Treat your doubts like collaborators

Creativity lessons from a Constantly Successful Eternal Beginner who has Never Known Failure

Feb 04, 2025

Welcome to Blackbird Spyplane

Our new Home Goods Report, bursting with things to enliven the place you live, is here.

Mach 3+ city intel for traveling the entire planet is here.

The B.L.I.S.S. List — a helpful rundown of Beautiful Life-Improving Spyplane Staples, from incense to sweatpants to underwear — is here.

Blackbird Spyplane is beloved for all kinds of correct reasons. Many have to do with the “content” of the newsletter, which is our provocative yet deeply humane investigations into the mechanics of style, and our attention to dope developments across culture generally.

Then there’s what advanced semioticians would identify as the newsletter’s “form,” i.e. the incredible way we write itself.

Yes — day in, day out, Erin and I (Jonah) flicka da wrist at the damn keyboard. Out come sentences at once aerodynamic and effervescent… reasoned and delirious… enlightening and delightful.

The result is “Blackbird Spyplane Voice”: protean, pathbreaking, much ballyhooed, widely imitated, and deemed “annoying” by no one ever. That’s right. During the Plane’s nearly 5 years of existence, exactly zero people have talked s**t about us, publicly or privately. It’s amazing, because people go through all kinds of hardship and struggle, and this can manifest in all kinds of myopic and misguided behavior, and yet no one has ever tried to go catty mode and flip a “hurtful zinger” at the Plane. Probably this is because there are better things to get worked up about than a reader-supported independent publication with ~millions of subscribers, and because we simply keep it too real and emit the radiant, sun-like warmth of too much love.

Chromolithograph rendition of readers encountering Blackbird Spyplane’s sun-like spirit of Radiant Love and Realness, by Henry Courtney Selous (1803-1890) for an 1844 edition of “The Pilgrim’s Progress.” Photo via Getty

Anyway. Some writers might find a prose style that works, then lock in and clock out. Not us. We don’t ever want to go Autopilot Mode with these high-wire phrasings and jewel-like bon mots. So we’ve spent the last few years refining Spyplane Voice, naturally and gradually, modulating some of its excesses, examining it for outmoded elements, probing it for new expressive possibilities.

In part that’s because Plane Voice at its most maximally amped-up served various purposes when we were starting out that it no longer serves. It’s also because language is a living thing, and you never want yours to devolve into pure undead shtick.

There’s no greater reward for how good we are at newsletters than Spy Nation, the most kindvibed and literary-minded readership across all media. To that end, whenever we’ve put out “Personal Spyplane” open calls for reader questions on IG, some Spyfriends have requested our wisdom not about wearing cool clothes but about writing cool words.

It’s never felt quite right to do a whole Plane about writing. (This ode to P.G. Wodehouse, a.k.a. The Seinfeld of Books, kind of counts.) Over the past several weeks, though, I’ve been working to finish my latest magazine story, a profile of a GOAT-tier filmmaker for the New York Times Magazine. I started reporting it in Seoul back in July 2023, and it is finally making its way toward publication.

Toggling between the Spyplane sletter-writer part of my brain and the generalist feature-writer part is always… stimulating. The upshot right now is that I’ve got “paragraphcraft” coming out of my damn ears. So I’ve decided to devote today’s Plane to some key unbeatable lessons about writing and creativity that I’ve learned over 20+ years as a humble Constantly Successful Eternal Beginner who has Never Known Failure.

I’m harnessing these lessons to two specific reader questions concerning Doubt and Motivation. Hopefully my answers will be useful to fellow Spy Nation Scribblers, but at the very least, they’ll be revelatory to anyone interested in the mysteries of Creation.

I. Doubt

“What do I tell my doubts?” — bhabipluto

This question isn’t explicitly about writing, but that’s where my mind goes. Maybe this reader is referring to the kind of doubts one might feel before approaching a baddie to spit game, but this simply underscores that doubt is central to all creative risk-taking, from writing to Putting that S**t On to painting to songwriting to filmmaking to skateboarding to working up the nerve to swerve charismatically on someone hot, and so on.

Here’s a True Spyplane Confession about doubts as they relate specifically to writing. Since my early 20s, several nights a month — and during some periods, several nights a week — I’ve woken up at ~2 a.m. in a state of thrumming dread. It must be chemical. The dread is outsized and irrational in a way that seems connected to whichever neurotransmitters the brain pumps out (or cuts off) during nightmares. Whatever the cause, though, this dread grows tendrils that slither around in my brain and coil themselves around any and every thought that sits unsettled in my consciousness, whether it’s minor (“I forgot to pay my credit-card bill”) or major (“a sense of comfort predicated on the absented suffering of others is corrosive and false,” “the people who mean the most to me will die and I will die, too”).

When I’m in the middle of writing a big piece, the dread invariably attaches to that, and transforms into a psychopathically nasty inner editor: “You set up a question in the first section and your ‘answer’ is an unsatisfying dodge — idiot,” “You didn’t grapple with this glaringly obvious counterexample — dumbass,” “That paragraph is so choked with leaden metaphors and banal insights that anyone halfway intelligent who reads it will see right through it and know that you are a bulls**tter to the acute degree that you have forfeited all claims to kindness and love — b*tch!”

Like I said, outsize and irrational. Eventually I drift back to sleep, and the next day, I’m able to put my anxious awareness of problems that need solving in its proper perspective. But at 2 a.m., in the throes of a fight-or-flight-style physiological stress reaction, it feels real.

And here’s the truly twisted thing: Even though it’s so unpleasant, there’s a sense in which I’ve come to rely on this nocturnal dread to make my writing stronger, to keep me sharp, to literally “stress test” a work-in-progress for fissures and flaws. My doubt is, among other things, a sign that I am not simply phoning it in.

Over the past couple years I’ve gotten better at taking deep breaths and asking my 2 a.m. doubts what they have to teach me… taking the high road on these f**kers and thanking them for their help … replying that I will think through their notes in the morning … and telling them to chill out with the other aggro extra s**t. Taking 240mg daily of Nature’s Bounty Magnesium Glycinate helps, too.

So my answer to this reader is to treat your doubts like collaborators. Ask them what they have to teach you. Take them as spurs to work harder, to “be your own worst critic,” and to get your weight up. Work on identifying the signal within their noise: what to listen to, where to push back, what to ignore. Because doubts have an extremely useful side. It’s when they tip over into masochistic and paralyzing that you need to tell them, “Shut the f**k up and let me cook.”

II. Motivation

“Any tips on staying motivated through creative endeavors?” — dcnso

Here’s 4:

1. Break when you’re feeling good, not when you’ve run out of gas. Sometimes you are humming along on a project, well-oiled, powerful and Swiss-watch precise. It’s tempting to ride this feeling all the way til it sputters and crashes, then call it quits for the day. But it is much better to learn how to step away before that spell of excitement and forward momentum ends. This way A) you will carry that productive hum of excitement with you as you do other things, i.e. it will keep running pleasantly like “a background function,” and you can keep a notebook on hand to catch any new ideas and epiphanies related to the project even as you run errands, read a book, watch a movie or whatever, and B) the fact that you left off on a high note will make returning to the project later much more appealing. Relatedly,

2. Rotate between activities that stimulate different parts of your brain. My personal example of this is that when I’m working on the newsletter I am not only writing it — I’m also thinking about the Photoshops I will whip up to accompany it. So, say, I’m four paragraphs into an essay. At that point, the idea for some illustrative graphic might occur to me, and I’ll stop writing and start Photoshopping. Switching gears in this harmonious way — puzzling through the question of how to express a point through a graphic — feeds beneficially back into the writing. But you could embrace this principle even if you don’t do a sletter with Photoshops: As an exercise, try to illustrate, explore and express an idea through different media. But less creative, more maintenance-style tasks are perfect for this kind of Endeavor Rotation, too, e.g., vacuuming the crib, washing dishes, weeding, repotting a plant, patching a pair of jeans, etc.

3. Keep work hours and honor them. This is familiar advice for a reason. Show up, sit down, start pushing around words or paint or musical notes. Even though we think of creativity as a stochastic and unschedulable visitation from the astral plane, we also know it responds well to all manner of earthbound “productive constraints.” Committing yourself to clock in every day at 8 a.m. sharp is as simple and productive a constraint as they come. On any given day the results of this clocking in might rip, and they might suck, but even when things feel like a dead end, remember that s**tty work is a pathway to satisfying work.

4. Curiosity feeds fun, and fun is its own motivation. Earlier, I alluded to several purposes that were served early on by Spyplane Voice at its most amped-up. A big one was that writing in a heightened voice helped me keep things feeling loose and fun, not just for readers, but for myself. Any creative pursuit you routinize will at times feel like gear-grinding. Keeping things fun will grease those gears, baby. How best to keep things feeling fun? Not by going on to Twitter to complain about how miserable writing is for the hollow reward of 67 likes. No! What you want to do is create and nurture the ideal conditions in yourself, and in the work, for as much discovery and surprise as possible. Discovery and surprise feel good, and when things start to feel like a slog, they will help to propel you through that slog. The key to unlocking discovery and surprise is a sustained sense of curiosity.

Curiosity is its own reward, and it is also the opposite of death.

P🖼E🖼A🖼C🖼E til next time !

— J & E

Treat your doubts like collaborators

Creativity lessons from a Constantly Successful Eternal Beginner who has Never Known Failure

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