This is your friend Sasha Goldstein.
And you are reading the kinda-sorta-first instalment of The Night Letters — irregular missives about creative experimentation and invention, literary, visual, and otherwise, from the foggy shores of British Columbia.
This is only the sorta-first instalment because it is actually an early version of the introduction to these letters that I wrote on The Desk, and nearly didn’t publish. Yet, here we are. I suppose this is more like a prologue.
Few people, even among my close friends and family, know me as a writer. Most know me as a designer — or at the very least as some sort of digital freelancer. Although I studied journalism and have been an intermittently practicing writer for most of my life, writing never fit neatly into my public persona and so it was something I rarely shared or acknowledged. The nature of this obfuscation is so far-reaching that it is worth saving for future digressions (hint! The next letter), but for now, you might consider that this project represents a sort of public coming-out that has been years in the making.
What to expect?
Good question. I’ll tell you when I find out. Even as I write, the form of this thing is still taking shape. I am writing to you from inside of it. I have some ideas about how it might turn out, but we won’t know until it has matured a little.
I feel a little like Jonah, broadcasting live from inside The Whale.
The acoustics are pretty good in here, so allow me to start by sharing the story of how (and why) a designer with no intention of publicly becoming a writer launched a writing website, filled it with essays, and found his way into your inbox.
An Identity Crisis, an Idea
It was April, and I, like everyone else, was wallowing under a stay-at-home order in BC. I had shut down my news feeds (too apocalyptic, depressing), and in the resultant silence I began reading newsletters, just like this one. In the solitude of lockdown, it felt good to receive letters from intelligent, articulate people, wondering aloud about the state of the world, sharing their fears, their challenges, their ideas. It was gratifying over time to get glimpses of the humans that lived beyond the keyboards. Even though none of us knew each other, it felt like I belonged to my own little society of correspondents, reporting from different walks of life and from far-flung corners of the world.
It had been years since I’d published any substantive writing of my own. At one point I had been very sure I would be a journalist. Later, I lived overseas on the volcanic coasts of South-East Asia and wrote long-form letters to friends, partially to help fight the pervasive loneliness of distance. Writing those letters was therapeutic, and putting my thoughts onto paper helped me understand them.
I decided to write a daily newsletter, from myself, to myself, inspired by those voices in my inbox. A little like a journal, but more literary.
I sat down to write one quiet spring morning. There were flowers blooming outside my window.
To my chagrin, words did not immediately come to me. They came haltingly, like water flowing from a well’s nadir: drip, drip, drip. I managed 300, maybe 500 words on a good day. I struggled to come up with ideas, so I began by observing things. I wrote about going for walks, the trees and the neighbourhood around my house in East Vancouver. I wrote about graffiti. I wrote about not knowing what to write about. I wanted to publish these creative hairballs somewhere, and had not yet developed the endurance required to write for more than an hour at a time, so I moved them to a Substack feed.
On good days, the drips would turn into a trickle, or even a steady flow of writing. On rare, inspired days, the words would gush, tumbling over one-another to get onto the page. I would finish exhausted, and come back the next day to a slow drip, drip, drip once again, hoping desperately that there was water left in the well.
Usually, there was. Plumbing the depths was difficult sometimes, made me want to light myself on fire sometimes, drove me to hysterics sometimes, but I persisted, resolved to lash myself to my chair if necessary. I continued to write daily. I began tripping over inspiration in things I encountered. As is so often the case with creative pursuits, once your antennas are attuned to the right frequency you start finding ideas hiding everywhere. I began spending more time on each piece.
I published a long-form piece on why we still use email, and realized that I wanted to publish more essays. Suddenly Substack — an email newsletter platform — seemed like a poor fit. I looked for alternatives. I considered Medium, but it felt too crowded. I wanted a space of my own.
Fast-forward some months. The Desk was live. I was writing daily, feverishly, struggling to publish twice a week while maintaining my design business. Why? I had decided that this was a reasonable schedule. It was not.
Even as I scrambled to maintain my output, I wrestled with questions of form and scope. Was I penning a blog? A newsletter? An online magazine? A portfolio of work? Was I hoping to get published? The writing was no longer observational. It had gotten more digressive and expositional, grown hair in strange places. I barely recognized it. It had morphed in a matter of months from a benign daily ritual to an all-consuming many-tentacled monster. The worst thing was, I didn’t know why I was doing it or where it was leading me. I just knew that sticking with it felt like the right thing to do; that I had accidentally discovered a well-spring of creative energy, and that I’d damned if I didn’t put it to work, lest it be lost.
Yet, this writing practice didn’t fit into any of my plans. I had started a busy web & UX design company two years prior that needed care and feeding. I had convinced myself that my mission was to succeed as a designer, to rise independently to the top of my chosen craft. There is a lot to unpack about my duelling fixations with independence and corporeal success, but suffice it to say that they have often been at odds.
As time wore on, I grappled with a growing fear that, like other creative endeavours before it, this would never reach an audience. The many unfinished projects sitting in storage boxes and on old hard-drives haunted me like spectres even as I tried desperately to imagine how to bring this one to life.
I know a thing or two about shipping and launching digital products. I’ve done it. I’ve helped others do it. I’ve built a career on doing it. One thing that is so universally true that it is practically canon is that in order to succeed, a product must serve others.
But this wasn’t a digital product per se, and the narrative didn’t make sense, at least not to me: a designer masquerading as a writer, publishing long-form essays about old Japanese cafes and mountain bikes. I was barrelling towards an identity crisis, one paragraph at a time. When friends and family asked what I was up to, I would mutter a few vagaries about writing something and change the subject immediately.
I continued to struggle. I knew that the writing was giving me permission to explore things that I found curious; to turn over stones and look underneath them for worms and centipedes. But I wanted more. I wanted a mission to give meaning to my efforts: a goal against which I could measure some sort of progress, day by day — and that meant figuring out how to use writing to help people.
And then I thought of those letters that had compelled me to begin writing once again. Of how those voices in my inbox inspired me to find my own.
It occurred to me that perhaps the not knowing, the striving, the ambiguity, the “in-progress” part of “work-in-progress” is precisely what's important, rather than a polished final product or a perfectly staged narrative or whatever. To be committed to creating any sort of legacy at all is to live with the cosmic pain of not knowing whether one’s work will leave a mark; whether it is worthy of an audience; whether the path one is on is right.
I have many projects and experiments to finish, some literary, some not. Perhaps, in sharing that in-progress part, I can enable you, and you can enable me. Perhaps we can do this together.
I can promise you this: I don’t know any of the answers. I know a few things about technology and research, about foreign culture and off-grid travel, about writing and design and branding. I don’t want this to be a “brand” — some sort of contrived, commodified experience designed to sell something or capture market-share. I want this to be authentic, unfiltered, honest, personal, and messy. I don’t know how to build an enormous following. I don’t know how to write a Best Seller, or how to achieve celebrity-level success at anything.
I do know what it is like to be closing in on thirty and to be deep in the bowels of the whale, feeling my way through the shadows, trying to build a life of fulfilling, meaningful work on my own terms; trying to navigate without a map. I know what it’s like to want to be the best possible expression of myself, and to wonder if this is it. I know, deeply and completely, what it is like to not want to waste this puny existence I have been graced with.
I don't have the answers, but I can share the questions, the process, the progress, the experiments, and the moments of “Aha!” as I continue to write and create and work it all out. It will be vulnerable, maybe a little weird. It might digress, it might ramble a bit, and it might mutate a few times before it finds its voice.
The path through this life is dark.
It is different for each of us. Finding your way requires no small degree of tenacity and fumbling. There are many wrong turns and false trails. Courage is required. So is faith. It can be tempting sometimes to just check out. To anesthetize and give up. To follow the herd.
But here, in the darkness, I can hold a light: this letter, its brood. As I attempt to create in the service of others, to build a scaffolding around it all, and to bring some beauty into this world, I hope our correspondences will be revealing; that you might learn from my fumbles, share the successes, and know that there are others out there trying to make sense of it all too.
I cannot show you your own way, but I can shine a light on mine. And maybe that will help you, in your own darkness, feel a little less alone, a little more brave.
Until next time
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