50 Writing Lessons From Aaron Sorkin Cover

50 Writing Lessons From Aaron Sorkin

In the fall of 1598, Robert Blakewell had a problem. He set down his hammer and looked at the red evening sky, lost in thought.

Despite being the one out of every three men in England who could read, his dream of becoming a writer, like his idol Shakespeare, hung in the balance.

As a blacksmith amid the war with Ireland, his profession forbade him from overindulgence in his art. The Act for the Relief of the Poor had just raised the monthly tithe for all those employed; paper and quill were rather expensive.

To top it all off, his town of Plymouth was 237 miles away from London. It might as well have been halfway around the world.

The latter mightn’t have posed a problem, had it not been for the gossiping villagers. Rumor had it the bard himself were to teach a drama class come spring. Not that Blakewell could’ve afforded the presumed ten shillings to revel in Shakespeare’s presence.

Heartbroken, he shook his head, took his hammer, and returned to his anvil.


I have no idea who Robert Blakewell was. In fact, I made him up.

But I know among the billions of people who came before us, before you and me, there were millions of Robert Blakewells. Most of them didn’t know their heroes and even if they did, they could never have reached them, let alone partake in their wisdom. But today, all that’s changed.

We don’t just have a vast selection of idols to choose from, we also have the time, money, and means to observe them. 24/7/365. We can follow them, contact them, and, for less than those ten shillings, they will even teach us—at least those who give an online course, like Academy Award winning screenwriter Aaron Sorkin. That’s the first lesson I learned from taking his masterclass.

Here are 49 more about writing, creativity, and what it takes to make a great story:

  1. Intention and obstacle shape the story in drama.
  2. To start the story, show us the intention. To start the conflict, show us the obstacle.
  3. The story hasn’t started before we know the intention. The conflict hasn’t started before we know the obstacle.
  4. Showing the intention is better than stating it. Showing the obstacle is better than stating it.
  5. To find out if your drama has potential, put pressure on intention and obstacle. Is the intention strong enough? The obstacle formidable enough? Is there a conflict of two opposing, equally strong ideas?
  6. If you want to write about a place you admire, like a startup office, a butcher shop, or the Grand Canyon, chances are your story is a TV show. If it’s a recounted event, like passing the bar, it’s likely a feature movie.
  7. Tactics make characters. How people tackle obstacles shape how we see them. Those tactics can be avoidance, action, honesty, bluntness, etc.
  8. Reveal character details only when they’re useful to the story. Don’t get lost in biographies.
  9. Characters don’t have to be like real people. They can be overdrawn. Don’t make them singers trying to sound like instruments. Exact replication is boring, even if it’s successful.
  10. Don’t pretend to know something about a certain ethnical group you don’t. If you can’t represent it accurately, make it irrelevant.
  11. The bad guy has to make a valid point. So you have to believe you’re making a valid point when you’re putting words in their mouth.
  12. Nuts and bolts research is easy. Look up the type of screw and move on. Inspiration research is hard. You’ll only know what you’re looking for once you’ve already found it.
  13. What’s the more important truth? Only change truths that don’t matter. Do we care what the killer drank or what he felt? Ask if the lie is unfair.
  14. The best paintings involve our perspective when we look at them. So make the audience part of the experience.
  15. Give the audience the same clues Sherlock has, let them figure stuff out, but then try to catch them with a twist they can’t see coming.
  16. If the audience doesn’t know they’re not possible, all things are possible.
  17. The worst thing you can do is tell the audience something they already know. The second worst thing is confusing them too much.
  18. Drama is different from story in that it adds conflict. A story can be without conflict. It’d be a lame story, but a story nonetheless.
  19. Exposition is a character as fresh as the audience. They’ll learn with them.
  20. For a screenplay, the first 15 pages matter most. If they suck, you can’t sell it. For a movie, the last 15 minutes do. If they suck, it’ll bomb.
  21. Every writer thinks they’re fooling everybody. Just write like yourself and keep your finger’s crossed people will like it. That’s all you can do, really.
  22. If you write action people are supposed to read and follow along with, make it last roughly as long as it would in real life.
  23. A probable impossibility is preferable to an improbable possibility.
  24. To get out of an improbable possibility, acknowledge it to the audience.
  25. The audience knows the rules without knowing that they know the rules.
  26. Reward patience, but make sure scenes connect. Think about launching points. How can the end of one scene set up the beginning of the next?
  27. The best jokes are set up early and pay off late.
  28. Embed the theme in the opening scene. Make it something that grabs people, either by dropping them into the middle of the action, or the conversation, or showing them something they’ve never seen before.
  29. Courtrooms are a great representation of drama. Intention and obstacle are utterly clear and the jury acts as a stand-in for the audience. How can you turn what you’re working on into a metaphor for courtroom drama?
  30. We love ordinary people in extraordinary circumstances and extraordinary people in ordinary circumstances. Show us either, but decide which one.
  31. Dialogue is music. When we speak to perform, the rules of music apply.
  32. What the words sound like is as important as what they mean. Read lines out loud. Do they sound ‘off?’ You don’t know why, but you can tell.
  33. In dialogue, don’t imitate real people talking, but don’t censor them either.
  34. To find out if dialogue works, perform it.
  35. Michelangelo looked at a block of marble and then “took away everything that wasn’t David.” As a writer, you also need to write that block of marble. It’s called your first draft.
  36. The hardest part of rewriting is killing your darlings.
  37. Be careful who you listen to. You’re the expert, not the audience.
  38. Build a circle of editors you can trust. Even then, always ask for specific notes and revise them one by one.
  39. Never start with “is it good or bad?” Start with “did you understand it?”
  40. Never make the character perform the emotion the audience should feel.
  41. If everyone’s happy with what you wrote but you, retype the whole thing. Once from the page, once from memory. You’ll know what to change.
  42. Avoid “once out of the well” moments. Don’t just mention that a huge crisis got solved. Show us how it gets solved.
  43. Your protagonists, however many, can never be victims of circumstance.
  44. Specificity in dialogue is important. How would a character refer to another character? Would they say “call Bob” or “call that lazy slob?”
  45. Never write in order to change someone’s mind.
  46. Once you get your foot into the door, don’t forget why you wanted to write. Don’t settle into whatever job happens to pay the bills.
  47. Take chances now. Write your worst pieces without consequences.
  48. Don’t run your work through an algorithm that tries to determine what the audience wants. Your writing will be bloodless and you will be unhappy.
  49. “You’re never gonna make everyone happy so I would urge people to not try.”

Online courses don’t absolve us from the hard work it takes to build a true career. But they can teach us the principles and show us the tangents.

Before Aaron’s class, I had heard of Aristotle’s Poetics. Now, I have a copy. Before Aaron’s class, I fantasized about moving to LA and becoming a screenwriter. Now, I’m not. Descriptive storytelling is where I want to be.

I know that you could have the best teacher, but learn only one really useful thing in a 5-hour class. But even if that were the case, wouldn’t it be worth a few nights of sitting on your couch, watching videos?

Had Robert Blakewell known what video was, I’m sure he’d have thought so.