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Searls of Wisdom for July 2023

Whenever you read something I write, please know that I was having exactly this much fun writing it for you: This is what I look like when I write this shit.

Greetings! It was a slow month in the content mines, as I've shifted my focus back to Top Secret work at Test Double, the fruits of which will probably not be apparent for six months or longer. As a result, I can't really answer what July was "all about", because I was squirreled away working on stuff I can't talk about just yet.

So here I am, lifting my head for the first time in a few weeks. Let's check in with how the planet is doing by reading a few headlines from the last 48 hours:

Neat. Good to know I haven't missed out on much.

You may be relieved to hear that today's newsletter is not about current events. Instead, I decided to finally take the time to document my peculiar approach to creative work. Most of the following essay refers specifically to writing, but it applies just as well to other stuff I've done like conference presentations and videos. I hope you enjoy it.

The Justin Searls Creative Process™

I've engaged in recreational creative writing since I was in middle school. It all started when a friend of mine roped me into writing Zelda walkthroughs for his Nintendo fan site. I proceeded to bounce around a bunch of videogame sites after that—including several where I collaborated with the (even younger!) Brian Stelter, who later went on to be a New York Times reporter and CNN host. But as soon as I got my driver's license, I traded in the glamorous life of getting paid in review copies of B-tier Ubisoft games for a "real" job that remunerated its employees with U.S. currency. There was one immediately-apparent drawback, though: working retail stimulated far fewer brain cells than writing about videogames on the Internet. It didn't help that the store I worked at was so low-traffic that it wasn't uncommon to go an entire eight-hour shift without seeing a single customer—and one quickly learns that a Blockbuster Video can only get so clean. Driving home at 1 AM each night, I found myself with so much pent up mental energy that I'd collapse into my desk chair and witness as my fingers furiously spewed all my suppressed creativity into blog posts and comic strips.

I don't enjoy writing, mind you. I want to be very clear about that. I don't like the creative process at all. It's painful, time-consuming, and distracts me from building more practical, useful things. But every one of us feels some need to be understood by others and, unfortunately for me, my thirst for validation is apparently insatiable.

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Anyway, having such early experiences "as a creative" absolutely paid off later in my career. Not because they made me an especially skilled writer, but because they gave me total permission to publish my thoughts from a young age. A lot of people I run into—even people of similar privilege—have their own interesting things to say but nevertheless seem to be waiting around for permission to say them. Not me. Game on.

Given that I've gone on to write quite a lot for work—blog posts, conference talks, technical documentation, overwrought email replies—I can see in hindsight that something resembling a repeatable process has materialized over time. But because I'm too impatient and disrespectful to educate myself in any traditional way, I made up everything as I went. So while I can't attest that any of my habits will work for you, I am reasonably confident you won't find them taught elsewhere.

Listening for dangerous ideas

As a mammal, I can't speak from direct experience, but I imagine that having a creative idea is bit like laying an egg: inevitable but unexpected, necessary but uncomfortable. And while excreting it from one's body brings temporary relief, it also signifies a thousand new things one must worry about.

Nor is there an active verb I would assign to "creating" an idea. "Invent" more aptly describes physical, tangible things. And "innovate" works better when contrasted with well-worn problems as opposed to brand-new ideas. Instead, the verb that sits best with me is "listen". I listen for new ideas. I'm not in control over what they are or when they arrive, only over what I choose to do with them.

I've also identified certain preconditions that result in the generation of more ideas or better ones. Ideas flow more freely when I force myself to experience boredom, which usually requires me to both unplug from my devices and deny myself the dopamine drip of checking tasks off my to-do list. My most unexpected ideas emerge when I spend time exploring new and foreign environments, especially alone. Interesting synthesis tends to occur when I divert conversations with smart people away from mundane topics and toward unfamiliar territory. And of course, it's hard to listen for ideas unless I take off my headphones and go about my day in Silent Mode. (Conversely, if a new idea is likely to distract me from the one I need to focus on, I play podcasts as white noise to drown out the sound of new ideas.)

So that's step one. Listening for ideas.

It's one thing to have an idea, but quite another to know what to do with it. Or even more basically, whether to do anything with it. I try to start by asking, "is this worth writing home about?"

Personally, I most enjoy investing in dangerous ideas. Ideas that threaten to change how people think. That shake up deeply-held beliefs. That challenge the status quo without unrealistically rejecting it. I know I'm doing something right if I find myself exploring concepts I've never heard articulated before but nevertheless feel obvious once stated. I also love a thesis that feels shaky and tenuous: a tightrope walk that could easily go in either direction and which forces me to precariously dance on one side of a knife's edge. My favorite topics have just the right amount of heat—they risk infuriating people if I'm careless, but come across as eminently agreeable when tamed by thoughtful rhetoric. To the extent possible, I sprinkle in playful irreverence that belies deeper critique.

In plainer language, I like my takes hot and salty.

The final question I ask before I pull the thread any further: how do I want people to feel afterward?

If I don't love my answer to that question, I toss the idea in a to-do list labeled "Ideas?" and go about my day. (I have never once looked at my "Ideas?" to-do list.)

Letting it Simmer

Once I decide to do something with an idea, I give it some breathing room by not acting on it for a while. If it's a major commitment like a conference talk, this phase could last months. If it's a straightforward blog post, I might only give it a day or two.

In either case, I find it's really important to let my mind wander and explore a topic from various angles asynchronously. Thoughts will pop up. Maybe I'll think of a joke that could break the ice in my intro. Or a clever title. Sometimes, I think of counter-arguments and pressure test them in my mind. Maybe I'll envision a color palette for a slide deck. All of these get dictated as Apple Reminders via Siri and are later ingested into Things.app.

(I will use almost none of these ideas.)

While things are simmering, I'll find a way to work the idea into unrelated conversations—partly to play-test my ability to convey the idea and partly to feel out the contours of discussion around it. If I haven't thought things through very well, this is when I'll typically find out. Maybe the topic is too narrow to be interesting. Or so broad and diffuse that it feels banal. Maybe my assumed rhetorical strategy falls flat in practice. After years of subjecting countless friends and acquaintances to this form of semi-consensual workshopping, I've identified a half dozen "muses" who are especially good at helping me process and develop a half-baked pitch into something workable.

Whether or not I use any of the one-liners or puns I collect in the weeks leading up to breaking ground on The Actual Writing Part, these artifacts are by no means the intended goal of the simmering phase. No, the real purpose this gestation period serves is to strengthen my mental muscles and prepare my brain to react to the rapid succession of disparate thoughts it will encounter in the course of my writing. By marinating in it sufficiently, I'll be comfortable making the countless split-second decisions needed to express myself cogently. I don't need to be an expert on a topic to craft a useful argument, but I do need to be prepared to triage, organize, and weaponize a cacophonous barrage of unrelated thoughts if I intend to successfully bring an idea to life.

All this simmering gives me what I need to undertake the next step…

Making really bad outlines

Before I start writing, I outline. Depending on the topic, a particular rhetorical structure might present itself too, whether that's traditional narration, description, compare and contrast, or persuasive argument. I will map out an introduction, body, and conclusion. I will enumerate some number of points I want to make. (Always three. Three is always the number of points.) I will love my outline, because it will make a messy thing feel tidy and reassure me I am approaching the finish line. Me and my outline, together forever.

(Later, I will go behind my beloved outline's back and cheat on it in keyboard-clacking passion as I indulge myself in a flurry of tangents and digressions.)

A little advice about writing that is most relevant at Outline O'clock:

  • Trust yourself and build your argument from first principles informed by your own experience as opposed to third-party sources. If research or fact-finding must be done, keep citations to a minimum
  • Disregard other people's opinions. Don't read their posts or listen to their podcasts. All it can do is sand down whatever was novel and interesting about your idea. If you're worried someone else had exactly the same idea and wrote exactly the same essay, think through the math on how unlikely that actually is
  • After every few points, ask yourself "could anyone read what I just wrote and think anything other than what I want them to think?" If so, that's an opportunity for your audience to fall off your Idea Bus in favor of the Dissent Express. Rework it until the argument is airtight

Of course, an outline is more useful if you actually follow it. But I've found that the act of writing a thing inevitably causes me to veer and digress, if not swerve, in unexpected directions. For example, everything you've read to this point is the result of exactly two bullet points, neither containing more than a sentence fragment (one just says "simmering / festering"). Right now, in the back of my head, I'm thinking, "I have 3 pages left in my outline and I'm already at 1600 words, what am I doing to these poor people?"

As a philanderer who's serially unfaithful to his outlines, my solution isn't to stop wasting my time writing outlines, it's to waste even more time outlining. In order to embrace improvisation in writing, I started treating outlines the same way a painter might treat pencil sketches: I keep drawing them until I'm confident I won't be wasting my paint when I finally pull out the canvas.

I typically start with a few bullets in the Apple's Notes app. The next day I'll put on some jazz, lean back contemplatively in my knock-off Eames chair, and start a fresh outline in my notebook. Later, I might get excited and scrawl "TOP THREE THINGS" in all caps on a whiteboard before I remember all my dry-erase markers are out of ink. If I'm prepping a keynote, I'll draw storyboards of slides onto a legal pad and map each to a corresponding plot beat in my latest outline.

The outcome of all this outlining is a deep familiarity with the bones of my argument, as well as plenty of practice assembling them into different kinds of skeletons. I'll know I've spent enough time with my own asinine outlining process once I've followed each potential argument's path far enough to see where it would ultimately lead. Incidentally, by that point I'll be so bored with the original idea (why did I think this would be interesting again?) that the thought of finally putting meat on these bones and writing real words begins to feel exhilarating.

"Hold me back!" I will shout to no one in particular.

You might think at this point, "finally, it's time to start writing!" but you'd be wrong. That's a classic rookie move, right there. The next step is, obviously, to come up with some kind of entertaining gimmick or conceit by which to deliver the message. Sugar to help the medicine go down.

Earning people's attention

If the outline represents the skeleton (or possibility space of skeletons, in my case) of a piece, then its "format" is the party hat and fake nose & mustache glasses that your eighth grade science teacher inappropriately put on his classroom skeleton in a lazy attempt to make STEM seem fun.

A few examples of light-hearted formats I've developed to surround dense topics:

  • Symbolic: in 2014, I wrote a talk to encourage people to think more creatively about organizing tests into purpose-built suites. In order to break out of the mostly-useless-but-nevertheless-dominant metaphor of "testing pyramids", I designed a Google Earth zoom-level widget that encouraged attendees to visualize software at varying levels of magnification instead—up close, far away, and at every meaningful increment in between
  • Silly: in 2015, I was slated to give a talk about software testing anti-patterns, so I naturally spent fifteen hours figuring out how to emulate Mac OS 9 so I could build my slide deck with the long-abandoned AppleWorks suite, all in service of a stupid intro joke based on the fact "iOS 9" was due to release that fall
  • Saucy: in 2017, in a talk that aimed to empower attendees to deploy metacognition to improve how they think about work in the same way they deploy tools to improve how they perform the work, I created a satirical Myers-Briggs-like quiz to get people thinking about how their approach to programming differs from others (tens of thousands of people have taken and continue to take this quiz, and the satire is lost on most of them)

In any of the above cases, I could have just recited an outline and conveyed all the information I wanted to. But would it have gotten people's attention? Would they have listened until the end? Would it make them feel any less dead inside?

Nope.

All this elaborate window dressing around The Thing You Really Want to Say isn't to trick people into eating their vegetables. Nor is it a cynical ploy to grab people's attention and generate clicks. The reason I put this work into my creative output is to give people a reason to engage with an idea that they don't care about yet. (And before you judge them for not caring about your idea, recall that you also did not care about your idea before you had it.) You're not debasing yourself by making the content fun. Making it interesting for others is how you buy your ticket to ride. The audience gives you 15, or 30, or 45 minutes of their time and in exchange you give them the salacious details of how they rank in a silly personality quiz.

Okay, so that's a bit about format. Finally, finally, FINALLY, we can talk about the thing that has the biggest impact on creative work: ✨mood lighting✨.

Setting the right mood

There are a number of things that enable and disable my ability to work creatively. I try to be mindful of them along with my general mindset before I sit down to work. If there's a knob that's in my control to twist, I'll adjust it to my liking. But if something outside my control is sitting between me and flow state nirvana, I won't force it… I'll go do something else instead.

A few things I keep in mind about my mind:

  • If I have any stressors, worries, or relationship strife on my mind, I need to settle them or else they'll keep bubbling up as I work, and every task will take me ten times longer to complete
  • I use music and lighting to adjust the tempo of my brain to match the tone of whatever I'm writing. If my brain is being too manic and restless, I'll calm it with some chill music and a darker room. If what a piece needs is some gratuitous keyboard violence but I find myself feeling lackadaisical, I'll switch from sitting to standing (or walking!) and pick up the pace with some upbeat music
  • My morning energy seems to be best for generating new ideas whereas my afternoons (once life has gotten in the way) are generally less valuable for deep, uninterrupted thought. As a result, I make it my goal to write as much as I can first thing out of the shower and save editing for later on, after my focus has inevitably faltered
  • If I find myself reflexively tabbing over to Mail, Messages, Slack, or social media, it's normally a sign that I want to procrastinate. Rather than give into the urge to obsessively scroll-to-refresh all my Skinner box apps, I take this as a cue that my mind needs a more substantive and restful break instead (by which I mean, I go work on something else until that thing bores me enough that I'd rather be writing)
  • Finally, when I'm really stuck, I think about how pissed I'd be to have sunk all this time into something only to die before finishing it. I think about my demise a lot, generally, but in this case I can make my fear of death work for me

Okay, you're probably ready for it. The moment you've all been waiting for: the part of the creative process where you actually make the thing!

Making the thing

I have nothing to say about this. Writing is simple but hard. Other creative work is, too. Get better at keyboard shortcuts if you want to save time.

If you've done everything else right, the act of creating is just a numbers game. Multiply Time × Toil until the work is done.

Whatever you do, don't give up. Unless you feel like quitting.

Editing your work

As a "digital native", I never had to worry about squeezing big ideas into an economy of column inches. Had I been born ten years earlier, I might have more appreciation for the traditional art of editing. If anything, the Internet has taken us in the opposite direction by incentivizing more words, not fewer. This has led me to approach editing as an act that's more about refinement and perfection than one of prioritization and distillation.

My personal approach to editing is pretty straightforward: I repeatedly read my work. I read it on the device I wrote it. I read it on a phone. A tablet. At different window sizes, to force the line breaks to land on different words. In large type and small fonts. As I read, the instant something doesn't land exactly how I want it to, I switch to my editor, fix it, and switch back. I am aggressively deliberate. If I can't get a particular turn of phrase to evoke the right sensation, I might spend three hours renovating the real estate surrounding a single clause buried in the middle of a 4000 word essay.

I keep doing this until I can read the entire piece front-to-back and find absolutely nothing that I would change.

Then I hit publish.

Immediately, I scramble to read the published work. I become flush with preemptive embarrassment, certain that I missed something. Sure enough, I find a dozen more issues I missed before. So I go back and fix them.

I share the piece with a friend, excited to see what they'll say. I read the piece again while I await their reaction. I find more problems. I publish those edits while they're still reading. I consider asking them to refresh the page so they get my latest edits, mostly out of worry that—much to my shame—the friend will identify typos I'd already fixed. (And I should not be penalized for typos I manage to catch myself!)

I am reminded of the time I built a clock in wood shop in eighth grade. It was a semester-long class and I completed the clock within a few weeks. I then spent nine weeks sanding it. Yeah, that checks out.

This process is inefficient

For being so driven to maximize efficiency and throughput in other facets of life, my creative process is stubbornly, almost gallingly, roundabout. I burn weeks and months from the calendar before even starting. I duplicate numerous planning tasks that most people only do once, if at all. I spurn existing research and prior art. I defer the work a day or two or three if I'm not "feeling it." I edit and re-edit until my fingers are numb.

Sometimes, people who don't know how much time it takes me to write a three paragraph email tell me that I'm a good writer. But now that I've pulled back the curtain, you might agree that there is probably room for improvement here. Whatever I lack in training and talent, I clearly compensate for in sheer effort and exertion.

On the other hand, when I look back on my life and career, it brings me a lot of joy to know that the breadcrumb trail of things I've left behind is full of unapologetically earnest reflections that were deeply meaningful to me. That's not worth nothing.

Until next time

Before I forget, last month I teased that I was wrapping up a blog post I had initially intended as my June newsletter. Here it is: The looming demise of the 10x developer. Because I chose a salty title, it got a lot of play. (I forgot to mention salty titles in my Justin Searls Creative Process™ above, but sometimes you gotta hook people.) I actually wrote a far saltier follow-up link post that nobody read because the title was relatively benign. I think there's some wisdom in burying explosive ledes when you don't have the energy to deal with their splash damage.

Anyway, let's call it. I'm about to get on a plane to go on a normal-ass, longer-than-a-weekend, nothing-to-do-but-sit-by-the-pool vacation for the first time in a long time. If you take the time to reply to this letter with your thoughts, then I promise to not only read it, but to respond—phone in one hand and daiquiri in the other. 🏖️