that’s amore

You might have noticed that I didn’t send an essay last week. No, I wasn’t being lazy. I’m never overwhelmed and I never procrastinate, either. The truth is, I was engaged in a period of quiet contemplation.

Impressed? You should be. In fact, you might even say I was taking a sabbatical from my newsletter. (Stefan Sagmeister and I take sabbaticals now and then. Deal with it.) It doesn’t matter what it is you make or how crass, commercial, or outright bizarre it might be: If you stop doing it for a “sabbatical,” everything you’ve ever done in your life achieves retroactive profundity. Taking a sabbatical—or, at least, announcing that you will be on social media or, even better, on stage at a TEDx event—is like dying and getting to attend your own funeral. I highly encourage it.

(Here’s hoping Nic Cage never realizes the power of the sabbatical. We need movies like this one now more than ever.)

In the current arms race between designers, writers, and Silicon Valley product managers all loudly practicing what you might call conspicuous contemplation—our bible is How to Do Nothing: Resisting the Attention Economy—I’m coming out ahead, winning at the art of looking like I’m not trying to win. Have I humble-bragged about quitting Facebook lately? Those of us who quit Facebook are very wise.

The only real problem with quitting Facebook is that after the initial announcement—which makes you look like a combination of Pema Chödrön and Warren Buffett—you can’t rack up any more too-wise-to-chase-success-yet-still-successful points from your social network. If only there were a tool for sharing these kinds of announcements on a regular basis so that people I know could continually be alerted about my astonishingly virtuous and ascetic feats of self-care? (Oh right, I’m still on LinkedIn.)

The only way to get ahead nowadays is to visibly stop trying to get ahead. You have to treat yourself like a delicate little hothouse creativity orchid sage and then let the world know you’re doing it. We need acclaim and respect for our lack of interest in either, but we also need enough space and alone time to recharge our souls, which apparently hold their charge about as well as a five-year-old Nissan Leaf.


Despite being exiled to camp every summer, a.k.a. “Lord of the Flies, Catskills edition,” I never really learned to swim. So, a few months ago, in a fit of middle-aged self-actualization, I decided to sign up for lessons. While I’ve read and written about skill acquisition before, it still surprises me to have to go through the same “stages of learning” every time:

  1. Unconscious Incompetence
  2. Conscious Incompetence
  3. Conscious Competence
  4. Unconscious Competence

It’s easy to get the idea that knowing how learning works will somehow make it easier to persevere. It does not. Only bullheadedness does the trick.

After two months of weekly lessons, I count myself firmly in the “conscious incompetence” category. As much as I abhor schlepping to a cold pool in the dead of winter to flop around like a child surrounded by human dolphins effortlessly gliding through lap after lap, there’s nothing for it but to keep doing it until I get it right and then, as cheerleading coach Monica Aldama advocates in the Netflix docu-series Cheer, keep doing it until I can’t do it wrong.

Mr. Rogers swam regularly. It’s supposed to be great exercise, especially if, like me, you have knees made of crêpe paper and Elmer’s glue. As I’ve pieced together my freestyle stroke, I’ve started wondering whether I could feasibly maintain a regular swim schedule. The blog SwimCompetitive advises the following:

A good guideline would be about 20-30 lengths for beginners, around 40-50 lengths for intermediate swimmers and roughly 60 lengths for advanced swimmers.

This is where the progression of learning gets toxic in every category: swimming, writing, everywhere. Mr. Rogers only swam twenty-five lengths a day, and he considered that “a long, long swim.” Now I’m told that I won’t even be “intermediate” until I’m swimming forty or more.

I can swim the length of the pool about five times (with breaks) before I feel like dying. So now I’m a pre-beginner, lower than low. If you make a habit of reading writing advice, you’ve had the experience many times of having the starting baseline placed well above where you currently are. It gets worse:

Swimmers who are at the beginner levels should aim to swim two to three times a week. More experienced swimmers should make it their goal to swim at least four to five times a week. Many competitive and elite level swimmers train about five to ten times a week.

In other words, I’m not even a real swimmer until I’m at the pool four or five times a week. And if I want to be “competitive,” I should be swimming multiple times per day. It’s exhausting to contemplate. (There I go again with the contemplation. I can’t help it.) This is where we get caught up in our writing. We receive this very rigid idea of what it means to be a “professional” that is totally at odds with the necessary mindset to explore our creativity and improve our skills. Professional is always positioned in sharp contrast with amateur, but guys, what does “amateur” even mean?

Hint: it has something to do with yesterday’s holiday.

Amateur derives from the Latin verb amare, “to love.” Amateurs do it for the love of the thing. When did that become bad? How are you supposed to get better at doing something you don’t love doing, at least some of the time? Professional also derives from a Latin verb, profiteri, but that one’s obvious: to profess. A professional makes a kind of promise to someone else that they can get the job done. I’m not sure why that takes the love out of the equation, but we do tend to get tangled up in our egos when we’re writing for others. A true professional should simply take the ego out of it.

This week, if you’re a professional, bring that Valentine’s Day romance back into your writing. If you’re an amateur, relish in the ardor you and your writing have for each other. And if you’re a pre-beginner, get in the pool and do some laps. Give it time. You’ll learn to love it.

one about words

Lately, I’ve been pondering the difference between thinking and contemplation. Thinking has more than its share of negative connotations. For example: If someone shouts “Think!” at you, they’re not too happy with whatever it is you just did. (In my experience, anyway.) No one’s ever shouted “Contemplate!” at me, but it wouldn’t feel as bad, would it?

“Sure,” I’d reply. “That’s a great idea, Jim. I’ll be out in the garden, contemplating!”

If I tell people “I need time to think,” it sounds wilted and pathetic: “You’re a grown man, Dave, but go have your little tantrum and let us know when you’ve figured the universe out!” On the other hand, if I solemnly announce that I’m taking a week off the Maven Game for a “period of contemplation,” I’m a bona fide thought leader. (Yes, thought leaders don’t actually think, they contemplate. In the words of the Canadian thought leader Alanis Morissette,  “Isn’t it ironic?”)

I’ve got to give more contemplation to the nouns I use. Verbs, too. Heck, all the Mad Lib categories. Adverbs? My choice of words says (conveys) a lot (a great deal? a muchness?) about me, my taste, my education, my philosophy of communication. This might be a whole new avenue (boulevard? thoroughfare?) of personal branding I’ve never really…contemplated before.

Recently, I finished Anne Fadiman’s Ex Libris, a slim collection of essays about books and the people who love them. Fadiman’s a strong writer. She’s also wordy. I can’t stress enough that this is a distinct attribute. In one book, she uses enough ten-dollar words to buy herself a complete OED. (I’d link to the page where you can buy the twenty-volume Oxford English Dictionary, but I’ve discovered that the link on their site is dead. How am I supposed to get any writing done with a one-volume dictionary?) It’s a bit much, Fadiman’s recklessly profligate verbiage. It’s tiring to read over long stretches.

As a young reader, I’d look up new words immediately and commit them to memory. As a kid, you don’t have a good way—when, for example, reading classic literature—to distinguish between the words you actually need to know and the ones that are long out of fashion. You end up using outmoded words in conversation with deleterious effect. To paraphrase our president: lugubrious. As a professional writer, I have to be judicious with the archaic and needlessly obscure. Words like recondite and otiose are linguistically charming, but actually using recondite words in your prose is otiose. Dead words died for a reason—leave them buried. 

Strike a balance. You want to be seen by others as insightful, educated, and wise. The directest path is through your choice of words, not in what you say but how you say it. Like silver nitride, words are fussy, delicate, and highly combustible. They matter. The sizes of our individual vocabularies vary, but each and every one of us parses language with the ferocious perspicacity of a Talmudic scholar when those sentences matter to us. Just watch the participants on the Netflix reality show The Circle obsessively analyze and reanalyze each other’s gnomic social media utterances for signs of deception. Who’s the catfish?

We’re all the catfish. If you contemplate about it.

the time-accountant

At the age of six, I wanted to be a cook. At seven, I wanted to be Napoleon. And my ambition has been growing steadily ever since.

Salvador Dalí

You like cancel culture? Try canceling everything. No more side-projects. No more project-projects, either. Marie Kondo didn’t go far enough. Get rid of each and every thing regardless of its joy-sparkles. Down with goals. Death to visions and the boards they rode in on. Come to complete and utter stillness.

(Tell me a part of you didn’t sigh with relief at the idea of doing this. I often dream of opening my task manager and hitting Cmd-A, Del.)

By my estimate, this one-step transformation will clear your to-do list, bring your project completion rate to 100%, and get your messy inbox down to zero, all for free and in no time flat. McKinsey would singlehandedly devastate human society to achieve results like that. (Too late.) Am I truly crazy to suggest such a radical move? Ask yourself: how many of your creative dreams have you actually fulfilled doing things the old way: suddenly feeling motivated to do X, deciding on a whim to do X, and then stuffing X into your life like one last milk carton into the recycling bin, hoping you can make it fit if you just push on the lid hard enough.

We all want to have done all the things. For me, simply writing this newsletter every week takes up about 112 percent of my surplus motivation, energy, and time. How’s your scorecard looking? Don’t be hard on yourself. This isn’t a lack of discipline. It’s an overabundance of ambition and enthusiasm in the face of exciting new tools. You can record, master, and distribute an entire album on your phone! You can publish a book internationally in a few clicks! You can become a TikTok star in minutes just by doing whatever TikTok is! In the face of all this unprecedented possibility, it’s hard to face reality: ten fingers, two eyes, 24 hours in a day.

If we’d just wanted to do one thing in our lives, we’d do it and get back to everyday life, content. To Kill a Mockingbird: One and done. As for those who do all the things, take Winston Churchill. Politician. Military officer. Historian. Best-selling author of a novel, two biographies, and three volumes of memoirs. Accomplished painter of Impressionist landscapes. Amateur bricklayer. Butterfly breeder.

You know what else Churchill did? He drank twenty ounces of champagne and a brandy at both lunch and dinner plus three or four ounces of whisky at 11 a.m., tea time, and bedtime. He wasn’t very nice to India, either.

Know who else did all the things? Isaac Asimov. Asimov wrote 506 books across all ten Dewey Decimal categories. Know what else he did? Grope. Prolific author. Prolific groper.

So let’s not lionize the polymathic high achievers, shall we? It comes at a cost.

I’ve been stopping over the last few weeks. Half-read books, half-finished projects, into the bin with everything non-essential, turning my ambition way, way down. Clearing the decks is energizing. My problem is that it doesn’t last. Ambitions multiply. Squash one and two more skitter out from under the floorboards. Give up on learning to play the harmonica and soon you’ve decided to code an app that let’s you play your iPhone like a harmonica. (Tuesday nights are free for coding lessons because that’s when you used to have harmonica lessons.)

There’s something inside of us that makes it impossible to leave a blank space, on our calendars or in our minds. None of our dreams have the opportunity to ferment before we act on them. We habitually jump the gun and then wonder why we sputter to a halt. We’re so optimistic and vigorous and excited about making amazing things happen that we go from whim to turning the bathroom into a podcast recording studio in one click. Next day, we realize we’re not all that excited about interviewing famous authors in our bathroom. Here’s a typical night in front of the TV for us:

Wife: What are you doing on your phone?

Me (tapping away): Almost done. I’ve decided to become a chess boxer because I read a blog post about the pro chess boxing circuit. I’m just ordering boxing gloves and a chess board on Amazon. Oh, and…chess…pieces. There. Also, I signed up for chess lessons and boxing lessons. You’re not going to see me on weeknights for a while.

Wife: Gotcha. Good luck with that.

Sound familiar?

There needs to be a hard limit. We should budget our time and energy as closely as we budget our money. Otherwise, we’re writing checks for a resource we don’t have in the bank. It would be one thing if you could set some time aside each month in an interest-bearing account and then, boom, you’ve earned like an additional year for a sabbatical. But no. Time is stubbornly finite.

With all this in mind, what we really need are certified time-accountants to help keep us on track. Mort works out of a dilapidated office in downtown Brooklyn surrounded by old gray file cabinets and boxes filled with manilla envelopes:

Me: Mort, I’ve decided to write screenplays for Kevin Feige at Marvel. With all the movies they’ve got planned for Phase 4, they’re probably desperate for the help. Step one, learn how to write screenplays.

Mort (pulling out a calendar): Sorry, Dave, you just don’t have the hours for that particular whim. You’ll have to let go of one of your other commitments. Granted, chess boxing was a good decision now that you’re a champion chess boxer, but your harmonica iPhone app is still in beta and the reviews haven’t been kind.

Me: Find me more time, Mort. Who’s going to write She-Hulk if I don’t step up and learn how to write screenplays, Mort? Are you suggesting I wait until Phase 5? By that time, Marvel movies will be way too popular for a total amateur like me to get the chance to write one. Now’s my chance to get in on the ground floor.

Face reality. Try canceling everything and see what happens. Wait for one thing to aggressively insist on being reinstated. Even then, be suspicious of your ambitions, your “side hustles.” Make your ideas work for the privilege of being realized. Wait till they beg and claw their way back into your mind. Then, defend the winner from all the other notions trying to seep their way back into your calendar and your brain. Ready your fists. Arrange your pawns. Chess-box your way to writing She-Hulk.

writing for the king

Do you want me to strike this?

Ron Albertson, Waiting for Guffman

I took a few stage-directing classes in school, but I didn’t learn much in the way of formal technique. (The theater department of my liberal arts college abhorred all things “pre-professional.”) When directing a play, I’d sit and watch the actors run a scene, tell them what to do differently, then have them run it again. It wasn’t elegant, but it got the job done.

At my school, theater majors were given only one opportunity to direct a full-length play, as a senior project. In my eagerness to get my theatrical career off the ground—unlike my peers, I’d never done any theater prior to college—I mounted six or seven indie productions in various spots around campus before my senior year. Mamet, Pinter, that sort of thing. Good times. Nothing beats putting on a show.

Forging ahead like this without any oversight and without much experience as an actor being directed, I developed an array of bad habits as a fledgling director. It was only during my senior-year project that the directing professor himself had the opportunity to watch me work outside of a classroom exercise.

“You’re directing for the king,” he observed, glumly. My first instinct was to take this as a compliment—who wouldn’t want to be royalty-oriented?—but no. “In the past, the king would sit square in the middle of the audience,” he explained. “All the action would be directed toward him. Everyone else would just have to deal with what they got. Today, things are a bit more democratic.”

“Oh,” I said, still unsure where he was going with the history lesson.

“You might try sitting somewhere else,” he clarified.

“Ah,” I said. “Yes.”

So I moved and watched a scene. Moved again, watched again. I discovered he was right. Arranging the scenery and blocking out the action, I hadn’t given any thought to the people on the right, let alone the people on the left. Or, for that matter, the poor bastards in the back. I’d only been interested in optimizing my own experience as an audience member, and I had the best seat in the house.

A theatrical production has to “play” to an audience of hundreds or even thousands of people. Great stage directors—Bartlett Sher is one of my favorites—handle this challenge so elegantly, you often forget about your lousy seats. It just doesn’t matter. You’re right there, having an experience. Unless, of course, there’s a column in front of you. (I’d like to see Bart direct his way around that!)

A book also has to play to a group of readers, an audience. Might be 5,000, might be 500,000, but it’s not infinite and it’s not just you. Don’t write for the king. Move around the “auditorium,” Imagine the various perspectives of all those potential readers. Do they know what you’re assuming they know? Do they enjoy what you’re assuming they enjoy? Will they find this or that aspect of your subject quite as fascinating as you do?

The eyes of a reader are the ultimate proscenium arch. As “director” of the reader’s experience, you’ve got an unlimited budget for sets and props. You can cast literally anyone you want. You can mount a production of extraordinary scope, spanning eons and galaxies. Writing a book may not be as fun as mounting a play—or, well, at all—but it’s an extraordinary privilege.

My professor may not have taught me much in the way of technique, but he identified a blind spot in my working style that still hinders me today. No matter how good you get, you can’t see what you don’t see; I wish I had more teachers like him.