Writing Coached

At some point in high school I realized I was a good writer. It was the partner exercises in English class. I’d write a first-draft essay for homework and exchange it with a partner in class the next day. Drive a red pen through each other’s work and exchange feedback. At first I thought it might be a fluke, that the bright girl across from me had produced something so uninspired. Surely she hasn’t read this back to herself, or she’d hear how awkward it sounds, right? But this continued to happen, with almost all partner combinations, over the years. If the writing of my peers is poor, maybe that means mine is good…?

It adds up. My parents are two of the best writers I’ve ever met. My brothers are all strong writers. And we genuinely enjoy grammar. Many a family car trip has seen a heated conversation around some grammatical intricacy. (Um, do other families do this?)

There were some memorable stand-out papers in high school. One on the abundance of animal imagery in A Tale of Two Cities that received top marks and made my teacher’s red pen go “wow, I can’t believe I never noticed this.” (Oh, to be able to recover those mid-2000s Word docs…) A clever take on the effect of audio correction on the music industry for my college essay. While others lamented the inclusion of writing in the SATs and opted instead for the ACTs, I delighted in my newly elevated score.

I took one English class in college, a Shakespeare elective my first semester that was one of my favorite classes of the entire four years. But I was caught up in math, French, and psychology classes. To dissect Titus Andronicus, or to unravel correlation from causation in psych studies, or to prove the existence of the irrational number e with my Analysis cohort? I leaned away from the literary.

A few years pass after graduation and I yearn to be a writer. Not as a job, necessarily, but generally. The possibility feels lost to the past. I’d need training, more training than a simple college elective here and there. Something intense, rigorous, from an expert, with a certificate attached. How to get this training, without doing something wild like quitting my job and embarking on a Master’s? It all felt so far away. The plot of an alternate timeline that I’d long ago bid adieu.

Because I had a lot of blockages. For one, I didn’t know the words. Missed my chance there. As a kid, when I read the most, my dad always encouraged me to keep a dictionary alongside; look up the words I didn’t know and write them out on a piece of paper for retention, he suggested. I tried this and hated it. It completely disrupted my reading flow, pixelated the story. I didn’t want to step in and out like that. So this became one of my blockages. The “I Don’t Have a Good Vocabulary” blockage.

I also didn’t know if my ideas were any good. I had this one idea about the meaning of “I miss you.” How many different ideas we throw behind this one phrase. How much suffering is knotted up in those words. How full of love, or resentment, or just about anything, that phrase can be.

One sunshiny Saturday I sit down at my laptop and try to get these ideas out. It comes out as a short, bulleted list. I read it back with disgust. At the writing, the execution. The words are boring, shy, flat. Whatever was floating around in me hadn’t found its way onto the paper. I feel blocked and dissatisfied. I delete the doc, close my laptop, embarrassedly pretend it never happened. The “My Ideas Might Suck” blockage.

Sasha Chapin’s existence is surfacing on my radar around this time. I’m following him on Twitter, which leads me to his blog, and his writing quickly becomes a favorite. He has this ability to throw descriptive, unusual, peacocky bright words into meaningful phrases, full of wisdom that feels well beyond his 30-something years. And yet never soapboxy. Quite the opposite. “What the fuck do I know” airs, even though you get the feeling he definitely knows some stuff. Unusual subject matter; in fact, classically difficult-to-describe subject matter: the psychedelic experience, smells. (How do you describe smells?! Other than “it smells like this other thing.” It makes me think of The Giver, and Jonas’s complete dearth of vocabulary for his newfound ability to see the color red. All he can say to describe it is that “a quality of the apple… changes.” But Sasha finds a way.)

In my career explorations, I consider copywriting. I DM Sasha for advice and he quickly sends a lengthy reply. Full of his best tips and tricks for freelance copywriting. Apart from the clear insight, I’m blown away by his generosity and friendliness, sharing all of this on the fly for some random internet stranger with 0 tweets on her avi-less profile. I feel so grateful that I order his book, kind of as a thank you.

Sasha bills himself as a writing coach on his Twitter bio, so I make a vague mental note in case I decide to pursue copywriting seriously.

A few months pass and this writing blockage intensifies. Something in me is calling out to be expressed, to find a way out of this body. I daydream about having a blog, about connecting with others out there in the world who like to think about this stuff, too. I’ve never had online friends, an online community. On Twitter, where I was consuming without participating, I enviously watched so many others form community without me. I was not one of those people, like so many I knew, who grew up on internet forums. My “real-life” friends don’t feel the same pull to Twitter that I do, so I felt alone on there, not sure how to dip my toes in. I knew that my people were out there, waiting to be found. If I could somehow shepherd my ideas towards them, we could exchange so much beautiful energy.

So this is another major blockage. The “Being Myself Online” blockage. It’s also keeping me from starting a blog, because of the public-ness, the inherent vulnerability.

It’s kind of amazing how often I follow an unwritten rule, without realizing I’m doing so or questioning the rule. But eventually I start to notice the rule. Then I start to think, why am I following this rule? Who wrote this rule? What happens if I break it? And the rule dissolves into thin air.

The rule I was subconsciously following for a while was that paying for writing coaching would only make sense if I were to pursue writing professionally. Why not get coached for writing as a hobby?

Sasha and I do a consult. We talk about my blogging goal and some of my writing ideas. He is charmed by the “I miss you” idea. Charmed! A bona fide writer!! One of my favorite writers!!! Is charmed by an idea I want to write about!!!! Even this simple validation makes me want to open my laptop and give it another shot.

Later that night, I’m too excited to sleep. My mind is expanding outward in all directions. I could be a good writer. In this lifetime, even. A real writer who I respect seems to believe it’s possible. A few nights later, I lay in bed with my then-partner, Ryan. He notes that I seem really inspired lately, excited and motivated. “Did you know,” I ask him, “that you can just reach out and grab things that you want in life?” The surrealism of the transition is overwhelming.

The coaching turns out to be as effective as advertised. Well, you’re reading my writing this very second, decide for yourself. It’s also more fun than I had expected. My idea of becoming a good writer had been sitting down with an Expert Writer and their red pen. Going sentence by sentence, talking structure, grammar. Quibbling over word choice.

And it’s nothing like that with Sasha. Our sessions are fun, friendly chats. Feels like they’re more about life than about writing, and I also happen to exit each conversation a stronger writer. Writing isn’t really separate from life. The “Being Myself Online” blockage is blocking my writing, but it’s also blocking me generally. Another example: shortly before working with Sasha, I met Ryan and Walker, two of my closest allies in the world, and also two of the most playful humans I’ve ever existed around. I never realized how seriously I carried myself through life until I started getting constant exposure to their silliness. Just as I’m learning this about myself, I start working with Sasha, who immediately picks up on the seriousness behind my words, and invites me to bring playfulness to my writing. A life goal that doubles as a writing goal.

Like any good therapist, he helps you identify your blockages, conscious and un-, and probes at them with you. Like any great therapist, he provides tools that you can run off with on your own. We only did four sessions.

Sasha continues to care, long after the Venmos ceased. He follows me on Twitter (where I post all the time now!), subscribes to my Substack, checks in on me and my writing process from time to time. That genuine decency that came through in his copywriting DM, persists.

There are a million ways to find self-expression. All kinds of modalities. Maybe for you it’s throat chakra-opening yoga. Or learning to sing. Or finding the right therapist. For me it was getting writing coached by Sasha.

Cover art by Sílvia Bastos.