JR writes: I've been an appreciative reader of your blog for a couple of years (love it!), throughout which I also worked in NYC television and film development and production as a production assistant. I originally went into the industry because I was in love with the idea of doing something for a living that was grounded but involved creative decision-making. My ultimate pipe dream job: be Jennifer Lee.
I left the industry about a year ago because I didn't even see my bosses making any creative decisions; they were coordinating logistics and playing to the lowest common denominator audience desired by advertisers - basically what I was doing, but for more money and under more pressure. The long hours didn't leave me time to do any of my own creative work, or to have any kind of social life, for that matter. For the last almost-year, I've been doing some teaching and soul-searching (aka the ultimate pastime/disease of our generation). I'm not happy teaching, and can't quite shake my vague TV/film dreams as I watch former coworkers move up and become "accomplished."
Do you know anyone who left the industry with similar frustrations? How did they find creative fulfillment and pay their bills? As a Hollywood insider, have you heard any solid advice on grappling with this? As I see it, I have three options:
1) Kill the dream, find something else to do with my life and continue to write email stories for my friends.
2) Stay in the industry, keep paying my dues, and hope the right opportunity comes along someday.
3) Find a flexible day job and do as much creative work of my own on the side as I possibly can.
I completely understand what you're going through. Working at a job you don't like can be soul-crushing, especially when you're not making enough money to build savings. The only reasons for a writer to stay at a low-paying entertainment job are to learn about the industry and to make important connections who can help you get a better job, buy or produce your material, represent you, etc. If none of these things are happening, it's time to quit the job and find a better one. You mention that your former co-workers have moved up, but in what way? If your dream is to be a writer or writer-director, it's not necessarily worth your time to try and get promoted in development or production. If you do want to work in these areas, as you've found, it can be a long and political struggle. I'm afraid I don't have much specific advice for that, except that you have to find a job in a place where there's room for advancement and where your bosses like you and actually want to promote you. I do think, though, that after a year or two in the industry, you need to have a specific goal (writing, directing, producing, etc.). Yes, there are lots of people who do multiple things, but if you're hoping for a kind of amorphous "success in entertainment," that might be a problem. You say "grounded but involved in creative decision making" (is that development?), but then you mention Jennifer Lee, a writer-turned-writer-director.
Yes, I've had some development friends leave the industry for good because it just wasn't working out. I'm not sure about their creative fulfillment; I feel like they were people who liked movies and TV but weren't as creatively obsessed as my writer friends. It's certainly possible that you could find a fulfilling career in another industry...maybe teaching just isn't it? Meanwhile, I know writers who left their industry jobs but still pursued writing careers. They work as babysitters, tutors, Apple Store geniuses, translators, receptionists, baristas and delivery drivers, but they all hope to quit these jobs and Just Write someday.
You've already kind of answered your own question with the answers you've laid out. If you decide that becoming a screenwriter is too challenging, maybe you've reached the end of the road and now you just need to find an outlet for your creative urges -- like the emails to friends you mentioned. You can also blog, take writing classes or make videos, but with no hopes of this hobby resulting in a professional career. Maybe being part of a book club or attending panels and screenings would be fulfilling, too -- or maybe they'd just make you wish you were still in the industry. I don't know. Only you can answer the question of whether creative hobbies will be enough for you.
If you decide you want to continue to pursue a screenwriting career, then you need to choose whether to find a day job in the industry or outside of it. But if you do get another industry job, you can't expect it to magically turn into a writing career. "Hope the right opportunity comes along" sounds a bit passive. Even if you're working in entertainment, you need to be doing creative work of your own on the side. I left my agency day job not because I couldn't write in the off hours, but because I had learned everything I was going to learn, had made valuable connections, and could find a better salary pretty much anywhere else. If your new job is simply too exhausting, you might decide to leave the industry once you've made some connections, because you need to find time to write. Did you really put in the effort with your writing? How many scripts did you write? Did any industry professionals ever give you feedback? Did you ever try to apply to a writing program or fellowship? Have you ever tried directing or producing a short?
Then comes the hard, endless part: monitoring your success and continually deciding to persevere (or give up). I've had to find comfort in small achievements, reminding myself that 2007 me would be impressed with little things like getting a manager, finding a producer to develop with and getting hired for an assignment. These intangible milestones have made me think I'm not totally crazy to believe I can do this. But if a decade goes by and I'm still writing script coverage about hookers and teaching grammar to teenagers, maybe I'll change my mind.