Leaving McKinsey to Write Full-Time | Paul Millerd | How I Write Podcast

I'm not writing for you. Writing is an act of ego. You might as well admit it. Everyone just agrees to pretend everything is figured out. In the book I called a silent conspiracy to like not bring up your insecurity. That's so good. I started just paying attention to writing. How do I write? Do I write better when I wander more? How do I set up my life? Who am I with? What kind of work destroys the creative energy? And how do you know when you're writing from the heart?

Eventually, you cry. If you haven't cried yet, like you haven't written enough. You might be feeling like you're bogged down in your job. You're doing work that doesn't inspire you with people who you don't really jive with. You want to write. You want to be more creative, but you just don't know what to do. Well, Paul Miller is our guest today and he wrote a book called the pathless path because he was feeling that same thing.

And this was a guy who had done all the big credential things. He went to MIT, he worked at McKinsey, he worked at GE, but he said, "No, this traditional path, it's not working for me. I want something else for my life. I want to write full-time. I want the space to think, to talk about ideas, to read, and I'm going to cultivate a life that's all about that, where I'm writing consistently. And he's gone on to publish a book that's been a grassroots success. It supports his family. It's self-published, and he's sold almost 50,000 copies now without a lot of marketing. So, what do we actually talk about? Well, we spoke about tactics and we spoke about some deeper stuff. How do you think about writing a first draft after you've had an epiphany? How do you edit so that your writing reads like you're talking to a friend?

But it was the deeper stuff that really resonated. Like how do you write in a way that stirs your soul? How do you put words onto the page that don't necessarily just come from your mind, but come from your heart? You know that you're doing it right, Paul says, when you're moved to tears. So, here's my conversation with Paul Millerd. Few months in, I'm writing the book. It was around when I talked to you, actually. I feel really excited about the book, but I feel like something's missing. So, I actually reach out to Sasha Chapin, who's a writing coach, and he's just incredible.

He read through everything, and he

didn't really give me much feedback. He's like, "It's really good, Paul. Uh you should definitely write this and publish it, and I want to read it." He's super supportive in that way. He's like, "The opportunity here is for you to go into your personal story." And as soon as he said that, it was so obvious. But then it turned into this like, "I'm going to write a three-month ebook. I don't really know how to do this." And pushing my edges in writing personally was very challenging, but that was also what made the book writing process so fun.

And the way I would do that was like I'm writing, and I'm just sitting there sort of like remembering. And like trying to go back to that moment. And like, "What was it like? What was it really like? What was it really like?" I'm just interrogating myself over and over again. And then like trying to put the words to it. Right? And so, like right at the beginning, there's a part I think like page four. Like, "Growing up, I thought making $100,000 a year made someone rich." That was like something I felt so deep for all of growing up. When I made that amount for the first time, I felt like I had more than I could ever need.

Yet I opted into an identity that didn't accept such complacency. That took a really long time to understand myself enough to write that. And then everyone around me was always moving forward to the next achievement. Right? And like so connecting that personal I opted into that identity that didn't accept the complacency, and you can sort of like feel there's a tension there with me already. But at the same time, everyone around me is like going, going, going.

And that's sort of like the tone for the book. But like understanding what I was actually feeling in those moments and then bringing it alive in a way I think thought people would connect with. Like that was what I was trying to do. And how did you go about doing that? Was that a process of editing? Was it a process of of walking and wandering? Yeah, so it was all of that. I think a book is a incredible portal. It opens up a very unique perspective to a specific

topic while you're writing it. Right? You open the draft and as soon as I started the draft, I'm seeing things everywhere. Everything sort of being filtered through that. So, the conversations, the books, the like people I'm talking to. I'm seeing ideas everywhere. And every time I'm talking to them, I'm basically like taking notes and dropping them into specific chapters. Like the book is just chaos at times. Tell me about that. Taking notes, dropping into specific chapters.

So, I might talk to you and bring up something around like writing online. And I would just drop a note. And a lot of times these are in unintelligible to me later. But I sort of always trust that like the good ideas will bubble up and emerge. And I'm not super detailed around like making sure I capture at the essence of everything. So, I'll drop a note, put it in like a chapter, create a chapter heading, and then revisit it later.

And a lot of my writing is just rewriting. I rewrote some chapters 50, 60 times. 50, 60? Well, the way I would put that is I'm not the kind of writer that just goes and writes a draft and then lets it sit and goes back and then re-does does the I read a chapter and then I'll pop in randomly to that chapter and just start reworking sentences, reworking sentences, reworking sentences. And so I come back and forth to that now. Now I'm actually working on another small book, but the way I did that, I was actually doing that this morning. I put my book in ebook format, brought an iPad, and then I'm highlighting stuff I want to revisit, then I'm going back to the document, rewrite, rewrite, rewrite.

Writing is very verbal, too. So at the same time I write, I read it out loud. And so I'm feeling, how does this feel in my body? Does this one feel true? Does it feel like it's flowing? Does this something that sounds true to me, right? And if it sounds I don't believe it or it doesn't even feel good to say, like I know it's not there yet. So my entire book was just a process of just paying attention to that feeling.

And then just chipping away, like slowly, all throughout the book, over and over and over again. And also, I think a model for my book was Tuesdays with Morrie. Have you read that book? I haven't. It's a story about Mitch Albom. And it's a story about Morrie Schwartz at the end of his life. And it's an incredibly powerful book that has stuck around because it's actually two transformations in one. One is Mitch Albom.

He was He opens the book with he's working all the time. He got the the better car, the better house, and he was obsessed with the work. I think he was newly married and not really present at home. He was getting book deals and getting his name all across sports publications. And then he sees his professor, this person that had powerful impact on him in college, and it was his opening. He sort of documents his own personal transformation while sort of unloading the wisdom of this guy at the end of his life, which to me is really inspiring.

Like he was living on his terms. He has this idea like don't buy the culture. And we live in a world where people complain about the culture all the time. Well, like don't buy it. Don't open your phone and scroll. But the thing is you have to create your own culture. Right? You have to flip it and take responsibility. And that's hard. And it might be lonely. It might suck. Other people might not join you on the journey. It might be financially costly.

And that book stuck around because follow Mitch Albom's life now. He's adopted people from orphanages in Haiti. He volunteers. He started writing about like religion and spirituality and awakening and all these things. He slowed down his career. He pivoted away from sports. And so the book is true. Right. In the deepest sense, right? And I wanted to write a true book. Right? Not a research-backed book. Yes, I want to follow this because that's exactly what I was hoping you're going to say because that is what you and I always gripe about is this nonfiction approach to books that's become eye-rollingly common where you have an anecdote, then you have a research study to back it, and then you have a clear takeaway, and that same cycle happens over and over and over again.

And you're talking about truth. And sure what they're saying could be like, "Oh, you know, if you do this for 17 minutes in the morning, you perform 8% more productively." That's true, but whatever. What really matters is exactly what you're saying. The kind of truth where you're saying something from your core that you believe strongly, and you're finding the words to express that clearly, and what you're saying lines up with your life, and lines up with a deep observation about the nature of reality. And there's space for both things. But this second kind of truth, this capital T truth, feels like it's missing from a lot of book publishing.

Well, it's a spectrum, right? You're going from like personal raw memoir to like there's a commercially viable book. I didn't write my book to reach the biggest audience. Maybe it will, but maybe it won't, right? But there is a playbook to do that. There is a playbook to write a book around work that will reach more people, that is easier to market, and might also work. But I couldn't write that book. Like it wouldn't have been true to like what I felt.

One of the things that you've been orbiting around in this conversation so far is not writing for the masses, writing for your people. And there's a moment fairly early on in your career where you publish something and you get roasted and then you become discouraged. And you have this moment of epiphany

where you say, "Hold on, I'm not writing for those people. I'm writing for a specific kind of person." And you lean into that. And by doing that, you become liberated. And I want to hear about that emotional arc. Yeah, so so someone I respected emailed me. It was like, "You're naive, you're missing the point. This is not good." And it hurt. It made me very defensive and it made me want to run away. But at the same time, I like I thought it mattered, right? And so I wrote a big email replying and trying to argue, right? But I realized it was a blog post and it was a really a letter to myself.

And so I created this blog post, I'm not writing for you. Right? I am not writing for the people that are thriving on the default path who have more than enough money to meet their needs and desires, right? I am writing for the unconventional weirdos that need a different way and need friends along the way. Around the same time I read William Zinsser's book. Right? And he has this line, "Writing is an act of ego, you might as well admit it."

Right? And that was the second thing. It's like, "Okay. Yeah, I mean, if you're going to write and share your ideas in the world, you want to be heard." And you can pretend like you don't, which I did early on, and I think part of that was just my own fear as well. And that was a big release, too. And so around the same time, both of those things, I'm just like, "Let it rip, baby." And the next 2 years, I really sort of found my groove. I found my people. I started leaning into them. I got more and more clues. I went from like one curiosity conversation every month to maybe a couple every week, right? And this sort of like curiosity conversation flywheel just started taking off.

As you were writing the book, I guess you were restructuring it all the time, huh? My idea was I'll write an ebook. Huh. I was calling it ebook just to lower the stakes of my self, I think. So I took all the things I'd written, started structuring them in a work doc, and started creating chapter headings and structuring it, and moving it around. And if you want to write a book, this is a great exercise just to see if you actually want to keep going. So as soon as I put it in there, I was like really excited about the document.

So you looked at the structure, and then you were jazzed. This is such a cool puzzle. I want to try to figure this out. This will be fun. And so I put it in there, and the biggest problem with going from internet writing to a book is links. Links, right? Cuz you're linking to different pieces. It's sort of lazy. Right? You're saying, "Oh, this this YouTube video you reference." And you just link or this person, right? And so when you're writing a book, you need to actually say what you think and just tell the reader.

Right? And the other thing is you sort of have moves and riffs. And so you can only tell the the same story around like your relationship to work. You can't use the same story 10 times. And so you start to see like your patterns and overlaps and for me it was an interesting puzzle because it actually felt like a consulting project. So you can think of it as like two modes, right? Bottom-up and top-down. Brandon Sanderson talks talks about this as discovery writing. You just go in and figure it out as you go or outline writing, right? You figure out the top-down architecture of the book.

I'm a bottom-up person. I like to just go into the weeds. I don't get overwhelmed by information. You can throw infinite amounts of stuff at me. In consulting, it's the same thing, right? You're going into the data and then popping up and trying to figure out the story and then going down and getting more data and popping up and going back down. And it's the same thing I was doing with the book. So I felt somewhat comfortable with the process early on and confident that I could do it.

It's like I can work my way through this. And I think that's a hard thing for people who haven't had that experience. Like in a 3-month consulting project, you actually don't know where you're going to end up. You start with hypotheses and a problem statement. And you're letting the data and the story guide you. Right? And eventually you need to learn to trust the process. One of the things that I always think about when I'm writing and if I look back at a successful writing session and I say, "How productive was that?" It's really easy to think about how many words did I write or did I figure something out? But I think a more interesting way to evaluate is how much was I able to surprise myself. You know, Ray Bradbury

has this nice line where he says, "Don't think at the typewriter." You should be surprising yourself. You should be out of your head. And I think that writing at its best, that's what it's doing. You're in something. You're restricting yourself to some narrow object of focus. You're diving deep into it and all of a sudden you discover how contoured that idea is and all these little nooks and crannies and caves that were hiding inside of that idea.

And that the point of writing is the surprise. I think flow is the word for me. When I'm sort of stumbling into maybe a yeah, a sense that surprises me that I'm capable of. It's like, "Whoa, that feels good." Right? It's like a feeling. And I often am saying it out loud as I'm writing it. And it's like, "Oh, this works." And that it's like you've sort of solved like that puzzle. And then you move on to the next piece. And writing it took me 16 months after quitting my job to become aware that writing was such an important thing in my life. And I've been calling this like finding your good work. What is good work, right?

Good work has this deeper um feeling, this connectedness to it. Right? This relationship to an activity you know you can do sort of over a long period of time. There's no goals with the activity and the goal really becomes like protecting that. And that's good work. I stumbled upon that. Like my awareness quit my job, wandering around the US, sort of doing all these experiments and writing along the way, but I moved to Taiwan about uh 15 months after quitting my job, and I had no work. I had no plan.

And I'm sort of sitting there one morning, just absolutely delighted that I am writing, sitting there with my coffee, and no plan. And I'm like, "Oh my th- this is a thing. I can live my life like this." And that was it. It was like I had found something. Right? And then from that point on, I'd never experie- I'd experienced flashes of that in my former work. When I was talking about the consulting projects, I flashes, but the context was wrong. From that point on, it was like, "I need to protect this. Like, this is so much better than what I experienced in my previous path in life that like this is everything. Like, I need to protect this. I need to build a life around it." And so, I was revisiting something I wrote in 2018, and I it's interesting to see how confident I was.

I think that year I made like 30 grand, just like hacking random stuff just to pay very basic bills. You're talking about good work, and one sign that you're doing that good work is that you're getting downloads. Because you could think of it supernaturally that a download is a revelation from God, and God is basically telling you do more of this, and that there's a connectedness there. Or you could think of this very rationally and logically, which is to say, you're in a place that your subconscious wants your mind to stir on, and it is only when you're aligned with those shower thoughts that you're really doing the right kind of writing for you.

I started just paying attention to writing. How do I write? Do I write better when I wander more? Do I write better when I'm talking to people? Right? What How do I set up my life? Who am I with? Right? Who inspires me? What books inspire me? What kind of work destroys the creative energy? How do I avoid that? How do I get that out of my life? Right? And so, when I'm writing my book, I would often just go for long walks, or sometimes actually just take weeks off from writing my book.

Just peace out. I would just feel stuck. And it's just a total vibe. There's no strategy or approach. It's just like I don't know. Feel stuck. I need to like move. It just not work on it for like a week. And then it always comes. It always comes back. And so, it's sort of trusting that it's there. The intro was like this puzzle. I couldn't figure out. What is it all about? How How am I connecting this whole idea? What does it mean? Why does it matter?

And so, I'm just I'm sitting at the desk. I'm like, "Oh my I don't know if I can get the intro." We're sitting in the southern tip of Taiwan by the beach. We were I was living there with my wife Angie. And Angie goes, "Go. Go. You need to go wander. Like go for a scooter ride." And she's usually knows. Like she knows me so well. 2 minutes, I go out with the scooter. I go on this main road. And it just like came to me.

And I pull over. I open my notepad. And I just start writing. And like it's it's basically the section why this matters in my in my book in the intro. And it's about my parents, but it's also me actually just saying this matters. Right? So, the the passage is basically me proclaiming that. And so, if you go to end of page 11, "Helping people live courageously so that they can thrive is one of the most important things in the world. I want to see people live the lives they are capable of, not just the ones they think they are allowed to live."

And so, that part and the whole part before it basically just flowed to me in the side of the road and it was like I basically resolved all my insecurity and shame around sharing ideas in public in that moment. Like, it just went went away and like I was like, I care. This needs to be said. It doesn't even matter if people hear it. Like, I I didn't care if people ever read the book because like I admitted it to myself. I had come to sort of this resolution of a lot of these things I was dealing with and I think on my previous path a lot of my achievement was driven by trying to avoid emotions.

Right? And the being on what I call the pathless path, like I had to sit with my emotions. But how do you actually really sit with them and experience them fully? And I think writing has been that portal for me to help me sort of transcend those and show up in the world as like who I'm meant to be in the world. The two words that are coming to mind are wandering and space of creating a life for you for yourself and your process where you can meander

and find things just by following some internal compass that you can't really always understand where it's leading you. And then the other thing is just space, having the buffer so that Angie can say, "Hey, get out of here. Go Go on your Vespa ride." And then you can be there, you can pull over to the side of the road, you can have that moment, then you can write down the thoughts, and then the thoughts can pour out, and you can get into a flow, and it all comes out there. And in order to do that, you need space. And I've been thinking a lot about why aren't business books better? And one of the reasons that business books aren't better is very simply that the people who write them don't have space.

They work full-time. They work full-time. They don't have space. So, you end up with the good business books tend to be when people retire and they look back. This was sort of an aha for me early on, which was I follow all these work writers, but something just seemed off. Like there's all these thought leaders that write and talk about things. And if you notice what they do, they get paid speaking to corporations. Right? So, they're in that world.

And so, what is the assumption of the corporate world and the successful path? It's that you work continuously for all of adulthood. So, you're on the clock for all of adulthood. And so, I sort of asked, "What if that's not true? Right? What if you create space for wandering, reflection, thinking, like the natural seasons of life and creativity and all these things?" And to the world I was in before, that is radical.

Right? To creative people, they're like, "Oh, yeah, obviously. Of course." And so, I realized I could just take that all the way. Just go all the way with that. And I did that by actually just living that as if it were true. What if you're not on the clock? So, take 2 months off and don't do any work. How does that feel? Turns out at first it feels absolutely terrible. Right? You feel the pressure of the world telling you to get back to work. You're a loser. You're not worth anything.

And so, a lot of my path over the past 7 years has been just like asking those questions and seeing what it feels like. And then writing about it. One of the things that shows up in your writing process is what you do is you look for clues from other people. The pathless path comes from the three marriages and you find these different phrases, words, ideas. And the way that your brain works is you find these things and they're these little nuggets of potential and you take them and then you mine them deeper, deeper, deeper, deeper, deeper, deeper.

And the way that that shows up is you're very good at building upon other people's phrases and coming up with phrases yourself. I think when you're exploring ideas, you naturally coin stuff all the time. So, I've coined hundreds of terms. Most of them don't resonate, right? And I am finding out through conversation. The pathless path, when I read it, I was like, this is this is incredible. I texted my friend Johnny Miller who gave me the book.

It's sort of like a magical gift in the first place and I was like, this phrase. He's like, I know, it's incredible. He had resonated with it, too. And so, I I had this friend from the beginning and we would talk about the phrase the pathless path. When I met my wife a month after moving to Taiwan, she loved the phrase and it resonated deeply with her. When we got married a year later, her gift to me was a journal with the phrase the pathless path on it.

And the the quote that's in the beginning of the book. Right? And it's like we're treating our life as a pathless path. And so, it is actually real because it's sort of like the living vision for our family, too. And yeah, every time I put it in writing, people be like, "Oh, I love this phrase." Or I'd use it in person and people's eyes light up. Well, it's such a good phrase. And I've spent a lot of time trying to deconstruct why. One of the things that I think you have going for you is that it clearly means something, so it sparks an insight in somebody's mind, but it also keeps me curious about what the phrase is. So, for example, if I hear something like Thomas Friedman's The World Is Flat, the problem with that phrase is it gives me too much. But, the pathless path has the right combination of I get what it means, but I also don't get what it means, so it sparks curiosity.

And it's funny because of that, I've probably recommended your book more than any other book at parties. And a lot of it is I know how easy it is to pitch the book because the title is so good. And every time it just has somebody say, "Oh, that's interesting. Tell me more about it." I wasn't super intentional about it. It was just obvious that this was the title for years. I mean, Osho has a book called The Pathless Path.

You're exploring the pathless path or something, right? It's a word from spirituality, right? Gateless gate is the phrase in Zen, right? And I I think it does capture I think it's perfect for the world we're in because my sort of angle on it is everyone's on a pathless path. Right? The problem with the default path isn't the default path. It's that people think they're on a safe, secure, steady, and linear path. Doesn't exist. Have you talked to anyone that actually has that? Talk to 60-year-olds.

And the crazy thing is you talk to older people. I would sit around in these conversations. I remember this one conversation I was a part of. Someone's talking about their friend getting laid off a month before their pension hits and losing it entirely. Another one's talking about like friend that had to go back to work cuz social security wasn't enough. Another one was talking about having to move their family in the middle of their career for a job change and restructuring.

And then they turn and sort of like mocked like how I was approaching my path. Not directly. I think a lot of it is their own insecurity. And they're sort of buying into this idea that they're on stable, smart, secure path. And I think like my angle on that is that it's not actually broken. It's that everyone just agrees to pretend that everything is figured out. Right. I In the book I call it a silent conspiracy to like not bring up your insecurity. That's so good.

So, actually, you just did something very interesting there where you took something the way that you were explaining it I was like, "Sure. Sure. Sure. I've heard that." But that is what the work of editing does is when you just said a silent conspiracy I'm like, And the juxtaposition between what you were saying and the way that you phrased it, it just ignites that idea with life. Yeah, and so I I had this feeling in the on my previous path that like everyone was crazy.

Like no one's actually talking about what's really happening. In one of my first internships, I remember going home and be like, "Nobody's doing anything." And like people will be like, "What do you think? You don't have to work, buddy?" And it's like I feel like everyone must be thinking these things, right? And then when I'm in my like full-time path, like thinking the same thing, and then discovering after I take my leap and when people are talking to me about work and I sort of have the position of random internet stranger that talks about work, everyone is finally telling me, "Oh yeah, of course we question it all."

And so it it is a silent conspiracy. And so yeah, I remember writing that in the book and sort of trying to capture like what is that like? What is it like knowing all this information and nobody acknowledges it. Right. You wrote a piece with 18 reflections from listening to the show How I Write and you wrote something so interesting. You said, "What I love about this show is that I disagree with what so many people say because it helps me clarify my own writing process."

So I'm curious, what sorts of things have you heard we've said, "I don't do it that way at all." And how has this show helped you think about your own creative process? Yeah, everyone just has a different relationship to writing. Other people like writing everything in one draft. I don't do that. I write randomly. If I don't write every day, it's fine. I write what I say most days. That's sort of my mantra. I don't need the mantra anymore because I write most days anyway.

But if I don't write, I don't write. The thing that makes all that work is I think you really enjoy writing. It's so fun. And so what what about it is so fun for you? It's sort of like the joy of finding out, right? Or Richard Feynman says, it's figuring out more about my life, figuring out more about the world, and there's this cycle where it actually just makes my life better. I share about what I'm finding, the questions I'm asking. I put it out there, and I find people asking the same questions. Those people have become some of my best friends, and I love these people, and it makes my life more fun.

And then I have more stuff to write about, and I can just sort of like keep doing this. Right? And so it's it's helped me sort of like steer a cruise ship into a new way of life. And it's just so much better than making PowerPoint slides for a client I don't care about. The work of that in the first couple of years of my former career in strategy consulting was super fun. I loved it in the first couple of years. It's like a puzzle you're figuring out how do you fit pieces of data and tell a story.

It's all the stuff I like in writing. But eventually you're you're incentivized to care about what a senior partner care cares about for a client paying them a lot of money, and they're freaking out, and they're anxious, and they're emailing you on a Saturday, and you're out with your friends, and it's like I can't care anymore. But like my writing, it's it's part of my life. It's so inseparable at this point. I just love ideas.

Yeah, it's funny cuz I love ideas. I agree that writing makes my life so much better. I love that phrase the joy of finding out, because that is writing at its peak. I have an idea. I know that there's something there, and by sitting with that thing, I begin to discover new terms, new ways of phrasing things that I would have never thought. That to me is a joy. But also there's a stuckness around writing that really, really frustrates me. And I bet if we did some personality assessment, you're all the way on the right side of the x-axis on patience, and I'm probably all the way to the left side. And I just struggle with the patience of I'm going to sit through this as I get stuck.

And I find the stuckness of like, I know I can SAY THIS SO MUCH BETTER, but I can't find it out right now. I find that to be so frustrating. I mean, we have different stories, too, right? You You got frustrated and quit pretty early in your path. 7 months. 7 months. So, I lasted 10 years. And so, I was so fed up with that path that like, I'm just so grateful for writing. It's so much better. And so, even the stuckness, I love the stuckness is fun for me.

So, what if I get stuck? It's better than a job. Right. We all go on our own journey, right? I didn't find or become aware that writing was my thing until 33 years old. Walk me through a typical day if you're going to be focused on writing. How much of that time is spent talking to people, ideally, walking, reading, typing? I don't have a typical day. Like today, I woke up and I'm working on this book sort of around the idea of like losing my edge. Right? Everyone's so afraid of losing their edge.

The truth is, you can you might lose your edge. You might accomplish less, but it might be also be awesome. Right? And so, I woke up. I worked on that for about an hour before my daughter woke up. And I didn't write anything after that. After that, I Actually, I wrote a little more, so maybe about an hour and a half of writing today. Then I went to the gym. And And because I knew we were talking, I left space open so I could sort of like slowly ease into a conversation that matters to me.

And yeah, I sort of approach every day like that. Like, what is what's coming in the day and how do I design my day? I think more recently, because I had a daughter in the last year, I am trying to get more structure in my life. Before I had bountiful time. And me and my wife sort of always took care of her own things. We're good at being independent and like finding the things we want to work on. It's harder with a kid. With goes without saying. So, I'm needing to structure that time a little more. So, I'm actually moving towards like how do I have three blocks of writing a week?

Got to wake up at 4:00 a.m., man. No, I'm going to do like So, I work 3 days a week. Nice. We split child care, me and my wife. I work 3 days a week, she works two. She's also working on a book, which is beautiful. So, those 3 days Right now, I'm not doing it, but I want to get to, okay, 3 hours 3 days a week. That's enough. One of the things that you and I connect deeply on is this love for ideas and a desperate yearning to find to bring people into our lives who share that.

And it's easy to romanticize, "Oh, you write on the internet. You publish your ideas. Share things." It's like, no. We need these people in order to feel like we have life. Because if I can't have these conversations, if I can't explore ideas with my friends, if I'm

not around people who are intellectually stimulating, I just die. I just die. I wither like a plant that hasn't been given water in 6 years. That is why we write. And it shows up in the way that you write and how you write, which is you're writing for friends. Your writing is a bat signal for the kinds of people that you want to attract. And it shows up that you're not saying, "I want to get the biggest readership in the world." You're basically saying, "I'm going to share my story. I'm going to do it with honesty and vulnerability.

And by doing that, I want you to email me. I want you to reach out to me. And I want to spend time with you. Because if you like my writing, the chances that you and I are going to get along well is very high. I mean, the crazy thing is I thought the reach for this book might be like 500 to 1,000 people. And now so many people are reaching out. And I have a daughter now. And I just don't have as much time to connect with these people. So, I am thinking about like what does that look like? Like how can I serve this audience? And I don't have an answer to that. But it's very alive question.

We're talking earlier about emails. And the quantity of quality emails is the best metric for how my writing is resonating. And I like quantity because obviously you want to like you said, you just want to admit that you have an ego. And listen to me, world. I want to be heard. That's why we sit down and write. So, you get that with quantity. But the quality thing matters, too. As writers, we have a visceral sense of how well-written thoughtful the emails are. And when you get a lot of those well-written thoughtful emails, your stuff is resonating. It's It's hitting somebody at their core. It's making them respond. And it's doing it in a way that is counter to the way that so much of the internet is going, which is soliciting a hot, temperamental, short-lived response, rather than a slow, thoughtful response that has somebody say, "Consider me a fan for for maybe even life sometimes."

Yeah, and I I think this is the part people don't understand, right? Cuz people get caught up in not a world of ideas, but a world of the media's ideas, right? Or the scripts in their head about how life should work. And they'll reach out to me and say, "Don't you think people can't do this if they have like a home and a mortgage and family?" And it's like I can't explain to that person how badly people need to take an unconventional path. Of the people that are emailing me and also myself. Like I felt really alone at the beginning of my path. And I had a few people that really rooted for me.

They went out of their way to email me each week, "Keep going. This is so exciting. I love what you're up to." My writing was objectively not great. It was interesting, maybe. Some people saw that I was headed in a direction. And I had a handful of these people. And they're so important. And I actively reach out to people, even if they have a big audience or small audience or no audience. And I really try to proactively do this with a lot of my time. I read a lot of people's early writing and stuff and try to just send them a message, "Hey, this is really powerful. I hope you keep going. Let me know how I can help." People need that.

The more people that have belief that they can keep going, it's just good for the world. You've made me reconsider editing in the sense that I never considered that too much editing could be so destructive. And you have a line that I really like where you say, "As a writer, you need to trust your own taste." There's two phases for writers. Phase one, you haven't put stuff out in public. You're both super insecure about it and also as soon as you put it out there and realize no one's paying attention, you want people to pay attention. Right?

So, you care a lot about what people think. Is it good, bad? Like, you're really unsure about it. And so, a lot of people really crave feedback. But then, phase two, you're going to find a rhythm and you're going to find an ability to continue writing. If somebody's posted a hundred of something, they could probably do a thousand. At a certain point, you just need to trust your own writing. And the thing is, like, some people ask for writing and I see other people's feedback. A lot of feedback's not good.

Because the best feedback is really about, like, pointing the writer in a different direction. It's either, like, oh, this paragraph is gold. And then I know, okay, how do I strengthen the ones above and below it? Because they're probably not as strong. Or there's a big chunk where nobody comments at all. It's like, maybe this is a little boring. Maybe I need to rethink this. Or somebody says this is confusing. That makes me think, and I might rewrite the whole thing or reframe everything based on that one comment. I mean, I still have not found like great editors.

I found a good editor on my newsletter who edited my stuff for my book. Uh but I don't ask for feedback for 99% of the things I write. I only had five people read my book before I published it. And all I had them do was say, "What do you love?" And I told the editor, "Don't delete any of those." How did you know that your book was ready? It's so hard. It's just sort of like a feeling. It probably wasn't 100% ready. This is the the benefit of self-publishing. Uh but minor errors. The book was ready in story. I thought I'd be ready. I thought I was at 98% done when I was at like 90% done, right? And that final stretch can take a long time.

And that's where having people help you can be useful, but I was doing everything myself. So, what I was doing was printing out the book and reading it straight through and making edits. Then I would put it on Kindle and I would highlight things I wanted to revisit and just like go through the book. And then I would read the book out loud to me to myself. And noticing things that don't flow and make sense. And then when you're reading an entire book, you repeat stuff, right?

Oh, this doesn't match this. This This is sort of planting the seed to this point. How does that connect? How do you tighten that up? And so it's very very much just like feeling. I probably read my book I don't 25 times in the in the last month. And the crazy thing is when you do that, like you're sort of looking at hieroglyphics at the end. This doesn't make any sense. This is nonsense. But then you just have to trust it and I just posted it. I find that it's time to ship when I feel one of two emotions. Oh my goodness, this is the best day I've ever written in my entire life. Everyone needs to see this. Or I absolutely hate this. I'm looking at hieroglyphics now. I can't even read.

And just get out of my life and it's time to publish. I just have no more patience for it. And to switch gears, I think that one of the things that you've hit on is how many contemporary bloggers are publishing books that are really resonating. Tiago Forte, Mark Manson, Ramit Sethi, obviously James Clear. They're getting cycles of feedback. They're talking to people. They're spending years in conversation with their readers

before they ever publish and it seems to be quite an advantage. I mean, it's just an obvious advantage, right? More iterations of really fast rapid feedback are going to be better than publishing a book every 3 years and then getting mass market feedback. Right? The big publishing houses require you to give them a pitch on non-fiction books. Right? And they want to make sure that it maps to something that will already resonate.

Right? So, that can work, but like I mean, their heuristic they're using instead is like they just scoop people up that have already validated ideas with an audience. Right? But if you are just cold pitching an idea, the odds are you're probably not going to write the most powerful thing. Right? Cuz they're going to pick the things that are safe and already resonate that they can validate. Right? The best ideas, and this is why like I think there's a promise of self-publishing is a lot of the best ideas might be people with smaller audiences like me who are on to something powerful that doesn't map to how the media or the popular narratives see it.

Right? I had 5,000 newsletter subscribers. I wouldn't have gotten a book deal. But like I I felt this urgent need to like I have to put it out there. And I was keeping a blog after college. I had a blog in grad school. I had a blog when I had Lyme disease. The thing is I was always writing, but I wasn't paying attention to the feeling of writing. I was so embodied in the worker identity or not embodied that I wasn't noticing that writing could be a thing.

And I think maybe it couldn't have been a thing then like the way the internet exists and the way you can put ideas out now. But yeah, I've written about tons of stuff. Yeah, you and I are so different in this way. I I never had that passion for writing. I think I do have a real passion for communication, for framing ideas. Writing for me is such a slog. It's really hard. And I actually think that's part of the reason that I can teach writing well is when I talk to a Write of Passage student, they're like, I don't really like writing very much or writing is incredibly difficult for me.

I go, ah, I know that feeling. And I know that writing is supremely useful and having written something that you're proud of such a good feeling, but the process of doing that for me is always hard. So, you talk about not needing discipline, I totally need discipline because if I don't put time into my calendar, do some sort of streak of trying to write, I just won't do it because it's the hardest it's the hardest thing. And when I look at my day moving forward or what I'm in the mood to do right now, it's never writing. But if I were to look back at a year and I were to say, what is the best thing I can do with my time, it's writing. So, I need to build systems and structures into my life to make sure that I do it.

Do you think this is your writing? This show? Yeah. I love doing this. I think this is your writing. Love doing this. Yeah, when I see you doing this, you come alive with the same energy I have for writing. The conversation, I just have the conversation with words. Like you're so good at the conversation with to like talking, bringing out of people. I find it so interesting how every guest has a radically different way of approaching the craft.

It's astonishing that how I write can yield so many different answers. You know, like you always think of how a like a card deck you throw it on the

ground all the different combinations. That's how I feel about the writing process. Yeah, like Mark Andreessen he talks about like reading all the current stuff and then all the old stuff. It's same with me, too. I read a lot of current stuff. It doesn't really bother me to take away my energy. I found it kind of fun. Early on in the book, you pull from the canon of people who've written about work. And you talk about Max Weber and different people who had written about what you had written about.

I don't think you get enough credit for how well read you are in the canon of this topic. Oh, I just snuck the nerdy internet book into my personal memoir. What? The Protestant ethic? No, like it the book is this combo. Like chapter three, I didn't really know where to position chapter three. Chapter three is a the it's called work work work. It's basically a deep dive into the history of work. And so when I started the book, that was the book. I was going to write this like nonfiction deep dive about the history and philosophy of work, right? And then I realized it's about the personal story.

Right? And so chapter three really could have gone anywhere. But I was like I need to hit the reader with this deep dive in the history of work. And it's going to get super nerdy. And we're going to go all the way back. And it's my telling of like how things happen and piecing together all these things through like Thomas Aquinas and the Protestant work ethic and all these things and like the quotes from Eric Fromm on The Escape from Freedom and like how freedom sort of changed in the 1950s. And then I'm sprinkling in like organization man and how they're talking about how people thought about work right after World War II and how that's led to today and leisure and peeper and all these things.

And so yeah, it's it's a super nerdy book. I mean there's over 200 references. So I sort of tried to pack like many books in one. I think my challenge with a lot of traditionally published books is they're sort of light on depth. And I wrote this for nerdy internet people exactly like you. Where I'm tossing in super nerdy quote knowing that you're going to write it down and go on your own rabbit hole. Then I just move. I just keep moving.

It's like nerdy quote, personal reflection, another nerdy quote, horse historical fact. Like boom boom like I I really thought about like just going super dense. And so you could easily have expanded the book to like three different books. Right? There's the default path in the history of work. There's like the creator economy and exploring all that. And then there's also like falling in love with writing and all that. And yeah, that's sort of what I wanted to do. Mainly cuz I just don't like most of the books that are coming out now. Will you coach me on my book? Sure. You need to go into your personal story because your personal story is where the power is.

Like when you talk about how frustrating school was, like that is so powerful. That is the truth that gives the credibility to the journey, the writing, the sharing ideas, all that. How did you learn how to tell your personal story with so much fidelity because that's just not something I've experienced with telling the story of a life. A health crisis, feeling lost and alone. Yeah, really just being broken over open. And also after quitting my job

feeling alone and feeling this jolt of reality. Like wow, I'm really lost now. I don't have a story for my life, and I had to get to know myself. But, I had started that process years earlier through a health crisis, when I sort of had to sit myself and sit with myself and figure out who I was. And then, through writing about that, and over the years, like you just reflect so much. And a lot of what I'm doing is just reflecting.

Right? And you write hundreds of posts about yourself. Eventually, you figure out something. How do you think about the pacing in your stories? I do have research in my book. This study from David and Gilovich talk about the ideal self and the ought-to self. Right? The ideal self is who we want to aspire to be. The ought-to self is like, I ought to take care of people. Right? And so, I could have went three, four pages.

These guys did this study, and it was these conclusions, and they found this. But, really, I'm just telling it through my own personal lens. Right? And it's like, oh, I leaned heavily on the ought-to self. Oh, I ought to stay employed. I ought to do these things. And then, as soon as I took the leap, I realized, oh, like your ought-to self is always there. It always takes care of what it needs to take care of. And if it does make mistakes, oh, you didn't make enough money the last few months, it will course correct. You can take actions, right? And so, not pursuing your ideal self, as I'm telling it in my personal story, it's like super powerful. Right? So, I'm moving through that quickly.

I'm not trying to linger on the study. I'm trying to just like keep the action moving. Right? You know, a lot of it's my own impatience. Like, I want to just keep moving. I want things to be easy to read. When I read it, I want it to flow. I want it to feel conversational. Your writing doesn't have a lot of friction. I learned this from Nick Majouli. I asked him one time, "How do you edit?" And he said, "I read, and I read, and what I read for is every time that I get caught on something.

Yeah, same. And whenever I get caught, I say, "Something's up there." So, I'm just going to polish. It's like ironing a

shirt, okay? I'm going to iron that part of the shirt. I'm going to get the wrinkle out, okay? I'm going to keep going. I'm going to get caught on something else. And then editing, at least the final rounds of it, are making sure that you don't get caught on things. So, that then you have that flow and that ease. Yeah, this morning I was editing something. It started out, "Most days uh I was waking up not feeling great."

And I would decide to do something each day. So, I don't remember the specific sentence, but like day day, like I'm like, "Ah, that Like in my brain like it stuck." And so, I highlight days that I'm going back and I'm like, "Okay, most days most days most days." I'm like saying it out loud. I'm trying different stuff, like typing as I'm going. And until I get to that flow, like I'm not going to ship stuff. Now, my newsletters and like Twitter and stuff, I'm just shipping stuff. I'm not really editing that. But for a book, I'm going back and a bit again until I remove all that friction.

And it was cool to see when I read my audiobook, there were probably three times I felt friction. Which felt It was like, "Okay, I I didn't think about that beforehand." Like I didn't actually think about recording an audiobook until I published it. But um yeah, it was like, "Oh, that is my approach to sort of just sound things out as I'm going." Yeah, and then the other kind of editing, this is the one that I find much harder, is mapping the intensity of an experience. So, I feel something deeply, something happened that I want to put words to.

And the lazy thing to do is to go to a thesaurus and go from interested to curious to fascinated. Okay, that's that's not what I'm talking about. I'm talking about finding some analogy or knowing what moment to zoom into to really make that experience come alive. And I've learned from Robert Caro when he would do interviews with people who were in the lives of his subjects, Robert Moses and then LBJ. He would keep asking, "What would I see if I was there? What would I see if I was there?

What would I see if I was there?" And he'd say over and over and over again. And what I got was make the reader see the scene. And the way that you get people to see is not by being comprehensive, but by being descriptive when it matters and using words and references that everybody knows that are super specific and that's what injects life into the writing. I don't think I do that well. So, It's something I struggle with, too.

I think what I do is give different context. I'll sort of switch tense to like abstract idea to then personal reflection to then broader application. I was reading that phrase earlier in the interview. I had opted into an identity that didn't accept complacency. Personal feeling and then next reflection ever around me was going to keep going, right? So, people can sort of I think what I'm looking for is like people can feel that connection. And a lot of it is like I'm just trying to talk to somebody like I'm talking to a friend.

You really do that. And for you, you're pretty plain and direct in your speech. Yeah. Get to the point and your writing feels like that. What do you take from Seth Godin? I don't have like role models. What I think I have is many sort of like possibility archetypes. It's knowing that certain ways of doing things are possible. Right? So, Seth Godin, later in life still actively engaged, energized by

creative work. Okay, file that in my head. That's possible. Right? Someone like Derek Sivers writes books on his own terms, sells them sells them directly to his audience. Okay, that's possible. Right? Sort of this like possibility through implicit permission. Right? Tim Ferriss is somebody I look to. He's reinvented himself many times. He's walked away from like angel investing. That's very hard to do. Walking away from more money is and an identity of success is often much harder than not having an identity.

Right? So, people like that, like David Whyte, like leaning into to being a poet, and like literally just being bold enough to do that in his 30s and call himself a poet and write so beautifully. Right? And knowing these things exist and having these role models, like we talked about Ramit Sethi before. He's still talking about I will teach you to be rich. He wrote that book in 2009, I think. It's 15 years ago. What I get from that book, I don't want to be Ramit, but just the fact that that's possible. Oh, you can remain engaged and excited about a book and a set of ideas. That's cool. Because most people move on. A lot of our entrepreneurs and creators, and there aren't many that are like 15 years plus on these paths.

It's that they he gives permission that oh, of course you can remain engaged in an idea. I don't need to search for the next thing. Right, I might still be talking about the pathless path in eight years. That's kind of cool to think about. And it sort of releases the pressure to like, oh, you have to have a next book or do all these things. It's like, no, you can actually just let that evolve naturally and see where it takes you.

It's this concept of a core idea. Which is such a focus of what we're doing at Write of Passage because it's not that you need to say the same things over and over again, but it is really nice to have a central idea that is true to who you are, what you stand for,

and you orbit around it, and it's just a theme that emerges. A question that I like to ask people for them to find it is, what does your head want you to write about? What does your heart want you to write about? What does your wallet want you to write about? So good. And when people have alignment between head, heart, wallet, they end up finding this core idea that they don't get tired of. And it's easy to look at somebody else's and they say, well, I get tired of writing about how to teach people to be rich or I would get tired of writing about the pathless path, but that's because that's not your core idea.

Right. And when you find it, your internal experience of that idea feels very expansive, but then to the rest of the world it's super specific and legible, and that's a good place to be. I think the trap people get into with this is they think there's a niche they can aim at. Like they think they can aim at a niche like it's a job. Right, I'll just get the application right and I'll get everything right and then I'll get there and then I'll be set.

Really, the best niche is like the niche of you. Right? Because and you can land in a niche, but often they can be very constraining, right? You can feel like you can't publish stuff, and this is why sometimes people blow up stuff they've been working on for years to try and create that space of exploration, right? I don't really feel like I have to write about the pathless path. Like the niche is really me. It's the niche of what I'm actually curious about.

And so people ask, "Do you worry about like what your audience wants you to write about or what's going to" It's like, "No, I don't I'm just writing about what I'm curious about this week. Some stuff resonates, some doesn't, but I'm just going to keep going." If you were to teach a class on writing, what would be in the syllabus? Non-work. Everyone would have to stop writing and go for a 3-hour walk. Oh, that's great.

No destination. And just wander and see where where it

takes you. The mission there is really just to sit with the discomfort and see what comes up. Because if you want to write, that is a creative act. And a creative act is very hard to do in rational mode. Of like playing tactics and going after it, right? You really need to connect with like you said, the heart. You need to awaken the heart. A phrase you say, "Heart's on fire." Know it You need to know that that state exists and play with your state and try different experiments and see how you can get closer to that state.

And the thing I tell people is, "If you knew there was a relationship with work that would feel so good that you knew without a doubt you could do it for the rest of your life, wouldn't you try to go find that?" So a lot of the exercises would be around trying to find that. And how do you know when you're writing from the heart? I think eventually you cry. I think eventually it breaks you because you get so deep and this is sort of one thing I might tell people. I actually did this exercise a couple years before I wrote my book where it's you write your life purpose until you cry.

You write you write it you write it you write it and it took me about 21 times to write it and then I cried. And the mission I came up with I won't get it correct exactly. But it was like explore ideas and creativity that matters to me and share them with friends, right? And it was all about like something around connecting with friends and helping people realize that things matter them. It's exactly the phrase that appeared in my book that I sort of had to re learn. And yeah, I think if you haven't cried yet like you haven't written enough.

What a place to close. Thanks, man. Thank you.