On Writing

I never thought i’d be writing articles and books, or even worse, giving writing advice. I was always the worst student in my literature class in Russia, and I never received a grade higher than a C on any Russian essay I ever wrote. I have a theory that my teachers got sick of reading and grading my horrible essays, so they stopped and automatically gave me a passing grade out of pity. Honestly, I don’t blame them.

When I came to the US, my grades in English class in college were not spectacular either. In fact, English was the only class I failed in college and I actually had to retake it in my senior year.

My writing has improved slightly since then – and you now get to be the judge of my scribbles. However, if the prequalification for giving writing advice was based solely on quantity – on how many words have blackened a perfectly fine white screen or besmirched innocent paper – then I am beyond qualified. I have been at it for more than a decade now.

My writing “career” started in 2004, when I was hired as a writer by

TheStreet.com. They didn’t hire me because I was any good – believe me, I wasn’t. But I had an investing background and TheStreet.com was not very picky; it needed warm bodies (ideally with CFA – Chartered Financial Analyst – next to their names) to comment on the markets and stocks. TheStreet.com paid almost nothing, and it was overpaying me.

I had zero experience, but I was ambitious. I took writing very seriously, and therefore my articles were serious. They were filled with big words, and, quite frankly, they were enormously boring. In addition, I was extremely self-conscious about grammar. Sentence structure and punctuation drove me nuts, and I was afraid of confusing words that were spelled similarly but had unrelated meanings (like comma and coma).

This brings me to the first lesson that I want to impart about writing, and it’s one that will drive English teachers insane: Don’t worry about grammar.

Once I stopped worrying about grammar, I felt a huge weight lifted from my shoulders (as all those little punctuation marks emptied themselves from my brain). I completely gave up on a, an, and the (my son does a great job at fixing those for me), I stopped obsessing about commas (and comas), and I stopped trying to ferret out all the other marvelous secrets of English grammar. I let copyeditors – who are very talented and oh so skilled at this – catch me out in all my little peccadilloes.

Writing is a very creative process, and more importantly, I love writing. But grammar is the least creative part of writing. I found that I spent a third of my writing time fixing grammatical errors. And the sad part is that even after I put in my best effort, I still don’t catch all the nitpicky stuff.

I broke the writing process into two parts: the creative part – downloading thoughts from my conscious and subconscious and crafting them into an article, client letter, or book. And then there is the less creative part, the nuts and bolts. I started to worry even less about grammar than before and began bringing talented copyeditors (they are editing this, so I have to say that – though they are!) into my writing process much sooner. This allowed me to write more and, in my humble opinion, the quality of my output has not suffered at all.

Instead, I channel my energy into being a storyteller and making my writing interesting and funny (when appropriate). As I mentioned, when I started writing, my articles were technical and boring. I still feel sorry for the people who read them and especially for my dear friends who felt an obligation to read them.

Then, my TiVo accident happened.

It was six months into writing for TheStreet.com that I wrote about the digital video recorder company. In that article, I dared to use a little bit of humor to describe the painful experience I had getting TiVo’s phone autoattendant to understand my Russian accent. I had to ask my then-three-yearold, Jonah (who by that time had already acquired a perfect “Disney” accent), to talk to the auto-attendant instead, and of course it understood him just fine.

That article was not brilliant – it contained as many or as few insights as my previous articles did – but it was not “proper,” and it was not boring.

Suddenly, though, the feedback from readers was much different. I received a ton of email. It was then that I understood the power of humor. But it was not just humor: I had been able to deliver my otherwise-boring message in an interesting way, and it connected with my readers.

This article singlehandedly changed how I write. I realized that knowing what you want to say is not enough; you also need to figure out how to say it.

To this day, I spend hours staring at the computer, trying to come up with an interesting analogy or a compelling angle on how to say something I already know. I often use analogies to tell a story, especially if the topic is complex. They help me relate complex ideas through simple examples.

Let me illustrate. I have a very smart investor friend of German ancestry. True to his roots, he is very efficient in everything he does. (Yes, I am stereotyping here, but why not?) He has written a very smart investment book; if you read the whole thing, you’d learn a lot.

But that is a big if. His book is as efficient and properly structured as you would expect from a well-engineered German car, or an instruction manual for that car. It doesn’t have an extra word or a superfluous sentence. But unfortunately, in the process of making it efficient, he sterilized his book. I was excited to read it but could not get past Chapter 3. I got terminally bored… and I do investments for a living.

Our brain naturally looks for the most efficient way to communicate a point, the one that consumes the least amount of energy. A story that contains a metaphor is not always the most efficient instrument (judging simply by word count and the writing time needed), but it is usually highly effective, because it lets us connect with readers on a very different and often more personal level.

In other words, the reader may actually finish reading what you wrote.

There is an unintended benefit to a writer when he communicates through a story. Storytelling taps into the right, creative side of our brain and thus stimulates the construction of mental models.

Identify your favorite writers, the ones whose voices you can really relate to, and learn (steal) from them.

In his book, Steal Like an Artist, Austin Kleon writes: “Nobody is born with a style or a voice. We don’t come out of the womb knowing who we are. In the beginning, we learn by pretending to be our heroes. We learn by copying.”

Kleon quotes Paul McCartney: “I emulated Buddy Holly, Little Richard, Jerry Lee Lewis, Elvis. We all did.”

We’re not talking about copy and paste here, but trying to emulate the best qualities of others. Kleon adds, “Don’t just steal the style, steal the thinking behind the style. You don’t want to look like your heroes, you want to see like your heroes.” In our effort to copy our betters, we’ll mostly fail; but this very partial success, which makes us draw upon and improve upon our own qualities, will ultimately lead to shaping who we become – this is how we evolve.

Carefully choose the people who you are influenced by, but don’t settle on just a few. Kleon puts it so well: “If you have one person you’re influenced by, everyone will say you’re the next whoever. But if you rip off a hundred people, everyone will say you’re so original!”

Read to write. My father has been painting since he was seven years old. Being an artist is deeply embedded in his mind and heart. Whenever we traveled he took an easel with him and always looked for places to paint. We’d be on vacation, out walking. He’d stop, close one eye, squint with the other eye, stretch out his arms in front of his face and form a square with thumbs and index fingers – framing his vision for a painting. He was looking for beauty, for the next picture to paint.

When I started writing articles, I noticed that I began to read differently. I started to pay much closer attention to sentence structure, to the voice and the stylistic tricks the author was using. I started reading not just as a reader but also as a writer. Writing also rewired how I observed life around me. I started to pay attention to little things, often turning them into metaphors.

Be respectful of your environment. This is not an ecological statement; I am talking about your writing environment. If you write long enough, you start to appreciate the importance of your external and internal environment. Stephen King, in his book, On Writing: A Memoir on the Craft, said that he listens to heavy metal band AC/DC when he writes. He feels it walls him off from the external world and helps him build his own worlds. I listen to classical music and, if I am really stuck, I start listening to opera.

And if that isn’t weird enough, I write only in italics. This little trick makes my letters look a bit friendlier to me. If you find that you like your font to be pink, go for it. We writers (and thinkers) need any edge we can get, and you can always change back to a color and format that is acceptable to society when you are done.

Create your own quirks. Walter Isaacson, author of many of my favorite books, including biographies of Steve Jobs and Albert Einstein, writes at night. He writes on the computer and then prints out everything he has written. The next morning, he reads it on paper out loud to himself. He says, “That way it is easy and fun to read, because if you just read it on the screen you don’t edit it properly.”

Turn off the spell checker and just write, write, write. I don’t always follow this, but I have found it to be very helpful when I’m stuck. I don’t stop for anything. I don’t correct misspelled or missing words. I just write; I keep moving forward and never turn back. I am doing a word dump. See, you cannot edit nothing; you can only edit something. This word dump fishes ideas out of your subconscious and gives you something to edit.

Be prepared for pain. Writing is a very personal process. Some of us are great thinkers, able to puzzle through very complex ideas in our heads and lay them out logically on paper. I have tremendous respect for those lucky ones. For most of us, writing is usually a painful endeavor that involves staring at a blank screen for hours on end and writing and rewriting multiple times.

In fact, let me take it a step farther: I think through writing. A quote from George Bernard Shaw comes to mind: “Few people think more than two or three times a year; I have made an international reputation for myself by thinking once or twice a week.”

As I have mentioned previously, if you ask me a question about something I have not thought about before, even if you give me a minute to think about it, my answer will usually, well, suck. I have not written about that topic yet, and so I may not have thought it through, and the logical links may not have been made. That’s just how my mind operates.

Quite frankly, I am embarrassed for my brain. It’s like the dirty apartment of a confirmed bachelor, with unwashed clothes, empty pizza boxes, and beer bottles all over the floor. For an idea to be developed to the point at which it can leave the room, I have to clean it up, organize it, and put things in their rightful place. That is why I write. Sorry, dear reader – it’s not about you, it’s about me, me, and me again. That is how I think.

When you sit down to write, your thoughts may not be quite ready to come out – it’s okay if they just haven’t come to a boil yet. Don’t blame it on writer’s block. Author Tom Clancy once said, “Writer’s block is just an official term for being lazy, and the way to get through it is work.” Just take some time off, do something fun and then get back on the writing horse.

One last thing. When you read this (or any other) well-polished book and the words are smoothly flowing along in perfectly lyrical sentences, you need to realize that you are most likely reading a 47th revision. Writing is rewriting, with a lot of pain in between rewrites.