While my journal-writing sessions are relatively effortless, there is another type of writing session that is very effortful.
Those are the sessions in which I’m repeatedly hitting mental roadblocks. In which I’m not limited by my knowledge with the subject nor comfort with the truth, but but by my ability to find an insight.
I sense something is there, and methodically approach the subject from various angles. But that source of irony, that contradiction, or that surprising juxtaposition remains elusive.
It’s when I’m regularly doing effortful though not always fruitful writing sessions something else happens. While on a walk or talking to a friend or in the shower, I’ll have frequent aha! moments. Not always about what I’ve been writing about, but about any random thing.
The more hours I spend effortfully forcing myself to write, the more seemingly-random moments of inspiration I experience.
Inspiration is a muscle. You must perspire to be inspired.
Aphorism: “We’re smart enough to invent AI, dumb enough to need it, and still so stupid we can’t figure out if we did the right thing.” —Jerry Seinfeld
Book: Nobody should read Sex at Dawn without also reading Sex at Dusk (Amazon). It’s a less engaging yet more rigorous takedown of the former.
I’ve been journaling for seventeen years now. I’ve amassed quite the stack of full journals.
When I flip through these, I sometimes find something interesting. But most of it is boring, and almost all of it is poorly-written.
But my journaling habit has improved my writing immensely. Mostly because it shows me what it’s like for writing to be easy.
Writing in a journal is easy because you just write what’s on your mind. After enough practice you realize, something is wrong when writing is hard. Sometimes writing is hard because you don’t know the subject. But sometimes it’s because you refuse to acknowledge what’s on your mind.
In this way, journaling helps you practice the most basic but important writing skill: writing what you know.
Aphorism: “Write when there is something that you know; and not before; and not too damned much after.” —Ernest Hemingway
If you want to be a productive person, it seems you should have an elaborate task-management system.
It seems you should choose goals, formulate a plan to carry out actions that will lead to those goals, then execute that plan with your flawless discipline.
But the world changes too fast to stick to a plan, and who among us can perfectly execute what we plan?
People who you think have elaborate project- and task-management systems often merely have an array of habits, routines, and rules that keep them moving in the general direction their goals lie.
Don’t pick the perfect plan, install systems for strategic stumbling.
Aphorism: “You do not need anybody’s permission to live a creative life.” —Liz Gilbert
Cool: These indoor bug zappers (Amazon) are effective at attracting and killing mosquitos in your house.
One of the most fascinating displays of the follies of the human mind is the cargo cult.
In WWII, the U.S. military landed on various islands in the Pacific. To the previously-isolated societies who lived on these islands, these soldiers were like aliens from another planet, arriving through never-before-seen technology.
After the soldiers left the islands, cargo cults cleared forest areas to make runways, and made headphones out of coconuts and air-traffic batons out of sticks.
They believed if they recreated the scenes they had seen, planes would once again land with food, clothes, and equipment.
One such cult is the “John Frum” cult. To this day, on the island of Tanna, there are festivities, worshipping rituals, and even false prophets claiming to be the reincarnation of “John Frum.” (A now-mythical American serviceman whose name apparently derives from introducing himself as “John, from…[place].”)
The bizarre beliefs of cargo cults come from the same wetware with which we in industrial society are equipped. So, cargo-cult thinking is everywhere:
Dating: Searching for a set of qualities we imagine we want in a partner, rather than thinking what it would be like to be with such a person.
Politics: Choosing candidates based upon appearances and sound bites that fit an ideal, rather than asking what makes an effective leader.
Productivity: Looking and feeling “busy,” regardless of whether it produces the results we desire.
Entrepreneurship: Following trends and hype. Copying style, not substance.
We often merely mimic appearances, without understanding what will cause the effect we want.
Do you see cargo-cult thinking in other areas?
Aphorism: “Anyone who in discussion relies upon authority uses, not his understanding, but rather his memory.” —Leonardo da Vinci
It’s an anxious feeling to not be on top of things. And it’s a vicious cycle.
When I don’t have a clear view of what needs to get done and how I’ll ever do it, suddenly more needs to get done and I have less time and energy.
If anything, there’s less that needs to get done when I feel on top of things. Because when I don’t feel on top of things, I invent things that need to get done.
The sense of urgency I feel when I’m not on top of things comes not from there being more to do, but from the anxious feeling that results from not being on top of things.
When I’m anxious from not being on top of things, every little thing is a potential answer to the question, “What needs to get done?” Every fleeting thought or glance at a scrap of paper makes me say, “Oh, there’s the culprit! Once I take care of that, this feeling will go away.” (Of course, it won’t.)
Give yourself time and space simply to get on top of things and make a plan for how you’ll use your time and space. You’ll feel less anxious, and everything will seem less urgent.
Book:American Psycho (Amazon) is the oddly-hilarious-yet-gory dark comedy upon which the movie is based.
Recently, I did my first set of open-mic stand-up comedy.
I had fantasized about doing it for years and had always found a way to talk myself out of it. But given all I write about creativity, I could no longer stand the feeling of hypocrisy for not following this creative whim.
As I searched myself, I found an irrational desire standing in the way of actually doing it: I wanted to be good.
I realized I had pictured my first stand-up set going a lot like the specials of my favorite comedians. Which is ridiculous.
I know from listening to interviews of hundreds of comedians that it takes at least ten years of consistent practice to be good at stand-up comedy. Twenty to be great. And by the time I see a comedian’s special, they’ve spent a year or two testing the material hundreds of times.
I don’t see being a stand-up comedian in my future. I would hate the lifestyle, and in any case, I live in a non-English-speaking country, where there are almost no opportunities to perform in English – and even then it would be an hour drive away. There are simply no ways for me to get in the reps it would take to be good.
But just because you can’t be good at something doesn’t mean you shouldn’t try. Even if you don’t do well at, say, stand-up comedy, it doesn’t mean you won’t learn from the experience: about writing, performance, fear, and creativity.
So while I was in some U.S. city recently, I put together a five-minute set, and performed at an open mic. I didn’t tell anyone I was going, and I used a stage name.
How did it go? It doesn’t matter. Good is not the goal.
Aphorism: “Make an effort. Just pure, stupid, ‘No idea what I’m doing here,’ effort…. Swing the bat and pray is not a bad approach to a lot of things.” —Jerry Seinfeld
Cool:Exploding Topics is a free newsletter that tells you about trends and products before they’re popular.
For non-Americans and the under-forty, Doogie Howser, M.D. was a television sitcom/drama about a boy who’s such a genius, he became a doctor at fourteen.
And at the end of every episode, Doogie would write in his journal, which was sooo high-tech at the time.
I didn’t start journaling till I was twenty-eight. And it’s because Doogie Howser, J.R. (Journaling Ruiner), well…ruined it for me. Every time I dared put pen to paper, I expected to wrap something in an insightful package, with a pithy takeaway. Like Doogie’s various maxims:
It doesn’t matter whether you think too much of yourself or too little, either way you lose.
Before my first solo surgery, thinking I wasn’t perfect was my greatest fear. But knowing I’m not perfect has become my greatest asset.
A physician searches others for signs of illness and disease. A human being searches others for signs of himself.
Worse, these would be pretty much the only things Doogie wrote in each journaling “session.” He’d just switch on the computer and, boom: insight.
You’d think I’d cut myself some slack, since Doogie was supposed to be a genius. But I guess that was the appeal of the show for boys like me: We wanted to be and believed we were like Doogie.
I’ve since learned the insightful packages and pithy statements are few and far between. You don’t pick up the journal and instantly write something brilliant. In fact, not knowing what you’ll write when you begin a journaling session is why you write. Most of it is a mess.
But that’s how you get to the occasional insightful package and, yes, pithy takeaway.
Aphorism: “If I cease searching, then, woe is me, I am lost.” —Vincent van Gogh
Cool:Mail A Letter is an ugly website. But it saves so much time I’d use it to send snail-mail even when in the U.S.
There’s an old documentary of Jerry Seinfeld that captures the essence of the creative process.
In Comedian, you follow Seinfeld as he builds an hour-long act from scratch, relying on none of the material he has heretofore created.
He struggles on stage. He loses his train of thought. He gets heckled. Over the course of several months, he builds up to three minutes of material. Then ten, twenty, forty. My favorite moment comes toward the end, as he’s riding home from a show:
That, for me, is what it feels like every time I write a book. I’m workshopping material on Twitter and in these newsletters, and early on, I’m getting nothing. No likes and no replies, and even I’m not loving what I’m saying.
It’s like the proverb about the two mice that have fallen in a bucket of cream: One drowns, and as much as the other moves his little legs, he can barely stay afloat. But eventually all that activity turns the cream to butter, and the second mouse crawls out to safety.
I’ve been through it enough times to feel confident that no matter how desperate, awkward, and hopeless it feels to bomb, eventually cream will turn to butter and I’ll be standing on solid ground.
Only to dive off that precipice of butter, back into another bucket of cream.
When I wrote, most my energy was spent trying to come up with something clever, or trying to choose words I thought a writer would choose.
Now, I spend most my writing energy trying to mine my mind for what I’m actually thinking. If I’m spending energy choosing words, it’s to balance simplicity with precision.
Figuring out what I actually think is still not easy, but it’s gotten easier. I consistently find two mental roadblocks standing in my way: One, what I want to be true. Two, what others have told me.
When I want something to be true, it’s usually because believing otherwise would tell me something inconvenient about the world or myself. Or, would portray to others a version of me I don’t want to be. Letting go of the desire for certain things to be true has been a journey towards humility and comfort with uncertainty.
You’d think you’d remember that others have told you what’s true, but usually you don’t. We’re full of assumptions we’ve made based upon observations others have made explicitly, or that we’ve gleaned from the collective assumptions of others. For example, the rise of cryptocurrencies has shed light on collective assumptions we make about the value of numbers on our online banking dashboards.
There are many other ways to get stuck while attempting to write, such as not having sufficient knowledge, not knowing the proper grammar and punctuation rules, or not having the vocabulary to say what you want. But beyond those, the biggest obstacle is simply knowing what you think.
Once you know what you think, writing is easy.
Aphorism: “Readers should always feel that you know more about your subject than you’ve put in writing.” —William Zinsser
Cool:God is American is a fascinating documentary of a cargo cult on a remote island in the South Pacific.
Best, David P.S. My blog turns twenty years old on Friday. Much of what I’ve learned and am telling you in this email is said accidentally in my first post.
