50 Writing Lessons From Aaron Sorkin


Mark: “There’s a difference between being obsessed and being motivated.”

Erica: “Yes, there is.”

What Mark is obsessed with, according to his girlfriend, is getting into one of Harvard’s elite social clubs. She doesn’t think it’s healthy. Mark, on the other hand…

Mark: “I want to try to be straightforward with you and tell you that I think you might want to be a little more supportive. If I get in, I’ll be taking you to the events and the gatherings, and you’ll be meeting a lot of people you wouldn’t normally get to meet.”

Erica: “You would do that for me?”

Mark: “We’re dating.”

Erica: “Okay, well I want to try and be straightforward with you and let you know that we’re not anymore. Mark, you are probably going to be a very successful computer person. But you’re gonna go through life thinking that girls don’t like you because you’re a nerd. And I want you to know, from the bottom of my heart, that that won’t be true. It’ll be because you’re an asshole.”

This is the first scene of “The Social Network,” a movie about the foundation and rise of Facebook. The Mark in question is Mark Zuckerberg. He would indeed become “a very successful computer person.”

The script for the movie, however, was written by “a very successful writer person.” In this opening scene, said person — none other than Academy Award winner Aaron Sorkin — shows us the most important rule of storytelling, drama in particular: Intention and obstacle shape the story.

In this case, Mark intends to get into a final club. His obstacle is not just to figure out how but also to convey the importance of this goal to Erica. When he fails to achieve the latter, Erica breaks up with him. She also reveals Mark’s true intention, which will color the whole movie from this point onward: He desperately wants to be liked, particularly by women.

Resting on this setup, it’s easy to see the movie unfold: Mark does something with computers that’s cool enough to get him into a club. He makes it bigger. It works. People like him. He finds success. Friends. Love. And then, because his obsession never stops, everything collapses around him.

That’s the kind of opening scene you want: An extensive preview that draws you into the story. It’s great writing, and it’s great because it follows from a great lesson: Intention and obstacle shape the story.

I picked up this lesson in Aaron Sorkin’s MasterClass  (not affiliated). Here are 49 more.

1. To start the story, show us the intention. To start the conflict, show us the obstacle. Reveal intention and obstacle early on to kick things off.

2. The story hasn’t started before we know the intention. The conflict hasn’t started before we know the obstacle. As a corollary of #1, the journey only begins once we know intention and obstacle. This isn’t to say you can’t set it up in other ways before, but real engagement tends to first happen after this point.

3. Showing the intention is better than stating it. Showing the obstacle is better than stating it. “I want to get into a final club” is not as strong as a five-minute rant about final clubs. A desperate attempt to look cool in front of others is even stronger. “You can’t get in” is not as strong as someone shoving and shooing Mark out the door. Show, don’t tell.

4. To find out if your drama has potential, put pressure on intention and obstacle. How strong and sturdy are your intention and obstacle? Ask some questions to probe them. Do they hold up? Or fall apart at the first speck of doubt? Is the conflict you create one of two opposing, equally strong ideas?

5. Writing about places leads to TV shows. Writing about events leads to movies. If you want to write about life in a startup office, the inner workings of the Hollywood industry, or every crevice of the Grand Canyon, chances are, you’ll create something episodic, like a TV show. If you’d like to recount a singular event — passing the bar, free climbing El Capitan, getting married — it’s likely a good fit for a feature movie.

6. Tactics make characters. How actors decide to tackle their obstacles impacts how we see them. Is the sultan’s advisor lying a lot? Does the pretty girl avoid the guy she likes? Honesty, bluntness, deceit, aggression, creativity, laziness — all of these traits should shape how characters act.

7. Stick to useful character details. If a fact about a character doesn’t move the story along, ask twice if you need it. It’s nice to add a little color around the edges, but, generally, readers’ imaginations are fantastic. They’ll fill in whatever they need, so don’t get lost in biographies.

8. Characters don’t have to match real people. It’s okay to overdraw a character, make them seem a little over the top. If it helps portray what they stand for, go for it. Sorkin says, “Singers don’t try to sound like instruments. Exact replication is boring, even if it’s successful.”

9. If you can’t be accurate, make it irrelevant. Don’t get too deep into ethics and ethnics you don’t fully understand. If you have to, do heavy research, talk to people, but don’t pretend you’re a funny black guy just because you’ve seen one on TV.

10. The villain must make a valid point. The reason Heath Ledger’s Joker from “The Dark Knight” has held up so well over time is, in part, because his rationale is excellent, even if his means are twisted. He and Batman are both trying to save Gotham, each in their own way, and that’s gripping. What’s hard about creating such a villain is that when you put words in their mouth, you too have to believe you’re making good points.

11. There are two types of research: Nuts and bolts and inspiration. Nuts and bolts is easy. Look up what type of screw it was and move on. Inspiration research is tough. You need time, and you’ll only know what you’re looking for once you’ve already found it.

12. What’s the more important truth? If you’re re-telling a real story or rely on nuts and bolts research a lot, you’ll find the truth won’t always do it. Sometimes, it’s not poignant enough. Punchy enough. Ironic enough. So when can you twist it? Sorkin suggests you ask if the lie feels unfair. Do you rob the reader of something with your lie? Or do you give them something? Only change the truths that don’t matter. Maybe, the killer drank beer, but vodka better reflects her feelings. Which one do we care more about? Listen to your gut, and you’ll know which details to change.

13. Make the audience part of the experience. Great painters think long and hard about the perspective from which the viewer will look at  the painting. Don’t forget the viewer.

14. Give everyone the same clues. Sherlock doesn’t get more information than you do, but you only hear his thoughts once he articulates them. If you can give your audience the same clues as your protagonist but then hit them with a twist they didn’t see coming, that makes for a great, engaging puzzle. “Ahh, I knew it!” “He did not just…” Both are good reactions.

15. It’s only impossible if the reader knows it’s impossible. And really, how much do we actually know to be impossible? Time travel, wormholes, different dimensions, and superheroes are 99.99% unlikely, and yet…

16. “The worst thing you can do is tell people something they already know.” The second worst thing is confusing them too much.

17. Without conflict, it’s not drama. Sorkin says this is where story and drama differ. A story without conflict may be lame, but it can still be an intact story. A drama without conflict is not a drama after all.

18. Turn exposition into a character. When Alice falls down the rabbit hole, everyone must explain stuff to her. That’s good because Alice isn’t the only one who benefits — we do too. If you can include a blank slate character with no clue what’s going on, you’ve basically written the viewer into the story (#13!). Slowly fill in that character, and you’ll slowly brief the reader.

19. The first 15 pages. If they suck, your book/screenplay won’t sell.

20. The last 15 minutes. If they suck, your book/movie will bomb.

21. All writers think they’re trying to fool everybody. Everyone suffers from impostor syndrome. Just try your best to write like yourself and keep your fingers crossed that people will enjoy the end result. That’s all you can do anyway.

22. Make the action last as long as it would in real life. If you’re writing about movement, allow the reader to follow along at a realistic pace. Don’t say, “When he kicked down the door, it landed on the floor with a loud noise.” Say, “POW! The door flew out of its hinges.” If the action lasts way longer than it would in real life, that’s a bad kind of slow-motion.

23. Probable impossibilities are better than improbable possibilities. That’s not Sorkin’s lesson. It’s Aristotle’s. Tell us about the impossible that happened with chutzpah, not the already-possible that “seemed unlikely.” John Wick killed 100 men alone? No way, I totally believe it! The nice butler killed the rich baron? Of course, again, whatever.

24. If you must use improbable possibilities, acknowledge them. The only way the butler gets away with being the murderer is by acknowledging the stereotype. Last scene, the cops handcuff the culprit. They shove him into the back of a police car. The officer slams the door and sighs in irony. “Well, well, well. Who would’ve thought? I guess the murderer is always the butler. Goddamn butlers.” If it has to be mundane, at least make it funny.

25. Readers know  the rules despite not knowing they know the rules. Stories are innate to humans. We connect with them at a deep level. Even if we don’t know the first thing about the craft, we know a good movie when we see it.

26. Think about launching points. Each scene sets up the next one. Each paragraph prepares the next one. How can you reward the reader’s patience while making sure all elements connect seamlessly? Make it easy to jump off one vine and grab another. Allow the reader to keep swingin’.

27. The best jokes are set up early and pay off late. You know what’d make that butler joke from #24 better? That same officer saying, “I’m telling you, Joe, it’s gonna be the butler. It’s always the goddamn butler,” five minutes into the movie.

28. Embed the theme in the opening scene. In “The Social Network,” the opening scene happens in a bar. It’s a metaphor for the clustering, changing, sometimes mutating nature of human relationships. Facebook is one big bar. You can chat. You can laugh. You can also get punched in the face. Grab people, drop them right into the action, or show them something they’ve never seen before. That’s how you open a story.

29. Courtrooms represent the ideal structure of drama. In a courtroom, intention and obstacle are utterly clear. Two sides, opposing goals, and the jury is a stand-in for the audience. What’s the courtroom metaphor for your story? If your story was an episode of Suits, how would it go down?

30. Ordinary people in extraordinary circumstances or extraordinary people in ordinary circumstances. Show us either, we love both, but make sure you pick one of the two. Usain Bolt outrunning a freight train isn’t cool. A former 300-lb. guy outrunning Usain Bolt is cool. Or, you know, Usain Bolt at a bar. Maybe he’ll meet Mark Zuckerberg.

31. Dialog is music. When speaking is a performance, the rules of speaking take a backseat to the rules of music. Sorkin says he hears dialog as music, and that’s how he writes it. Does it feel like waves? Does the rhythm flow? Is it lopsided? Muffled? What’s that thumping sound in the back? Pretend you’re on Spotify. Would you hit repeat on this conversation?

32. How words sound is as important as what they mean. Which intonation of “goddamn” makes the butler joke (#27) sound the funniest? Read it. Read it out loud. Again. Again. As with a good movie, you won’t know why, but you’ll know if something’s off (#25).

33. Dialog is neither imitation nor censorship of real conversation. You don’t need all the “umm”s and “ahh”s of everyday small talk, but if “this shit sucks,” then “this shit sucks.” Don’t go all PG-13 on us.

34. If you want to know if your dialog works, perform it. There’s no one there to laugh at you. You’re already alone in your room. Just get up, take the script, and perform the words out loud. Who cares? No one will see it. But you’ll know if “this shit sucks.” You’ll know if you need to make it better.

35. You have to get your own marble. There’s a great, probably untrue Michelangelo quote. When asked how he found David inside a block of marble, he supposedly said, “I took away everything that wasn’t David.” That’s great if you’re a world-famous artist, dead, and misquoted, but for the rest of us, it’s probably not that simple, starting with the fact that, first, we have to get our own damn marble. If you’re a writer, that block of marble is called your first draft. Get something on the page! Anything, really. Then, you can start looking for David.

36. The hardest part of rewriting is killing your darlings. You know the drill. If it makes you feel better, create a file where you keep all your witty, unappreciated chirps of genius. But if it doesn’t help the story, don’t keep it in the story.

37.Be careful who you listen to. At the end of the day, you’re the expert, even if that’s hard to believe (#21). Not the reader, not the audience, not your fellow writers, not your investors, not the producer, not the editor. You. Be careful who you listen to.

38. Form an editor’s round table. Have a small circle of people you trust in critiquing your work. When in doubt, don’t doubt yourself, but clarifying whose opinions you’ll consider in advance will make #37 a lot easier. Even so, always ask specific questions and weigh their answers one by one.

39. Don’t ask, “Is this good or bad?” ask, “Did you understand it?” It’s easy to make gut judgments about a story and form a subjective opinion. What’s hard is questioning if we’re well-equipped to do so. Don’t let people get away with, “I didn’t like it.” Maybe, they just didn’t get it.

40. Never perform emotions the audience should feel. Imagine the over-the-top actor who dramatically breaks down on his knees, raising his fists to the skies and forever cursing her wretched name. Yeah. Emotions are the result of actions. If you show us the right actions, we’ll feel the right emotions. No need to hold up a “clap now” sign and paper tissues.

41. If you’re the only one who’s not happy with your work, retype the whole thing. Retype it from the page once. Word for word. Leave it as is. Then, retype it again, this time from memory. Between the two versions, you’ll know what to change.

42. Avoid “once out of the well” moments. Sorkin recounts a lesson from Bill Goldman, back from the time when most movies were short, episodic, and came with text cards at the beginning to catch viewers up to speed. In one such movie, the hero fell down a well at the end. The next movie started with a slide that read, “Once out of the well…” If you can’t figure out how to reasonably resolve a crisis your hero is in, it’s probably not a crisis they should face in the first place. Don’t just mention a big dilemma was solved. Show us how it got solved.

43. Protagonists can’t be victims of circumstance. Like, ever. Of course, everyone has their bad moments. Everyone’s a downer sometimes. But if your story is mostly some dude lamenting his own fate, that’s just…sad.

44. Dialog must be specific. Would John really say, “Call Bob!” or would he say, “Call that lazy slob and tell him to get his ass in here!” Let people refer to people the way they’d refer to them in real life.

45. Never write to change someone’s mind. You can’t. Period. If what you write happens to land in the hands of someone who wants to change their mind, that’s luck, not your job.

46. Don’t forget why you wanted to write. If you keep at it, you’ll likely find some form of success. On whatever scale that may be, once you’re “in,” don’t settle into whatever opportunity presents itself. Don’t stick with the job that pays the bills. Remember why you wanted to write and use that to steer your career. Chances are, you can do what’s fun and make money.

47. Write your worst pieces without consequences. Sorkin says that, in a way, he was unlucky because “A Few Good Men,” his third screenplay, was such a big success. After that, he never got to fail in private anymore. Now, he views that as a luxury. “Take chances now,” he says. Few to no people will ever see your worst creations.

48. Don’t magic-8-ball the audience. It’s impossible to know what the audience wants. Know what you want. If you run your work through some algorithm in hopes of getting it just right, it’ll only come out bloodless, and so will you.

49. “You’re never gonna make everyone happy so I would urge people to not try.”

Previously published on Medium.com.

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Photo credit: Screenshot taken from MasterClass


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