Malcolm Gladwell explains why outlining, writing and rewriting is so hard.

“[It’s]a question I’m obsessed with: Why don’t people work hard when it’s in their best interest to do so? The (short) answer is that it’s really risky to work hard, because then if you fail you can no longer say that you failed because you didn’t work hard. It’s a form of self-protection… Most of the psychological research on this is focused on why some kids don’t study for tests. If you get drunk the night before an exam instead of studying and you fail, then the problem is that you got drunk. If you do study and you fail, the problem is that you’re stupid — and stupid, for a student, is a death sentence. The point is that it is far more psychologically dangerous and difficult to prepare for a task than not to prepare.”

Malcolm Gladwell, From an interview with Bill Simmons.

A friend of a friend has a great script. It’s funny, it’s sad, it’s fresh, it’s original, and he loves talking about it. His friends, industry kids, say “Write it and send it,” a sentence that is rarely said. Whenever this happens, he disappears for a while. I’ve thought a lot about this, and my read is that that script, that dream project is his lottery ticket, his last and only chance to escape the sad life of normalcy and errands he lives in, the last avenue left that could make him the supermodel-fucking rock star that youth in the 90’s prepared him to be. To write the script, to suffer through it, would be to see the flaws in it. He might get a project, but he would kill the warming dream that gets him through the cold days of endless, ordinary struggle.

It’s a sad thought. But my motto has always been “whatever gets you through the day.” That guy is not a screenwriter. He’s a guy with a screenwriter fantasy, and if it’s anywhere near as awesome as my personal James Bond villain fantasy, I can see why he doesn’t want to leave it. But there comes a time to put childish things away. If you want to be a writer, you must write and write well.

The vast majority of newbie writers are both careless and slow. Their drafts take forever, they refuse to be nailed down by best practices like an outline or a careful plan going in.  When they get notes, they start a new project, continuing on an endless cycle of first drafts.

That’s the hardest and most important work I do with clients. I get them to slow down, get the fundamentals, take a fearless look at themselves, and get them to kill the “brilliant but lazy” self image they have of being a misunderstood boy (or girl) wonder, and get them to see the real person, flawed, imperfectly skilled, and able to improve. It’s the cave that you don’t want to go into that contains the dragon.

I could end the article here with a pithy quote, but I’d like to add my own name to the list of people who’ve let fear for their own stupid, shitty ego slow them down. When I was young, I was praised for being “bright,” but never for hard work. I was facile, but sloppy, always rushing ahead to the next step by cutting corners on the previous. I never learned the fundamentals, a part of me knew it, so I kept going fast to hide my deficiencies. As a result of this sloppiness, I spent most of my 20’s watching people less “gifted” but harder working become more successful than me.

Writing was my saving grace – I might be single, fat and dateless, but I had my spec. And yet, perfection, heck, competence eluded me. A common thought for me was/is, “I’ve spent my entire adult life writing, mortgaged my entire future, missed out on so much fun, how am I this fucking bad at this?”

Eventually, after many false starts, missed opportunities, and incredible failures, I finally took the blow to the ego, saw my flaws, and endeavored to improve every aspect of my writing, bit by bit, slowly and meticulously, so my fundamentals would be deeply ingrained and unconscious. It’s a work in progress, but I feel like I’ve built a base that will allow more interesting development. I’ll leave you with a quote from Cus D’Amato, the man who trained Mike Tyson.

“You must understand fear so you can manipulate it. Fear is like fire. You can make it work for you: it can warm you in the winter, cook your food when you’re hungry, give you light when you are in the dark, and produce energy. Let it go out of control and it can hurt you, even kill you…“Fear is a friend of exceptional people.

You are fucking exceptional. Go and write something. Slowly and carefully.

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10 thoughts on “Malcolm Gladwell explains why outlining, writing and rewriting is so hard.

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  1. “endeavored to improve every aspect of my writing, bit by bit, slowly and meticulously, so my fundamentals would be deeply ingrained and unconscious” …how are you doing this? What fundamentals, and what specific steps are you taking to improve them? (marvelous writing…rare among even the most popular ‘writing coach’ blogs, thanks)

  2. Thank you for the nice compliment. When I started, my blogging was a little rough, but I’ve been working at getting better. I guess “What are the fundamentals” will be my next blog – or next after the one I’ve been writing on development culture.

  3. I hate to say it but what you described there is me. I have good ideas and I have the ability to become an adequate writer, but I lack the motivation. When I do something i get part way through and stop because it isn’t good enough straight away. Can’t wait for your post on how you worked through that stage.

  4. Pingback: QOTD | theOffice

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