​Sasha Chapin is an award-winning writer, writing coach, and recovering chess enthusiast. Sasha is the author of All The Wrong Moves; he publishes on Substack and has appeared in The New York Times Magazine, BuzzFeed, and Hazlitt.

Is writing a priority for you this year? Do you want to work on a book or be more consistent with publishing your blog or newsletter?

Many of the blocks to consistent writing are psychological, not practical. Sasha shares techniques for narrowing the gap from your brain to the page and making the writing process more enjoyable.​

For the video recording, resources mentioned, and conversation transcript, visit https://forcingfunction.com/podcast/sasha-chapin.

Welcome to Forcing Function Hour, a conversation series exploring the boundaries of peak performance. Join me, Chris Sparks, as I interview elite performers to reveal principles, systems, and strategies for achieving a competitive edge in business. If you are an executive or investor ready to take yourself to the next level, download my workbook at experimentwithoutlimits.com. For all episodes and show notes, go to forcingfunctionhour.com.

Today I'm really excited and honored to be joined by Sasha Chapin. Sasha is an award-winning writer and writing coach. He's the author of "All The Wrong Moves," a memoir about his forays into the tournament chess world. Currently, Sasha is publishing on Substack and writing for publications such as the New York Times Magazine, Buzzfeed, and Hazlitt. Our topic for today is "awaken the writer within." The key here is that you are already a writer. The words already exist inside of you. You just need to remove the barriers preventing those words from ending up flowing onto the page. And we could not have a better person joining us for that purpose today. Sasha has a true knack for removing those barriers, both practical and psychological. I worked with Sasha as my writing coach last year, and he was instrumental in improving the clarity and structure of my articles. Most importantly, the process of writing now feels much more effortless. So, it's an honor. Sasha, thank you so much for joining us, we're really excited to see what comes up today.

Thank you for having me. I'm excited to be here.

Cool. Let's just start by sharing a little bit about your story, how you got here. How did you get started as a writer?

The beginning of my journey was kind of rocky. So, I was always pretty verbal and I think it was clear to people around me that I wouldn't really be good for anything that wasn't creative. I didn't seem like the normal job kind of person, and so I was pushed and pulled in various directions, but I always came back to writing. I thought, "I'm going to be a writer." This was a thought that was mirrored by people around me, but my early creative life was pretty miserable. I went to school for Comparative Literature to, like, be a great writer by studying the great writers and imitating their tricks. That didn't go very well. The average writing day for about six or seven years was a lot of chain-smoking and giving myself gastric ulcers and producing a couple of tortured sentences. That went on for a while. And then in my mid-twenties, I had this sort of flip. Everything started going quite well, within a couple of years I won the Gold National Magazine Award, the Silver National Magazine Award, I got a book published, it was well-reviewed, seemingly, I suppose.

So there's a really powerful bimodal distribution in my life between miserable, non-producing artist and fairly happy consistently-producing artist.

So let's start with what didn't work. You mentioned going to school, trying to imitate the great writers, becoming one of them through this process. Why do you think that this imitation didn't work for you?

Well, I was making a mistake pretty consistently. I should tell you before I launch into this that I think imitating other writers is a great exercise. It's a good way to like notice the differences between your natural setting and somebody else's natural setting, and being influenced by other writers can be great in the same way that, you know, you hang out with somebody charismatic and interesting and you find yourself mimicking their structures of thought and speech. But it's sort of a blend of your own and theirs. What you can't do is slavishly imitate people you feel are amazing. And that's what I was doing. I was completely neglecting my own personality and my own priorities and my own strengths as a writer in favor of whoever I admired that week. Right? I wanted to be a carbon copy of James Joyce or David Foster Wallace, or whoever. That was the problem. Like, abnegation. Everything I was doing stylistically was trying to be less like me.

How did that factor into your difficulty with output at this time? You said that you were kind of making yourself a little bit miserable, your health was suffering. Presumably you weren't happy about the way things were going. The words weren't flowing. What else was going on at this time.

Well, I mean, my mental health overall was pretty poor. I wasn't sleeping a lot. I think it would be easier to ask, like, what was going right than what was going wrong. And what was going right was not much. In terms of writing, though, I think the simplest way to put it is just that everything was insufficient. Like, I spent like six or seven years writing a novel and a half and writing essays for school, and just everything was torture. Everything felt torturous. Nothing I did felt right.

So during this time, it feels like your mental health was suffering. Words weren't on the page, not a lot was going right. When did the tide start to turn for you? When did writing feel less torturous?

I think one thing that happened that was very significant — So, after a bunch of personal crises in my life, I swore off writing. I told myself, "I'm not a writer anymore. Writing is terrible. I will never do it. It will never be a part of my life ever again." And then I spent some time in music. I was a singer/songwriter for a couple years. And that was a healthy state of mind for me after spending all of my time thinking about how I was going to be a literary artist, because when I was a songwriter my job was obviously just to entertain people. Like, the test of whether a show went well wasn't whether I was entered into the canon of the great geniuses of history, it was whether people clapped or looked at me instead of talking or being on their phones. And so, after a couple years of that I went back to writing, and part of what I brought to it was just an entertainment mindset. Thinking, like, what I want to do is show the readers a good time. Everything else is immaterial.

I also worked with editors for the first time. I mean, I worked with editors before, but like had real collaborative relationships, and then I started to understand the profound degree to which people don't do this alone, and the degree to which collaboration is powerful. I had always wanted to be like a lone genius stalking the landscape, you know, emitting perfect transmissions from my mysterious brain. But it's not a great strategy. And so I discovered that.

Yeah. What strikes me is just having much healthier expectations. Maybe a much more gentle touch, right? If you're comparing yourself with the greats, and the greatest of the greats' work after years of publishing and you know, decades of practicing their craft, that would cause, I imagine, a lot of fear and hesitation and sort of self-judgment in not measuring up to that. And it's cool you talk about the shift that happened after music where the goals were different, of "giving them a good time," as you say. It seems like releasing some of those expectations of being an artist and more having the listener, the reader in mind was a huge shift. Is that something that you see often? The common advice is "write to someone." But is that a shift that's been useful for you?

Yeah, definitely. It's been a very useful shift. I don't think there's anything wrong with striving for greatness, but ironically people often strive for greatness by imitating greatness when usually great artists are just utterly themselves. Over time they lean more and more, they incline more and more into all of their eccentricities, all of their experiences, they bring every part of themselves to the work. Right? Where when you're trying to imitate someone great, you examine all of the components of your mind and you pick a couple, you pick this like tiny wedge, the tiny wedge of you that resembles whatever author you're trying to duplicate. And that's not going to work.

Yeah, I think people can get a lot of mileage out of demystifying writing. Like, people think of it as like this prophetic, mysterious act. And it can be that. There are moments that can feel, like, very mystical, like channeling the universe. But the way you're going to get there is by simply regarding it as communication. It's another kind of conversation, right? When you're writing something you're not sealing off the subject matter with a bow and forever enshrining yourself as the last word on that thing in the universe, you're just contributing to the ongoing conversation that is human life. You know what I mean?

Yeah. I think this is a really interesting thread about leaning into your eccentricities. I think the kind of prerequisite is how do you discover what makes you unique? I think that could be a sticking point for a lot of people too, is like, what, you know, what do I know? What experience have I had, what makes me different? And I think that leads someone to fall into that comfort zone of imitation rather than let's say authenticity. What was this process like for you, to discover, come to terms with your own eccentricities, and starting to let those shine?

Yeah. So individually—One thing that really helped was when I started writing for magazines, I thought, "This is gonna be a fun side gig while I continue my life as a singer/songwriter." And so the first couple of essays I wrote for publication were about things that were very obvious to me. Like, I had just spent years struggling with bipolar disorder, so my first essay was about bipolar disorder. And then the only music I was listening to all day was Elliot Smith, and so I wrote an essay on the career of Elliot Smith. And it just went like that. And I think unintentionally I stumbled upon a piece of wisdom that, you know, is not mine, but I think it's really powerful, which is that if you're looking for what's special about you, you should search for the obvious. Things that are obvious to you. The more you know something, the more a truth is obvious to you, the more expertise you have in it but the more it sort of fades from view. It becomes just like the language through which you view the world. You know what I mean?

So when people are looking for what's interesting to write about, often they're looking for an image when they should be looking for the lens. How they see stuff, their experience, like what they genuinely think about. You know, don't index for what in your mind is interesting. Index for what tends to be on your mind most of the time.

Yeah, I think there's an interesting meta point, too, in the more time that you have spent with an idea the more dimensionality that you'll be able to bring to it, the more experiences that touch on it, and probably the more nuanced view. It's not something that's been inherited from someone else. Presumably it's emerged over time through a set of experiences.

Yeah, for sure. For example, you know, you're a top ten poker player. That's an unusual experience, but you know, there have been probably like a couple of hundred people who share that description on earth. We were once having a conversation though where I said, "One day I'm probably gonna become a bad poker player for a couple months." And you said to me, I've never forgotten this, it was memorable, you said, "Actually, you'd probably be a good poker player, but the thing is to be a good poker player you have to develop a killer instinct, and it's not easy to turn that off." And it's like, well, if you think about writing about poker in the abstract, maybe that's not super interesting, because lots of people have written about poker. But you could write about being a kind person who adopted the killer instinct and now is learning to work collaboratively. Right? That's just you. But like that's so obvious to you that you would never come up with it as like a part of a list of ideas, because that's just your history. It's the lens through which you see the world. But it's a good idea. You should write that essay. Or consider it.

It's very top of mind right now, and I think that's a really cool way of framing it, is you know, write about what's obvious. Write about things like, "Oh, they couldn't—" The thing that you are probably least interested in. Not that—It interests you a lot, but that it doesn't seem very interesting to you, that's probably what's gonna be most interesting to others, because they're a lot less likely to have had that perspective or even have thought that that was a perspective to have.

Yeah. The things that are most obvious to you are obvious because they are surrounded by this corona of individual data that nobody else has. That's a good place to start.

Talk to me about the creation of your book. What was that process like? I know the temptation, "Hey, I'm writing about chess. Like, let's write about the history or the strategy of chess," which as you said has been covered by many, and you gave the only dimension that you could write when you wrote "All the Wrong Moves," is, "Here's my experiences delving into the chess world with all of my foibles and failures and perhaps mistaken perspectives but unique perspectives." What was that process like for you?

Yeah, so this is an exemplary case for a principle of mine I try to advocate to all my clients, which is instead of thinking about what a good idea is, just start writing. Just treat every first draft as an experiment. You know, don't sit around wondering like, "What would a perfectly compelling essay about this subject be?" Venture forth into possibility space and then iterate towards the thing only you can write, the thing that turns out to be the most interesting.

So, the book started as an essay I was going to write for a magazine about the mental lives of top chess players. And I started writing the essay, and it was like perfectly serviceable, but I discovered that the mental lives of chess players are pretty boring. Like the top ten chess players, they're like really nice nerdy guys from Europe. That's it. That's who they are. Lovely people to talk to, but like not—We have this image of the crazy chess genius, but that's just Bobby Fischer and that lady from Queen's Gambit. So, I was stuck. And then I thought, well, people like reading about when you're bad at things. That's relatable. I'm bad at chess. Maybe I should write about my life as a bad chess player. That was not what I'd thought I was going to write about, but it's the way things went.

And so, again, I want to belabor this point because I think it's important. Like, if I had thought about, "Uh, what's an essay about top chess players going to be like?" And I did a bunch of research, and then I decided not to write it, my book would have not existed. But I just sort of plunged in and then did some pathfinding and then I wrote this essay. And I was not planning to write a book about being a bad chess player, but of all the essays I wrote at that time it was the one that was most well received. To my, like, bewilderment, and then it snowballed from there. The essay was me performing very badly at one chess tournament, and that made for entertaining writing, and so it was the opinion of the publishers that me performing badly at lots of chess tournaments would also be entertaining writing, and I think that was correct.

Yeah. I think there's a couple lessons there. First, just the importance of diving in. That you'll just have no idea what final form the project will take until you've begun, that all of these diverging paths will appear as you explore the landscape, as you try to identify the possibility space, as you so eloquently put it. So the only way to start to converge upon the final product is to start to wander down some of these paths. And you mentioned the importance of feedback and hearing what resonated with the readers. Both what grabbed them, what they found entertaining, but also presumably what you found the most interesting. Where you went in with a hypothesis that this is going to be really cool, and it turned out that your original hypothesis perhaps was incorrect. Or at least like you were less excited about it, you didn't think there was much depth there. And the experimentation led to you going into the wider world of chess and finding that the real stories are at the lower levels or the up and comers or all the characters and aspirations that occur there.

You mentioned earlier the importance of not going it alone, of, you know, I think I'd be interested to hear more about—What do you find makes a successful collaboration? Whether this is with a professional editor or even with just a kind and loving friend who's willing to, you know, read your words and tell you which words they like.

Yeah, so those are very, very different situations. In terms of getting good feedback from friends, from colleagues, who are not you know, professionally obligated to read your writing, people by default do the worst thing they can possibly do, which is just say, like, "Read this and tell me what you think." Which is really—Like, that's a really hard question to answer. If you're looking for feedback from individuals, you want to ask questions like, "Are there any places you got bored? What do you want to see more of? What are the parts that you found most engaging?" And there are questions that they can answer without feeling like they're being mean to you, because sort of by default, like, if you're searching around your personal life for feedback, which you should be doing, there are two groups of people, both of whom you have to accommodate. There's a group of people who never want to say anything mean to you ever, or anything that they think can make you feel bad, and then there's a group of people for whom criticism is very high status. By default they approach other people with a corrective agenda. So they'll just say a bunch of stuff just because they want to say stuff. Those failure modes can be completely avoided if you ask specific questions.

What specific questions come to mind when you're looking for feedback on a piece?

Like, what do you want to see more of? What's the emotional core of this piece to you? That's a really important one for me, because I find that—So, this is a bit of a sidebar, but a lot of people approach the revision process as exclusively a process of deletion, but I find that the most important element of the revision process is finding what's really important and then abandoning yourself to that. You know, it's not necessarily obvious in the first draft of a piece, whether it's long or short, what the real meaning of it is, or what about it is really gonna break someone's heart or break their prefrontal cortex or whatever it is you wanna break. And so discovering what that is in the minds of the readers can be huge. And then just, you know, leaning in that direction as voraciously as possible.

So when you receive a piece of feedback that, "Hey, I like this part the most, this is what really grabbed me," it's not just stripping away the things that didn't grab, but going in much deeper into the thing that did. Do you have an example that comes to mind?

Yes, I do. So recently I had some big changes in my own mental health, and I wrote this big post about it which was received quite well, and during the editing process—So, the short story behind the post is that I did a bunch of alternative therapies and completely changed the way I thought about myself for the better. And I wrote this piece, and part of the piece was despairing over the state of mental health where we as a civilization seem to agree that life must be painful and that just like hating yourself a little bit forever is sort of the level of mental health you should expect. And when I wrote the piece the beginning was saying, "Well, I don't know what to recommend for everybody, this is just my own path." I was being very self-effacing. And then somebody commented like, "Well, actually like maybe you should recommend something. Like what do you think—I like the places where you're actually more prescriptive."

And then I completely redid the intro and then it was really prescriptive, because I realized I did have a process about how people should improve their mental health. I was just being shy about it. But that shyness, while it was maybe partially motivated by not wanting to do harm, it was also just like me being ungenerous. Like, there was something in my heart and I didn't want to put it out there. I was—Somehow—So, allowing the reader to know what I actually thought. And that completely changed the tone of the whole thing. It made it a lot more urgent, a lot more heartfelt.

Yeah, that strikes me. Both the vulnerability and the comfort with talking about things that are maybe a bit discomforting. You know, things that—We wanna always put ourselves in this light of an expert or rather the all-knowing scribe, and being comfortable sharing, having a position on something even if we're not certain about it. And obviously understanding that a lot of our position will reveal itself through the process of creation. I'm interested, as someone—I really respect how genuine and authentic you are with your writing. How have you been able to remove those filters, those barriers to being yourself, to sharing what you really think, to not hiding behind being intellectual or hiding behind couching your opinions?

Yeah. So it hasn't been super easy, and it's an ongoing process. Like, I still catch myself writing something that's—Like, fairly frequently writing something that's more about self-image management than it is about, you know, being who I actually am. But there are a couple things. Like, one thing is that I've noticed that my intellectual heroes don't seem to have certainty as the goal of their intellectual lives. So one example for me is Jonathan Haidt, who wrote "The Happiness Hypothesis" about Stoicism, and then he wrote "The Righteous Mind" which is about the moral behavior of groups of people and group selection as a way of looking at human evolution. And as I understand it, he was walking around thinking, "Happiness is in your hands as the individual. You know, stoics figured out this happiness thing in Roman times, so I just have to write about that." And then he finished the book and like literally at the end of the book he was like, "Oh, I'm wrong. The key to happiness actually largely lies in community. Understanding humans as individuals is terribly short-sighted. So I'm just gonna write that other thing. That book corrects my last book."

And by iterating on himself, he was able to develop more original thoughts than if he had said, "What I'm going to do with this piece of writing is shield myself from all objection, say all of these things that I'm sure cannot possibly be incorrect in any possible world." The other thing is just disaggregating your own personal goals with writing and your own feelings from how it actually functions in the world. Like, when readers read your writing, unless they're assholes, they're not like looking at every single sentence to make sure that you thought about something rigorously. It's not like they're reading it to approach you as an attack surface. They're reading it because they're motivated towards some end, there's something they want to learn about or think about, and your piece of writing is a tool for them. Right? And like if it's poorly considered, it makes them angry, that might lead them to form their own thoughts that are, you know, better than yours. If you write something they agree with but it's from a little bit of a different angle, it might help them reify their values and make what they already know more alive to them.

And so if you think, like, "How am I advancing the conversation?," it's a much more generous frame of mind than, "How am I going to end the conversation? How am I going to be the last person who says this?" You know what I mean?

Yeah, advancing the conversation versus ending it. A big failure mode for me with writing is sitting down and trying to write the definitive piece about something, and, "Hey, this is the only article that I am going to write about this, and that way I can just—Anybody asks me about it, I can just send them the link." And you know, you can see the recipe for failure there is you know, we'll never completely converge on certainty, and our views are going to shift before and after writing. So it puts the piece on a pedestal that it can't possibly live up to.

It brings up a question for me. You talked about this kind of disconnecting from goal orientation. I think a lot of people get into writing, I think myself included, because we have larger career or personal goals in place. So I'll talk to a founder and they're like, "I need to be writing to make it easier to raise money or to hire more engineers." Or I talk to someone who wants to be creating online. Maybe they want to have a course or some sort of product, it's like, "I need to be having my ideas out there so people can see that I'm an expert, that I know what I'm talking about." And in a lot of ways that can create a mental barrier as well, because especially in the beginning it's unlikely that you are going to—That the Internet's going to blow up because you published a post. Right? What advice do you have for someone to kind of stick with something like writing that especially in the early going can sometimes feel like you're shouting into the void? It's that very interesting shift that happens right before you hit publish, it's like, "Oh, man, I'm kind of nervous and don't necessarily want anyone to read this." And then as soon as you hit publish, it's like, "Oh man, why is no one reading this?" How do you deal with that kind of releasing of the goal orientation?

Yeah. So, I think it's important to specify that I'm not necessarily against goal orientation. I like, intelligent goal orientation. Like, picking the right goals and being goal-oriented at the right level of resolution. So the best way to become, like, be goal-oriented in writing, like want to produce excellent work and wanna be—Reach people, there's nothing wrong with that. I think that's a noble aspiration. But the best way to get there is release outcome sensitivity in the short term. Like, if we think about a founder writing a fundraising document, they could spend a week writing something and slaving over every single word and imagining the extremely mean-spirited VC picking it apart, and that will probably result in an extremely constipated, unstylish, boring piece of writing. Maybe that'll still get them funded, I don't know. You know, but it's not going to be as good as it could be. What they should do instead, if I were their coach, I'd say, "Have two conversations about this this week. Write the version that's an email explaining what you do that's dashed off to your wife. Write a version that brings your emotions to it. Like, play and see what emerges."

The—What a piece of writing should be before it's written, I don't know it, you don't know it, nobody knows it, and the way you determine its high-yield form, the way you find that version of the thing that's gonna take on a life of its own is by playing around. So it's alright to be perfectionistic. In fact it's good, right? Like, perfectionism is just having some interoception about whether you're meeting some standard. But it's in the interest of your perfectionism to have some chaos and play, some experimental data to perfect, not just to assume that perfection will obtain in a linear fashion right away. It never works like that.

Yeah, it reminds me of a piece of advice that you gave me, and I'm adding this metaphor, and I kind of visualized it as adding in pieces of a puzzle, where I had such a difficult time getting that first draft, right? Staring at the blank page, and I have all these thoughts in my head, it seems like there's something there. How do I get it into some written form? And you know, first was the suggestion of, talk it out, you can record yourself, turn it into a transcript. But also think about writing different versions of it. The bringing different selves to it, say, different states of mind. Some day you had a bunch of coffee, someday you really oversleep, some day you're feeling really euphoric and some day you're really angry and you're writing a rant. You're talking to a friend, you're talking to a boss, you're talking to yourself, you know, ten years in the past, ten years in the future, you're talking to a younger person. Right? All of these perspectives allow you to assemble different pieces of the puzzle, start to plug those gaps.

And that seems like a good tip that I know has worked for me whenever I get stuck, which is super often, is to just try to find a different angle to approach.

It also reminds me of a different piece of really tactical advice that you gave me, I forget the specific thing you said to write, it's like, when you get stuck at something essentially just like putting a bookmark there. Just writing like, "return," or something like that, and then like moving on to some place where you're not stuck with the trust that the answer will come to you likely when you're not sitting at the desk. It's probably a good time to talk about some of these, I don't want to say "tricks." Let's say "techniques" for just keeping things flowing, to not letting yourself get bogged down.

Yeah. So, I think the ultimate sort of meta-tactical rule I have with all of this stuff is "no grinding." If you're grinding, something is going wrong. Like if you're, like, if every sentence is like agony and you can't find the right word, like, you need to do something else. Don't grind. The more grindy, terrible writing experiences you have the worse your writing will become and the more you will hate writing. You don't want to have an aversive relationship to something you want to be good at.

The other thing I think that's related but different is being all right with whatever mood you're in when you're in the chair. So a problem that people run into, one piece of difficulty, is people have had this idea for a long time. Let's say it's a meta-skills endeavor, or whatever. And then they think, "Well, I'm going to write the definitive piece on this, but it's really hard right now because I think this idea is deeply shocking and surprising, but I don't feel shocked and surprised by it right now. I just feel like it's sort of obvious." Well then, the question is can you let the obviousness of the idea be a mood that informs the writing? Like, then can it become a sort of frankness and a kind of honesty? Maybe you can spend more time writing about the implications of the idea which excites you than the background that you think you ought to write about? Basically, just removing all of the "ought." "I ought to be in a certain mood." That these ought to be framed a certain way. That doesn't exist. There are a million possible great permutations of a given piece of writing. You just have to go with the permutation that makes the most sense to you, like, this hour.

It is very, very easy for smart people who are analytical, which is probably the entire listenership of this podcast, to slip into a mode where they imagine the ideal form of the thing, but it's always precise enough to be punishing but vague enough to be unhelpful. You know what I mean?

Yeah, I see that. And let me know if this makes sense as how you're thinking about it. It seems like with a piece there's lots of gathering in the early stages of just pulling things in, seeing what's interesting, seeing what sticks, and just like having lots of material to work with, and kind of having it in front of you and seeing, "What do I have here?" Is there kind of this inflection point, this shift, where this gathering kind of shifts more towards convergence of, you know, stripping away things that maybe will be left for a future episode or, like, "All right, this is like really what resonates, let's dig into this here." If so, if there's this shift, how do you find that, "Hey, it's time to move towards converging on a final product with this material that I've gathered?"

I don't think there's a rule that's consistent, and this is why deadlines are helpful. You know, because you just have to make that shift at some point. Yeah, that could never end. You know, your ten page essay about something could be a five hundred page book, could be an epic sonnet cycle. You can go in lots of different directions. I think you just have to decide on where it's appropriate for this use case if I have to do it by Friday.

Talking about tactics for a second, I think as writing productivity strategies ,daily habits are overemphasized, publishing schedules are underemphasized. I think the most important kind of forcing function for writing is the releasing forcing function.

How do you create that publication deadline? I agree, it seems like without a deadline not a lot of things happen, but what I think you would want to avoid is (one) either just creating a fake deadline that you don't actually respect, or (two) kind of generating unnecessary stress or anxiety that will take away some of that fun of making the piece. Like, how do you create this forcing function of a publication deadline that's more helpful rather than thwarting?

So, I have a somewhat funny one that's idiosyncratic, but it's actually been incredibly helpful for me, and I think more people should consider it, which is that if I don't publish a newsletter every week, I send my friend Ashuda a thousand dollars. And if I do it for a year, she sends me a steak and a bottle of wine. And I felt weird about establishing this, but then I realized that for a year of my life I had a book deal, and a book deal is just a situation where they give you forty thousand dollars, and if you don't give them a book they take your forty thousand dollars back. So you're going to make a book.

And it's very, very natural for me to write. I'll write things like that all day and night. It's my favorite thing to do. But releasing newsletters every single week is not as intuitive. But having that deadline seems like it could be imprisoning, but paradoxically it's freeing. It's like, why, I have to do it. If it's kind of bad this week, it doesn't matter. I have to do it. And one thing you learn when you have a regular publication schedule, too, which is a little terrifying at first but becomes comforting is that you really don't know what's gonna be popular of what you publish. Sometimes you know. Sometimes you think, like, "Oh, this is excellent work." But like a couple of days ago I wanted to chill out in the hot tub with my wife and I had to publish something. It was Sunday night, Monday's the deadline. And so I just threw something out there, it was like four hundred words about my problems with note taking systems. And it was immensely popular. It did really well. And I just dashed it off.

And then there are other things you slave over that are like beautiful works of art that go totally unappreciated. That's one wonderful thing about publication schedules. It's humbling. You know, it's not yours. The work you put in is not so you can control readers and make them like it. You're always leaving it up to them. You know?

Yeah, there's an importance to raising the stakes, and having a schedule creates a natural cadence. It removes a lot of the willpower to get yourself to do something. It's more of, "Well, I've—" You make the commitment once and then all of the future actions—So it's really, taking away that perceived effort. Because, well, I have to do it. I'm not gonna give back the forty grand, so I guess I'm writing a book. It's just a question of what and when.

And yeah, you mention this thing that I thinK we hear often but don't actually internalize of not knowing how something is going to do until it's out there, and that has the natural conclusion of, "We need to just be putting more things out there because we can't be the judge." The whole point is having the others in mind. So yeah, I think that that's really valuable, and just acknowledging that, hey. You've been doing this for years and sometimes still you're faced with a deadline, it's, "All right, what are we gonna write about?" And sometimes the results will surprise you, that our best selves can come out when we raise these stakes for ourselves.

Yeah, absolutely. It's raising certain stakes and lowering other stakes, right? Like raising the stakes of, "Oh gosh, I've got to publish this thing." Raising the stakes in terms of producing more work, lowering the stakes in terms of your self-image management, lowering the stakes in terms of like what it means for you as an artist personally that you're doing this post because you know, you don't have time to fucking think about it, you just gotta do it.

Yeah, I think one trap people get stuck in is thinking about authenticity and pleasing the audience. Those are two, like, contrasting values, and you have to pick one or the other. You have to make the form of art that is closest to you, or you have to pander to the masses. And I like to think of it more as like a dance. Like you make a gesture, and then the world responds in some way, and then you respond back, and then the thing you make is some interpolation of what you would make if just left to your own devices and the appetites of your readership, whether that's your email list or the editors of a given publication. And when you look at it that way it's freeing, because then it can just go on for your entire life. You never quite know, but there's always a new direction to move in.

I think one failure mode people go in, people have, is like—And this was very much mine—Is the aspiring novelist mode, where they think, "Oh, the thing I make has to be this shape. That is my true art. I'm gonna spend like six years alone doing this thing, so the world will understand me in my totality." It's like, no, that's not what art is about. It's part of the conversation of daily life. It's not that mysterious.

Yeah, it's an interplay of structure and messiness, right? Having some sort of container, some sort of shape for a lot of things to get thrown at those container walls and see what sticks.

Totally. One story not from writing, that just sticks with me as an anecdote that I think about a lot when I think about creativity is, you know Richard Feynman, the cafeteria plates? If I can tell that story for your podcast audience, so like—

Yes, please.

Richard Feynman—I think it was at the Institute For Advanced Studies. Maybe I just think of that because it sounds like a convincing name for a place. But anyway, he walked into this building and it was in the cafeteria, and there was this dishwasher and he was tossing plates up in the air for fun. And he looked at the plates. They're wobbling in the air. And he thought, "That's weird. I can't figure out why they should move in that way. Maybe I should try to model that." And he wrote a bunch of equations, and then it ended up being actually important math. But the point is he didn't know it was gonna be actually important math when he saw the plates wobbling, he just thought, "That's fun. I'm gonna pursue that thing."

And I think, again paradoxically, the best way to achieve near-term or long-term outcomes is in the short-term prioritize experimentation and play in chaos. Have faith that something's going to emerge in time, and that, you know, what's not going to work is trying to make sure that everything you do is gonna be perfect and indefensible. Because it's not gonna be, it never works that way. And that's a little painful. Like part of that is you have to—You'll bring all these uplifting little speeches, but I feel like it is important to point out that it is painful at times. You have to get used to being fallible. It hurts at first, but it's freeing when you do.

How do you get over the pain?

Experience it. Multiple times. And then one thing I find myself telling my clients a lot is like, sometimes they feel ashamed because they write something and it doesn't go super well, and theN they feel ashamed of being ashamed. They're like, "I should be totally free, I shouldn't feel ashamed of my failures." The thing to remember is that we're tribal creatures. In the ancestral environment, social ostracization meant dying alone in the wilderness. Right? That's the part of your brain you're contending with, is the part that's like making sure everything you're doing is acceptable so you aren't cast out into the wilderness where you will perish of like starvation or you'll get eaten by a wolf or something.

And so like, you can conquer that, but it just takes some time. Like, it takes emotional learning. You have to do something that people don't like or that people ignore multiple times, and they'll learn that like literally you don't die. You're not abandoned in the wilderness. You'll be okay.

That brings up something that's personally interesting to me, is like what it looks like to be a writing coach. When I work with performance coaching clients, executives, investors, to me at least—And again, I think this is a meta point—It feels somewhat obvious, and, "Hey, these are the things that seem to work really well. You have good structures in place for knowing what your priorities are and making sure those things come first. You have processes for all the important aspects of your business and you start to systematize them." And so for me it's—I'm almost going through this mental checklist. And there's obviously some psychological barriers that can creep in, but for the most part it's sort of sharing things that tend to generalize and figure out how we can streamline it so they can implement those things.

For me, at least from the other side, like writing feels so psychological and individual and there are some tactical principles that seem to work well, but on the other side it's really like what seems to work well for one person in particular, and that everyone's kinda mental psychological bottleneck has its own unique flavor. So I just wanna know, 'cause I'm super curious, when you're working with a coaching client, how do you discover what that blockage is for them in getting those words out there and onto the page? What are you looking for?

Yeah. So, as I have said sort of over and over again in different ways in this conversation, I feel like people perform best as writers and do their best work when they bring the fullness of their being to it. So this is where individual writing education is really fun. If I interact with people and then I see their writing, it is very obvious to me whether the fullness of their being is going into it or not. And it is very often the case that the things they think of as negative idiosyncrasies of theirs or their work end up being redeeming factors, and the things I want them to lean into. And once you bring somebody into alignment with their characteristics, the things they actually want to write about in the ways they actually want to write about them, the ways that are most congruent to their personalities, magic starts to happen. And sometimes that happens really, really fast. Sometimes in two sessions something really great happens, and then sometimes you're wandering in the wilderness for a while and then something clicks into place.

But it's a heartbreakingly consistent pattern that people come in seemingly trying as hard as they can to avoid what's good about their writing and ignore their own magic. I have a client who writes memoiristic stuff and she writes about these extreme experiences that she's had with incredible frankness and humor, and she's like, "I'm such a simplistic writer." But she sees it as being simplistic, I see it as being honest and forthright and clear, and that's what's magical about her work.

And so it is sort of systematized, but there's no checklist that works for everybody.

So, when you reveal what makes someone uniquely them, their magic, how do you encourage that magic to go out? How do you help the person to sort of get comfortable with that and to feel comfortable expressing it?

Well, individual permission is nice. You know, like it's interesting. Like a lot of the Writers of the world, like capital W, are people who come from an Ivy League background or they took an MFA and they've been basically like—From day one of their lives they've been told that their like individual thoughts are interesting and worth hearing. And that's just something that people haven't heard.

One thing I do sometimes is sort of like—I have an assignment which is sort of a sneaky assignment, which is I tell people to write about something that's not interesting. Like I tell them to write about like pizza, is a classic one, or like, you know, whatever. Something that is very, very ordinary, and just let go of everything in their mind. And almost invariably when I get people to write about something boring, there's a glimmer of something interesting. One or another like fundamental facts of their existential condition and how they see the world. And I'm like, "I'm interested in that part." And they've never heard that before, 'cause they've never thought of exposing it. And if I said, "Write something about your basic existential condition," they'd just completely go blank, because you're thinking it should be a certain shape. Sorting your mind based on what's superficially interesting to other people is a great way to make your mind go blank and forget everything interesting that you know.

Yeah. It does seem to come back to giving yourself permission to get away from expectation, to being curious rather than judgmental, and really leaning into those parts that are exciting. That was an interesting meta point you made, where if it feels really hard or sticky then you're probably doing it wrong, and just try anything else and see, you know, see what you like about that.

Absolutely. I wrote this post a little while ago, which I think is a good post, I think it was accurate, about writer's block. Most people think that writer's block is like a lack of discipline. Like, "Real writers just work harder. They just get the words down." But I think usually what's happening with writer's block is that you're misaligned. Like you're trying to write something about a subject, but you're trying to write an opinion that is not actually deeply held, or you're trying to imitate something else you think ought to have—Like, it's usually pretty easy to just call up an image of something or like a memory of something or the idea of something in your head and just write down the mental impressions. The impressions are there. The problem is if you disagree with them. That's where you get blocked as a writer. Right?

Like, you want to write like a zeppelin crashing in your short story, and you're like, "Well, gosh. I can't describe that in a fancy way, so I'm just not going to describe it." Right? But you could just write, "The zeppelin crashed." "And then the blimp went down." And then you could fix it later, or not. Writer's block is usually lack of self-acceptance.

Yeah. It's something that I say often around procrastination, is that procrastination is giving you very valuable information. Right? All of the feelings that we're having, there are no positive and negative feelings. These are just feelings from our subconscious, so that we feel stuck or unmotivated or confused, that we can treat this as a very valuable signal and try to figure out what it's trying to tell us. I think that's the sort of—A meta habit with this that I try to build, is rather than, you know, flinching from that, thinking of this feeling as negative, something to be avoided, and particularly not identifying with it. You mentioned this, like, "Oh, I'm not able to sit down to write. I must not be a disciplined person." That's a really easy leap to make if we aren't being curious, if we aren't interested in what these signals have to tell us. That if we can work with them, presumably we can incorporate them, and anything that we end up with on the page will be much stronger for it.

Absolutely. Yeah, like procrastination, people's response to it is like, "Do it harder." And then doing it harder never works. It's funny, a number of clients I work with, and I expect this to continue, have a story where they think like they can't write, writing's really hard, they have no discipline. And I'm like, "Well, have you engaged in written communication in the past?" And it turns out they had great careers as writers on forums or like on Twitter, but they don't think of it as writing somehow. And I say, "Well, no, the point is to make what you think of as writing aligned more with the way your brain works, not the other way around. Like, it's not like you have to learn this new weird thing that you don't like doing and then make yourself like it."

Yeah. And then I think there's something interesting that happens when you adopt the perspective of a writer. I'd be interested in your thoughts on this. I know personally when I have a piece that I'm working on, everything that I see is a potential solution or breakthrough or metaphor that I can throw onto the fire. And it creates this just more living intensely, this more rich experience of reality, because I'm looking at things through this fresh lens of not knowing. And I think that was an interesting point you made around, we're already doing all of this writing, and that all of these interactions that we're having—This could even be conversations. I think for me, having a conversation about something that I'm thinking about that could even become a piece is really key to start to hone in on what those points of resonance are, is treating all of these as opportunities for discovery.

And I think that that takes a lot of the pressure off, and also starts to dismantle the notion that the writing only happens when the fingers are hitting the keyboard or the butt is in the chair, that this identity of a writer is more just a way of looking and being curious about things.

Yeah, definitely. Definitely. I cannot overstate the extent to which you are right about that. That's totally true. Yeah. Like, the more you write—It's like, when you get seriously into photography, you start composing the world. You start seeing it aesthetically. The same thing is true if you write a lot. You start seeing the world verbally and you start to, you know, it creates new vectors of interest. And understanding your life verbally, assuming there's any change in your life that happens at all ever is like a life complete issue. Things never stop changing, and then the opportunities to examine what's going on around you never end. If you're broad enough about what the relevant subject matter is. What you consider relevant. You should consider your whole life relevant.

Yeah. I'm also—What's coming up for me too is like to be a writer, and thinking about like—We kind of went, at least I did, like not being too goal-oriented. Like, don't be too myopically focused on what you're hoping to get out of doing this. I think it's important to recognize that, hey, to one extent you're already doing some of this. You're already having conversations, you're talking to friends, you're having arguments or exchanging memes in Discord or on forums. You're having this exchange of ideas that is inherent to writing. You're already doing it in some form. But if you think about, hey, what you're looking to get out of it, you might find that there are other supporting verticals to achieve these goals that also can take off some of the pressure. It's like, I don't need to get all of this from my writing, right? I can build relationships, I can start to get some clarity around my ideas, I can start to build a brand, I get some awareness about what's going on in the world, all this type of stuff through lots of other mediums. It doesn't need to be confined to, like, "I need to be writing a book, I need to be writing Twitter threads, I need to be publishing a newsletter." That these things can support each other, but they're not necessarily mutually exclusive.

Yeah, definitely. I think, like, adopting the identity of "writer" can be a bit of a red herring. Like, people thinking, "Oh, I'm not a writer, so I have to become a writer." Like, well, writing—It's funny. We live in this hyper-verbal culture that also sort of deifies writers as this special class of people, and that's totally anachronistic and totally wrong. Yeah. And one thing is that if you look at a lot of the great genre-defining, culture-influencing writers of history, what you find over and over again is not a narrow focus on goals. You find good books, bad books. Like, lots of great writers have like voluminous correspondence, they work in multiple genres. You know, Karl Ove Knausgård is like one of the most famous novelists of the past twenty years. He wrote this five-part autobiographical series. But he also wrote a book about angels, and he's also written books of poetry. And you know, you see this over and over again. The writers who do great work are not insistent on everything looking like work, and they're not insistent on every single word of theirs being publishable, they just get in the habit of loving words and communicating a lot.

You have this program coming up that sounds really cool called "Make Something Scary," and the idea of someone who's taken on a large creative project. It could be writing, it could be just something that requires a long period of creation. And I'm interested, if someone's listening to this and let's say they chose that this is the year to write a book or to create a beautiful documentary or ceramic pot, whatever it is, and what is your kind of starting advice for them to increase their chances of success on this journey and to make that journey a little bit more enjoyable?

Well, I think part of my thing is an accountability group. The program is now full, which is great. I'll be running another one later this year, probably. But understand the degree to which—Well, first of all accountability is important. But understand the degree to which failure is okay. Failure is an important part of our artistic life. If you're free to fail then you can do much more interesting things. And one of the points of Make Something Scary is not necessarily doing something more difficult, it's doing something that you don't know whether it will be popular, you don't know whether you're even capable of doing it, but you're gonna try really hard and just see what happens. That's the scary part of scary. Like, the people in the program are accomplished people who can do difficult things. It's more like doing mysterious things, doing things where the output is unclear.

And one thing I talk about sometimes is that it's strategic to be anti-strategic, occasionally. Like you have implicit strategies for how you live life, produce things, run your relationships, and those strategies might be pretty good and they're based on a significant degree of learning and you get blind—Blinded? Not blinded. Blinkered. That's the word I'm looking for. You get blinkered, you get fixated on like one way of doing things, one way of existing, and remembering that anti-strategy is a part of strategy. If you think you're gonna fail, if you think like, "It's gonna go badly and people won't like it," there's probably more to learn in doing something like that than there is to doing something where you're sure that people will approve of it. You know?

Yeah. It brings to mind just the long-term orientation that rewards lots of experimentation and growth and taking lots of shots on goal, where the final destination is so unknown that it makes sense to explore a lot of paths and to try a lot of things in the meantime.

Yeah. Yeah, precisely. The point of creative life shouldn't be to release a bunch of little blog posts that nobody ever disagrees with that are like all roughly the same. The point is to have an exhilarating journey towards the heart of who you are and who you are in the world. Which never stops changing, so you can do it until you die.

So on that note of having an exhilarating journey of exploration, Sasha, thank you so much for being here, for sharing yourself and your wisdom. I know that I really appreciate the help that you've given me, and I think you had a lot to say today that'll help many others. Is there anywhere that you'd like to send people if something you said today resonated, or a place that you'd send them to learn more?

Yeah, if you want intermittent transmissions, then my Substack is the best place to go. If you want constant blathering about whatever, then my Twitter is the best place to go. And I am most reachable over email.

Cool. We'll drop those links in the chat. So imsashachapin.com, sashachapin.substack.com, and I believe it's @sashachapin, is your Twitter?

Yep.

Cool. So yeah, definitely check those out. Sasha, as you could tell, has a very fun perspective on things, and I think there's a lot that can be learned from his lens of looking at the world as a way of discovering your own lens. What do you find obvious that might not be obvious to everyone else. Sasha, it's been an absolute pleasure. Thank you so much for being here today, for sharing, and yeah. Very much looking forward to continuing the conversation soon.

Thank you. Yeah, always good to be here, always lovely to talk to you.

Thank you for listening to the Forcing Function Hour. At Forcing Function, we teach performance architecture. We work with a select group of twelve executives and investors to teach them how to multiply their output, perform at their peak, and design a life of freedom and purpose. Make sure to subscribe to Forcing Function Hour for more great episodes, or go to forcingfunctionhour.com to sign up for our newsletter so you can join us live.