Only 758 hours (that’s 45480 seconds for anyone counting) left until December 31st, and the year will, inevitably, be over.

Are you hanging in there?

What a ride. There are a novel’s-worth of words to write about 2020 and the changes it wrought. Germ invasions, cultural contortions, political skulduggery, and general tumult the likes of which we may never see again on this scale. In some ways it feels like the we’re nearing the end of a very strange, very engrossing single-season Netflix special.

It’s me, Sasha Goldstein, and a short while ago, no doubt in some odd state of seasonal mania, you signed up to receive The Night Letters. If you’ve joined up in the last couple of weeks and want to read the story of how (and why) this endeavour began, I’ve archived it here. If you somehow found this page on the internet and haven't yet joined the mailing list, head on over to the secret invitation page for a better primer on what this is all about.

If you tuned in last time, you’ll know that this newsletter is a bit of a caterpillar: a little blobby squirmy thing that is hoping to one day disappear into a chrysalis and emerge as a luminous butterfly. Right now, we’re still in the blobby squirmy phase.

A case in point: I’ve written three entirely different versions of this very letter so far, two of which got so digressive and complex that I had to spin them off into essays, which I hope to some day actually finish. My intention has been to cap each of these letters at around 1,000 words, but based on every attempt I’ve made so far, that seems impossible.

In fact, most of the difficulty I’m having at this early stage is related in some way to word count — by the time I’ve arrived at the final draft of a single letter, I’ve also written two to six others that I’ve thrown in the trash or had to figure out how to repurpose, along with numerous drafts of each. This has the inevitable side-effect of producing multiple spin-offs, which require sustained efforts of their own to complete. Such convolutions demand more than their fair share of energy, complexify my intended send-schedule, and steal time from other projects that I really, really need to be kicking out the door.

My hope is that over time this word-churn will diminish and I can stop writing novellas each time I want to send a letter, but I’m not holding my breath. As the Qaran says: Inshallah.

Failing and… unfailing?

The year was 2017. I was working for an apparel company by day, pushing pixels around in a never-ending game of digital conversion whack-a-mole. My head was ballooning with grand ambitions that had nowhere to go. I was tired of conversions. I wanted, so very badly, to create something real, something that was not pixels.

So, naturally, I chose the most complicated and difficult idea I could think of and threw myself into it with a fury: I wanted to produce designs based on textiles from cultures around the world and work with artists to screen-print those designs, by hand, onto 11x17” sheets of paper, which I could then have cut into quadrants, embossed, and sewn, as covers, to eighty pages of fine writing paper; pocket-sized notebooks — sort of like a Moleskin — but also carryable pieces of art.

There is an elaborate origin story here… one that followed me across continents and took many years to germinate and seed before it sprouted. Like all ideas, it wasn't entirely original. But that’s a story for another day.

I laboured for well over a year. I flew halfway across the world on a Boeing B787, found inspiration in the mountains of Japan. I cycled back-and-forth from my tiny flat in East Vancouver to production facilities in neighbouring cities, I designed and re-designed and re-re-re-designed. I reviewed samples. So many samples. Infinity samples: paper samples, binding samples, finishing samples, pre-print samples, print samples. I spent thousands of dollars and innumerable hours. The project seemed illimitable — and yet, I was so absorbed in the joys and difficulties of bringing my vision to life that I barely noticed.

Then, on one bright wintery November day I received a truckload of boxes with my notebooks. I was overjoyed. I waited breathlessly for imminent applause. I called my mom.

My mom congratulated me. We hung up. The applause never came.

The silence was awful.

In the weeks and months that followed, I did nothing. I froze up. The project, that I had worked on so furiously for so long, stagnated. It entered the the do-not-ask-me-about-it phase with friends and family.

It eventually dawned on me that I had misunderstood where the finish line was… that producing a product is not the same as producing a business. I had devoted more than a year of my life to teasing an unfathomable vision out of my head and transmuting it, miraculously, into the something that I could hold; something that I was proud of bringing into the world; something worthy of existing and of being shared and owned and used. It had taken nearly every ounce of courage and fortitude I had to get out of my own way, to stop over-perfecting, to get to that moment when I could hold the real thing in my hand.

And yet, without execution it was an empty victory. I had merely reached the starting line. And I couldn’t move past it, because I wanted to continue obsessing over every tiny detail. I wanted the experience of discovering that product and buying it to be just as impossibly perfect as I had wanted the product to be. In short, without realizing it, I wanted to skip being a scrappy indie startup and begin as a fully-mature consumer goods company.

But I had no time, energy, or money left to shoot artistic, drool-worth studio product photos or design or design & code a bespoke high-touch e-commerce website. So I did nothing.

The silly thing about the whole endeavour is that it failed before it even had a chance to fail. It failed — not because I had produced something that nobody wanted, but because I was so obsessed with my vision that I let it strangle me. My version of “good enough” was so unattainable that it suffocated my momentum until I was so burdened by inertia that I couldn’t move forward.

What did I learn? I learned that it’s better to hit roadblocks early, better to fail quickly and cheaply, at 10% completion instead of 90%. I learned that execution is more important than creation and concept. I learned that origin stories are hard to document after-the-fact. I learned that good products are useless without good marketing, and good marketing is useless without good content. But most importantly I learned that “good” is subjective, and that it can imprison you if you let it.

Hold for applause

I’ve decided to try again. This time, with an emphasis on kicking this project in the butt and getting it out the door, and a de-emphasis on all of the things that were getting in my way.

This means: simplifying e-commerce, simplifying product photography, doubling down on the narrative and most importantly… a commitment to stop getting hung up on small details.

To that end, I’m currently working on a light re-skin of Shopify’s aptly named Simple theme. I’ve also decided, in the interest of not having to maintain numerous domains for this and any future projects, to build a brand-agnostic storefront, which I am, in the spirit of not getting hung up on details, blandly calling “The Workbench.”

Which leaves only narrative and photography left — photography should be relatively simple unless I let myself get hung-up on it: I plan to shoot the books as lay-flats on some kind of smooth, lightly grained wood surface. I shot some test photos using an old moveable kitchen island (pictured below) and they turned out just fine. I just need to find a more suitable backdrop and I should be, as they say, “off to the races”.

Narrative is proving a little more difficult. The story of these notebooks is surprisingly long and involved, but my intuition is that they need some narrative to justify (or perhaps explain) the price-tag and bring some context to their existence — especially in lieu of remarkable photography or special packaging, which I am almost guaranteed to get hung-up on if I try to produce. The quality of these books is truly tactile — to hold one in your hand is a compelling enough sales pitch — but their story (I hope) will serve as a good enough substitute.

A few folks have asked me why I don’t simply wholesale the books. These are, after all, the sort of items that might sell nicely in certain small boutiques and gift shops. The answer is that they are far too expensive. I plan to sell these books online for $53.00 each, and as astonishing as it may sound — this price barely allows me to break even once I factor in marketing costs, payment transaction fees, etc. If I had to add a 30-50% wholesale markup on top, the books would be absurdly expensive and, at least in my estimation, a waste of retail shelf space.

I am planning to launch these and wash my hands of the maddening paralysis that my blunders have wrought, a week from Monday. This date lines me up — just by the thinnest of hairs — with last-minute holiday shopping, but more importantly, it leaves no time for me to spin out or iterate endlessly on non-critical details.

I’ll report at the end of next week and let you all know how it went.

So… hold for applause?


(Ed — I did it! See the follow up email from the following Monday here)

Did you enjoy this?

Subscribe to The Night Letters to get occasional newsletters about creative invention and entrepreneurship