Why Write Memoirs | Review of All the Wrong Moves by Sasha Chapin

Photo by mouad bouallayel on Unsplash

A good memoir is entertaining, insightful, and relatable. A great memoir changes you because you see yourself in it. 

All the Wrong Moves by

Sasha Chapin

is a great memoir. 

It is nominally a book about a guy who becomes obsessed with chess. But to me, it’s a book about the profound, persistent awareness some people have that we are never in the right place, at the right time, doing the right thing, and that obsession, self-loathing, and delusions of grandeur are all just different veneers on our constant attempt to escape this awareness. 

But it’s a fun book. I loved it so much that I was tempted to fashion this review like a binder full of Pokemon cards–where I am just an excited kid whipping out my favorite vignettes and quotes going, “and here’s Sasha in Thailand–the alienation is funny, but here’s Sasha with his mentor–the neediness is what makes it sincere, oh and here’s Sasha in India–what a great existential twist on a fish out of water story!”

There is so much to take from the book, I couldn’t possibly get it all into one review that wasn’t prohibitively long so I will focus on what I liked and how it changed me. (Also, I am going to talk about the author using his first name instead of what I usually do where I would say “the author” or “Mr. Chapin,” because I DM’d him on Twitter once and he answered, which means we’re basically buds now.)

This was a great memoir because it fundamentally changed how I feel about the nature of art and being an artist. It made real to me not just the value of reading memoirs, but the transformative power of writing them as well. But before I make the case that it was a great memoir, I want to make the case that it was a good memoir, one that was entertaining, insightful, and relatable. 

Entertaining

When I say a book is entertaining I mean it is funny or engrossing. 

This book was very funny. I love to laugh but very rarely do I laugh out loud when reading by myself. I laughed out loud a lot in this book, and even more often I did a smile and hard nose exhale. The first example of the wry, self-aware humor came in the first few paragraphs: 

“Anyway, like most people, I became obsessed with chess after I ran away to Asia with a stripper I’d just met.” 

Little jokes like this keep showing up, even in tandem with more sincere subjects, like when he talks about one of the main contradictions of adolescence:  

Back then, although I still didn’t like myself, I was sure I had one redeeming feature: being smarter than everyone else on earth.

He drops a similarly funny line when discussing the pros and cons of marriage: 

As an abstract principle, marriage wasn’t something I had wanted, because, well, there are lots of attractive people in the world, and I haven’t seen them all naked yet. 

The book also has a lot of great descriptions. Common writing advice on the internet is “show, don’t tell.” This means instead of saying, “it was hot,” you say, “the sun beat down on the sidewalk,” or something similar. I’ve always thought this was advice for amateurs. 

A good writer can tell with style, can tell in ways that are additive, and so allows you to own the scene in your mind. Showing is good, but telling can be better, and I think that Sasha has mastered telling with style. Like when he went to Bangkok, Thailand: 

I suggested we take a trip to Bangkok, Thailand’s capital, which is literally the hottest city on the planet. The heat feels like reality is exaggerating.

Or when he describes Hyderabad, India:  

It’s maybe not the most superficially pleasant place, but the extremity is appreciably extreme. I was having trouble fitting all of the new reality into my reality holes. Time felt slow and squishy, and my few legible thoughts crawled slowly out from under the weight of a jewel-toned blur of sensation.

He blends the ability to be funny and to tell with style in a lot of places. One of my favorite places it shows up is in the abundance of short character sketches that make up the book. One of my favorites from early in the book is this brief bio about the kid who was the king of the Pawnishers, the chess club that Sasha was in during high school: 

The Pawnishers were brought together by Liam, a boy who could bend the world to his will. Everywhere he went, a situation began. This is perhaps best exemplified by the fact that he somehow had an Internet fan base who held a real-life convention in his honor. They, a dozen or so people, flew him out to Virginia, just so they could get him drunk and make out with him in shallow, cold water. He was influential like that. So, when he informed the bookish contingent of the school that they were in his chess club, we basically all agreed to this interpretation of our lives.

If this was all there was to the book, I would probably still recommend it, but there was a lot more. 

Insightful

Beyond entertaining, the book is insightful. When I say insightful, I mean everything from going, “hmm . . .” while you’re reading because you encountered a new or clever way to explain something you kind of knew, all the way up to, “holy shit!” when some turn of phrase rearranges the value system you’d been using to navigate the world.

Some of the insightful things are little bursts of “hmm . . .” like you might get after reading the following sentence and thinking to yourself, “that’s funny but he’s right”: 

You should never do this. Never tell yourself you’ve been through the worst of anything. 

Or when he tells the story of his first discovering chess, there is an insightful and funny comment on the mercurial nature of destiny and how it shows up in our life: 

That’s when life as I now know it began. Not that I knew that at the time. The future never announces itself. Your destiny is quietly prepared offstage, until the hour when it emerges, saying something like, “Knock knock, motherfucker.”

A lot of times you can tell an author is swinging for the fences, trying to generate quotable lines, but instead they are just sounding pretentious. That does not happen in this book. It is full of one or two-sentence insightful comments that are eminently quotable, like my favorite one below, but all of them add to the story and emerge organically from it: 

Without a little friction, life is just lunch.

For me, the place where the insight of the book really shows up is in the discussions of chess. I have always daydreamt about being an intellectual, so I just took it at face value that chess is important and has value. But I never really grew to like it myself, and I never really understood why people revered it beyond poker or playing a musical instrument or any of the other hobbies that aspiring intellectuals take up. This book changed that for me. I get why people love chess now. I combed through all Sasha’s meditations on chess and picked my two favorites. 

In this first one, Sasha relays the excitement of chess not by comparing it to other hobbies or putting it into a historical context, but by arguing that chess is a compulsion because it appeals to the way we as humans evolved:

Psychologist and author Steven Pinker says something about music that I really like. He calls it “auditory cheesecake.” Just like cheesecake is so satisfying because it’s more sugary than the foods the taste buds were evolved to experience, music overwhelms eardrums that were designed merely to track the movements of predators and the grunts of our loved ones. It seems like there’s something similar going on with chess. Chess pours pure sugar down cognitive pathways that were originally forged for the sake of simple survival. Our sense of pattern recognition, crucial for making our way under the stars, is tickled when we see lethal potential lurking in an innocuous-looking pawn structure. Our sense of geometry, crucial for anticipating the flight path of a potentially delicious bird, is pushed to its limit when we calculate a complex tactic. And perhaps most importantly, our sense of social status, evolved for the wearying task of navigating the pecking order, finds satisfaction not only in the competition itself but in the hierarchy of the pieces—in the thrill we feel when our queen savages its inferiors on our opponent’s team. 

In the second excerpt where he discusses his love of chess, Sasha is discussing what humans can and can’t do–where we fit in the world–and explains that the most human ability is abstraction, and chess is abstraction dialed up to 11: 

In light of all this, in my opinion, if there’s one particular thing that distinguishes us, it has to be abstraction. The way we take our fleshy, silt-covered world and cover it with metaphors, maps, formulas, and poems—how we incessantly make wickedly complicated models of everything we live in. According to us, the sea is wine-dark, the earth is composed of metropolitan areas, and some numbers are irrational. If you accept this, I submit that chess is about the most human thing you can do. Lots of animals fight. But we say, okay, just as an experiment, instead of fighting with our actual bodies, maybe we could spar with teams of funny little wooden dolls, each of which moves in a different fashion, in a simulation of the stratification of human society. Then perhaps we’ll come up with a whole language describing our imaginary battles, such that we might say, “Sasha played a subtle knight maneuver in the Czech Benoni.” Eventually, someday, it’s even possible that we’ll develop computer programs that play this game better than we do. Chess takes the most banal act of all—violence—and makes it a symbolic ballet with a culture entirely of its own. 

Relatable

So far I’ve discussed the universal appeal of the book, but I want to dive into why the book touched me so much. In the early part of the book when Sasha moves to Thailand, I could relate a bit because I spent three years in Asia after my undergraduate–albeit in China. But some of the lines like this one where he’s discussing trying to learn Thai were relatable to me and made me laugh: 

[O]ccasionally I overheard one of the maybe one hundred words in my vocabulary. “Oh,” I would think, “someone is discussing pork.” 

But it went a lot deeper than that. I don’t know where I first became aware of Sasha’s writing, but the first thing I read by him that was a real gut punch was Review: CK One on Substack (open it in a new tab–finish this review first). In it, he talks about being fundamentally aware, as a child, of a separateness between himself and the rest of his peers. I was also aware of this separateness. I did not expect him to also write about this theme in his book, but I found that it was pervasive, and explored on a much deeper level than in the original essay. 

I really felt this anecdote about how his enthusiasm for things, life, ideas–whatever it was, made him somewhat disagreeable to his peers: 

As much as it might have seemed so, I didn’t want to be disliked. What I wanted was to communicate my constant excitement about all the slivers of reality I could touch and gather with my overactive mind. Nearly everything thrilled me. Sometimes I would become so possessed by my private thicket of thoughts and associations that I’d start sprinting down the street, chased by some fulminating notion, and would often collide with a mailbox or a stranger. Like instantly blooming clutches of bougainvillea, refractions of the world sprang all over my insides, and I wanted to get them out. But the only result of this instinct was my social unacceptability.

This is a feeling I still carry with me, to an extent. It is why I write things and publish them, to share that enthusiasm.

Sasha goes on to talk about how this feeling of your enthusiasm separating you from others compounds over time, until it turns into shame, a feeling that you are unwelcome and being judged: 

This gave me a pervasive shame: a feeling that the project of my very being had been given failing marks by some invisible and final council. And this shame never really disappeared completely, and in fact only abated slightly, even as my social standing improved.

And this discussion of his feeling of not being a part of, but being outside of, is what opens the door to his obsession with chess, of which the book is a chronicle: 

And when I played chess, I felt, like, different. On the chessboard, the shame that plagued me was temporarily dispelled.

In a funny way, I think that this sentence might be the one in the book I relate to most. So many people I know, myself included, have spent large swaths of their lives running away from something. The problem is they do not realize that’s what they’re doing. They’re trying to escape, and indulging in escapism, but not in a fun, harmless way like reading romance novels or playing Dungeons & Dragons. Instead, they glom onto the first thing which deadens the noise and captures their attention completely, and I don’t need to parade out example after example to tell you that this doesn’t usually end well. 

The obsession becomes a kind of proxy for life, taking it over:

Badly played chess is kind of like badly played life. Real problems are dealt with poorly or not at all, while much effort is expended on avoiding imaginary danger. Rather than dealing with the reality of the situation, you act as if you were playing the game you wish you were. Then you collide with the boundaries between the actual and the hypothetical.

Like I said earlier, to me it’s a book about the profound, persistent awareness some people have that we are never in the right place, at the right time, doing the right thing, and that obsession, self-loathing, and delusions of grandeur are all just different veneers on our constant attempt to escape this awareness. And I think Sasha probably agrees: 

Even in the most exquisite moments of my life, I had always wanted to leave for somewhere else, or be something different.

For Sasha, the attempt to escape this awareness came with a move to Thailand first, and then with a consuming obsession with chess. The tricky part is that there are funny, beautiful, edifying facets of the escape, as there are with most escapes. But ultimately it is just that: escape.  And (spoiler alert, sort of) in the end, he doesn’t draw some big conclusion about why the escape is great or why it’s terrible. He simply tries his best to stop escaping, to enjoy what’s happening, and to say, “this is nice.” 

Yet still, he remembered the escape for what it was: the highs and the lows, the grandeur and the degeneracy. And this nuance, to stop attempting to escape and to simply be, but to appreciate those parts of you that you forged in the escape, this is the place where life is lived for most of us. 

Two Arguments

I am currently a big fan of Sasha’s Newsletter and writing course. In early 2022, he wrote an essay called How I Attained Persistent Self-Love, or, I Demand Deep Okayness For Everyone.

Being the kind of writer I am—a memoirist, I guess—has always struck me as a little sad, because it means that I’m constantly wondering whether any definable portion of my experience is marketable. I’m forever observing myself from a mercantile perspective, noting whether any of my minor melancholies or brief discomposures might be salable. Essentially, I’m a parasite on my own life. Any compelling character I meet excites me not only because they’re exciting but also because I might describe them profitably. If I met you, I’d probably wonder how I’d condense your characteristics if I needed to put you in an essay.

As someone who similarly aspires to write memoirs, to make and share meaning out of the little vignettes of my life, I understand how it can feel like this vocation—nay, this compulsion—detracts from the experience of being present in one’s own life. I have felt this in a real way. Specifically, as someone prone to looking for a way to “escape” in the way I am and I assume Sasha is, becoming a memoirist can be a great rationalization for never being fully present. Under the rationale of logging an anecdote and withdrawing from the situation, you have a credible excuse to escape at any time.

I want to grant that there is some truth to this, but I want to offer two arguments for why I think that writing memoirs is still a good and noble pursuit, why I will keep doing it, and why I think Sasha and others should as well. 

I’ll start with the weak argument, which is that this constant examination of the people who fit in my life and how I might record them as a character has made me more present in a more purposeful life. I also am afflicted with constant thoughts of, “how would I write about this person? How would I introduce them to this story? Does this vignette in my life have value to be written about?” However, I was such a space cadet before, that doing this has made me more present in my life, not less, because I am actually contextualizing things I’m doing. Another totally unexpected side effect is this persistent contextualizing also has encouraged me to start planning and doing more noteworthy things. 

The stronger argument is this: everything isn’t about me. The primary purpose of an artist (and I believe writers are artists) is to be a conduit. An artist opens a channel for people who consume their art, so that during and after consuming they can feel something, and connect to something. The artist’s cause is to entertain, challenge, and educate. To do this, to become that channel, they have to bare a part of themselves. And while there may be riches and fame for a small minority of artists, most of the great artists of history never got a check and only reached a few people, but in making the art, in making themselves a channel to something bigger, they enabled the people who consume what they make to be a part of that. 

And for me, I keep writing as a way to pay forward the experience I have had as a witness to art, the times when a story someone else tells opens me up and lets me see myself and the world in a new way. So I would like to offer a small consolation to Sasha and other similarly-minded memoirists. Yes, you may be losing a small part of yourself as you observe your own life, attempting to anecdotize everything that happens for a project later, but that’s okay. 

The little bit of you that you lose by the persistent attempt to record and share parts of your life is a small sacrifice when you consider that this practice—this drive to figure out what matters then distill and share it—may someday result in a work of art which reshapes the way someone feels about the world, or even defines an entire era of their life. 

Like you may write a book that finally convinces someone to try to learn chess. Or you even may write a book that inspires someone to write their own.

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Note: if you made it this far and enjoyed this review but are worried I already shared all the good parts of the book, I assure you I did not. The initial list of highlights I made that I thought were top 1% in quality was three times this length. You can buy the book here.