Sasha Chapin on Self-Love, Divorce, and Spiritual Awakening

an introduction to a new kind of spiritual writer

Photo by Christina Brinza on Unsplash

“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.”

–Sasha Chapin, All The Wrong Moves: A Memoir About Chess, Love, and Ruining Everything

In All The Wrong Moves, his globe-trotting, literary memoir of the competitive chess world, Sasha Chapin writes, “Essentially, I’m a parasite on my own life.” But if Sasha was ever a parasite, he’s been through a bit of a metamorphosis.

Sasha is an award-winning (former) journalist, a memoirist, a writing coach, and, most recently, someone who’s written a lot about self-therapy, psychedelics, and spiritual awakening in his popular Substack newsletter.

As a therapist, meditator, and seeker myself, I’ve been moved by Sasha’s willingness to self-experiment, his candor in sharing his results, and his poetic flourish for describing the qualia of consciousness. In this post, I’ll introduce you to three of my favorite pieces of his writing, why they matter to me, and why they could matter to you, too.

How I Attained Persistent Self-Love, or, I Demand Deep Okayness For Everyone

“Deep Okayness is not the feeling that I am awesome all the time. Instead, it is the total banishment of self-loathing. It is the deactivation of the part of my mind that used to attack itself. It’s the closure of the self as an attack surface. It’s the intuitive understanding that I am merely one of the apertures through which the universe expresses itself, so why would I hate that? It’s the sense that, while I might fuck up, my basic worth is beyond question—I have no essential damage, I am not polluted, I am fine.”

This is the first of Sasha’s essays that I read, and the one that made me a fan of his writing. Now, the idea of "persistent self-love" or "Deep Okayness" may sound to you like a mushy glob of ill-defined woo, or it may be a state you're already, to some extent, familiar with. But for most people, the idea will just seem weird. I think the best way to explain it is through contrast with its opposite, which is self-hatred, self-loathing, or chronically beating yourself up. 

There’s a story about the Dalai Lama. At a small conference in India, in 1990, the meditation teacher Sharon Salzberg asked him, “Your Holiness, what do you think about self-hatred?” The Dalai Lama appeared confused, and asked, “What’s that?” After Salzberg took the time to explain this experience that so many of us share, he simply responded, “How could you think of yourself that way?” 

This anecdote has been bandied about in the Buddhist world for decades. But the reason it's proved so popular, I think, is that it captures the idea that there might be something uniquely modern and Western about self-hatred. Now, plenty of people have criticized that conclusion. But if it’s true, it’s a problem, because it means that traditional Buddhist training might not have an antidote for it. 

In the experience of many meditators, self-hatred means we can use the traditional teachings to fuck ourselves up. We flagellate ourselves for not being good practitioners. We use meditation to anesthetize or try to destroy parts of ourselves we don’t like. We use the teachings to spiritually bypass our emotions, relationship needs, and past traumas.

So Deep Okayness, at least the way Sasha frames it, isn't necessarily the same thing as “enlightenment” or awakening in Buddhism or the yogic traditions.¹ It's more like the opposite of the self-hate that some of us experience as our baseline orientation. And when that self-hate is healed, spiritual practices can become much more fruitful.

So how can we get from self-hatred to persistent self-love? Sasha writes, "The way I attained Deep Okayness has nothing to do with what normally happens in a therapist’s office. And that is of concern to me."

As a therapist, it's of concern to me, too. For over 100 years, the dominant paradigm in clinical psychology has been, as Freud put it, "transforming your neurotic misery into ordinary unhappiness." But the ordinary unhappiness of a bourgeois in turn-of-the-last-century Vienna--or even 21st-century California--is no longer enough. Not when we have alternatives. 

Some of the alternatives that Sasha pursued included Existential Kink, “introspection” techniques, MDMA, and LSD. As a therapist, I feel like I should say “don’t try this at home,” but that’s exactly what Sasha did. And to his credit, it seems to have worked for him. He reached a level of subjective wellbeing that would be rare to achieve through traditional psychotherapy.

To be fair to therapy, though, some of the techniques Sasha used to achieve Deep Okayness do have their origins in therapists' offices. Specifically, Sasha talks about using a form of parts work that sounds a lot like IFS (Internal Family Systems therapy) as part of his psychospiritual tech stack. And a growing number of therapists are using psychedelic-assisted therapy in their practices. There’s also a long history of psychotherapists who have gone beyond “ordinary unhappiness” as a goal for their clients, arguably stretching all the way back to Carl Jung and including the humanistic and transpersonal psychologies of the 1970s, as well as more recent approaches.

I had my own experience of “the closure of the self as an attack surface” in my twenties. It wasn’t anywhere near as dramatic as Sasha’s–in fact, it’s almost embarrassing to relate, because it happened in an NLP life coach training. 

You see, up until that point in my life, I had periodically beaten myself up with negative thoughts about myself. Not coincidentally, I also suffered from frequent bouts of depression. At some point in that 120 hour training–which was crammed into two weeks in a business hotel–I realized how counterproductive those thought patterns were. I saw that not only was I torturing myself unnecessarily, but these thoughts also kept me from making progress toward any of the goals I cared about. And somehow, a switch flipped in my brain, and I stopped doing that. 

Instead, I replaced my negative thoughts with thoughts that supported me. It’s not that I adopted a Pollyanna-ish focus on positive thinking–when I had problems, I would analyze them and try to come up with solutions. But I didn’t beat myself up for having the problems I had. Instead, I started talking to myself more like a good friend. It was a fundamental shift in my orientation toward myself, and one that has remained consistent ever since.²

I agree with Sasha that more people should be able to find Deep Okayness. In fact, I believe it's our birthright as human beings. 

I also believe that psychotherapy has an important role to play in this collective upgrade, especially if more therapists can experience Deep Okayness for themselves and learn how to help others get there. In order to do that, we need a massive tech update, one that might include trauma-focused therapies like EMDR, IFS and other forms of parts work, contemplative and nondual approaches, indigenous healing traditions, and for some people, responsible use of psychedelics. 

But as Sasha demonstrates (and my own experience confirms), psychotherapy isn’t the only viable path. Most of my clients come to me to solve a specific problem, not to find Deep Okayness (though some of them may find it along the way). And plenty of people looking for an experience of self-love or Okayness seek it–and sometimes find it–outside of therapy. By sharing his own experiments and experiences, Sasha is serving as a guide for other travelers along this road.

My Recent Divorce, and/or Dior Homme Intense

"In May in Silverlake, the jasmine blooms enormous, and its thick glamorous treacliness, along with its armpitty undertones, cradle you while you saunter amongst the hot people and overpriced real estate. Guard dog urine and puffs of weed accompany the jasmine, and the sun sweeps clean through you, animating colors so vivid that your meagre awareness feels unable to hold it all, like it might spill over at any time."

I'm including this next piece not because of what it has to say about relationships or personal growth, but because Sasha's writing is so damn good. This is where his background as a memoirist comes in, as he writes about the breakup of his (previous) marriage with memorable precision and poignancy. One element that stands out in this essay is Sasha's extended digressions on Dior Homme Intense: "It’s the pale core of spring earth, the slender butter of morning, the lightest air breathed from the mouth of a slightly musty hallway."

As someone new to Sasha’s writing, I was a bit bewildered by his seemingly encyclopedic knowledge of fragrances. (Like, is there some kind of backstory I'm missing? Did he spend ten years apprenticed to a master parfumier in rural France?) But the fragrance writing serves as what the poet Jane Hirshfield calls a "window"--a unique angle from which we can see the subject matter--in this case, Sasha's divorce--in a different light.

"In the end, Dior Homme Intense winds down beautifully—while it’s quite large and stately in the opening stages, it falls, after a period of hours, like an elegant melancholic onto a therapist’s sofa, into a prettily crumpled little package.... It curls into a new resolution, a small cloudy pearl, its giant mass seemingly collected inwards, as in the formation of a quiet star. That’s what I hope the better memories of these years will do—fold and gather, losing all of their heat but not all of their light."

Ultimately, it's a compelling meditation on the end of a relationship--something all of us have experienced, though in an infinite spectrum of variations. But as I've found many times, both as a reader and a therapist, the very specificity of one individual's experience often helps me reflect on my own.

Hey, why aren't we doing more research about spiritual awakening

Awakening is a phenomenon described in some of humanity’s oldest religious scriptures, including the Buddhist suttas and the Upanishads. It’s a persistent change in consciousness, from ordinary, self-centered, thought-based existence to one of greater openness, compassion, and freedom. But it’s not just the domain of long-dead sages: thousands of people around the world report experiencing this way of being on a day-to-day basis. 

In this essay, Sasha and Kathryn Devaney (co-founder of the Berkeley Alembic) make a strong case for doing way more research on this phenomenon. They open with a hilarious, and apt, analogy: 

"Imagine that there were a bunch of intelligent people trying to figure out how best to kill other people. This isn’t hard to imagine, since this is the world we live in. But let’s add another fun little wrinkle: imagine, also, that in this alternate world, some people are capable of killing other people by shooting deadly lasers out of their eyes.… But imagine that, for some reason, there wasn’t much interest in this in the mainstream combat community, and thus, laser-shooting remained underexplored and poorly understood. Imagine if you asked some professional martial  artists about the death lasers and they said, “yeah, don’t know much about that, it’s not really my research area so I haven’t looked into it, anyway, spinning back kicks are cool.” That would be odd, right?"

In other words: spiritual awakening is to conventional psychotherapy as shooting deadly lasers out of your eyes is to a spinning back-kick.

Given that the results of spiritual awakening are, reportedly, orders of magnitude better than those of conventional forms of therapy like CBT (“ordinary unhappiness” again), why aren’t scientists more interested in it? Shouldn’t we be trying to help everyone experience this level of psychological freedom?

While noting the extant research on meditation, Sasha and Kathryn raise some really important, unanswered questions about awakening: “Is there any way to tell which practices will be most effective for which people?” “Is there one kind of awakening, or multiple kinds?” And importantly, “How can we prevent adverse meditation effects?”

While Sasha and Kathryn call for more research in this area, they don't spend much time discussing the folks who are already doing some of that research. They do mention Shinzen Young and Jay Sanguinetti’s work on sonication-enhanced meditation, which is fascinating. But a number of other researchers have addressed the questions Sasha and Kathryn raise in their essay.

One of the most well-known experts in this area is Andrew Newberg, MD, author of the book How Enlightenment Changes Your Brain. Another is Dr. Jeffery Martin, author of The Finders and founder of the Center for the Study of Non-Symbolic Consciousness. And then there’s Richie Davidson, who’s been scanning the brains of adept meditators for decades and co-authored the book Altered Traits with Daniel Goleman. 

Sasha and Kathryn are right--we need way more research on awakening. And not just on expert meditators and those who’ve already gotten there, but on how ordinary people like you and me can experience this fundamental shift in consciousness. 

As a long-time spiritual seeker, I’ve had my own ups and downs on this path. There was even a brief period in 2020–after some intensive meditation during the lockdowns–where I thought I might have reached stream entry, the first of the four classical stages of awakening in Buddhism. During this period, I felt a remarkable sense of ease and well-being. But it eventually faded, as I got caught up in day-to-day stress and identification with thoughts. Sometimes I question whether this experience was real, but temporary, or whether I was just fooling myself. Is it still there somewhere, in the background of my experience? 

As Sasha writes in another essay, One Year of Okayness:

“Feeling that you are done is a trap. Feeling like you have permanently attained some permanent clarity is a trap. It is a confusion about how the mind works, perpetuated by our insane desire to be a static thing under our control, and our insane desire to get a ribbon for some way we are. It’s a trap for me as much as it is a trap for spiritual gurus who declare themselves perfect and then fuck their students or whatever. Self-compassion, or any other practice of self-development, is a day-by-day practice. It requires renewal.”

I agree with Sasha and Kathryn that we need more research on spiritual awakening. But we also need more first-person, narrative writing about these experiences, and that’s ultimately why I’ve come to value Sasha’s work. If you’re seriously interested in spiritual and emotional growth, I think you’ll find value in it, too. Any of the essays I’ve linked to here are good places to start. And if you’ve read this far, I highly recommend subscribing to Sasha’s newsletter and following along with his journey.

---

Thanks to

Charlie Becker

,

Ishan Shanavas

,

Steven Foster

, and

Latham Turner

for valuable feedback on this essay.

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1. Unless it actually is. I’m not 100% convinced on this one, especially because one of the core features that people living in some kind of awakened state describe is a sense that everything is fundamentally okay.

2. As Seneca wrote in one of his letters (quoting Hecato of Rhodes): “What progress, you ask, have I made? I have begun to be a friend to myself.”