Mark Frauenfelder and Kevin Kelly recently invited me onto the Cool Tools podcast to share some of my favorites apps and services. I’d welcome any excuse to chat with Mark, one of my favorite authors from my publishing days, and Kevin, whose work I’ve always admired. I’m also a long-time fan of the site, which has been around since 2003 (!) You might find the discussion interesting, so check it out.

Every writer has a crutch, something to push them through the discomfort of getting the words down. Mine’s always been coffee.

I started drinking coffee early, which was maybe not a good idea, and it’s been integral to my writing process as long as I’ve had a writing process. Get stuck = time for another cup. Since I’m constantly getting stuck—when am I ever not stuck?—that consumption adds up. Sure, the output gets a little bubbly when those neurons are sizzling, but any self-indulgent flights of fancy can always be edited out in the next pass. In theory.

Even in middle school, I’d regularly make myself a cup of Taster’s Choice whenever the mood struck. Morning, evening, whenever, and yes, it wreaked havoc with my sleep schedule. (Mystery Science Theater 3000 wasn’t going to watch itself.) And, once I discovered the (sometimes) joy of writing in high school, coffee made a natural pairing.

Is coffee bad for you even if you’re not an adolescent? I don’t know. As with red meat, you can find research to support your position either way. Coffee has been seen as cause or cure, poison or panacea, ever since its discovery in the 15th century. When I had the opportunity to work with the Chopra brothers on their shared memoir, Sanjiv, an eminent Harvard hepatologist, told me in no uncertain terms that I needed to drink at least six cups a day for a host of health reasons. I always had, but now I was under doctor’s orders. (Here’s the full reasoning behind Sanjiv’s suggestion.)

After graduating from college and entering the workforce, I spent my Saturday mornings writing plays at a coffee shop/roaster north of Union Square in Manhattan. Jittery with caffeine, stomach in knots, I’d peck at my tangerine clamshell iBook wondering why my thoughts refused to cohere. When I got my first full-time writing job, I decided to try the Atkins diet before I got to point of resting the keyboard on my belly. Dr. Atkins said you should cut coffee out at first, so I did.

There were no real withdrawal symptoms, but the mental craving was intense. I missed the ritual. At the time, every workplace was divided into smokers and non-smokers, the former tacitly permitted to work 20 percent less than the latter and, what’s more, spend that free time networking with senior employees who, naturally, had worked their own way up the ladder in large part by hanging with senior smokers themselves. I’d always been excluded from that elite society. Now I didn’t get coffee breaks, either. Would Atkins take my watercooler next? Where would I go to discuss the latest episode of Friends?

As the weeks turned into months, the weight came off, but at a price when it came to my creative work. Everything felt slower, more deliberate, more conscious—I hated it. I’d been writing a blog called Fancy Robot at the time, around 2003. With coffee, I felt like I could chug a mug and riff effortlessly for ten or twenty minutes before crashing. Now, blogging was starting to feel like work which, at the time, was an absurd notion. Blogging could never be a job! More important, I couldn’t tell whether I was as good at writing without coffee. The work you do while caffeinated always feels more interesting, witty, and worthwhile. Writing without coffee is like turning the overhead fluorescents on during a dance party. You see what you’re doing a little too clearly.

Eventually, I became fed up with being mentally present while writing—to hell with Atkins and his damnable rules!—and decided to pour myself a Venti cup of verbal brilliance. Whoosh! I can still remember that rush after a long period of abstinence. Boy, did writing feel fun again. And if what I got down was a mess, well, that would surely even out once my body chemistry adjusted.

It never did. I’ve been riding that caffeine see-saw all this time. While that wasn’t too much of a problem as an editor, as a full-time writer for four years now my reliance on caffeine has become an issue. I’d even taken to stashing packs of caffeinated mints everywhere to up my dosage without bothering with the coffee-maker. Anything to push through and hit that word count.

A few weeks ago, I stumbled onto the r/decaf subreddit, a community for people trying to quit caffeine. I hadn’t been consciously planning to do anything about my coffee consumption but, on the spot, I decided it was time to let it go. No more busysauce. In a way, I’ve always used coffee as a crutch for my work. In that moment, I began to question whether productivity is something one can drink.

A recent study found that caffeinated bees are busier and have better memory, but are less effective at actually gathering honey. (No, the scientists didn’t give the bees lattes. Many plants in addition to Coffea arabica produce caffeine naturally, and this research may point toward why.)

It’s been a few weeks without my crutch. Again, the physical withdrawal wasn’t terrible. What I’ve been worried about is the effect this might have on my work. So far, I’m keeping up on output and, if anything, my energy levels are more stable. What I still miss are the little manic boosts, the self-indulgent flights of fancy. I just don’t think my readers will. Also, I continue to wonder whether I really am missing out on significant health benefits that might outweigh the drawbacks of caffeine. (Then again, if coffee is so wholesome, why does the Starbucks mermaid have two tails?)

In the end, I’m sticking with it for the time being, happy to be free of my crutch. A crutch becomes a self-fulfilling prophecy. Every time you run into a block—a difficult sentence to construct, an indecipherable note, a moment of mental exhaustion—you turn to it for relief. If you’d only sat with that discomfort a moment or two more, you’d have pushed through it anyway. But now you give credit to the crutch for something you could have done on your own, reinforcing your dependence. Meanwhile, the crutch brings its own problems. In coffee’s case, anxiety and other physical symptoms.

What’s your crutch? What do you turn to when you can no longer face the page? Maybe you don’t need it as much as you think you do. I’m not telling you to stop drinking coffee. Enjoy it. Enjoy six cups’ worth! It isn’t about the coffee. It’s about what you think you need to write, whatever that might be. Ask yourself: what would my work look like if I were willing to face it alone, one warrior entering the arena? What would happen if I tackled my writing with my own bare hands?

the jerry rig

The enemy of a good plan is the dream of a perfect plan.

—Carl von Clausewitz

In high school, I didn’t participate in any extracurriculars. Doom wasn’t going to play itself, after all. It was only when college applications rolled around that I realized I’d made a minor error in judgment. You see, kids, back in those days you couldn’t just get your head photoshopped onto an athlete’s body. You had to do the work. And, since it was too late in the year to join any existing clubs or teams, I’d have to take the DIY approach.

It never fails to amaze me how a genuine deadline organizes my thinking and directs my energy. In short order, I’d wrangled some equally uncurriculared friends to help start a literary magazine. I knew soliciting entire stories from unmotivated high school students would take too long, so I decided we’d relay-write them. Each contributor would write a chunk of words and then I’d revise the text until it was presentable and finish it myself. (Who knew I’d turn this into a career one day?) 

Convergence was a grand idea with middling execution, but it did the job. After pestering the neighborhood stationery store and the new Mexican place into running some ads, I printed a few hundred copies and brought them to school, triumphant. It didn’t matter that almost all the issues sat unread, even by the “staff.” I’d published a magazine. Ethically, I felt fully justified in claiming credit for the feat on my college application. And, in the end, I was accepted into some schools. Who knows? Maybe Convergence closed the deal. “Hey, maybe this kid is about more than just Doom,” they decided. “You could even say he’s well-rounded.”

A clear, near-term objective with consequences. Why is that so powerful, so necessary? In Skillful Means, the Tibetan Buddhist monk Tarthang Tulku writes:

Whenever we start something new, we may find ourselves anticipating the many obstacles that could arise and the limitations we feel we must face in ourselves and others. Although we feel enthusiastic about our work, we may also be constrained by an underlying fear that we might not succeed [emphasis mine]. This fear hinders the free flow of our energy and prevents us from fully appreciating the excellence and inner value of our work.

Damn right it’s scary to write something new! It’s always scary. Forget my client work, I’m even scared before writing this newsletter, which is hilarious because the only people who read it are pretty much you, whoever you are, and my Mom, and I sometimes wonder whether my Mom only says she reads it to be nice. She’s more of an Agatha Christie type. Tulku continues:

Because we are afraid to put all our energy into our work, we begin to undermine the force of our involvement. We may find ourselves leaving our work every few minutes to eat something, to get a tool, to have a drink of water, to remind someone of something. Although we may realize that none of these things is really necessary, we may still continue to interrupt and distract ourselves. When we fall behind in our work, we may then try to find the quickest way to complete it, giving it only enough energy to get by.

In other words, once that deadline gets close enough to give us a clear, near-term objective with consequences, we act. We stop trying to find the perfect plan and we figure out a way to achieve our objective in the time remaining. It’s the fear of getting it less than perfect that keeps us stuck. It’s only when we match that fear with an equivalent one—not getting into college, for example—that we can proceed. This is how noise-canceling headphones work: they play an equal but opposite frequency and the two sounds balance out into silence.

The problem is, many creative projects don’t have a deadline, and even if they do, by the time our brain accepts that the deadline is near enough to be scary, we don’t actually have enough time to do a proper job. Our brains are terrible at estimating how long things will take.

If you don’t have a deadline or if the one you have is simply too far into the distance to emotionally register, find one for yourself—a contest, an MFA application—and commit yourself to it publicly. Tie in a financial incentive with Beeminder. Make your commitment public. Whatever it takes to incite an equal and opposite fear. To escape from the pit, you must do as Bruce Wayne did: make the climb without the rope.

Creativity is a terrifying, abstract concept. Problem-solving, on the other hand, is something you do a hundred times a day. You just have to activate it: How am I going to get this done in time? What do I do first? What do I do after that? You don’t need a perfect plan, just one that’ll do the job.

p.s. If you want to write a novel, you have a full month to prepare for National Novel Writing Month in November. If not, look for alternatives or start your own.

save your sparkle for the page

Last week, I misspelled meshuggaas. It was a real meshuga thing to do. What a pisher I am. Sure, I’ve fixed the post, but what’s that worth? Bupkes. I am both a shlemiel and a shlimazel. If only you could edit the past as easily as a WordPress post! This is an embarrassment to my ancestors. Oy.

I suppose I should get on to this week’s megillah, but why you’d listen to a putz like me, who can say?

The weather in Brooklyn the other night was lovely, so my wife and I decided to take a stroll. (“Alexa, babysit the kids.” A little-known feature that works surprisingly well.)

Weaving our way through the labyrinthine industrial byways of Red Hook and the Columbia Waterfront District, we stumbled upon a used bookstore. Freebird Books sits on an isolated stretch across the street from acres of shipping facilities along the East River.

Only in New York will you, after a lifetime in the city, randomly discover yet another used bookstore that’s been around for years on a random walk in the middle of nowhere with only a handful of other storefronts nearby and almost no foot traffic. Only in New York will said bookstore be open for business at eight in the evening.

Remember my definition of the perfect bookstore? This place had it all, minus the cat. (With the rats you see in that area, you’d need yourself a lynx, minimum.) In the back, the owner was watching that episode of Star Trek: The Next Generation with the aliens who communicate only in metaphors. He’d rigged it up so that the dialogue played throughout the store, a soundscape which felt even more appropriate, i.e. customer-unfriendly, than the usual hard bop jazz or discordant classical. Freebird is really something special: They just don’t want you in there. (Maybe it’s because they love the books so much it hurts to sell them.)

Right off the bat, I spotted a number of weird gems face-out on the shelves, but only one was worthy schlepping along for the rest of our walk:

The Executive Look: How to Get It—How to Keep It

Magnificent, isn’t it? The contents don’t disappoint, either. If you want to look like any late 70s/early 80s older male TV villain, from Highway to Heaven to The Incredible Hulk, this book will show you how. (Expect a whole new look from me in the coming weeks. In a word? Turtlenecks.)

“Who wrote it?” my wife asked.

“I’m guessing…a haberdasher?”

She opened the book to the back flap, and my life was changed…forever.

Remember those Dos Equis ads for The Most Interesting Man in the World? That guy was a tedious bore. Mortimer Levitt may not have surfed killer waves or wrestled bears, but by god he lived:

Mortimer Levitt opened his first Custom Shop in 1937 and is still the sole owner of this nationwide, 43-branch chain. He has also produced plays, films and television features, and is involved in many cultural and philanthropic activities: a founding member and producer at both the Manhattan Theater [sic] Club and the Levitt Pavilion in Westport, Connectict, and owner of the Mortimer Levitt Gallery; board chairman of Young Concert Artists…He is an avid skiier, tennis player, sailor, and pianist, and lives with his wife, Mimi, in New York City and Westport.

Remember how Fred Sanford used to feign a heart attack whenever he didn’t get his way? “This is the big one!” Reading this, I experienced a paroxysm of panic and regret that left me similarly reeling.

What am I doing with my life? Why haven’t I produced plays, films, and “television features”? Why haven’t I founded anything or been on the board of anything else? At the very least, why don’t I play the piano? (Unless he was talking about playing “Chopsticks.” I can manage “Chopsticks.”)

“This is the big one!” I cried, staggering under the weight of missed opportunities. “We’ve got to get out of this city. I’m not going to be able to get any of these things done here with the time I’ve got left—I’m already 41! We’re going to have to move to an easier city: Pittsburgh, or Cleveland. I need to learn how to play tennis and I need to start some sort of nonprofit. Maybe two. Above all, we’re going to have to stop watching Netflix! People like Mort only existed when Netflix wasn’t an option. I’ll need that time in the evenings to produce ‘television features.’ How do you produce ‘television features’?

I have “reactions” like this from time to time. My wife has plenty of experience talking sense into me. An hour later, we were watching Netflix and I’d canceled my order for a pair of skis.

Writers crave affiliation, accomplishment, distinction. We want to be interesting. I know the pull all too well, and Mortimer was only the latest reminder. That said, actually chasing interesting, going after these markers of distinction, is a mistake, a dead end. When we get caught up in trying to be interesting, we’ve conflated creator and creation. An actor plays villains and we assume they’re villainous. A comedian makes us laugh and we assume they’re funny in person. A speaker wows us from the stage and we assume they can string an entire sentence together in conversation. Far more often, it’s the opposite, and there’s nothing ironic about it.

Pros save their sparkle for the page.

Back in college, the other theater kids were very dramatic. They may not have created many characters—as actors, directors, or playwrights—but they were characters. These characters now work at Goldman Sachs. When I took a video class at a nearby college with a reputation for its filmmaking program, all the aspiring Scorseses and Tarantinos dressed the part, but very few bothered to learn how to edit video in Adobe Premiere. Only a handful completed anything. They, too, are now cogs in the global financial system.

Brilliant authors are often boring in real life. Comedians are frequently humorless. Creators (who know better) don’t waste time cultivating appearances or racking up distinctions. Trying to be interesting leaves a hole in your bucket. Smart creators put everything they’ve got into the work. If they’re still funny, charming, fascinating, or distinctive, it’s only because of a glorious, overwhelming excess of talent. Personally, I’ve got none to spare. I’d love to be polymathic or “notable,” to have an award for something or join an elite club or get my name on a building—but any of that would take time and energy away from my work.

Only five Custom Shop locations remain, but Levitt’s legacy lives on with a foundation that mounts public performing arts events around the country. Even in death, Levitt outshines my accomplishments. I haven’t even begun to work on establishing a foundation, which is probably for the best. Mine would be more along the lines of the Foundation for Law and Government from Knight Rider. Do you think I could apply for a government grant to build K.I.T.T.?

p.s. I should add that my wife was embarrassed when I recognized the Star Trek episode just from the dialogue. I was embarrassed when she couldn’t tell if it was TNG or TOS.

p.p.s. Now I’m wondering whether you know what TNG and TOS stand for, and now we’re both probably embarrassed about the other.

accepting the meshuggaas

In response to my essay a few weeks back about how the easy way is actually the hard way, Nancy Larson, author of The PARDA Process, wrote to me about the difficulty of writing and publishing her first book:

That last project frequently found me weeping as computers fried, printers crashed, hiring and firing editors, etc. It was truly awful. I’m glad it’s done, mind you, but it was hard. The writing is (relatively) easy; it’s all the ancillary things that went with it that almost drove me to the edge.

The writing is relatively easy? THE WRITING IS RELATIVELY EASY

Nancy’s right. Once you’re at the keyboard and underway, writing itself isn’t all that bad. Usually. But, just as any fighting force is dwarfed by its support team—four thousand helpers joined the three hundred Spartans at Thermopylae—the artwork itself represents only part of the commitment to the work of art. You have to accept all that and factor it into your planning or you’re going to make yourself miserable.

Yes, we become more efficient in how we work over time. Less yak-shaving, as a programmer might say. But there’s a point of diminishing returns. It’ll never be anywhere near one hundred percent tappity-tap. There will always be a substantial amount of what you might call The Meshuggaas: thinking, planning, organizing, researching, switching from Word to Scrivener, starting over, regretting starting over, going back to an old draft, switching from Scrivener to Word, giving up on writing altogether, reading a great book and deciding not to give up writing after all, now where did I put that file and was it in Word or Scrivener format…

This is the meshuggaas of writing, and it never ever goes away no matter how many cumulative weeks you’ve spent on the best-seller list. When we don’t accept the meshuggaas, we suffer. Refusing to believe that all this craziness is an intrinsic part of the creative process, we drive ourselves crazy expecting the impossible. We set grand goals that we could never really achieve in one human lifetime and then beat ourselves up for not staying on track to achieve all of them in a timely fashion, i.e. prior to our own deaths.

Oh, it’s so easy to be seduced by the easy. As a reference librarian I order self-help books by the score for patrons. I scour web sites for writing tips and easy ways to keep my house organized. Unfortunately, few of them deliver on their promises. Slowly, I’m coming to peace with the fact that there truly are no shortcuts. Consequently, it’s becoming somewhat easier to step back and assess whether doing the hard work for a particular goal is worth the effort.

This is wisdom. Nancy is accepting the reality of writing as it is instead of writing as we all think it should be, one day, if only we read enough books or use the right software or find the right teacher or online course. We won’t be able to check all the boxes.

Instead, let’s check one box on our creative bucket list. Just one. Better, let’s work steadily toward that one check and be content with that state of enbucketment as long as it lasts.

Have you ever seen the expression “to take pains,” as in “Humphrey took pains not to lead the hunting dogs athwart Lord Chumpelford and his men”? Take pains to do your work. If it isn’t occasionally boring or frustrating, if it doesn’t feel like you’re wasting your time doing this or that, if you don’t suspect that the rest of the world is moving on without you while you fiddle with nonsense when you should be done already, you’re not doing it right.

Plod. The plodders will inherit the earth.

I was not a good student. I rarely sensed that I excelled relative to my classmates. That said, there came a point in high school when I realized that I played clarinet pretty well. I hadn’t gone out of my way with it or anything, but the old licorice stick came easily to me and I’d ended up ahead of most of the section. Eventually, I started to pin some self-worth to the ability and, while I still didn’t practice regularly, I started private lessons.

One day, I arrived early to my lesson to find a guy in his fifties or sixties sitting in my chair. He had a blue-collar look—bristly moustache, meaty hands, calloused fingers—and he held his plastic clarinet like a hammer or a saw. After he’d packed up and left, I asked my teacher why an old guy like that would bother starting the clarinet. (As you can imagine if you read this newsletter regularly, teenage-me was insufferable.) Starting an instrument in middle age made no sense. He wasn’t going to enjoy the prestige of being First Chair in his high school orchestra or anything like that. He’d certainly never have the opportunity to go pro. Would he really be satisfied squeaking out “Twinkle, Twinkle Little Star” for the rest of his life?

Except, he wouldn’t be squeaking for long. Whenever I arrived, I’d catch the end of the guy’s lesson and, lo and behold, he got better steadily. Soon enough, he’d caught up to me, and I began to feel self-conscious about starting to play until he was out of earshot. I’d always assumed that practicing daily and doing the assigned work were like vitamins: good for you in an abstract way but ultimately unnecessary. No, practice and effort were like steroids. They worked, fast. Natural talent had gotten me to a certain level without much effort. For more, diligence and humility would be required.

My freshman year, I auditioned for and was accepted into my college’s elite orchestra. At the first rehearsal, I sat down next to the other clarinetist and took a look at the sheet music. It was like a foreign language. I raised an eyebrow at her as if to say, “Are they kidding?” She didn’t even acknowledge my existence. I looked back at the music. There were markings and notations I’d never even seen before. I looked down at my clarinet with an out-of-body sensation as the conductor raised his baton. Was this really happening? Over the next hour, I made a few half-hearted attempts to play notes, but mostly I mimed: I had no intention of coming in at the wrong moment and revealing the depths of my ignorance. Throughout the ordeal, I kept wondering: How the hell did I even get in? Nobody could be expected to go from where I was at my audition to the level required by this music.

Except, someone could. That older guy had taught me that. Someone could get to this level with steadfast commitment and plenty of hard work. Someone could learn to play as well as anyone else in that room.

Someone could, but it wasn’t going to be me. At the end of the rehearsal, I packed up my clarinet and quit the orchestra.