The Magic of Writing with Sasha Chapin

[01:28] Paul: Welcome to the conversation, Sasha. Excited to be here with you. Uh, we are here to talk about my book, but really this is an excuse to go deeper into some of how you think about writing, uh, some of the things, uh, you've done in your path. You've written your own book, of course. I'm gonna throw a little plug for Sasha's book, play with the graphics here. Of course, All the Wrong Moves.

[01:59] Sasha Chapin: Fancy graphics. Thank you for having me. I'm excited to be here, and congratulations on your book. It's a thrilling feeling.

[02:09] Paul: Yeah, the question I keep getting from people is, how does it feel to have written a book? Which I was writing a little bit about yesterday. It's weird. Um, because it doesn't really feel like anything. I don't know if you went through a similar feeling, but I realized the dominant emotion is probably sadness because I miss the project of writing it. And I think this is something we'll dive into as well.

Like there's so many scripts about you're supposed to feel crappy writing. Um, but my experience has just been. It was pretty fun to do and kind of a nice puzzle. Did you have a similar experience? People asking you, how did it feel to publish a book?

[02:54] Sasha Chapin: Yeah. Yeah. When you're publishing a book, people think you're the most interesting person in the world. And it's like, it's like mentally very interesting, but superficially not super interesting. You're just typing a lot. And yeah, one thing you write about in your book so eloquently is arrival fallacy.

I think it's called. This idea— I'm not getting the words right, but I'm getting the idea right. This idea that like we think there's going to be some event that's going to fundamentally change the texture of reality, and then very few things do that, and writing a book usually isn't one of them. So yeah, I felt sort of postpartum depression for like weeks after I finished my book, because it was like my childhood dream. I did it. I was like, yeah, I'm the same person.

[03:41] Paul: Yeah, it almost has more of an impact on other people's narratives of you. I've found it kind of, um, has brought my own perception closer to other people now in the sense that they're like, oh, you've actually been doing some stuff, and now you have this like author script or author tag that kind of matches with what you have seemingly been doing for years. Maybe it's a little different for you given you had been doing writing professionally as well.

[04:12] Sasha Chapin: Well, I relate to that experience in a different way, which is I told people I was a writer for a long time before publishing my first article, and then I published and it was like, oh, they were like, you're not just a mess, you actually write things. So That's a nice experience. Yeah, people have proof that you're dedicated and passionate. I mean, that was already evident from your public admissions, but now it's extra evident, which must feel good.

[04:45] Paul: When I started to write my book, I thought I set out to write a book, but I was looking back and at the beginning I kind of hedged a little and said, this is gonna be a collection of essays. And I think my initial conception was I'll throw a bunch of blog posts together and tie it together. That doesn't really work at the scale of book length, mostly because blogs are interconnected and you can keep referencing back and linking back. And I realized there was a deeper story to tell. And I didn't know, I wrote for a month and was a bit stuck. And that's when I ended up reaching out to you.

I gave you my very messy draft and I don't remember everything you told me, but you told me one thing that really unlocked things for me, which was, Paul, you're a really good analytical, like rational writer. You can tie ideas together and make sense of it. Uh, but your emotional stuff, super powerful. You've only pulled it off in a couple places. Um, go all in, basically like let it rip. And I think in that I discovered Oh wow, that's actually the most interesting path to follow.

And that through line was basically what pulled the book off for me. How does that map to like— so I don't know like how you're thinking about it on your end when you're doing something like that.

[06:13] Sasha Chapin: Yeah.

[06:13] Paul: So you mean doing something like that, do you mean giving advice or do you mean So in my case, like you must have a mental model of like somebody that writes a book, right? You've been doing writing coaching and you have a sense of like what they need. And you could have easily given me 100 suggestions on how to improve my writing. But I think some of the best coaches I've encountered in many different disciplines don't touch on the mistakes. They tell you the like one thing that's, Exactly where the, like, I don't even have the word, but like where the heart of it is.

[06:55] Sasha Chapin: Yeah. Yeah. There's a failure mode I think that I used to stumble into as an advice giver, which is to think that it's like high status and that it makes you intelligent to have a primarily corrective agenda. Like saying things that saying what's wrong with the thing is what you should do. It's easy to say what's wrong with the thing. There is a specific failure mode that I've noticed while coaching the like tech adjacent and business adjacent population, which is this belief that like focusing on emotion is sort of obscurantist.

You know what I mean? Like it's occluding the idea, which is like the real point of the thing, but ideas take their power from social relationships and from matters of the heart. You know, it's, it's like stealing an analogy from Jonathan Haidt that he used for something else, but it's like watching an opera without the music. You know, it's like, what the fuck does it matter that you are not a consultant and you're a freelancer instead if it doesn't matter emotionally to you either way? Like, it's not really a practical decision, or it is a practical decision, but it's spiritually practical. It's not like materially practical or practical at an intellectual level.

There's no way to like logic yourself into the belief that being an international worker of the world is like better somehow than being a consultant, you know?

[08:17] Paul: Yeah. I, I was actually inspired by Amy McMillan's book, Reclaiming Control. She wrote this like 100, 150 page book around basically quitting her job and wandering around the US for a year. And our backgrounds are very different, but the emotional energy I felt from that book, it just made me think, I wish there were 100 of these. And that's basically what I was aiming for the entire time, especially after you— I mean, you kind of like gave me permission. I know I didn't need it, but it was like, yes, go in that direction and just kind of like lean into that.

Do you— did you aim for a similar thing when you were writing your book? Like, was there like a directional energy or kind of feel you wanted people to have?

[09:07] Sasha Chapin: Um, honestly, the, the sort of like tendency that you had, you have to get over, um, which is to just lean into your obvious strength, which is like analytical stuff at the expense of all else. Um, that was not my struggle. I think my struggle was like, well, no, as I'm saying that, I realize that that's a lie because What you wanted to do is, is wed intellect and emotion in that you wanted to lay out the benefits of living a Pathless Path type life, but also just like let people know that they're not freaks, you know, like give them permission to do it. And I think I sort of wanted to do the same thing with chess in that I wanted to like animate something that's dry for people maybe and show them the emotion behind it. There was actually a draft of my book that was like 80% chess material and 20% me. And then my agent took me out for lunch and she told me my book was boring.

She was like, I skipped 20 pages here and I'm not interested in this. And then she was for me what I was for you. Yeah.

[10:16] Paul: Yeah. And it seems so obvious as soon as they tell you that piece of information, right? You're probably like, well, of course I have to do this. I have this story. I have to let it rip. But I mean, Even for you, probably, I imagine there's a certain vulnerability in actually committing to that.

And I think one thing my book helped me do is basically just eliminate the shame of claiming to care what I care about. Because when you're writing blog posts, newsletters, like I had been doing, you can kind of always hedge a little and people are still going to be engaged and interested. But in a book, if you do that, it's just annoying. A reader doesn't want to be like, well, don't tell me why your ideas are not good. You kind of have to let it rip. Is that a big thing you see in writing coaching as well?

[11:13] Sasha Chapin: Yeah, for sure. Jeffrey Lewis in the chat said anyone can be a think boy, and I think that's true on multiple levels. If you just write little atomic essays about ideas, Well, anyone could have written that essay. And anyone, so that means you're not personally responsible for the contents, right? You're not really staking out a position. Somebody's like, the idea is wrong.

That doesn't really matter. You were wrong about an idea. That's fine. But if you betray your personal investment to it, you are committing to a set of values as opposed to other ones, letting people know what you're about on a deep level, and they can reject that and therefore reject you. You have to be at peace with that. Intellectually, we all know that not everyone has to like us, but there's knowing and then there's knowing.

[12:01] Paul: Yeah. Did you go through a shift with that? I, for me, it was, I actually read a quote from William Zinsser and he had this quote. He's like, writing is an act of ego. You might as well accept that and move on and say what you're here to say. And that really unlocked something for me a few years ago, which is just write for the people that like your writing already and write for yourself.

Did you have to go through a similar transformation? I mean, your writing is like, to me, like your writing is like 100% embodies that. Like you are writing exactly what you want to be writing.

[12:44] Sasha Chapin: Yeah, I try. I mean, it was an iterative process. Leaning into being sincere doesn't necessarily mean writing the same thing over and over again, right? It's like where your sincerity leads you at a given time might be totally different than the year before or the year before or the year before. One thing that happened to me is when I first started publishing, I wrote a bunch of personal essays about like how I was sad. You know, I had kind of a rough childhood and like my early 20s kind of sucked.

And then I was rewarded for that. So I had this urge to keep writing essays about how I was sad, but there's only so much alpha there because I'm like, I stopped being so sad. So then like what looked like sincerity at a certain point was no longer sincerity. Writing about chess was sincerity. I'm writing about something else. So it's not like, I think you have to make the commitment to incline towards it over time.

[13:41] Paul: Yeah. So in your current writing journey, um, and this will tie into how my book kind of happened. Do you, how do you see like a book emerging? Like maybe the first book for you is like, this is a goal as kind of a writer identity I want to do. Do you see a path to another book perhaps as something a little like more emergent? Um, something like that.

[14:09] Sasha Chapin: Yeah, for sure. I think, I think it's a valiant goal in and of itself to just like write a book for the sake of writing a book. But, um, that's not usually enough. That usually makes for a bad book. I think a book just sort of emerging fractally where you're like, I have this thing to say, at least this other thing to say, and then I appear to have a lot of text. That's probably the best way to do it.

After my first book, I desperately pitched book ideas to people because I was like, ah, now my identity is that I'm a book writer. That was a mistake. That was just a waste of months of my life where I was just running down blind alleys. What I needed to do and what I'm doing now is, you know, ask myself like, what are my enthusiasms today? Which is not necessarily obvious.

[14:59] Paul: Yeah. So I'd love to dive into some of those. I love like that you're really excited about perfume. Somebody asked in the questions they submitted, what was the question? Do scents affect your writing at all? Love to dive into that and then we'll go a little deeper on some of the interests you're writing about now.

[15:24] Sasha Chapin: Well, I wanna hear about the interests you are writing about now. I wanna hear about where you're going following the book, but briefly, if you know, you don't have to know right now, you can just take a fucking break because you wrote a book. Take some time off, Paul. But yeah, I mean, sometimes I wear a perfume before sitting down to write to embody a particular mood. I think in the same way that someone might put on like hip-hop beats if they want to get like hyped up or whatever. I have like a collection of including samples, I don't know, probably somewhere around 100 scents that I can apply on a given day.

And so it's nice to have this vocabulary of like invisible environments that I can adorn myself with. In terms of what I'm enthusiastic about now, like, yeah, I love writing about perfume on an ongoing basis, just in tweet form. And right now I'm really excited about mental health and contemplation. Which is a very, a very deep subject. People are now asking me whether I'm gonna write a book, which I'm sort of wary of at this point, but yeah, it might happen. What about, what about you?

What do you— are you just chilling out at this point?

[16:38] Paul: Yeah, so I think this kind of ties back to what's next, is I've realized like, I don't like— writing the book was cool, it's Basically all the ideas I'm excited about. So now a book is the greatest excuse ever to get even more people to talk to me about the things I'm already excited about. So I really just want to keep writing about these ideas. I think the way my book emerged was very emergent in that I've had this flywheel of I write, I have weekly curiosity conversations with people, And then I say stuff to people and they're like, I've never thought of that. And I'm like, really? Oh, wow.

I'll write about that. Would that be useful? So I did that for about 3 to 4 years and kind of ended up at a point where people were then changing what they were saying to me, which is, Paul, you have a lot of interesting stuff. Where do I start? How do I connect the dots? What's like the, The Paul Millerd view of like how to think about unconventional paths.

And I didn't really know, so I wanted to find out and that's kind of what drove me to do it. And I think I kind of figured it out, which is really cool. And I don't know what to do with that yet, other than continue to help people with this stuff, cause I get a total kick out of it. Um, so having a conversation with you is like, you're excited to talk about me, but like, it's so fun to hear about like your continued journey too. Um, so it's, it's this very meta, uh, drive for me, I guess. Yeah.

[18:29] Sasha Chapin: And that makes a lot of sense. I mean, one thing that's cool about this interest, The Pathless Path, is that You're interested in the possibility space, right? You're interested in everything that's not the default life path, which by definition includes a lot of paths, right? There are lots of ways to not drift into conformity. It's one way versus infinite ways. So yeah, I can see you going in a lot of directions with that, both in general theory specifics.

How do you make money doing this thing? What does this person do?

[19:10] Paul: Yeah, and writing another book, I have, I have no interest in that now. It would have to emerge organically. Yeah, I just want to keep writing, probably like newsletter and blog essays, and try to do harder stuff. I think I'm definitely inspired by you by just like really just trying to decrease the filter and between the ideas that are going on here and on the page. I think the more I've gotten rid of that filter, the better my writing has gotten.

[19:45] Sasha Chapin: Yeah, that makes a ton of sense to me. This is something I think about all the time. I actually wrote a post about this today.

[19:52] Paul: Oh, wow.

[19:53] Sasha Chapin: This is about the strategy of anti-strategy, this idea that over time, You form strategies in your head to maximize a certain kind of reward, but if you let that take over your life, then you incline away from your full breadth, right? I tend to think that the best creative work— there's a metaphor I use with my clients all the time, which is like, your best creative work is just like juicy, delicious fruit that comes out of a rainforest. And your inclination is like, oh, I want to figure out how to farm this fruit and do a lot of it. But it depends upon the diversity of the ecosystem. And so if you're aiming to produce one kind of thing, you're probably reducing the diversity of inputs and outputs that actually makes for the best work.

[20:40] Paul: Ah, yeah. And it's hard, right? Because I've kind of noticed this in like, okay, my background is in business. And strategy consulting, I know how to think about strategy in businesses and like all that. If you write about business strategy, you will get a lot more readers. So I purposely make sure that I'm like dropping in like anti-business strategy stuff randomly in my writing.

And then also just not writing about that because I know that like feedback loop will be almost too powerful to overcome. Do you have—

[21:23] Sasha Chapin: it gets to you. Like, I— there, there are creators on the internet whom I will not name, whom I have great respect for, but they pigeonhole themselves into being like this kind of guy, which I think is a good strategy for like business but a bad strategy for your existence as a whole, you know?

[21:43] Paul: Yeah, it kind of saddens me, right? It's like I think maybe you have the same impulse as me, which is like, I really like what you're doing. Please let it rip. Go back into the weirder, deeper stuff. I love when people are following those threads. I get so excited about it.

[22:03] Sasha Chapin: Me too. Me too. What were you about to say? I interrupted you.

[22:10] Paul: Yeah. I'd love to pick up, connect something you've been writing about, which is this deep okayness, right? And I think there's almost this story that you're attaching to it, which is that things can be awesome or things can be good, which is really interesting in the aspect of writing. So many people will say, said things to me throughout the process. Oh, it must be grueling. It must be like really grinding.

It must be hard. It must be painful. Like, how hard is writing a book? All these things. And they're very weird because one of the things I've kind of stumbled upon in my journey is this shift from wanting to escape work to actually designing for liking what I do. So I only wrote the book because I thought with high odds of it panning out, that it would be really enjoyable.

How do you think about that story of writing and it has to be painful? Do you think that holds people back? Do you think it's necessary for some people?

[23:22] Sasha Chapin: Yeah, I think there are different kinds of pain. There were moments writing my book that were definitely painful, but it was psychologically rich pain. Right? The kind of thing where you're like, this is like— I thought of it as a bit of a bullfight at times. Writing a book, a book is too big for— I don't know about everyone's head, but certainly my head. So it's this extremely taxing mental problem.

There's no way to do it perfectly, and nobody can help you at a certain point. You are alone. And that's like— it's wonderful. Like, it's like pain, but it's— It's the kind of pain that feels good. Like jumping in cold water is really painful, but then it's really refreshing and enlivening.

[24:04] Paul: Yeah, I love that. I remember just sitting at the table for 4 hours working on one paragraph, and it's like, can't find the word. And it's more than writing too. I found it was very physical too. So I realized really early on that I needed to like pair this with an entire lifestyle approach to like getting this book out there, which was, okay, when I'm stuck, it's not like power through. It's like perhaps take a couple of days off and wander, like physically get out of writer mode just to see what comes back.

And then one of the things I was writing about was just kind of like embracing non-work. So. I took like a month off in the middle of the book just to see how it would feel. And then I tried to inject that energy back into the book.

[24:58] Sasha Chapin: But yeah, my number one piece of general like process advice for writers is never grind. If you find yourself grinding, stop grinding, do something else for a bit. Anyway, sorry, I interrupted. Turn-taking is hard on this stream. Desert internet is not so good.

[25:13] Paul: No worries. Yeah, that's all I was gonna say. Maybe I'll open it up to questions. Let's see what people have. This is an interesting one to talk about by Edward. How do you know when you have found the correct writing voice and choose that rather than keep experimenting?

I know for me, finding my voice was almost a necessary aspect of the book. I think you kind of pointed out a couple things that were my voice early on, and I thought that was helpful. Like, I highly recommend just getting like a vibe coach at the beginning of your writing to be like, this is your voice. And then really leaning into that, because then you can start asking the question, okay, like what what does that voice say? What is that voice's version of how you tell this story? How do you think about finding a voice in your writing?

[26:20] Sasha Chapin: Yeah, I try not to think about it as a singular thing and more like I notice that tendencies that are almost like registers of speech, right? Like in life, you sound the same But you also sound different. You modulate it. Your pillow talk is gonna be different than how you talk to like an investor or something. It's gonna be different than how you would talk to like some guy who shows up to fix something at your house. It's distinctly you, but it matches the context.

And I found that you click into this sort of groove when you find a register of voice that's important for a given subject matter And that's trial and error for me. Like most of the things I post on my blog get fully rewritten at least once. And a lot of that is like me writing something and thinking, well, this is a bit too highfalutin or this isn't illustrative enough. It has a kind of intensity that doesn't match how I actually feel, but it's iterative. I usually don't know in advance.

[27:21] Paul: Yeah, that resonates. A question from Jeff, I'll put it on the screen. How do you dare to live out a personal brand? I reject the word personal brand, but of being crazy, experimenting, being someone new you aren't familiar with yet. And should we all strive to live at that edge? This is a pretty interesting question.

I mean, I kind of talk about this in the book. My life, if you showed my life to me 10 years ago, I would be like, how, what? How did any of that happen? None of this makes sense, but the day-to-day reality is very normal. Like, this is my normal now. I think if I were to like take a full-time job and like go back into like urban, like mode of like partying and like just doing all the things young professionals do, that would feel so weird for me now.

And that would be so hard. Whereas like now it's easier. And perhaps that's freeing for people, but I mean, I am purposeful about injecting spontaneity and serendipity into my life. So I'm always trying to do different things that will not feel like for writing, but like I've kind of seen that as something that is rewarding for the sake of it itself. How do you think about that too? I mean, you've been writing publicly much longer than me.

Did you go through a phase of like trying to like see things as like, oh, I could write about this? Or—

[29:00] Sasha Chapin: Yeah, I try to take— I realized that I tried to take a bottom-up, top-down approach. So it's not so much that I try to be crazy as I try to like just notice what's going on in my head and my environment and incline towards believing that I could write about that in some way. So it's like, The bottom-up stuff is just like, oh, what is actually going on in my day-to-day life? What am I actually thinking about? And the top-down approach is cultivating the ability to hone those into different kinds of transmission, which just sort of ends up being eccentric. Like, I think that most people— it's not that most people don't have crazy ideas, it's that they have too high a threshold for what they consider an idea.

[29:42] Paul: You know, I love that. Yeah. And is that just repetition, you think? Just like getting the gunk out and basically just shipping?

[29:55] Sasha Chapin: Yeah, just shipping. And I think just like learning to be a bit outcome independent. There's one thing I believe about creativity, which is I think the way to get the best long-term outcomes is to not care about outcomes in the short term. And that like the best work is gonna emerge from chaos. It is in the interest of your perfectionism to have lots of different kinds of material to perfect, right?

[30:22] Paul: Yeah. I, I love that. I think one thing for me that really helped my writing was just committing to a weekly newsletter mentally. And then I'd show up Friday with that thought, I have nothing to write about, but then you just sit down and you pump out something and Those often are the ones that people react to the most. And you start to see this loop of, oh, there's so many interesting things to talk about. I think I was listening to David Sedaris talk about this and he was like, I talk about the boring stuff.

He's like, my job is to make the boring, like the most incredible story possible. And I mean, he obviously pulls that off, But it just makes you realize, you take a step back and you think about some of what David Sedaris is talking about. It's like, oh, he's not really talking about anything. He's just talking about like conversations with his in-laws and family and his sister. And it would probably feel very normal to us if we were in that family, but he's able to bring it alive in an interesting way.

[31:28] Sasha Chapin: Yeah, and it makes sense to me. I think if you burrow down into anything in your life, you can find how it intersects with your values and with whatever your vision of the transcendent is. And like, you can get a bit heavy-handed with that. Like, there's a New York Times Magazine column which I've written for called Letters of Recommendation where people like recommend something and it's like they recommend like squirrels but talk about squirrels are transcendent. That can be a bit much. But I think, you know, you could go looking for unexpected depth.

[32:07] Paul: Yeah, do you have any favorite writing prompts to give your clients?

[32:12] Sasha Chapin: Oh yeah, the best one is write about pizza. So good. All the time I tell like people who don't think they're writers, so like write about pizza and you get some astonishing stuff because nobody feels like they're gonna be an expert on pizza, I've never asked like an Italian chef. I imagine it's true for them, it would be self-conscious, but like nobody thinks they're an expert. Nobody thinks their steak's there and they just let their mind wander where it wanders. And that's usually way more interesting than whatever they were producing before.

[32:42] Paul: I like that. Yeah. Especially in the American experience. I would, I would love to read my wife's essay on pizza because like in The first time she met my family, she's like, why so much pizza? Like, why is this happening? There's so much more food you could be eating.

[33:03] Sasha Chapin: Yeah, well, pizza has a certain welcoming character where it meets you where you're at. I mean, I just wanna read, like my friend Steven Fulvell is a Twitch streamer who plays strategy games and he doesn't consider himself like a writer, although he wrote a book. Recently, but at the time he didn't consider himself like a writer. I assigned him write about pizza. These are the first like 4 lines of his essay. Get ready.

For this essay, I will be writing about my favorite pizza. As is commonly known, pizza is the best food and pepperoni is the best topping. This is the straw man which I will obliterate over the next several paragraphs. A house has a foundation, walls, roof, and a staircase which descends below it. For a distance measuring more than the depth of the earth. Such is the central character of this story, the storm.

It is raining in a way that does not pour because the rain does not go down. It stays all around you. It's like, the fuck?

[34:00] Paul: I love that.

[34:01] Sasha Chapin: It's so like lyrical and intense, but he like felt the freedom to like let out that part of his imagination because he was like, well, it doesn't matter.

[34:11] Paul: Can you— you got to send me that. I'll put it in the show notes. I want to read the rest of that. Is there more to that? Oh, wow. That's so good.

[34:22] Sasha Chapin: Yeah. Yeah. So pizza is the best friend.

[34:26] Paul: Awesome. So another question from Kate. How did you know when you finished the book and there was no more left to say for the time being? I would disagree with your second part. I think The key is essentially deciding when it feels right that there's more. Okay.

Cause I think I definitely could have kept going for years on this. There's probably like 50 more books I want to read and like integrate the ideas. And I think there's a trap of like overstudying or over-researching. That was probably, that probably would have been my failure mode, I think. I, I really just went on feeling. Um, I had a sense from early on of like the book I was capable of.

I didn't know how to get there. I didn't know what it would look like and I didn't know what it would feel like, but I had a deeper sense of knowing that I'd know it when I saw it. And it really wasn't even until the final week before publishing. Um, I read through it 3 times in like printed out form and read it to myself live and made like 70 to 100 edits each time. And it was that final time and I was just like, it's ready. And that was it.

Like the, I think the final step was basically like removing 3 things. I removed like 3 different things. And that was also the feedback you gave me a couple months before I finished was like, just tighten this section up and it will make sense, make more sense. It will flow better. But yeah, that, that was my pro— like, I— this is something I don't know how to explain. It was just a feeling.

How about you?

[36:19] Sasha Chapin: I have very little more to say because I endorse that explanation. I also think that the magic of deadlines was helpful for me. But yeah, yeah, there's a feeling of You know that, you know those like weird chairs that like look like they're defying gravity, but it's just because of that called tensegrity. There's a certain kind of tensegrity when you're like, yeah, this has some sort of interior coherence where things are imbalanced, but that's just a— just you go on feel.

[36:45] Paul: Let's see, we'll grab, uh, another one. Oh, from Edward, uh, would love to hear about Sasha's drafting process. His articles have almost have a studied carelessness, uh, but I know there must be a lot of work going on there. You said before it was kind of a, you do like one turn on the essay. Is, does it take work to get to that carelessness vibe?

[37:19] Sasha Chapin: Yeah, I think so. The carelessness vibe is partially just me. I'm a person who tends to shoot from the hip, and I think of myself less as a truth teller or something than someone who's advancing the conversation. You think it's more— it's better ultimately for the reader if you provoke a response than if you try to be right. But ironically, that takes some revision. As you mentioned, You know, the work is generally like stripping away superfluity and coming to my actual level of seriousness and commitment to a topic, which is usually not like super, super serious and committed.

I'm just kind of like a playful person by nature. And so if I don't have that playfulness in my work, it's generally because I've gotten self-conscious for some reason about like needing to be serious about something. Got to strip that away. I still do that all the time.

[38:26] Paul: Awesome. Let's see what else we have. Here's like a very specific question. Do you have any actionable tips to make readers go from one sentence to the other? I think the thing I learned was basically read it out loud. Um, but I don't, I don't know if you have any other thoughts on that.

[38:46] Sasha Chapin: Yeah. So, oh my God, I have so many beefs with writing advice in general. Like I read something about this the other day that was very smart. I forget where, but it was like most writing advice today is like deletion focused. It's like omit unnecessary words, you know?

[39:01] Paul: Yeah.

[39:02] Sasha Chapin: Certain people think you should be like commercial copywriters, which I think is insane. Because nobody remembers reading a cereal box, you know. I think like the thing that keeps people reading— okay, so brevity has something to it. Like I think some repetition can often be eliminated from a draft, but like I think the thing to lean into is human presence. Like I think people typically feel like they're in good company when they're having a compelling reading experience. And in terms of practical technique, often that can involve inclining towards the rhythms of your vernacular speech.

[39:49] Paul: Yeah, like writing advice will say like remove really or adverbs like that and I found when I was reading stuff out loud, it was like, oh, I would say it like that. So why not write it like that? And it kind of adds emphasis. And it also avoids this trap, which I think a lot of people fall into of writing is like basically trying to pass the SATs with their writing rather than just talking like a human. Maybe if you're writing for like a very elite circle, it might matter to you, but I don't know. I want to write for like just normal people reading my writing.

[40:36] Sasha Chapin: Yeah, totally. Yes. Yeah, that advice is insane. Like, omit really. That's not what's going to make your work powerful. It is occasionally good to be blunt and pissy.

As a device, but they don't think that should be your default. And even when you're writing in a professional context, like people think standards are there that aren't really there. If you look at like, I've done this because I have some clients in business. Like if you look at like famous memos in business, often they're very characterful, not as much as like my crazy tweets about perfume or something, but like the peanut butter memo from Yahoo. One of the executives said, we're like peanut butter, we spread ourselves around on everything. Like those aren't really necessary words, they're just fun and cool.

And like Steve Jobs was such a master at being presentational because he just acted like a human being, even though he was like the culture, new technology.

[41:43] Paul: Yeah, I love that. What, uh, are there any other thoughts you'd want to leave about, um, or maybe a question is like, how are, how are you thinking about like your own journey now? I know you've kind of shifted into doing some of the writing coaching. That's how I found you, um, last year. How are you thinking about your Pathless Path and, uh, how to navigate your own journey?

[42:12] Sasha Chapin: Yeah, I am potentially shifting away from writing coaching because I think writers can fall into a trap where they become writing teachers. All they talk about is the craft and then that's— they become boring because obviously you just become boring. I'm increasingly doing general coaching type stuff, more like emotional coaching because unintentionally my writing coaching is often like therapy. People are like, You're better than my therapist. And I'm like, well, that definitely suggests a specific kind of direction. Um, but I don't know.

I'm pretty committed at this point in my life to meaning coaching, which is my day job at the same time. Um, wandering such as you advocate.