10 Things About Screenwriting I Wish I'd Known Sooner

These aren't exactly Hollywood "secrets," but hard earned wisdom that would have been nice to have... earlier.

Sundance is winding down and the vibes have been… weird.

But I wouldn’t take it too personally. The vibes have been weird in Hollywood for the past few years, and even though it may seem like everyone is hanging out and releasing movies without you (don’t compare yourself to others, remember last week?!) that’s not entirely true!

For example, I wasn’t at Sundance!

I’ve instead been extremely busy, obsessively playing Civilization VI (remember last week??!). Every time my wife walks into the room and sees me on my phone she mutters… “you’re obsessed!” She keeps asking me why I find this turn-based strategy game to be fun, and I keep trying to explain that it’s nice to make decisions about how to build a society, and what to research, and what to do when you have all of the resources of an empire at your disposal, and how the rules work… her eyes start to glaze over.

But! I think we all think rules are fun, to a certain extent! They help shape the world around us, our expectations, our emotional well-being and tolerance of uncertainty, and so I thought I’d write up some less-discussed, but I think very important truths that I have come to understand about how to make it in a career as a screenwriter.

These are not rules about “Writing,” per, se. They are more “the unspoken rules” that I wish someone had been kind enough to share with me before I embarked on trying to build a sustainable life in this crazy business.

So if you’re feeling like learning the rules of the game, let’s dive in.

10 Things About Screenwriting I Wish Someone Had Told Me Years Ago

1. Most of the job will not be writing. It will be convincing someone to pay you to write.

If you’re not going to read this whole post (I get it) this is the one that I would really like to impress upon the young, hopeful, bright eyed youths of the world. I don’t know how they do things at USC or any of the other big shot film schools, but in my little enclave of NYU’s Department of Dramatic Writing (721 Broadway, represent!) we spent hundreds of hours talking about the craft of writing. Story structure, character, Aristotle’s Poetics, act breaks, the theater, but what we spent VERY LITTLE TIME talking about is… probably the thing I spend the most time doing: pitching! I’m sure we must have covered it a little bit, but I do not think I had any idea just how much of a career as a writer (or director) is really… having a career in sales. If you want to get good at working in Hollywood, you shouldn’t just read Robert McKee, you should really read books about how to sell people things (like this one!). 90% of “making it” in Hollywood is actually about being able to be charming and persuasive in a meeting, and then repeat that over and over as you work your way up to the decision maker. You need to be talented, yes, but you also need to sell.

I would say my four years spent working in sales were EQUALLY if not MORE valuable than my four years spent in college. Food for thought!

2. Don’t be afraid to follow-up (respectfully).

This is also a sales tip (notice a pattern?!) but it’s not just about being able to make something really great and share it with someone else. It’s also about then being willing and able to send the dreaded “Just following up!” We’re all busy people, and I really do think for the most part people WANT to help you (if they can), so when someone doesn’t get back to you about the thing you sent them… rather than assume that’s a definitive “No” you need to actually get them to say that to be sure. Always always always follow up (once, not more!) if you hear nothing. People are busy! Bump your ask to the top of their inbox (politely) and you’ll be surprised how much getting good at this skill pays off.

3. Don’t let perfect be the enemy of good.

This isn’t about sales! This is about writing itself! Yes, you want the end result of your project to be a perfect piece of art. But… while you’re getting there, do not ever let “perfect” be the goal. It’s not possible! And more often than not, it will get in the way of you getting anything on the page. Forget about perfect, and learn to get to “this is pretty darn good” and feel happy with it. Every draft of every script could always be futzed with a little bit more… but sometimes, you have to just say “this is pretty good, let’s move on.”

4. Confidence is intoxicating.

You thought we were done talking about sales, didn’t you? Well, not quite! As an artist, I’m personally very interested in “the question” that a film or project is asking. I love a puzzle, and I love a challenge, and I love love love not knowing. But… most people, especially people who are trying to decide whether to invest a lot of time/energy/money into helping you… do not feel similarly about not knowing. A lot of them would feel a heck of a lot more secure if you could instead confidently tell them the answer. Who has time to question?! I think this was my steepest learning curve to try to overcome personally when I moved to Hollywood from working in NY theater. When you’re making a play, it’s all about getting to the bottom of things together! With a movie… a lot of money is on the line and we’d really all rather have someone in charge who can confidently tell us what we’re all doing here. You do not need to know all the answers, but you do need to be able to speak assuredly about what you want to do, and why. It’s the number one thing that makes people want to work with you. I really believe it.

5. Your first job (ok, several jobs) will still not be enough money to actually be considered a job.

Sorry to break it to you! But the first paid writing gigs I had were in theater, so they were, laughably small. And when you consider the number of hours that go into making a play… they were absolutely minimum wage level (or lower, probably lower). But even after that, the first paid FEATURE FILM writing job I had, was still not enough to quit your day job over. I had, because I had literally just moved to LA from NY, but as soon as I did in fact get offered a job… I did the math and… nope, not a sustainable living wage. So it was back to living with my parents, WHILE I was writing a film, for a major motion picture company! “Don’t quit your day job” may be hacky advice, but that’s because it’s good advice. SAVE YOUR MONEY, DON’T DO ANYTHING RASH, and even when you’re feeling like you’ve finally made it, remember your taxes and your fees and the fact that it took years to catch that first break and who knows when you’ll get the next one. Always make sure you are saving for a rain day, but especially remember that you’re going to have to after the first job (okay quite a few jobs).

6. Learn to say no.

Maybe the pay is bad. Maybe the people give you bad vibes. Maybe the project just isn’t interesting. We all have bills to pay and we all need to do what we can to survive, but learning to say no is a superpower and a gift. Saying no to the shitty opportunity / shitty manager / shitty producer is the only way to ensure you have the space for the good version! It’s very scary to say no in a world where resources feel so scarce, but remember, it’s also the thing that can set you free! And people really do admire someone who can set a boundary and stick with it. Be polite, but be firm.

7. There is no shortcut, and no sure thing.

About once a year I trick myself into thinking “this project will be the easy one.” And let me tell you, it never is. There is no such thing as a “slam dunk.” There is no such thing as the movie that’s going to be super easy to pitch, or to sell, or to make. Every every every movie (even the ones you think are bad) was a very very very difficult labor of creation, and took thousands of hours of time. Don’t trick yourself into thinking this one will be different. It won’t!

8. Your success depends on your ability to tolerate disappointment.

The longer I’ve worked, the more confident I am that the people who survive in the arts are mainly just that… the people who didn’t flame out. This is a career of so many near-misses, disappointments, heartbreaks, and failures to launch, and your ability to tolerate that is going to be the thing that determines whether you can survive. It’s a hard career of high highs and low lows. Learn to find a way to ride the waves.

9. It’s the journey, not the destination.

A great way to ride the waves is to remember that this whole endeavor isn’t really about getting anywhere. There’s no “now I’ve made it to where I want to be.” Over every mountain you are trying to climb is another mountain, and if you are waiting to get to the highest, best, most well-paid mountain, you will never be satisfied. Learn to love doing what you do. That’s it. It’s very zen, but it’s very true.

10. Nobody knows anything.

Who am I to give advice? What the hell do I know? If I said anything you disagree with, don’t do it! As William Goldman wrote about Hollywood, “Nobody knows anything,” and I think he was right, at least about that.

Any other advice you wish someone had told you much much earlier? Let me know in the comments below. And if you dug this post, please give it a share somewhere somehow.

At the end of the day, word of mouth is all we have in this crazy mixed up world.

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