"I have never regretted saying no"

The TPF Q&A with screenwriter Colby Day

Colby Day is a very busy person. This is a feature, not a bug. The screenwriter and filmmaker keeps multiple plates in the air, a necessity in today’s Hollywood.

In The Blink of an Eye, which he wrote and stars Kate McKinnon, Rashida Jones, and Daveed Diggs, recently won the Alfred P. Sloan Prize at Sundance. He’s on tap to direct The Comedy Hour with Tim Heidecker and Tatiana Maslany attached. Colby also writes Hollyweird, a newsletter that’s part journal, part advice column, and part demystification of Hollywood’s inscrutability. It’s excellent.

We talked about the correct number of projects to be doing at one time, when to say no, and the Medicis. It always comes back to the The House of Medici.

Which one is the real Colby? Image credit: Sela Saloni

Three Point Four Media: Hollyweird is very informative and helpful in explaining what seems like a confusing business. Back in the day, I wrote a couple pieces about the finances of freelancing. I hope they were helpful for other people, but I was surprised by how helpful the exercise of viewing my life/job/work through a wider lens was for me.

Colby Day: It’s very reassuring to be like, “Oh, it is this hard for everyone. Is this normal, right?” Doubly so in an ecosystem where you don’t ever get to know what anyone else is doing, except for the part that is most shiny and successful.

Whenever anyone asked me about freelancing, I’d always tell them one key to success was to treat it like a job and not an art project. Hollyweird has a similar point of view. You show your effort in a way that is truthful without being obnoxious.

That’s the perpetual artist problem. For better or worse, it is a numbers game. It’s easy to divorce the math from that equation a little bit. But it is still a math problem. And opportunities are one of the inputs to that, right? The more opportunities you create for yourself, the more statistical likelihood of success you have. That can mean living within an ecosystem where you are juggling 35 things at once. That’s good for the business, maybe bad for the art. For me, there’s a push-pull about what’s the livable amount of things that I can juggle. The number has to be high for it to be a sustainable career.

As your career has progressed, has that number gotten higher as you’ve gotten better at time management? Or lower because your success rate is higher?

One of the first things my manager told me is “What you have to consider with any opportunity is do you need this money? If the answer is yes, you have to pursue the opportunity.” The first three years I was living in LA, I said yes to everything. That’s why I started to write year-end reviews. I had so many plates spinning, and none of them were moving forward. I spread myself so thin that I didn’t have the bandwidth to pick the thing I cared about and push it ahead. Once I got the second job in Hollywood, I tried to recalibrate. I was able to raise the threshold for saying yes and give myself a bit more bandwidth to very actively focus on a project while also having a handful of less high-touch projects in the works.

Getting to the point where you can say no is very freeing. Saying no is a wonderful feeling.

The advice I give people early in their careers is that I have never regretted saying no, even when it meant I had to get a different job or quit a job. Every no I’ve ever delivered, I have felt relieved afterwards. But the first equation in a career is “Do I need it?” If you need it, there’s no no.

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I talked to The Black List’s Franklin Leonard a few weeks ago. In The Blink of an Eye appeared on the list in 2016. That’s a long time ago! And also maybe not? Time in Hollywood is strange.

It’s crazy that it was 10 years and also that feels totally right. The script was the first thing I had when I moved to LA that was really popular. I had a lot of meetings about it. Every meeting was, “This is really cool. Good luck.” It was brutal. After a few months of that, I had a meeting where someone said they weren’t going to do the movie, but they did vote for it for The Black List. It never crossed my mind that it could appear there even though I grew up reading all those scripts. I credit my manager and agent for sending it to everybody they knew. The Black List is a combination of movies that are definitely going to get made and movies that probably aren’t. Mine was in the latter category.

So many meetings ended with people saying come back when you find a director or money or actors. I was 25. How was I supposed to do that? It took a very long time to find the partner who thought we could make it and make it at a price point that wasn’t Interstellar. We went through three or four different combinations of potential directors and producers between 2016 and 2020. Andrew Stanton read it and got in touch, and all of a sudden the stars aligned. There aren’t many people like him who can command that level of studio attention with that level of creative freedom. He also really cared about my script and what I wanted the film to be. With Andrew, we had a path to do it that wasn’t there before.

Are you getting paid for all these fits and starts?

Here’s the issue with getting paid: The moment you get paid, you lose all agency. Early on, I had a couple of people offer to option the script. I felt like if I said yes, I would give up control of what happens. It could become a totally different movie. I asked if they could guarantee that I would be the only writer, and everyone said, “No, of course not.” So I said no. It was a lot of money to say no to, but it was a project that really needed an advocate. I didn’t believe that I’d found the partner who wanted to make the movie that I thought it should be. It was sweat equity for a very long time. There’s a trend in media to defer the development of the material onto the artist. I was in a meeting with a very senior person at a studio. They asked me who I could get to direct the film. Why is that my job? That’s your job. There’s a feeling that once the artist has everything in line and mostly guaranteed, then they sign on.

That’s risk-adverse, which isn’t surprising.

We have a system that was built by carnival guys in the 1920s who wanted to have a bigger circus than their rival. It’s become a business run by guys who have consulted for McKinsey. The business was started out by weird egomaniacs who loved entertainment, and now it’s run by weird egomaniacs who love spreadsheets. Doing less is preferred by a big business. In the current system, the onus is to make less than you used to make, which doesn’t compute with taking risks or trying things.

Now you’re on to The Comedy Hour, which will be your director debut. There’s a story about it in Deadline and actors attached, but how real does it feel? When do you breathe a sigh of relief that it’s actually going to happen?

A movie is only real once the audience is seeing it. It’s a really complicated puzzle to go get money for any movie, and especially for your first movie. We’re looking to close up the rest of the money that we need. It seems pretty likely that we’ll succeed but also: it’s Hollywood. I have to operate within the Hollywood ecosystem of “This is definitely happening. I will will it into existence. I am telling everyone that this is the date that it’s happening. They need to get on board and we’re going to go do it,” and also pursue a second, third, or fourth job at the same time, so that if it gets delayed and doesn’t happen when we hope it will, I can go do that other job.

I’m splitting my focus on prep for a movie that we want to go make this year, and also what else can I write that will pay my rent and keep me insured under the guild health insurance? The whole business pivots on the ambition to go make the thing and practicality of at any point, some rich person might stop me.

The rich people can enable you. The rich people can stop you.

We used to have Medicis. There are a couple Medicis left in the world, and we’re all hat in hand going to talk to them. If you have any billionaire readers, artists would love it if they ponied up a tiny bit to the rest of us to go make cathedrals.

A billion dollars is so much money. One of your bios reads, “He prides himself on writing generous stories that trust their audiences.” That’s a lovely sentiment, and seems very accurate.

I think audiences get it. I think they’re smart. They’ve watched movies their whole lives. There’s this weird trend of what if they’re not paying attention? That’s a race to the bottom and self-defeating. If you demand that people focus, they will either focus or not, and that self-selects who the audience is. I’d like to hope that the audience wants to watch the movie that they’re watching.

That reminds me of the cable industry destroying the bundle to try to compete with Netflix. They didn’t consider the inevitable outcome of sacrificing the cable bundle. There’s a parallel where if you don’t trust your audience not to be on their phones, they are going to be on their phones and eventually they stop watching movies completely.

There’s this tail chasing thing about trying to make more of what people want. I think people don’t know what they want. We don’t know what people want. It’s a losing battle to presume we could guess. That feels like a slippery slope. You should make what you want to make.