STIMY 126: Rejecting $200k/year for the Pathless Path?! | Paul Millerd (Solopreneur, Author & Podcaster)
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Paul Millerd: I think I called this the last stand. It's almost like I was trying to like test if I really wanted to walk away, and I just got fed up one day and I was like, I think I'm gonna leave.

I had been like planting seeds, but I just emailed them. I was in Florida. I don't even know if I told anyone I was going to Florida, but I was just so done.

My sole energy was on zero, so I had no choice. It was so easy to walk away. I knew I might have to pay back this signing bonus. I tried to fight for it and not pay it. The company sucked. They had a three year clawback. I said two and a half years, three year clawback on a sign-on bonus and moving charges.

These companies, like, they don't give a shit. And then the people in the company, they can't give a shit cuz the company's set up to not give a shit about you. And it's like, yeah, it was so painful writing a check. But man, I would do it again and again. It left me with less runway, but I still had about a year of cash in the bank to like pay to live in, well, not really New York. I ended up leaving New York and going somewhere else.

But yeah, it sucked.

Ling Yah: Hey, STIMIES!

Before we start, can I ask a favor? Please leave a rating and review for STIMIES on the platform that you're listening to this on. I would love for more people to know about this podcast, and that can only happen if people share and write reviews and, oh, STIMY's also on YouTube, so you can look us up there.

Now let's head into episode 126 of the So This Is My Why podcast. I'm your host and producer Ling Yah, and our guest for today is Paul Millerd. He's a former McKinsey consultant and creator, writer, and podcaster among many, many things. A few years ago, Paul thought that he had everything he could possibly want, but then he realized that it wasn't enough, he left his $200k a year job and went on the pathless path to build a life that he really wanted, and along the way, I wrote a book called The Pathless Path that sold over 20,000 copies.

At the time of our recording, I was just about to embark on my own great leap from the world of corporate. So as you can imagine, I slipped in a couple of my own personal questions on what to expect.

So if you're interested in learning what alternative career paths and lives exist today, then this is the episode for you now.

Are you ready?

Let's go.

Paul Millerd: I grew up in a very small town in Connecticut in the US and grew up in the woods around family. Had a pretty simple upbringing.

I was always good at school. I think in the zeitgeist at that time, like the American dream of like go to college and then get a good job, that was the path. And to be fair, that was the path that worked pretty well in the eighties and nineties and people remembering previous generations. So I was a generally curious kid about definitely technology, sports, things like that.

It's interesting though. I mean, I was really good at school, but like nothing really stands out as like, oh, this person has super deep interest in this. Other than I just spent a lot of time hanging out on the computer, which is what I do now too.

Ling Yah: I want to talk about your parents, your family, cuz they sound like they had a huge influence over your life.

You said before that your parents didn't go to college, but they sacrificed so much to let you have a chance to dream. I wonder if you could just share what you meant by that.

Paul Millerd: They're both pretty solid in like the default life path script and that was the story they grew up with, right? The man works, the woman takes care of the family and you just go about that and it worked pretty well. I think my dad probably got lucky a few times by not getting laid off. I remember the tension in the house around potential layoffs at many different points.

And by the end of his career he was making a lot of money. I was long gone by that standpoint, but I mean, I didn't have to worry about like clothes, school, food. Went to like a normal public school, which is free. I don't remember not having what I needed, which is to say I didn't grow up with a scarcity mindset, of I don't have enough.

I need to suffer for something in the future.

I realize now I was somebody that was dreaming about different paths. I was always curious about why people did things and what are the different ways to do things. But I wouldn't say that was cultivated at all.

It was kind of dormant and wasn't really aligned with like how my parents were approaching the world.

Ling Yah: I thought it was interesting how you had so many side projects when you were younger. In high school you did. Paul Says It Well. At College, you were DJ Popo Schitzel. How did these very varied jobs come about?

Paul Millerd: It all makes sense now, but it didn't make sense of the time. I was just trying to have fun. I always looked for ways to have fun. I remember I wrote this essay for the yearbook about me and all my friends who owned minivans. So we staged a photo opportunity of like six guys that had minivans and we all parked them in the back and like angled them like we had fancy cars or something.

It was kind of this fun little joke we had and I was helping to build the yearbook. So published this article how we were like a new trend of millennials who were driving minivans cuz basically all our moms wanted cooler crossover SUVs.

So I did stuff like that. I remember I declared for the NBA draft as a joke and my friend wrote this Article for the school paper.

Yeah, I created this thing called, Paul Says It Will, where I'd predict the weather. I never thought anything of these things because my entire conception of what life is supposed to be is like you get good grades to get a good job. I literally didn't have any clue. I had nobody saying like, Hey, this computer stuff, you're really into that.

You're having fun. Lean into that. No one ever pushed me. Nobody took it away from me. I think to my parents' credit, I got a computer in my room and I would just spend hours on it by myself, building websites, doing all these things, joking around, having fun. And it's a lot of what I do now, but I didn't see that as like a viable path.

The only thing I thought you had to do was work in a big company in a job.

Ling Yah: It must have been strange for you to have all these very fun side projects and then work at a gas station, which was a town away. You hated it.

Paul Millerd: It was terrible. I wanted to quit like everything when I was young.

I think this is now an underrated skill. I think the whole idea that you shouldn't quit things is default path mentality. And default path is the story you grew up with, which tells you do these things to be a good person in the world.

A big part of that in many countries is basically learn how to suffer at a job you don't like because this is the only option, and that's how you take part in society, right?

You take part in society by doing formal work, which means a full-time job for typically big company. I think this translates pretty well to Malaysia too, right?

Ling Yah: Yeah. Across the board for sure. But there are also certain instances where you have to suffer. For instance, you run a podcast yourself. I imagine at the start it is very hard.

It is a grind all the time, but over time you can see the value occurring. The same when I was learning the violin. The first two, three years, it doesn't sound like music, but once you get through that period, you put in the grind, then it just gives back so much more. But you have to not quit first.

Paul Millerd: I would push back a little. I think this is a problem of language. When we talk about grind, grinding on a stupid, pointless job, doing work that's not helping you grow as a person is not work worth doing. Mm-hmm. Grinding in terms of like figuring stuff out , like putting in the hours to edit. I edited my first hundred podcasts.

I was not disconnected. I was aligned with something I actually cared about. Like it didn't feel painful or coerced to have to do that. I was excited to do it. Sometimes it wasn't that excited, but it was so like, yeah, this brings meaning to my life. So grind, like put your head down, just pay your dues. All these things.

And most of that's just gaslighting from the previous generation that rose up the ladder in big companies a lot longer and just wants to either see young people suffer because they did, or they're just changing the rules and they wanna like not disappoint them. But this is a big thing.

And I didn't realize there was a different way to relate to your work until after I quit my job. I was so blind to this. I was doing all these side projects, right. Having fun. I actually liked school. I liked high school and I liked college. It was never hard for me.

Ling Yah: Why was it then that your mom is like, you just don't have ambition?

Was it because you wanted to quit other things even though you were good in school?

Paul Millerd: Because to her I needed to learn how to suffer and do things I don't like. That is the default script of work. Learn how to struggle through things you don't like because you need a paycheck. That is how you show up in the world.

And it's just not true. And it's even less true than ever before. You're doing this podcast and you're probably creating a lot of opportunities for yourself. You're just showing up and doing things that inspire you and you like. That was not possible 10 years ago. But it's more possible now. And even in many jobs, like you can design it around liking what you actually do, right?

So we have these legacy stories from our parents and our grandparents, and everyone's just going through life. They're going through life and saying, well, you have to learn to suffer. And it's just not true anymore. And if you're listening to this podcast, you're probably somebody that wants to improve their life, dream bigger, and you know it's not true.

And this is where I've shifted dramatically. Like design for liking work, which means I don't opt into doing work that feels like that grind.

I don't need to be the biggest podcast in the world, but I need to check in with myself each week and say, do I actually like this? Do the conversations I'm doing in my podcast, bring me alive.

For five and a half years, the answer has been hell yes. So I keep doing it . I broke even on my podcast. I did. I've done some sponsors here and there, but why am I doing it? I don't know. The things you keep doing, you don't have a good answer for. On the default path, everyone's got an answer.

Well, why are you in this job? Well, I'm learning a lot. Nobody's ever learning. They say, I'm learning a lot. Nobody's actually ever learning. You learn a little in the first couple of years of a job and then you plateau, and then all you're learning is, how do I behave in this company to get promoted? And people hate that.

Ling Yah: What was your thought process? I mean, this all came later. What was your thought process back when you were at university and you were an honor program and you were surrounded by people with this success ethic?

Paul Millerd: Yeah, so I went to a pretty crappy high school and I did well, I got a good S A T score and I got into the honors program at my state university. And yeah, I didn't really have a plan or any goals.

It was just like, yeah, this is easy. This is close. I got decent scholarship money, I'll go here. When I got there, I was in the honors program and I discovered all these people that were working so hard in high school and had AP credits and had already come in with 50 college credits and had plans to go to med school, law school, business school, all these things, top companies, and I'm like, what the heck?

You're just around those people. You absorb their goals, right? This is called mimetic desire. You want what they want. There's no source like truth for that. You're just sort of paying attention to things, and I don't think this is a hundred percent bad. I think when you're young, you have no idea what you wanna do.

It can be useful to just pick a path. I think the thing I've now learned is you need to make sure there's an exit plan if you're not enjoying that path 10 years from now. Right. I loved consulting and finance and all these things I was learning in the first three, four years of my career.

But 10 years in, I looked around and I see overweight men who are cynical, not inspiring, and I saw myself turning into a cynical, negative person as well and was like, I don't wanna be that person for money.

This is stupid.

Ling Yah: But you said you also really enjoy your time at say McKinsey, and that you actually were planning to move to Boston without a job, but this came about quite unexpectedly. What was that like?

Paul Millerd: I just kept moving around like crazy. I think I had this restlessness, which I now know is I just like working on many different things.

And I probably should have tried to design around not having a boss, which appears to make me very happy now.

At GE, I was in their finance program. I ended up in that program because I found out it was the coolest program at GE and I hacked my way into that when I was in college.

It was really just trying to optimize my options. I didn't know what I was doing. I didn't really have role models telling me anything except make a lot of money, get a job at a good company. That's all that seemed important to anyone. I wish I had mentors that had deeper conversations with me, maybe challenged me, maybe push me.

I tried to break into consulting my senior year of college and got denied. But once I worked at GE I was like, I'm still gonna try and break into consulting. And I got rejected from all the firms again. But somehow I got this analyst position at McKinsey and Company, which is this amazing firm.

And that sort of changed everything for me. It gave me all these opportunities and I loved working there. Like I really loved working there. My biggest regret for my career is I didn't work there a couple more years. Not go to business school and just like left and bet on myself a lot earlier.

Ling Yah: How long would you have wanted to stay on?

What else do you think you would have gained?

Paul Millerd: I think four or five years. I mean, the people that stayed that were sort of in my cohort got to lead teams, coach people. I love that kind of stuff. They opened an office in Costa Rica too, and there were a lot of growth opportunities and it's just a really good culture.

People care there. They're aiming high and you get a ton of feedback and you really do actually grow.

Ling Yah: Weren't you known as the lean guy?

Paul Millerd: Yes. Yeah, like our office was interesting. It was all these people, different specialties in the office. We were this like new research hybrid group, which was like you specialize in a topic and you work with consulting teams on very narrow topics.

So I was doing lean manufacturing globally. I was working with teams in India, California, Africa. Remote at the time. So it was Pretty interesting to start working remote then. Doing a lot of video stuff and I was lean manufacturing. My colleague was doing supply chain, another colleague who's product development.

I sat and acted as somebody doing US general like economics research. There was another guy doing agri-business. It was all over the place. There was a Mexican research team. There was a geospatial analytics team. All these things. And it was just a vibrant atmosphere. And I think after that I was always just trying to recreate the atmosphere. I still miss it.

But I don't think I would take a full-time job to get back into an environment like that.

Ling Yah: What was for you, the reason that you decided it was time to leave McKinsey at the time?

Paul Millerd: Everyone else was. I just absorbed the goals of the people around me. Everyone's always moving in these prestigious companies.

You're going to business school, you're going to law school, you're going to get an mph, you're going to work at some fancy global company overseas. And my boss was like, Hey, have you thought about like doing this MIT program? And I really wanted it. And I also just like wanted to be in school again.

I've always had this bent of sort of anti work energy. I just like didn't wanna work. School seemed way more fun. And what better excuse than going to a good school where like everyone would give you a pass for basically not working for 27 months. So yeah, I got super into that. I remember just being totally absorbed with wanting to get in.

I don't know why I was ready to leave the company. I was just like impatient. I wanna keep moving. Like, I was drunk on achievement.

Ling Yah: What was curious for me was that your boss had asked you whether you wanted to do an MBA at MIT. You did. But you were also clear you didn't wanna go back to McKinsey.

Did you have a thought of what you want to do then?

Paul Millerd: I don't know. I had this story that maybe I'd work in manufacturing. I really just wasn't thinking that deep about what I really wanted. I don't think I had the tools then. I was pretty emotionally unintelligent. Typical just guy in his twenties that didn't really understand like what was going on in here.

Ling Yah: Did you also question your decision when your grandfather passed away and he was larger than live you described? Because that was the time you went to MIT, right?

Paul Millerd: Yeah, it was the month before I started. So I took a weekend off between McKinsey and MIT. That whole month was pretty intense.

Like, I lost my grandfather. It's very sudden. And I think it popped my bubble for the first time. This bubble of just sort of floating through life. I think I had a very easy life. I was always good in school. People liked me. I had friends. I was kind of good at everything I did. And then losing him just opened me up emotionally for sure.

Like, I don't think I cried more that summer probably than I did in the previous 10 years. It sort of just opened up this hunger, like, there's gotta be more.

And I think that was always in me, but I was scared to admit it. I was still scared to admit it or talk about these things to other people.

And I just became more aware and I wanted more out of life. I'm not afraid to say that now, but I was then.

Ling Yah: How did you figure out what that more was in making that into reality? Because I did notice on your LinkedIn you were bouncing from one to the other to the other. Constantly searching for something. Retrospectively, looking back,

Paul Millerd: I didn't, I had no idea what I was doing. I just kept looking.

I think that is the one consistent theme in my entire journey. Is I never settled. I kept moving.

Toby Luca, the CEO of Shopify said this on a podcast recently. He said, change is information.

So change for the super curious person that wants to reflect and go deeper is vital. So I kept making changes, but I was making changes in a very narrow context.

I was moving from one consulting firm to another and like changing the topic, but still in an area is very good at. Knew what I was doing. It was very safe, it was high paid, it was respected, I now know there are a hundred ways to live your life, and I attract and talk to people who are on all sorts of unconventional journeys.

It turns out there are other ways to live life other than as a corporate worker in a city working for a consulting firm.

Ling Yah: How did you figure out how to quit?

You say that you're very used to change, but a lot of people who listen to this find that really hard. I found that really hard as well. And you even had to return a 24 k signing bonus and missed on the 30 K bonus. You walked away from a lot.

It wasn't something small.

Paul Millerd: Yeah, I had a lot of practice quitting. When I was younger I did quit that gas station job. I quit soccer. I quit various things growing up.

Yeah, I quit every internship. Like every internship. I was like, I don't want to go back and do this. Like my freshman year in interns, there were like five of us, and they just all went back and they ended up working at the company.

I was like, I am not settling for this. I was always dissatisfied. And I think I just kept searching and I think I was smart enough and we talked about this before we chatted, but this idea of like a hoop jumper, William Deresiewicz, he coined this term in writing about his Yale students in the early 2010s.

You're basically just trying to do X for Y, And the problem is you never actually arrive at Y, you're just doing X for X for X. It's like this infinite loop. And so I just kept trying to improve my situation, okay, I'm gonna go from this company to ge, GEs better reputation. I'm gonna go from GE to McKenzie.

Okay, I'm at McKenzie. How do I parlay that in the m i t? And then, okay, this other consulting firm, how am I gonna tell that story of how this all fits together?

And I was always just moving towards the next step. I was never quite happy in any job. After six months, I was always quite bored.

And yeah, it just was very unsettled. And then walking away from the signing bonus was actually very easy. I was miserable. That was the worst job I had.

It was good in some respects. I liked some of the work, but the environment was awful. Like I just didn't gel with my boss and I was trying to get promoted and create this custom career path for myself, and I was totally just like self sabotaging my own success because I didn't want those things.

I don't know. I think I called this the last stand. It's almost like I was trying to like test if I really wanted to walk away, and I just got fed up one day and I was like, I think I'm gonna leave.

I had been like planting seeds, but I just emailed them. I was in Florida. I don't even know if I told anyone I was going to Florida, but I was just so done.

My sole energy was on zero, so I had no choice. It was so easy to walk away. I knew I might have to pay back this signing bonus. I tried to fight for it and not pay it. The company sucked. They had a three year clawback. I said two and a half years, three year clawback on a sign-on bonus and moving charges.

These companies, like, they don't give a shit. And then the people in the company, they can't give a shit cuz the company's set up to not give a shit about you. And it's like, yeah, it was so painful writing a check. But man, I would do it again and again. It left me with less runway, but I still had about a year of cash in the bank to like pay to live in, well, not really New York. I ended up leaving New York and going somewhere else.

But yeah, it sucked.

Ling Yah: It makes me think of, I guess I had her on recently, Lydia Fenet, and she said when she was working at Christie, she thought of them as family until 10 years later, so she realized that actually we're just a number in the P&L and that's all that you mean to that company. When you decided to quit without any regrets, did you know what you wanted to do?

Were you ready at that point to embrace being your own boss?

Paul Millerd: I don't know. I had just like given up. I just wanted to run away. I still had that question of like, there's gotta be more than this. But I didn't have an answer for like, what that actually was.

I had done some experiments as a coach. I sort of knew, okay, I can do freelance consulting, but none of what I'm doing now. I did not expect to write a book. I did not expect to do like, online courses or like writing a newsletter and have these things be so fulfilling. A podcast, like I was listening to podcasts, but I never imagined like, oh, I can do that.

I thought like, maybe I'd do a blog cuz I had done some writing. But yeah, I had no imagination. It took me six months to really just disconnect from work and start to re ignite that imagination to start thinking about oh wow. I forgot things I liked. Some of that joy of childhood screwing around the computer started coming back to me and I started like easing into it and I was like, man, I feel good.

I don't know if I can make money. And that's scary, but I don't know if I ever want to go back and I'm willing to go broke doing this.

Ling Yah: Would you say your priority then was less just finding your next job and more just reconnecting with yourself and figuring out what would actually bring your soul to life.

Paul Millerd: Yeah. I larked as a freelance consultant for the first seven months and like I took that seriously cause I knew I needed to make money. And I did a bunch of projects that were actually really fun and they showed me, okay, at minimum I can make money as a freelancer. And the working conditions are way better than being full-time employed .

I'm just, I don't know. I'm not wired to have a boss. I've had great bosses, but like the great bosses always end up leaving. And you always end up with the worst bosses, cuz the worst bosses are the ones that stay.

It took a long time. But that first year I started having this space.

I was on these freelance projects and I moved to Boston from New York and I'm wandering around and I'm just like, everything feels lighter. I'm feeling more playful, I'm feeling more imaginative. I'm writing, like ideas are coming out of me in exciting ways. I'm connecting with new people. Basically the last six years, I've just stayed true to that energy and for me, the pathless path, like my alternative to the default path is really about embracing that energy, given that a certain way of orienting toward the world is possible. Liking your work, feeling alive, not becoming cynical, knowing that that's possible. I think it's worth aiming at, and I think it's worth losing money.

I think it's worth losing friends if it means that. I think it's worth so much because if you can find a state where you feel connected to yourself, other people, the world, and feel alive, it changes everything and it's incredible.

Ling Yah: So I also mentioned this earlier as well, being fully transparent, I have one week left before I finish my notice, and I will have nothing actually scheduled for my future.

What is the kind of exercise or questions I should be asking to ensure that what I do in the future, I will have no regrets over.

Paul Millerd: I sense from your journey, you've been very intentional about this and it seems you've tapped into a creative energy that's like, that is what I wanna follow.

I would say pay attention to that. You're gonna get exposed to opportunities to make money. At a minimum level you need to figure out how to make money in the short term just to like make your fear go away.

But eventually you gotta figure out what level of discomfort am I willing to live with? Full-time jobs promise to make that disappear, but it never actually disappears. Everyone just pretends not to talk about it, right.

So yes, you gotta make money, get your bearings, and then figure out how much discomfort am I willing to deal with.

Given that you have to figure out how to be pragmatic and practical. But don't deny yourself the chance to not work. We live in a world that defines almost everyone by work. We are not workers. You are not a worker. I am not a worker. None of you listening are workers. If you're not a worker, who are you?

Question could last years. I'm still asking that. I'm still figuring out who am I? And given who I am, what kind of life do I need to build to continue to support that state of being.

Ling Yah: How do you evaluate the different opportunities that come your way? I feel like there are many different opportunities there are coming in, but it's all over the place.

And I feel as though to know what to say yes to needs to figure out who you are. But that's the reason why I even started this podcast. I don't actually know who I am. And when I talk to many people who have made many big pivots, they would say, actually, I just said yes to everything. And after a year or two I started saying no.

Would that be your path as well?

Paul Millerd: Yeah, I think the financial scarcity caused me to say yes to more things than I should have. I got really curious about the question of like, what does life look like if I don't design it around work?

So in the first month, I just moved abroad. I mean, I traveled in Europe and I just like burned some money.

It was kind of just like This income I earned is dirty. Like Owen, just like, it was just like disgusted and just wanted to like, spend down some of it. But then, yeah, all my consulting gigs for freelance and I was just spending a lot of time wandering.

I was working as little as possible and trying to explore like, what does it feel like to not have a job, not be a worker? Because when you don't have a full-time job, people basically consider you unemployed.

And that is hard to deal with.

That tension can cause people to become extremely aggressive in pursuing monetary goals because then they can just reach where they were formerly in terms of just ignoring their emotions and feelings.

So yeah, I think the key to me is, You need some heuristics because in a full-time job, you can do stuff you're two out of 10 motivated to do because you're forced to and you're being held accountable by a boss. You can't do that on your own. You need to be eight out of 10 excited or more. So ask yourself one to 10, how excited am I?

You can't pick seven.

Another way is hell yes or no. That's another metric I use.

Ling Yah: What were the things that were in eight of 10 for you? How did you figure that out?

Paul Millerd: Yeah. It's like writing. Writing the podcast. It's all the things I'm still doing after five, six years. Freelance consulting was very hard for I knew how to do it. I was good at it, but like my heart just wasn't in it, and I kept lying to myself. And over time I figured out how to, like craft offerings to do exactly what I want to do. I love teaching, I love coaching, I love creating things.

So I basically run a online training business for companies, and I only do it on my terms. I could make more money. I am always flirting with like, oh, I should hire somebody, but I never do. I just never end up spending any time on it.

Ling Yah: You mentioned writing. Would you say that writing was sort of the start for you to figuring out all these other different offerings that you have that you enjoy?

Paul Millerd: Yeah, it was writing and wandering. Wandering and non-work breaks. After I got all these consulting gigs, after seven months, I sort of created a secret sabbatical for myself. I didn't really tell anyone. I just stopped taking projects. I wanted to explore like what would happen if I just wandered around. Boston didn't work.

In my mind, my goal for the first year was like, okay, if I make 50 grand, I'm gonna break even. And I made that in like eight months. So I was like, well, what if I do nothing for four months? And you don't tell anyone this. You don't tell your parents, you don't tell your friends.

Cuz like, I was still so insecure about my path and I was trying to find my footing and I didn't really know other people thinking like this, but I was like, this is what I'm curious about. I'm gonna lean into it and see what happens.

It turns out people are really interested about it, but it took me writing about it for years to actually find the audience for that.

But I was 10 outta 10 excited about writing. I loved writing. Every time I wrote it was like this feels good. And that's it. That's all I was following.

Ling Yah: So it was as though you're doubling down saying, I'm going to be the productivity guru. I'm just writing for you what you really care about at that point in time.

Paul Millerd: Yeah, I didn't wanna create another job for myself. I had a job. I was very skeptical of work. Anything that reeked of a script or a story or a metric or a goal, I was just very skeptical of all of it.

I saw all these playbooks and I sort of knew like, okay, I can do these things to grow faster, get a bigger audience.

But I was like, I don't want to do these things. They aren't me. This is the thing, like people don't realize like, I'm really willing to go, go broke, continuing to win this path. Whereas like other people really want money, right? And they say, don't you worry about money. What they're saying is like, I like making a lot of money.

I can't relate to them cuz like, I made good money before I quit my job. But I didn't care about it. I was sort of disillusioned because everyone around me was so like, oh, I don't even make enough money. And I'm like, you're all crazy. This is more than enough. You just lack imagination.

Ling Yah: So what is that ideal life that doesn't have work for you?

Paul Millerd: Well, I'm sort of living it now. I sort of just ended up by defending against work that I don't like only doing things I like and Ali Abdaal again was writing about this skip test, right. Would you skip this time on your calendar? If you could just get the end product? I don't really have a lot of hours on my calendar or schedule that I'd want to skip.

It feels very good. I like writing. This conversation's awesome. You're asking great questions. I like writing my newsletter. and I design everything around that. Like, I don't want stuff, like people say, oh, you should do like a book launch. I don't know. I don't really like marketing.

I'd rather just focus on writing the book than worrying about a book launch. Right. I just wanna write a good book, and like put it in the world and like, we'll see what happens. turns out people like the book. I I did not expect that.

Ling Yah: You just crossed 20,000 sales.

Paul Millerd: Yeah, it's crazy.

Ling Yah: That's amazing.

Paul Millerd: I discovered a tweet for myself like last March. I was like, I sold a hundred over the fi first few days. Like, looks like I'm gonna cross a thousand. Like, this is like mind blowing. Far beyond what I ever expected. It's like really cool. I enjoy the journey so much because I really don't have any goals.

My goal is to continue doing things I enjoy. Continuing to play the game. And my mantra is still write most days.

If I write most days, things usually end up working out. And that's like Twitter, my newsletter, longer form blog posts, maybe another book, I don't know. But like a lot emerges out of that.

Ling Yah: Hey, STIMIES!

Interrupting this just to say I've left law and this is essentially my year of yes, to meet, to explore, to see what's really out there beyond the world of law. While, of course, also doing the STIMY, which comes out every single Sunday. Now the thing is I've started to also help other people to build their personal brand.

I've spent the past three years essentially digging deep to the lives of Olympians, C-Suite executives, four Star Generals, and now YouTuber and Viral TikTok is as well. And what I've learned is that LinkedIn is an amazing platform to allow me to tell these stories, to allow other people to share their stories, what they're passionate about.

What they're trying to do to change the people, to change the community, the world around them. So if you are interested in also learning how to build a LinkedIn personal brand, do, reach out cuz that's what I'm helping people do right now.

Just drop me an email at, [email protected] and let's get started.

And if you're not sure what that looks like, just head over to my profile, look me up Ling Yah. And you'll see what I'm doing so far, snippets past guests and also what it takes to be a great storyteller.

Now let's get back to this episode with Paul Millerd.

For the benefit of those who don't know in your book, what is the Pathless path all about?

Paul Millerd: Yeah, it's really my journey of leaning into this question, what if I don't build a life around work? Can you still make a life work? My conclusion is, it might suck. It might be financially awkward, it might be embarrassing.

Your parents may love you less, but it also might be worth it and it might be a feeling so true and so life injecting through your veins and your soul that you're willing to follow this path. And I think for many people, what they've found from my book is they're already on a path like this. Even if they're in a job, they don't feel safe.

They know they need to keep moving around, job to job, and they're like, oh my gosh. Somebody finally like put together a story and made me feel a little more sane, And that's what I wrote it for. I talked to hundreds of people in the process of writing over the years. I had these curiosity conversations where anyone could book a call with me every Wednesday.

And over and over again, people were like, oh, you're asking the same questions as me. I didn't know you could talk about this. I didn't know anyone who was thinking about this. So I had all this secret knowledge and I'm just like, it was just so overwhelmed with like, oh my gosh, like I need to share these ideas.

I need to put 'em out there. No one's talking about this. I didn't have a lot huge audience when I was putting it out there. I was kind of scared, people might still laugh at this. But it was just like, I, I gotta trust this. At least a hundred people will buy this book, maybe.

Ling Yah: Maybe 50 from family and friends.

Paul Millerd: Some in my family did. Most of 'em haven't really talked to me about it. That's the power of the internet. You can find the people that are actually interested.

Ling Yah: What have been the things that you learned that didn't make it in step book?

Paul Millerd: I think something that probably doesn't come through is I think finding my partner, Angie. Yes. And marrying her. I think we both think about life in similar and we have this deep punch that there's gotta be more something is deeply wrong with how most people are living.

If you don't have that in the person you're with, it can be very isolating.

Ling Yah: And you actually embarked on this journey, having not met Angie.

It was along the way.

Paul Millerd: Yeah, I visited Taiwan in that first year of " I'm not gonna work for four months break". I like Taiwan. Ended up moving back there. Ended up meeting her about a month after moving there. And then we pretty much aligned our paths after that.

We haven't really left each other's side for more than two weeks since almost five years ago.

Ling Yah: Wow.

And you just had a child as well.

Congratulations.

Paul Millerd: Yes, thank you. Yes. Seven weeks. I feel so grounded and so lucky that I have her. A lot of people say, oh, you have kids now. Aren't you worried now? Everything's gonna get crazier.

That is just another script in people's heads. That's a story they've been told about previous generations. Kids are hard. You're gonna suffer, you're gonna struggle. What we've found actually is while she was pregnant, we like craved safety and a place. But now she's born and we're like, okay, how can we be adventurous again?

How can we explore? How can we travel with her? That scares some people. For us it's more experimental. It's like let's test something.

We tested Austin for five months and we're like, ah, we like it here. We made some good friends. Let's stay for a few years and see what happens. But we'll likely live in other countries again.

Ling Yah: There is another person I follow sometimes moonmountainman and he and his partner would spend their whole lives just hiking these Grand Mountains until they had a child and he accept that I had this panic of, oh, does that mean I have to give up all my passion and my love?

And he found a way. They brought the baby up on all of their adventures and proved that it can work. If you really want it to work, you can still have those adventures.

Paul Millerd: Yeah, it's just a script. It's such a powerful script.

It's like, you have to go to college, If you don't go to college, you're gonna be left behind forever. Yes, that is true, but there's also alternatives and there's many more people taking alternative paths than ever before.

Ling Yah: What are some of the alternative paths that have really intrigued you?

Paul Millerd: So many people are sharing their paths. I think just living abroad with kids and how parents describing that is really inspiring.

Me and my wife are from different countries. We don't have an easy default script. A lot of people in these kind of relationships pick one or the other country. I don't know if either of us love the default script in either of our country. So we kind of like the idea that we can mix it up.

Ling Yah: Just before you had a child, I want to touch on this. You said that your past year had been the best year working. Why was it the best year? How did you make that a reality?

Paul Millerd: Well, it's gotten better and better every year, and I think it's just taking projects I don't like. Learning from it. Moving on, fine, tuning it. Getting to know myself better, reflecting on it and writing.

Like, I spent a lot of the last year going on a podcast, talking about my book, about ideas I'm super passionate about, I want to help people with and yeah, it's fun. And my consulting skills course, I got it to a point where like I feel great about it.

It took a few years. Like I wasn't always happy with it, but I got it to a point where I felt great and I was doing work from that. That paid well and the book took off and all those things at once.

I felt very alive and connected. I was able to support ourselves in the US which was super scary for me the year before.

Ling Yah: How did that consulting course come about? What was the impetus, do you think? I'm gonna create something for people when you didn't enjoy consulting

Paul Millerd: It all goes back to my time at McKinsey. I I learned so much. How could you teach these skills to anyone?

I was always like helping with training and doing things like that. Then I joined as an advisor to this undergrad consulting group. I developed a bunch of training materials. I coached hands-on dozens of people.

I worked with 10 different project teams over several years. And when I left my job, I ended up doing a gig, doing in-person training, teaching those skills. I just kept volunteering to help people with this stuff.

The biggest lesson is do free work that you care about over and over and over again, and seeing where it leads you. No one can compete with somebody who is internally motivated.

So like, somebody said, oh, I'm struggling with presentations. Hey, I'll do a two hour workshop with you and your co-founder. All I want is feedback. Would you be interested? And they're like, for free, you're gonna teach us this stuff. This is amazing.

And then when I was in Taiwan, I met Angie and I'm like, looks like I'm staying in Taiwan and I don't know if I wanna do consulting. So I spent a month in building the course. I launched that in December 2018 and been tinkering it for four and a half years now.

Ling Yah: One of the most important things on this journey is finding the same people. The kind of people who are treading unconventional paths. How did you figure it out?

Paul Millerd: I was lonely and I've always been social, so I just started reaching out to people. At first I met 'em at like conferences. And then eventually I set up this curiosity conversation.

I would meet people and say, Hey, I'll have a call with anyone. And people started reaching out.

Ling Yah: Can you share a bit about how you set that up to even get people to respond?

Paul Millerd: I just did a Calendly and put it on my website. At first people weren't finding me. But I would just like meet people in person and say, Hey, I do these curiosity conversations. If you want to chat, use this link. It was just fun to call them that.

As my website started getting some traffic on stuff, some people reach out. It was like very sparse at first. But yeah, over time as I kept writing, I got a bigger audience and more and more people would reach out. It still wasn't that many until like three or four years into it.

And then 2020, there were probably like a hundred people over the year that I talked to.

Ling Yah: What were some of the conversations that really stood out for you?

Paul Millerd: It's always the themes. I think the most powerful were like the people that were struggling.

I don't know if I want to do my career. We have this super expensive life, but I can't tell my wife. Something is terribly wrong here. People are building their entire life around work, but they don't actually feel like they can talk to their wife about it. That's crazy.

Ling Yah: And how do you advise them at this point?

Paul Millerd: I don't know. That's hard. I have a wife who likes talking about these things. I have no idea. I think the fear of talking about these things is because they sense, oh, if I explore this, I might end up blowing up my life. And that's what happened to me.

I blew up my life, but I was single and didn't have debt, so it was easier. I talk to people all the time who still decide they have these things, they have families, and they're like, you know, I, I am not the person I need to be. I need to blow up my life. I can't make that decision for people.

Ling Yah: For those who do wanna blow up their life in sort of a systematic way, what are some of the things or checklists they should be doing?

Paul Millerd: I think one of the most powerful things you can do in a positive way is go to it another country. Distance from your default culture. Get distance from your family who might be worrying about you for good reasons, but the worrying doesn't help you grow.

Expose yourself to new cultures, new ideas, new energy, new environments, new foods, all that. I think the most important thing is to make sure that even if you're escaping, you're planting the seeds for wonder to sprout.

Wonder about what if, what could happen if I lean in this direction? What are the positive things that might happen? Because if you're on a solo path and you don't have optimism or imagination, you're gonna struggle. These paths are really hard. Having a job and just doing that whole thing is way easier.

Ling Yah: Speaking of jobs, if you were for some reason having to take another full-time role again, what would that be? And why?

Paul Millerd: Why, it would be, I probably need money. But I think I'm at the point where like I know there are more ways to set up life than I thought before, which means I would just pitch something as a consulting gig, I'll work three days a week for you remotely.

There's way more flexibility after the pandemic too. And I think knowing what you're willing to do and knowing what to say yes and no to is vital.

Ling Yah: So how do you know what to say yes and no to? That is my biggest struggle.

Paul Millerd: Just screwing up. I think one thing I do is I call it ship Quit and learn. Which is design things to make 'em easy. Just get started, design it for quitting.

And the only goal is to learn what to do next, right? So don't launch a podcast with the goal of trying to be like Tim Ferris. Do exactly what Tim Ferris did. Launch six episodes and ask yourself, do I like this? How did that feel? What was good about it? What was bad about it?

Am I spending all my time on this and am I gonna go broke? Like be pragmatic and then figure out, okay, can I make this simpler so I can focus on other stuff? Can I make it more complicated or do I love it and I want to go all in? What does that look like? Right? So just experiment. Do small experiments and scale up from there.

Ling Yah: Who is someone that you think has redesigned their life in a really great way?

Paul Millerd: I don't want to be any other person.

But I like taking threads of ideas from certain people like Seth Goden, I think one thing that inspires me about him is a older man who's still creatively engaged with the world.

Oh, Kevin Kelly, I just interviewed on my podcast. Yes, I like that. Yeah. Kevin Kelly spent a lot of years wandering and he really embraced this like, curiosity mindset. He's early seventies and he's still energized with life.

Russ Roberts, he's in his mid sixties. He just moved to Israel to take a new job. He's been podcasting for 17 years. He is a professor, just really curious and wants to ask deep questions. These people inspire me because I want to be energized and soul alive when I'm older.

Derek Sivers. I don't want to live Derek Sliver's life, but he questions everything. Why do you have to have a family?

He asks crazy questions like that. And I'm like, well, there might be interesting things in that but I don't know why is he asking that.

I get a lot from all sorts of different people. But it's always like older men who are still creatively engaged.

Ling Yah: Basically just listen to the people on your podcast.

Paul Millerd: Yeah. Well, I interview the people I'm curious about. A lot of people inspire me. I think people like you inspire me.

I've been following some of your journey through like LinkedIn posts and stuff, and you seem to really enjoy what you're doing.

When I see that, it's like, that's cool.

That's worth something. Like I love when people follow that energy.

Ling Yah: Thank you.

That's very encouraging to carry with me as I enter this, whatever this path will be. The pathless path.

Paul Millerd: Yeah. I mean, what are you feeling right now? What's giving you hope in optimism for the future?

Ling Yah: I think what's given me hope in optimism is that I have just been following as you said, what really interests me and that interests me because I will stay up to 2:00 AM 3:00 AM almost every day doing this thing that gives me no financial benefit whatsoever.

And what I'm really grateful for, is that people around me have been very encouraging. They don't say disparaging comments, but I only learn now that they didn't think this was gonna last. They thought there was this little side project. You would die after five, 10 episodes.

But when they see that I've kept at it for almost 120, then they all start coming and they're saying, we really admire it. We really wanna help you. And it just opens doors I never thought was possible. It wasn't even doors I thought to think about, but they start to open. And that for me was the most exciting thing, realizing that actually they're really, really cool people. Really exciting things I would have never dreamt of asking, which I now have access to.

And if I spend more time doing that, because this is only as a side project, if I do it full-time, then who knows where I will be 1, 5, 10 years.

Paul Millerd: Yeah. This is why I tell people to do a hundred of something too. Mm-hmm. Like do a hundred because if you make it do a hundred, it's only because you like it.

You can't do a hundred of something creatively that you don't like. And if you start doing like a lot of something other creators pay attention and they look and say, oh, somebody that gets this weird thing like me, they have that thing where like they have this creative pole and they have to do this.

those are my favorite people. And nothing against somebody that's just starting, but the people that are playing the long game, were all sort of crazy. Like even people like Ali Abdal. I've gotten to know him over the past few years. He has an huge audience, but he was still struggling with like, how do I leave medicine?

What will my parents think of me ? Like being a YouTuber's not high status for previous generations. I know successful creators making a lot of money and they don't have the approval of their parents. So you sort of need each other. And when you see other people, oh, they're doing a hundred of this crazy thing, that's cool.

I wanna root for this person and hopefully we can support each other.

Ling Yah: This was something that surprised me. Just because I did a hundred plus of this one thing, podcasting. It feels as though people look at me and go, because you can do this. I trust you to do everything else that I've never proven or put out that I can do.

Just because you can keep at something and do it well.

Have you found that happening?

Paul Millerd: Yeah, because people that are alive and pouring positive energy into the world, it's rare. It's a scarce resource. Most people give up by their thirties. They're just like, well, what am I supposed to do? I just keep working a job.

So if you're alive and like practicing some agency in the world, people are gonna notice. Yeah. Yeah. I've gotten hired to do all sorts of things, like we're gotten paid for writing. Early on I wrote like a report In the future of work, I wrote part of a book on remote work before the pandemic.

I've gotten paid to speak. I've gotten paid to coach people. I've gotten paid for consulting. I've all these different things. It's crazy.

Ling Yah: What is the most serendipitous thing that's happened to you just before we wrap up?

Paul Millerd: I think Ali Abdal sharing my stuff for sure.

His brother reached out like three years ago and like, Hey, do you want to come on me and my brother's podcast, and I only knew his brother. Ali Abdo wasn't using Twitter, so his brother had like a big audience, his brother Tamer who hosts a not Overthinking podcast. So I'm like, yeah, sure, you seem cool Tamer.

And then I googled it the morning of and I'm like, oh, this guy's like a decent size YouTube channel, a couple hundred thousand. And got to know them through them and he started reading my stuff and replying to it and saying, oh, it's really cool, and sharing it. He's such a generous, genuine person.

I don't know, he likes my stuff and he keeps sharing it and it's selling a bunch of books. So I just feel really grateful. I've never asked anyone to share my book or leave a review.

And I think people just get a kick out of like supporting people that aren't asking for it.

Ling Yah: Just before we wrap up, I actually have one question from someone who also read your book. She has two questions, so I'm just gonna play what she said for you.

It's a slightly unconventional take.

Hi Paul. I like it. My name is Zuyin, and your message in the Pathless path really resonated with me. I'm currently a practicing lawyer and I genuinely enjoy legal practice, but at the same time, I am constantly thinking about my relationship to work and how I can improve my experience.

So I have two questions for you. One is, is it possible to create a pathless path in what may look like a default path? For example, in my case, legal practice.

Paul Millerd: I like it. That's a great question. I think that's a big misconception, which is like, you need to go full. My full pathless path. I think my contention is that everyone is on a pathless path.

The stories we're using to navigate our lives are basically hand-me-downs from our grandparents and parents who are just in a much more stable industrial economy. Everyone's on a pathless path. That's my starting point.

Two is, a lot of the people I talk to who are the happiest are the people at work who work in full-time jobs, And one, they either define what they won't do. I think that is the most important thing. What will I not do? What will I not compromise on? That is another way of saying, what do you actually value, right? If you're not dropping the ball on to any degree, you're just doing everything. You're just gonna work more.

You're gonna optimize for every achievement. You're just going to like float along in what the organization wants. So I decided my last two years of work, I would just not set an alarm because like I was still recovering from chronic illnesses and like I just wanted to rest. I definitely pissed off some people, but I didn't get fired.

It was like, oh, I can like stand up for what I care about. If we're working remotely as a deal breaker for you, hold yourself accountable for that. And the other thing to consider is that you probably need a break. To appreciate what you either value or don't value from your job.

Because if you're just floating along, you're working, you've done that your whole life or been in school, you've never paused and disconnected and been able to truly contemplate these questions.

So I think trying to ask your employer for like an unpaid leave at worst or like paid leave to take a sabbatical and then come back can be really powerful.

Not a vacation where you're at a resort or something, but like a true disconnect where you go and contemplate things. And there's a lot written on sabbaticals. If you search like sabbatical, Paul Miller, I have a big essay on that. It's also on the book as well. It's hard. And then finally I'd say find path role models.

A lot of people have remixed legal paths. She's lucky because she likes her work. Now, how do you design all the other parameters around that? You can do legal work as a contractor, Yes.

Americans pay a lot for stuff. You can work as a legal contractor doing a lot of stuff that you don't actually need to be a lawyer for, but people still wanna hire a lawyer.

Like setting up an L L C or something. You can do that to the US. You could create a package, create an offering but that's like the full self-employed. But like you could also freelance as a lawyer. I think you just gotta get enough information and see different paths, expose yourself to new ideas and all that.

Ling Yah: My second question is, are there any key principles distilled from your Pathless path experience, which you think would be helpful generally for anyone thinking about their relationship to work, including those who may not necessarily be seeking to step off the default path in such a clear cut manner?

Thank you.

Paul Millerd: Yeah, I mean, the biggest question is are you a worker? That one sends people into a spiral of like, oh shit, am I a worker? Is everyone just defining themselves as a worker first? People say, oh, I love my family, my family first, and then they're working till 8:00 PM Or they get a promotion to work more hours and make more money, and they take it.

It's like, is family first? Right. Yeah. I think also just writing down like what is work, what is good work, what is my de definition of work worth doing?

Just reflect on these questions, use some of the questions in my book.

Designing Your Life also has a lot of great prompts. They have a journal exercise. And another way to get at this is Ramit Seti. He has, I Will Teach You to Be Rich, but he also has a journal that has a bunch of different questions and money is often a proxy for work, right? And that will really expose the emotions behind what you're trying to do.

Ling Yah: Well, it's been such a pleasure to have you on.

I normally end all my interviews with the same question. So the first is this. Do you feel that you found your why?

Paul Millerd: Yeah, I think so. I'm feeling very alive. It's almost like, why not do what I'm doing? I'm having so much fun for the past seven weeks I haven't really been working and I've been able to spend time with my daughter and that is the whole point.

Ling Yah: Do you ever feel fear?

Paul Millerd: Oh yeah. Every day. I just recognize it and realize it's never gonna go away. It's uncertainty, it's fear and security, all those things. The point of life is not to make those go away or disappear. The point is to figure out when it's serving you and when it's not.

Ling Yah: What kind of legacy do you wanna leave behind?

Paul Millerd: I really don't think a lot about that question. The truth is like, I'll probably be forgotten in a hundred years.

I think if anything, I want to build a good family and that is the most important thing to me. Be a good father, be a good spouse, be a good member of my extended family and my community. And that is ultimately the most important thing.

My work, it's fun. I enjoy doing it, but I don't know, we'll see.

It's up to the world to figure out if it's worthwhile.

Ling Yah: And what do you think are the most important qualities of a successful person?

Paul Millerd: Somebody that realizes that there's nothing to aim at. There is no arrival and the only true success is really finding a path that is true to yourself.

And luckily, we're in a world in which that is more possible than ever, and I think it's worth finding.

Ling Yah: And where can people go to connect with you, support you by your book?

Paul Millerd: Yeah, so I run a similar podcast, the Pathless Path podcast. Would definitely love to have you on sometime, especially after you've stepped in, gone through the journey. Yeah, stepped into the unknown. But yeah, pathless Path podcast. Also, my book is that, just Google it. Paul Miller on Twitter.

And boundless.com is my newsletter.

I send most Saturdays.

Ling Yah: And is there anything else you'd like to share that we haven't covered

so far?

Paul Millerd: No, that was great. I enjoyed all the questions. Amazing. Rooting for you on your own journey as well.

Ling Yah: Thank you, Paul. I have people like you to look up to. Inspire me and encourage me forward.

Paul Millerd: Don't look up, just look sideways. We're all on the same journey.

Ling Yah: That was the end of episode 126.

The show notes and transcript can be found at www.sothisismywhy.com/126.

If you haven't done so already, please do leave a rating and review for STIMY. It's the only way that people can find out about this podcast and I'd be really grateful if you did so. And if you haven't done so already, please subscribe to this podcast and see you next Sunday.