you know have you got experience of doing stuff that would be considered a little bit weird or has your life really been a series of tick boxes where you've sort of done the conveyor belt thing that everyone around you is doing. It's not to say that if you're in that mode you can't like change your situation or whatever but often I find that the people that really have this urge to get onto the pathless path and that also tend to thrive on the pathless path tend to be more the ones who were like a little bit weird uh when they were younger. So, this is just something worth keeping in mind. And I think this might be a way to answer that question of like if you're concerned of sort of enamored by the idea of quitting your job because it seems cool versus is there something deeper underlying this that's like more core to who you really are or your personality or whatever in so far as your own personality is a sensible like barometer. So now before we make the decision to quit our job, we should probably do step four, which is to run the numbers. >> Step one with all of this is figure out who you are. Who are you and what do you need? I am somebody that does not need a lot in terms of money and material possessions and I've always known that, right? So that lowered the bar dramatically. That made it far less scary for me to quit and do my own thing. People will come to me and say, "I have a mortgage and I want to send my kids to private school and I want to save for a college fund, uh, but I also want to quit and do my own thing. How do I handle all this?" And I'll just be like, "I don't know. I'm writing from my experience. I have less desires. You need to find somebody with a similar path, right? And so for me, it was easier because I could live on less over a number of years. >> I have a I have a really great prompt for people in jobs. You can quit your job and not work for a year and I'll give you 25% of your current income. How do you feel? Now, to me, if you had told me that before I quit, I would have been ecstatic. Two things. One, I have all my time back. That's so exciting because I always have things I could do with my time. I already have an appreciation for things I would do and things I'm interested in and how to spend that time. Second thing, 25% of my income. Start doing the math. Could I live on that? Yeah, I could probably hack a living. Even if I dip into my savings, it's not too bad. You start doing the math and if that becomes reasonable, you can then just start looking at the question in a completely different way. Not how do I replace my salary or how do I create a successful path for myself. How do I hack a living on 25% of what I currently make over the next year? And if I can't, I'll go back to my job. Nice. So, at this point, it's worth pausing this video and actually thinking about this question. If your income suddenly dropped by 75%. Like you had to live on 25% of your current income, how does that feel? If your immediate reaction to that is 25% of my current income, okay, I do the maths on that and like, you know, I'd have to downgrade my lifestyle a bit, but like, you know, I could certainly make it happen. And maybe you feel a sense of relief that like, oh my goodness, imagine what I could do with all that free time that I'll have, then that's a very strong sign that maybe the time is right. But if you feel 25% of my income, like a quarter of what I'm currently earning, there's no freaking way I'd be able to survive on that for whatever reason, then that is also fine. But it's just like the more money you need to make to meet your life and your family's basic needs, the harder it is to do your own thing because obviously like the bar for success is higher and higher. So for you that question of like, okay, how would I feel if I didn't have a job anymore, but I did I still had 25% of my current income? You feel excited about that. What are some other responses that people might have to that question in your experience? >> Yeah. So if your response is that's ridiculous, I need to replace my salary before I quit. That's a that's just a much higher degree of difficulty leap you're trying to execute, right? I didn't match my salary until my sixth year of being self-employed. To some people that might be failure, right? So, you need to figure out what are the expectations? What does success look like? I often lead people through a series of questions. One of them is what is the lowest amount that would be considered successful if I made over the next year? What are the number of months you're comfortable earning zero income? Right? And it's all around just reframing your fears because almost everyone is thinking, how do I make it work? How do I go from successful job to successful pathless path? And it's sort of a crazy thing. Why would you be good at self-employment if you have no practice doing it? I'm 8 and 1/2 years into it now. I just feel like I'm getting my bearings. M yeah I think this is very true. I find myself kind of thinking in the same uh same sort of ways when I'm I'm I've sort of ended up becoming a pseudo coach to people for this exact problem as well cuz people now come up to me being like oh how do you quit your job rather than how do you be more productive and things like that and I like the way you framed it which is that if you're trying to replace your salary that's a very high bar and it's a difficult game that you are playing. the lower your bar is, like if you can get by with 10 grand, 20 grand, if you have a year's worth of savings so that you can actually dip into it a little bit, the game just becomes a lot easier because now you're not trying to get a six figure salary from day one, which is really hard to do. And I get all these people saying to me, but like, oh, you know, I'm I'm I'm making six figures in my law firm and I want to do my own thing. And I'm like, okay, cool. What how much money do you want to be making? And they're like, oh, you know, I have to be replacing my salary. I'm like, okay, within what sort of time time frame? Oh, ideally in the next six to 12 months. Like, okay, that's going to be hard. like you know it takes time to train up to do anything. If you want to be a neurosurgeon earning earning the big money, you can't do that within like three three to six months on the side and on the weekends and stuff. It's like a decade of training. Paul, how much money should I have saved up before I quit my job? >> I think the best thing to do is reframe that into a series of questions. So, if I'm going to quit my job, how long am I willing to go without making money until I consider this a failure? What amount of money would encourage me to extend the time frame from six months to 12 months to 18 months and just continue asking different versions of this kind of question and also run the numbers. I am shocked at how few people actually know what they spend. To be honest, I didn't actually calculate my spending before I quit my job. But as soon as I quit and wasn't making any money yet, I started going, "Oh crap, I need to analyze what I'm spending per month." And very quickly I lowered that amount. I realized I could live on 3500 a month. And so I had more than that to fund a year from savings. And for me that felt good. That felt right. >> So again, I think this is worth double clicking on. Paul is not saying, "Hey, follow your dreams and the money will eventually come." Instead, he's saying something more practical, which is you should probably actually run the numbers on this. Do the maths. Figure out how much do you actually need to live on. What if you lowered the bar to buy yourself time for that expiration? And so if you're going to go on this path, it's actually a lot easier to be on it when your lifestyle expenses are very low compared to if you have the requirement that you match your salary before you make any kind of decision cuz again it's really hard to get there. >> Over my 10year default path career, two years were in grad school, 8 years employed. I made somewhere around like $800 something,000 on my own over 8 and 1/2 years. I think the number was about the same. And the question I was asking myself and this sort of made me realize that this is a whole new skill is learning to work self-employed on the default path. As you get more skilled, you earn more money. As you're on your own path, there's a skill associated with it as well. And so it was just really interesting that the numbers were very similar >> over those eight years. >> And so once you have run the numbers, we move on to step five, which is to take the leap without a perfect plan. What was your impression of self-employment or like entrepreneurship or like starting but like sort of any of these like non anything that's not full-time employment? >> It's so weird because I was sort of memeing myself into these things subconsciously without I think intellectualizing it. I was so firmly winning prestige bingo and on that successful path that I had a lot of opportunities ahead of me and I was still like pretty good at what I was doing. But during my days, I was listening to Tim Ferrris podcasts. But I didn't make the connection that, oh, I could be one of these people that could go do these things. But I was loving that stuff. I was consuming it. I was eating up everything Derek Civers was saying, Tim Ferris. But then I would just go to work and it didn't occur to me that I could do anything else. And so this is one thing I think people get wrong about taking the leap is a lot of people don't actually know what the plan is after they take a leap. And the idea that you think you need a plan or need to know what you're doing after taking a leap holds far too many people back. My plan for when I quit was to become a freelance consultant. You know what I did for my day job? I was a employed consultant. I lasted about 6 months doing freelance consulting. And in that time, I had enough breathing space in my life and work to realize, oh, I have this creative itch. >> I like these other things I'm doing. I don't know how to monetize those, but this is really interesting energy showing up in my life. >> Yeah, cuz I I imagine an objection to that be, well, well, my the terms of my contract say that I, you know, have a non-compete pull. >> Same with mine. But they're going to they're going to fire me. >> Yeah. No one's going to know you're doing a pro bono project for a friend's company, >> but I have to declare it to HR. >> You're not wired to take the leap, probably. >> So, I I I feel like when when it comes to quitting the job and doing my own thing, for some people, it's almost like a kind of they're being pulled towards it through like following their energy and stuff. But for others, it's like almost this, man, I [ __ ] hate my job so much that I like I have to do my own thing. And it's sort of more this sort of like negative kind of thing which I see increasingly in my YouTube comments where people are like or in like Instagram DMs where people are like, "Oh my man, I've got such a toxic boss at work or blah blah blah. I've never I've never done anything on my own. Tell me, Ali Abdal, what is the simplest, most easy business you can start to become a millionaire in two years without having any skills?" And I'm like, "Uh, I think people should take a sbatical, not start a business." I think the way I reframe it is take a threemonth sbatical one time in adulthood. If we assume we work 500 months in adulthood, taking a threemonth sabbatical is a tiny tiny percentage of that working adult life. What if you put taking a 3month break first in priority and said that is the thing I'm going to pull off no matter what. I think it's more achievable for more people than ever before. And the task in those three months is not to start a business. It's just to get back in touch with yourself. So many people get so lost and absorbed in the system from going through school to college to work. And I actually recommend doing this in your 30s because you sort of have some experience. you have some attempts at trying to make work work and you can just pause and say, "Okay, who am I? What have I learned when I wake up tomorrow? What are my interests?" Right? And you might have to do it again. You might have to take a sabbatical again 5 years later. >> We actually have a lot of students in our lifestyle business academy that are doing our kind of online business school as part of a sbatical from work. Uh most of our students, I say probably 90% are trying to build a business alongside the day job. But for maybe 10% of our students, like they've actually taken an active like two, three, four month break from work and they're like, you know what, in this 3 to six month period of time, I'm going to commit all in on figuring out what it would take to actually build a business from scratch. So, if that's a possibility for you, definitely something worth considering. Or even if you're just able to straight up take a sobatical from work and not feel like you have to start a business in that time, just having that space to explore and figure out what you really want to do can be super helpful. And so, let's assume you've done all these things. You've run the numbers, you've maybe taken a little bit of a leap. We now move on to step number six which is to hack a living. >> The pathless path has visible costs, hidden benefits too, right? So the costs, everyone knows the cost of taking a leap and doing your own thing. Income, unpredictability uncertainty fear all these things, everyone prices it in. But the thing you can't see is the invisible benefits, right? The invisible benefits all occurred for me and sort of radicalized me to my own pathless path a year in my first year after quitting my job. And it was, oh, I made $100 on my own. If I could make a $100 on my own, I could make a,000. Oh, if I could make a,000, I could make 10,000. Right? And these things build and you start to feel excitement ownership autonomy belief in yourself, like possibilities start expanding. And so the formula for me was really I quit. I didn't have any income lined up. I tried to get freelancing gigs. Over the first nine months, I made about half of what I had made, maybe a little less than that, 30 to 50% of what I had made the previous year. And that could fund my lower cost of living. And I was like, "Oh, wow. I funded a year in 9 months. I didn't have to tap into my savings. I can go another year." And so, I just kept buying years. And the more time I had on this different kind of path, the more excited I was. I met more people. I started believing in myself more. And this kind of journey is possible for people too. >> I think this way of approaching it is much less scary than people normally think about. Like if you think about quitting your job, most people think about it as like this all or nothing decision like oh my god like I'm earning 100K a year right now and if I quit my job it suddenly goes to zero and then I'll figure out how to earn 100K a year for the rest of my life. And it's like this all or nothing. I'm going to end up broken, homeless, and alone versus I'm going to be okay. Like this. It's a it's very sort of binary thinking, at least when our fearbased brain gets involved with the process. But I like this idea of that you're just sort of buying gears of your life. Like you don't need to figure out your retirement plan if you're thinking of quitting your job when you're like 28. You just need to figure out like how can I survive for the next 12 months. All right, cool. Or or even the next 3 months or even the next like 3 weeks, you know, that kind of thing. I think those of us who were, you know, did well in school and stuff, we're so used to being like, you need a plan for your whole life, like medicine is great because it's employment for life and all that kind of stuff, that we're so used to thinking like, oh, you know, the thing I'm doing as an employee right now is going to be the thing I have to do for the next 60 years of my life. We just know that that's just not how the world works. And yet that is the default way that our subconscious mind thinks about this because of all the stories and stuff that we've been told throughout our lives. And so, it's really about running one experiment after another. Maybe you do it for 3 months and you decide, how much money did I make in those three months? Am I still enjoying this? How do I feel? Maybe you try it for another three months. Then maybe you do a six-month experiment. And you're always just running one small experiment at a time. Like even with me when I quit medicine, like it sounds like dramatic to say it like that right now, but I that's not how I thought about it back in 2021 when I made the decision. The way I thought about it was, you know what, let me take a one-year break from medicine, kind of like a sbatical from medicine, and then I'll see how it goes. Loads of people take sabbaticals from medicine. Some people go to Australia. That was was planning to go to Australia, but COVID, so they shut down their borders. And in the grand scheme of things, no one really cares about the gap in the resume, which is something that people are so worried about. Maybe in your case, your employer is different and they really really do care about a a gap in your resume. But honestly, I I think it's one of those things that holds way more people back than it needs to. And so now we're talking about how Paul actually made money, how he hacked himself a living during the last 8 years that he's been on the pathless path. >> My income sources over the years have shifted dramatically. The number one thing that's paid the bills has been different five or six times. Two years ago, book sales was the only year I made the majority of my income from books, even though that's what people know me for now. My first couple of years were freelance consulting on a much lower base. The next few years were an online course from teaching consulting skills. The next few years, I don't know, right? And so, it's just sort of committing to this continued experimentation. And I like the experimentation. So, you have to figure out who you are. If you don't like learning, experimenting, and connecting with others on these paths, doing something like a creator path can be very challenging. >> But what about the money, man? Like, you gota you got to feed feed the daughter. Like, aren't you worried you're going to get end up broke and she's going to end up starving? >> I think confidence from earning money on your own is very powerful. >> So, I talked a bit about early on making that first $,000. That first $1,000 is warps your mind. It's like, wow. I joke that earning a thousand on your own is way better than making 200 grand for an entire year in a salary. It makes you realize, oh, I can just do stuff, put it out in the world, and potentially fund a life doing those things, right? And so, one year doing that, two years doing that, three years doing that. I've tried to prioritize making money in many different ways. I've generated over a million dollars in revenue over eight years. Now, would I have made more in my previous path? Sure. But the confidence underneath how I've generated all that money on my own is just so profound. And so, I have some passive income sources now. So, I sort of have like my own basic income that like funds the experiments and continued betting on myself. And so, I just want to keep going. I don't know how long I can keep it going, but as long as I can continue to buy my freedom and buy time to spend with my family and buy time to create, I'm going to keep going. >> There is a concept I learned from my friend Dicky Bush, which uh I really vied with me a few years ago. It's like instead of thinking about financial security, instead think about financial confidence. For a lot of us, we're like so attached to this idea of security. And for a lot of us, security means you've got 10 zillion dollars in the bank so that at a 4% withdrawal rate, you never need to work again a day in your life. And like, good luck getting to zillion dollars in the bank. It's probably not going to happen. You're probably going to die before you hit that number. However, if you reframe it, I don't need financial security. I just need financial confidence. I need confidence in my own ability to actually figure it out and make money. That changes the equation. That means you can take leaps like this without having to have zillions of dollars in the bank. And this is one of the reasons why I'm so bullish on everyone at least dabbling with entrepreneurship at some point in their life. Like it's not about whether you start a business that you then run for the rest of your life. You probably won't do that. But it is about learning the skills of independent income generation. If you are a normal person, if you're an employee, you have never learned the skills of what it actually takes to make money because the only way you make money is once in a blue moon when you campaign for a raise or a promotion at work or when you apply for a job, which does not happen very often. But when you own a business, either as a freelancer or self-employed or having your own small team or whatever the thing might be, you are learning the skill of making money every single day because the hardest part about building a business is winning the work, not doing the work. Doing the work is easy. You can easily figure it out, especially with AI once you have paying clients. But getting those paying clients in the first place, holy moly, it's like hard to do because it's a series of skills. It's a muscle that you haven't yet developed. Last year, we ran this thing called the 1K challenge, which was like a six week live thing over summer where we sort of helped people make their first thousand dollars online. And we had a bunch of people who made their first thousand dollars and more online. And then one of our students, Kelsey, ended up joining our lifestyle business academy. She'd been on the default path working fancy tech jobs in her whole life. And through doing the 1K challenge, she realized, oh, making money really is just solving problems for people. Huh, I could use my existing skills to solve problems for people that I know. And so, she made her first thousand during the 6 weeks of the thing. She joined our lifestyle business academy. She's now made $40,000 over the last few months. And she did all of this without quitting her day job. She still has a fancy tech job, you know, working in tech. and I think has no plans to actually quit that job, but feels a profound sense of confidence at being able to actually make money. So, when you start making money on your own, man, that's one of those massive unlocks. It's just a series of skills that you need to learn and you learn those skills often by just trying to do the thing. Oh, and by the way, if you're interested in learning more about our lifestyle business academy, which is our online business school, where we help corporate professionals build sixfig lifestyle businesses, so that it makes your job optional. Uh there'll be more details down below and you can check it out if you like. One thing we sort of talked about earlier in the conversation was this idea of dipping into savings, which I've spoken to a lot of people who are like petrified of dipping into their savings. I have a friend who I know for a fact has like $80,000 in savings. Her house has a mortgage that's like $200 a month. She's absolutely terrified of dipping into her savings and has all for the last 5 years that I've known her has used that as as a reason as to why she can't possibly like do her own thing even though like clearly there's a lot of savings and like she >> hasn't got a partner or kids and doesn't have respons like so like all of the usual excuses can just be like canceled out in that context. >> Money on a spreadsheet does not solve emotional problems. There's actually a study recently out that showed retirees will spend about 80 to 100% depending on the income bracket of their lifetime earnings, but the wealth they build, they spend far less of that. And many people die with a bunch of money. Right behind that, I think it's just this rhythm of the paycheck reality. And so the paycheck reality says one, I am a good person and a worker and contributing and part of society if I'm earning a paycheck every every day, right? And then the other side of that is if I don't I'm a bad person. One powerful reframe helped me as well. A friend said this to me early on. He said, "Consider your savings a gift from your former self." He's like, "Paul, your consulting self, he did grind for you. He built up a little war chest for you to go out in the world. I had 50 grand in savings when I quit my job. And so that was sort of a gift from my past self. So you can really like close your eyes and be like, "Oh, thank you past self. I appreciate that. I'm receiving that." Another reframe is sort of labeling your life experiment as like I've called it a freelance year. I'm just going to do a freelance year, an experimental year. limit it like time frame it or just call it your life MBA or life PhD. I paid $100,000 tuition over 2 years to get my MBA in masters in engineering. I quit my job, broke even, made money on my own, didn't pay anyone for 2 years, and people thought I was crazy. Why not consider like a one or two year experience of betting on yourself trying new things as equivalent to like going to spend your own money on a masters? >> Yeah, I love that way of labeling it. Um, another way that I sometimes think about it is, you know, all businesses require investment. Just that, you know, you the the investment that you're getting is from a former version of you. Conveniently, it's used, so you don't have to give away equity for that. And that investment gives you the runway. So, how much runway do you want? Do you want three months? Do you want six months? Do you want a year? because it's like you're basically it's it's like raising money from a VC. It's except you're not you're not giving away equity. And I find that that framing helped for me and also has helped for a few of my friends who have sort of like mentored through the process. Interlude about how work can be good without becoming a fantasy. So now that we've dealt with this money objection, which is often the biggest one of like, oh my god, can I actually survive or will I end up killing myself because like I don't have any money. Once we've dealt with that kind of general sphere of rejections which often tends to be emotional rather than mathematical in nature, there is a deeper question underneath all of this that we have to contend with, which is what's the sort of work that you actually want to do? Because the danger with any kind of quit your job conversation is that it's easy for it to be framed as like, you know, job equals bad and self-employment equals good. And that the freedom to live life on your own terms means never having to do any hard things ever again. And that, oh my god, if you just find what you love to do, then you'll never work a day in your life. I know loads of people who are on the pathless path. A lot of them are super super super rich. almost none of them uh view work as, you know, this thing of you're it's always sunshine and rainbows and roses and all that crap. And so this is a little interlude where Paul and I talk about the idea that work does not have to suck. >> There's a I think think the opening line of good work when I first read it was like what is it? I'm quoting directly. Could it be this simple? Just do things you like. >> Like when I read that I was like I I I can't remember. >> You don't need to read the rest. I was just like I was literally grappling with that question in my journals like every morning being like can I in fact just do things I like and then I read this the first line I was like oh great Paul's about to write a whole book about this shocking to many people though because many people have internalized the idea that work has to suck work is a sacrifice work must be painful and so we internalize these things so deeply that we don't even question when we're suffering >> objection your honor uh easy for you to say uh work work can be on you. Paul Miller, tell that to the gas station attendant or the person working at McDonald's or the person sweeping the floors or the single mom working three jobs to make ends meet. >> I would say that the default story in most cultures, in most societies, is that work must suck. Work must be painful. All I am doing is pointing to an experience I have had and saying work doesn't have to be painful. By definition, many people in many different kinds of jobs do find joy in what they're doing. And so all I'm asking is that the margin to consider small decisions around what might be possible. And so trying to fit something like that in which you have to do things you don't want to do that is a job into this container of I want it to just be my passion. >> There are influencers that will sell you that idea. I will not sell you that idea. I don't think it's possible. What I think is possible is slowly moving more and more toward a larger part of that job-shaped container being things you enjoy. >> And so just just back up and like take off the labels and just notice what you're doing on a day-to-day basis. >> Yeah, I completely agree. Um, another line I found myself saying to a lot of people is that everything feels like work after a while. Everything is work, >> right? We're all just doing things. Humans work. When you change your daughter's diaper, you're working. You're doing things, right? But we don't apply special labels to that. It feels light and easy because you just do it. That's what you do as a parent. When we start attaching all the labels to work, when work has to be special, when work has to give me fulfillment, when work has to provide me infinite money, that's when it's just really hard to pull off. >> Now, I like this distinction Paul draws between good work and a bad work. And bad work being like, you know, the sort of stuff that drains your energy, the sort of stuff that makes you think, I really want to do this. You know, that kind of stuff happening repeatedly is a good signal. Good work is the stuff that you're like, oh, you know, this was actually quite enjoyable. you know, maybe not every aspect of the thing was like that like fun, but you know, broadly I felt energized by doing this thing and I can see myself continuing to do this sort of thing. And in every kind of job, there's some elements of good work, some elements of bad work, some elements of good enough work. In every kind of business or self-employed path or freelancer path, there are some elements of bad work, good enough work, and good work. And what the whole game becomes once you've been doing it for a while is it becomes basically a rebalancing the portfolio kind of game. For me, the question I always think about is if I had a h 100red million in the bank, what would I actually end up doing with my time? And then I look at the stuff that I'm actually doing with my time. And then I'm identifying, okay, cool. So, what are the things that I'm just doing for the money that I wouldn't choose to do ordinarily? And I try and make that list as small as possible. And it's not an overnight thing, like especially when you're starting out a business or starting out trying to make money. It's like there is a little bit of a shall we say, grind to it because you're probably not going to be doing stuff that makes money that like you're feeling super blissed out about all the time. But definitely over time if you keep on like just continuing on the path you start making these small pivots and a few years later you look at your calendar and you're like damn pretty much everything I'm doing is actually stuff I want to be doing whereas maybe a few years ago 30% of the stuff that you were doing was the stuff that you actually wanted to be doing. And so to make those pivots we move on to step number seven which is to follow your energy. >> I did some of the freelance consulting work and I found I didn't really like it that much. I was good at it. I could do it. It generated good money but there was this tension. There was this avoidance. I wanted to not take every project I eventually took. And so I was doing the consulting work just for the paycheck. And so one of the shifts I made in the first year was that I decided to do my best. I did fail at times. Do work that I actually just wanted to do for the sake of itself. Even in my first year of work doing consulting work. So before I did consulting gigs, I spent an entire month writing this essay called Crisis at Work. And it was this big long essay exploring the history of work. I hired an editor to coach me on my writing. I hired an illustrator to illustrate graphics for it. And it was just so fun. It was really enjoyable. But in my head, the story was that's not real. I can't make money writing. It's not something to take seriously. And so I look back now and it's it's so obvious to draw a straight line from that energy to what I'm doing now. >> Yeah. One of the things I think I read in one of like Paul Graham's essays back in the day was, you know, what's the thing that you find yourself thinking about when you're in the shower? That question can often lead you to what sort of work would you actually be into? And I was I think I read this like 10 years ago. Uh and I was like, huh, I've not once in my life thought about medicine while I'm in the shower. It was always about like the app that I'm building or like the software platform me and my brother are trying to build or like oh I really want to be a YouTuber and try and do these like music covers or whatever the thing was. It was never about the thing. It was never about the main thing that kind of default path that I was pursuing. >> Yeah. I have this idea on the pathos path where I say don't aim at a niche. Don't find a niche find a mode. Right. And I actually gave you as an example in this essay >> and I think one thing where you've succeeded is you found a mode where you can show up as Ali Abdal. You're not finding a niche >> cuz you change your mind every six months of what you're interested in. But that's how most humans are wired. Most humans are not hardwired for one niche throughout adulthood. For me, it was this proof of energy that it was like, I kind of like that. That might be some evidence I could do stuff on my own. I don't know where that will lead, but that's sort of one pro in the list of maybe I'll go take a leap and find out. >> It's a cool way of uh approaching this that it's not about finding a niche where you're sort of like just doing one specific thing for a very long time. It's more like finding a mode where the general mode of operation is figure out what I'm interested in, uh, do some teaching about it and see if I can maybe sell something based on that teaching that I'm doing. That's sort of the mode that I've sort of landed up in. I'm going to give some context here because I think it's interesting or maybe useful, but like so we've had this course that I've been running for the last six years, the parttime YouTuber academy, which is a basically a course that teaches people how to build YouTube channels. And then like last year, I was saying to Dan, I was like, "Dan, I really want to start my own online business school and I really want to do this lifestyle business academy thing because I'm no longer massively energized by teaching people how to do YouTube, at least not for like 40 hours a week, but I am really energized by teaching people how to start an online business that gets them to financial freedom. What do you think?" And Dan's push back on this was in general there is a good principle in business, which is it is much easier to do more of what works than to do something that is completely new. So Dan was like, "Look, if you want to make money, why don't you just triple down on the YouTuber thing? Like, you could do a YouTuber for businesses. You could do a YouTube for teams. Every business wants to start a YouTube channel. You could do a thing there. You could do a service, and it would make so much sense because you've already got this multi-million dollar asset in this YouTuber academy. Why would you start something completely new?" And I was like, "Well, cuz it would be fun and fulfilling." And he was like, "Well, okay, but then what what 6 months from now, are you going to start like a gardening academy because you're into gardening? and like 6 months after that, are you going to start a knitting academy cuz you're into knitting? And I was like, yeah, you know, that's probably not the optimal strategy to get you to zillions of dollars in the bank. But that kind of is the mode of operation that I enjoy for myself and for my business where the business basically follows the thing that I am energized about in the moment. Right now, I'm not massively energized by teaching people how to do YouTube cuz also because AI is taking over and I I need to like dive into that rabbit hole at some point. And so that side of the business is still running and we're still like updating the course and making sure the AI tools are updated and all that kind of stuff, but I don't need to think too hard about it because I've done the hard work of creating the initial thing and now the team basically runs that. But I'm currently energized by this lifestyle business academy thing. And so I'm spending all my time working on that. And at the point, you know, if it ever happens that I become less energized by that thing, then I'll hand that over to the team to continue running or maybe we'll shut it down like we've done with some previous product of ours or whatever and then I'll move on to the next thing. And that's sort of like the mode of operation that I've at least found myself landing on that like actually you just follow your own curiosity and make stuff around what energizes you which for the record is not the optimal strategy that I would advise someone if they're trying to make loads and loads of money. >> On my current path I have a set of activities I like doing. That's shifted over time and I'm always noticing oh I have interest here. I'm going to spend time doing this or that. But there's no story attached to it. I am not an author. I am not a creator. I am not a YouTuber. I am not a podcaster. I'm just somebody doing a set of activities that I like doing. >> I really like that. I have this is something I've started doing recently where I've started to internally drop the label of YouTuber cuz when I have the internal label of YouTuber, I kind of think sort of there's always a sub routine running in the back of my mind of like what's the next video uh and like keeping an eye on the analytics and all all of that stuff. Recently, what we've done is YouTube is sort of confined to a Tuesday. That's my filming day and that's a day where I think about YouTube videos and then the rest of the time I'm not thinking about YouTube videos. So I have like some slots on my calendar where I think about the various apps that we're building which is kind of fun and the rest of them these days I'm building this like lifestyle business academy thing which feels really fun right now and I'm sure it's not going to stay feeling fun and exciting for years because everything sort of at least at least for me sort of I have a period of excitement and then it sort of slowly waines over time. I I found it very helpful to drop to drop the noun and just focus on Yeah. I like I like I like like the way you put it like the bundle of of activities labeled work or whatever. >> Yeah. If you're aiming at trying to be a creator, you're going to end up frustrated and confused. I mean, so many people have gone allin toward these labels trying to basically just reinvent the default path off the default path, right? And so many people burn out and quit in a blaze of glory, right? Some people even shut down everything they've done even though it's generating money. To me, that that didn't make any sense for a while, but then I realized people are trying to kill off that identity they created for themselves, right? They're doing the same thing I did when I quit my job. I just wanted to get rid of that and start fresh, burn it to the ground, right? And so, I'm trying to avoid that. So, I hold the labels of like who I am and what I'm doing lightly. I'm just trying to carve a path in which I can continue to do things I like doing. >> So, now that we've done all this stuff, we figured out the portfolio of stuff that we want to do, we're not overly attached to the labels that we've like put on ourselves, we now move on to step number eight, which is to declare retirement. >> But Paul, what if it goes to zero? Like, and then you're going to struggle to get a job because they're going to you look at your CV and they're going to see that you're like this vagrant who's just been doing their own thing and you're a flight risk and then and then you'll your family will starve. I don't have this insecurity of like a fear of going to zero. Many people have it, >> but one way I cured it is by actually just making less and seeing how I felt. At first I felt terrible. For the first few years of my path, I made an average of 30 to 40 grand a year. I felt pretty bad. And so I did a pretty interesting exercise four years in. I sat down and ran the numbers of all the financial assets I have. And I'm somebody that's always been worried about like having enough money and saving enough. And I don't want to spend too much. I've always been very frugal. And in the first four years of my path, I basically just covered my cost of living. So I didn't save additional money. The money script I had in my head was that I'm reckless. I'm like uncontrollable, like out of control. And I just ran the numbers. And I had retirement funds. I had invested in investments and I didn't touch those at all. It was like I was so scared to touch those that I built my entire energy and life around just like making sure I made enough to cover my cost of living. In those years, it was like a huge stock market run and my net worth had doubled in 4 years. And so I had this huge moment of dissonance in which my net worth had doubled and I felt like a completely reckless person financially. A lot of why I write is self- therapy. And so I wrote this article in 2021, even before I started making more money from the book and stuff, and I just declared myself retired. >> What do you mean you declared yourself retired? >> So I called myself retired in the sense that I felt like I could keep going on my path and doing work I liked. I think I got this idea from you called the skip test. I love this idea. Would you skip this task if you could just get to the end result? So, for example, this podcast, I would not skip this just for a finished product. I I love this kind of conversation. >> And so, I wouldn't skip it. And so, in those four years, I had done a majority of the things I didn't want to skip. And so, I considered myself retired from bad work. Bad work is the stuff that drains my energy, the stuff that incites all the tension in your body, the resistance, the things you don't want to do. One one definition of retirement that I like is where I think I got this from Naval who I'm sure got it from somewhere else where it's like you're no longer doing things for instrumental reasons. Like you're no longer doing a thing for the sake of something else. You're only doing things because you intrinsically want to do them, >> right? >> And then if you can make enough money from those things that it funds your lifestyle, it's like, oh wow, now you're sort of you've got this infinite game going on where you no longer quote have to work if we define work as things that I would I wouldn't choose to do if I didn't care about the money kind of thing. And so we now move on to step number nine, which is to handle the people around you. You have a wife and a daughter. Paul, how could you be so irresponsible to leave a stable, high prestige, high status profession? Aren't you worried your family's going to starve? >> Yeah. So, this is a very common question I get. It It's actually pretty funny because before I had a kid, people would be like, "Oh, well, you can say what you're saying. You don't have a child. When you have a child, it will be different." And so, it is nice to have a child now. So I can be like same strategy. Still don't know. Still don't. Yeah, I had a kid. I had a kid for the story and the the street cred. But two things. One is you you can marry someone that is wired similarly and embraces uncertainty. I met my wife after blowing up my life, which was great because I was mostly failing at dating in my 20s. I would talk to people on dates and be like, "Wouldn't it be cool if we just like quit our jobs and traveled for 6 months and you could see them get like a little disappointed like this guy's not going to cut it. Income's probably not going to keep up." I was dating in like New York and I had I had a fancy job on the Tinder profile, so there were certain expectations and yeah, just like no matches. Blew up my life. started living values that felt very true to me and aligned and I attracted somebody that was wired very similarly. The first month I met my wife, uh, she was quitting her job and so she was texting me some mornings and being like, "Hey, I'm going to skip work today. Want to just hang out and wander?" Fell in love pretty quickly from that. And so it's been sort of a beautiful journey to have her alongside me very early. That is a sort of cheat code to this path because it can get lonely. It can get very challenging to do this on your own. I've had her by my side. She's never laughed at me a single time. Every crazy idea I've had, she's supported me and I support her dreams, too. And so we're sort of still figuring it out as we go. It's definitely harder and you do need a little more money with kids, but we've lived in seven countries with our daughter over the first two and a half years. And we've lived in many different ways over the first two and a half years. Done a lot of different experiments with how we're working, living, not always thriving perfectly, but it's still fun and we're enjoying the ride. My wife Izzy hasn't had the years of wealth building that I've had. And so for her it's like I see a lot of my former fears about money from like three years ago in her today where I would just like fly business class because I know like whatever and she would be doing the calculation about premium economy and stuff and feeling bad that oh my god like this is unnecessary. And it's it's interesting to see that mirror because I I think it took me about 3 years to realize that like have more of an abundance approach to money which came from the financial confidence of just having an internal sense of basic certainty that I'll be able to figure it out. >> Yeah, this is a really interesting thing. I have my money fears and future fears and then I have Angie, my wife's money fears and future fears. We actually had a similar thing with me paying for uh baggage overage, went over a certain amount of pounds, and I just didn't want to take stuff out and repack. She brings an extra bag, so we can do that. I was just a few years ahead of her in resolving that. A few years ago, I would have repacked. I would have gotten angry. I would have gotten frustrated. But you know what? I was just like, "Here, credit card, pay it. I don't I'm retiring from paying and worrying and micromanaging this expense. I know enough I have the confidence that I'm going to be okay spending this small amount. This is why in my last book, one of the whole chapters, chapter 4, is devoted to Angie's journey and her journey of trying to find good work. >> She's been years behind me on the almost same journey. And it's really hard because I literally wrote a book about this stuff and I'm a few years ahead of her and I just want to like solve her problems. >> It's like just just do exactly what I did. >> But she's a different person. She has her own journey. She has her own route. She has her own path to take. >> And we're going to have a lot to talk about over dinner tonight. Leah, in in Izzy's case, literally this morning, she was like lamenting a sponsorship that she had to do that had a sponsor deadline coming up and I was like "Ah hello there." And over time, I've learned to keep my opinion to myself and just be like, "Yeah, it kind of sucks." Um, rather than, "Hey, there's a whole process for this that we've already figured out cuz we've been we've been through this over the last 5 years." It's like, yeah. How does that feel knowing that like your peers who went to MIT with you and are were at McKenzie are now making more money than you and are more successful on paper with higher prestige jobs compared to you doing your little experiments in work and writing on the internet and books and stuff. >> Yeah. So, I'm probably one of the poorest of my business school graduating class. Almost guaranteed bottom 1% of that. And so, I get this question a fair amount. especially from my business class peers. They're like, "What what are you doing?" Yeah, I actually got a message on >> I actually got a message the other day on LinkedIn. Um I can read the LinkedIn. This is from somebody in my graduating program, the dual degree engineering MBA program. Do you ever feel you're not using all your potential compared to our fellow classmates? And so eight and a half years on this journey, I'm smart enough to know that's his insecurities, not mine. >> But still, I felt a little something. I'm like, am I am I a fool for doing this? Could I have made more money? I literally have friends making millions of dollars a year. I have classmates who have sold startups for hundreds of millions of dollars. And so I do ask, should I have done these other things? But then I just come back to the present moment, right? And it's like, would I have met my wife? Would I have lived in different countries? Would I have had all these experiences? Would I have so many days I didn't want to skip? And it just becomes so silly that I would ever go back to the previous life. So, at this point, it's worth asking yourself if, let's say, you feel the itch to go on the pathless path and do your own thing, and then 10 years from now, you're at a reunion for your college or university or school or whatever, and you find out that you're actually in the bottom 10% of earners. Everyone's crushing it in their high status, prestige jobs in hedge funds and investment banking and tech sales or whatever the thing might be. and you've been exploring this path where you're exploring your curiosity, exploring your energy, and you've just made less money than they have. How do you feel about that? How do you feel about potentially scoring lower on the scoreboard of status and prestige and money that the people around you are still using to judge the quality of their lives? Of course, if all if the things work out super well, then you'll end up making way more money than them. Like I've got a friend um he used to actually work at a hedge fund and so uh and then he switched to the pathless path and so he you know he and I often talk about this when we see each other uh once every few years of like you know the gap between his net worth and his friends net worth who by this point are now partners at the hedge fund and you know all of that stuff and he does say that it is difficult to deal with at times knowing that man if I just stayed in my shitty corporate job that I absolutely hated I would have a net worth in the tens of millions by now like my friend Johnny does. But then he sort of reminds himself that, you know, he's able to spend his days basically doing whatever he wants. Uh he was able to see his kids grow up. He's able to go surfing every day cuz he's into surfing. And he has to he almost has to remind himself that actually he wouldn't trade lives with his buddies who have been in, you know, who's who are overweight, whose hair is falling out, who've been in corporate hedge funds for the last like 20 years and who have a net worth of tens of millions because he has found his good work. even though he makes a lot a lot less money than them. So, I don't know, maybe it's just a cope, but it's worth like running that thought experiment. Are you the sort of person who would be okay with making less money compared to your friends uh knowing that you're doing stuff that energizes you, or are you very concerned about how your situation looks like to the people around you? >> Various other objections I would like to offer for your consideration, your honor. Uh firstly, my parents will be disappointed if I quit without a plan. Um, the aunts, the uncles, the cousins, the colleagues, people will laugh at me if I quit my job without having an answer to, "So, what's your plan, mate?" >> They might. Are you okay with that? Is typically what I tell people. Almost everyone who's done something more unconventional or experimental, in my experience, has had at least one family member who said something extremely painful to them, either in the process of quitting or after quitting. And sometimes those relationships never resolve. The parents have their own stories about work, about responsibility, about what you're supposed to be doing in the world. In my first book, I wrote, "Will they still love you?" And really question that because I think in taking a leap to do an unconventional path, there are people who have parents who are like, "Hell yeah, I'll support you. I love everything you do." Most people have at least some critics in their life and there's going to be a loss of something you can't anticipate, right? You're going to lose identity. You might lose status. I felt these things very powerfully. I felt like a failure. The thing I tell people is it might suck, but it might also be worth it. Sasha Chapen calls this love the moat of low status because on the other side of the moat is sort of an arbitrage opportunity of most humans don't want to pay that tax. >> Yeah. Chris Williamson just put out an episode this morning titled um what you want is on the other side of cringe. I was like oh that's nice as well. >> I love that. >> Yeah. That's uh cringe is the stuff you feel embarrassed to do. Every content person, everyone who's done YouTube, everyone who writes online has felt ashamed weird embarrassed. It's so hard early on. You feel like the world is going to attack you. Then what often happens is nobody pays attention to you. Then you do try to get attention. Then when you get a readership, then the critics come and you get insulted and you eventually just learn to deal with it and you realize it's worth it. And now finally we come to step number 10 which is to keep playing the infinite game. A lot of people like you and me who sort of whether or not we explicitly or implicitly encourage people to explore alternative careers. The objection might be that there's a lot of survivorship bias here. It's like it worked out for you and me. There's all sorts of people who quit their job without a plan and then they end up riddled with anxiety, losing all their money and then struggle to find a job again because like the job market is really hard these days. Dot dot dot dot dot dot. What's your take on that? I think what I found is those people are really hard to find because most of these decisions are reversible. Getting a job again is much easier than people think. What's happening is people's fears are beyond the reality. Most people have families to come back to. They have alternatives to come back to their job. Tim Ferrris's fear setting. It's like what are the steps you could take to get back to where you are now? Often for people it's like one email. And you see this there's data from multiple surveys I've written about in my newsletters. The regret rate for quitting your job and doing something new is so low. Career transitions, the same trend. People typically don't regret the decisions they make. People regret the decisions they didn't make. There's a nice line from Oliver Burkeman that just because a given path is unfeasible for the underprivileged does not mean that it's unfeasible for you. And I think I I do hear this objection from a lot of people where they're like, "Yeah, well, not everyone can just like quit their job and be an entrepreneur." It's like, "Okay, not everyone can, but you can." People will say to me, "What if everyone did the pathless path?" And I always reply, "Have you met the the humans?" Like, most people hate the idea of what I'm doing. Most people are triggered by it. They they're not interested. I'm mostly writing for the people that are already deeply curious. Okay, final objection. I think um what about healthare and retirement and responsibilities in that sense? >> There are hacks. So the advantage of a lot of the questions about healthcare come from the US where healthcare is outrageous. So I've been uninsured for multiple years in the US. I've uh been on state exchanges in many years in the US. I've had a low income in the US and had government covered insurance for me. It varies dramatically by state, but it's typically just a price. I've paid for healthcare out of pocket and you can buy it. I haven't paid more than 5 to7,000 a year >> for healthare. So, it's just a price. It's just another cost of your life. >> Throw it in your spreadsheet >> with your dining out or other things that maybe are more flexible >> and just figure it out. But, but the people that must take this path, they don't start with the excuses. They start with the okay, I'm gonna have to pay for healthare. I might not have healthare. How am I going to solve that? How am I going to take care of myself? How am I going to meet my needs? And so people are just denying their own agency. As soon as you take the leap and you don't have a job, you now have 40 extra hours of action per week. >> Y >> which you can figure stuff out. >> Even more than that if you have a commute and all the time, mental space, the whole the whole thing. >> Yeah. Okay. Nice. So for anyone who's gotten to the end of this video who's still feeling like resistance like oh I think I maybe want to do this but like I'm afraid because reasons ABCD healthcare retirement pensions privilege success rates what advice or rather what would you say to that person? >> I think it comes down to getting to know yourself. One thing I've always told people is just to go spend time with yourself. So I often assign people a wander. go out in an afternoon without a destination. And many people rarely walk without a destination. And so really lean into this. Just walk, take random turns, and see where you end up after a couple of hours. And notice how much your brain is just trying to aim at a certain destination or time or story of I need to be somewhere. I need to be back. And start with simple experiments like that. Host an event. Have a call with somebody that's on a path that you're curious about. Write something. Try and experiment online. Go to a meetup. That's a new interest. There's so many small things, right? And just start there. Don't think you need to solve everything in a moment and take the leap now, right? Just get to know yourself and continue asking, "What is the life I want?" >> One, I guess, objection I've heard a lot is, "Yeah, but I don't want to waste time trying something that might not work." >> Yeah, I've wasted tons of time experimenting in my life. And so if that's your prime motive in life to not waste time, then this probably isn't for you, right? Because it is very costly to do things on your own. You often waste weeks, months, years trying different things. We've experimented with living in different ways. Since having a daughter, we've had to reorient and rethink everything about how we're living. And it's very costly. It would be way easier if we just got a job and accepted the default way of setting up your life. But for us, there's more. There's that ah we must find out. We must keep experimenting. There's that drive and if you don't resonate with that like maybe it's not for you. >> Nice. Love that. >> So Paul has left at least a million dollars on the table. He is in the bottom 10% maybe even the bottom 1% of earners from his MIT MBA that he did many years ago. He does not have a plan for how he's going to make money six months from now. And he told me with basically zero irony that he genuinely considers himself retired. What I at least took from this conversation and what I take from Paul's reading and books and videos and podcasts and stuff that I've been consuming for years at this point. What I take from this is that it's not dreamy in the sense of like, oh, quit your job and then everything will work out great. It's more like you can totally quit your job and if you do, it's going to be messy and it's going to be hard and it's going to be confusing and you're going to cry yourself to sleep some of the nights because you're not going to know where money is going to come from. And if you have this requirement that you're going to replace a stable salary like overnight, you know, good luck. That's probably not going to happen. But if you're okay with living this life of uncertainty where you do not now have a yellow brick road that is in front of you and you're having to figure it out pretty much all the time, then that's what it's really like. Honestly, this is one of the things I sort of miss most about having a real job in medicine. Like medicine gives you a yellow brick road to follow. It tells you that like this is the path you're going to be on for the rest of your life. And there is profound psychological safety in at least the illusion of control. The illusion that there is a path that you can follow for the rest of your life. In reality, it turns out not to be like that. You know, like the latest intake of junior doctors in the UK, there were actually more uh graduates than there were places in medicine. And so all these people who signed up for med school eight years ago or six years ago being promised a job for life are now suddenly unemployed or they've got to get a job in the middle of like Aberdine or something where they don't want to go because their friends and family are all in London. And so like you do get rockpulled from time to time based on AI, based on the economy, based on recessions, based on layoffs, based on mergers and acquisitions, based on government policy. You can totally get rockpulled. But even so, the illusion of certainty is really quite nice. And that was one thing that I'd sort of underestimated when I went on this, shall we say, pathless path of figuring things out, that there's always a little bit of a concern around what's going to happen six months from now, what's going to happen a year from now. And it doesn't feel as stable as knowing you're basically guaranteed a corporate job for the rest of your life. Although, to be honest, I would argue that that world is becoming a lot less and less secure and safe than it once was. Now, if you're at this point in the video and you haven't yet seen my video about how to build your own $100,000 a year lifestyle business in, you know, somewhere between 12 and 24 months, then this video over here is going to show you the exact road map. And that's maybe one option you can choose to follow uh if you decide to go down this pathless path approach. Thank you so much for watching and I'll see you in the next