I’ve been posting a lot lately. If you only follow me via the newsletter, you’ve been missing out.
Hollyweird has also made its way onto instagram, and TikTok.
As I have been thinking about how I introduce myself to a larger / different audience, it’s prompted some contemplation about my own trajectory in this career, and what I’ve learned between my days as a middle-schooler with a VHS camera I “borrowed” from my dad’s office, and now, as a paid pro.
And looking back at it all, the number one thing that I think really, truly, profoundly held me back, for way too long was… a discomfort putting myself out there.
This manifested in a lot of different ways — difficulty asking for what I want (whether that’s advice, or help, or collaborators), difficulty feeling comfortable in social settings, difficulty talking about my self and my work, difficulty pitching projects… the list went on and on. And getting over that discomfort? Or at least more able to tolerate the discomfort? Absolute game changer. Because, let me tell you, as someone who didn’t used to feel comfortable asking for what he wanted… if you don’t ask, you will never get it. In fact, even when you do ask, you might not get it. But there’s at least a chance, now!
Where did this discomfort come from? Shame, I guess. Internalized shame. Embarrassment. The deep suspicion that even if I thought what I was doing was interesting, other people probably didn’t and I’d be better off just keeping it to myself so I wouldn’t get disappointed when nobody cared. Better to not even try to get attention, that way you can never be disappointed!
Despite growing up making movies and knowing I wanted to make movies (not just write them, but also direct them) I became a writer. That felt easier than being the person in the chair with their name on it, with a bullhorn, whose job is to tell everyone what they should do. I could pursue what I wanted, but… quietly! Without putting myself out there too too much! You cannot hide as a filmmaker. But you can hide as a writer.
I think a lot of writers prefer to disappear a little bit. Why else would we want to craft stories all day? It is a lot easier to put a piece of work out there than it is to put yourself out there. Sending some writing feels risky, sure, but not nearly as risky as showing up with a big dumb smile saying “hello, it’s me, the writer/director and most important person here! I bet you want to help me out, don’t you, person I’ve never met before?!”
That requires… confidence. And that level of confidence felt, to me, for a very long time, like an unusual amount of confidence. A level of confidence I simply didn’t have, and wasn’t sure I ever could.
I had that confidence, in my abilities. I always knew I could write well, that I could craft a story and characters. I even knew that I knew a lot about theater and performance and film. But for some reason… the vulnerability of going into a meeting and CONFIDENTLY saying “Hello, I’m here to knock your socks off!” and meaning it… felt impossible.
So I hid behind other directors. In the theater, because that’s the way it’s done when you’re making plays, and then still when I moved to LA to work in film. The first few years I lived here, I railed against the fact that the entire job of being a writer seemed to be pitching things… shouldn’t they just READ what we want to do and tell us whether they like our WRITING? Wouldn’t that make the most sense? I actually still do think that would make the most sense. But this business isn’t about what makes sense! It’s about putting on a show!
I worked in sales for a long time. And I also hated that. But the thing that standing on a street corner and trying to get people to stop and spend money on something taught me (that’s literally what my sales job was, sometimes in the snow, sometimes in the rain) was to get over myself. And fast. I could not be embarrassed or ashamed for very long, because if I was, I’d miss another three chances to make a sale. And I couldn’t worry about whether people wanted to talk to me or not, because I knew they didn’t want to talk to me! I was standing on the street interrupting their normal day!
I had to sell to a certain number of people every week in order to make rent. And to do that, I had to get over my awkwardness. Or at least find the tools to overcome it temporarily. And, it worked. I did manage to take the risk of hearing “No.” And when you take the chance that you might hear “no” enough times, it does start to bother you less.
Putting myself out there became, not necessarily my favorite thing in the world, but… tolerable. A lot easier. And it has only gotten even easier with time (and practice, lots and lots and lots of practice)!
And now that I have officially become a professional screenwriter, I can say with confidence that the number one skill I absolutely needed to improve in order to make it was not my writing but my SELF-ESTEEM.
Cheesy? Maybe! You could say CONFIDENCE instead. You could say SALESMANSHIP too, I guess. Because professional screenwriting isn’t really all that different from the sales job, really.
All of these things are interconnected. The best salesmen are confident, because they feel secure. They can tolerate hearing no. They know that the rejection isn’t necessarily a reflection on them, so much as a temporary setback.
You do not need to cure all of your demons to make good art, though doing it does absolutely help! Ask my many therapists over the years.
But… to be a good artist, who also GETS HIRED, you DO need to be able to walk into a room, make friends with some strangers, and confidently tell them about who you are, what you believe in, what you want to make, and why that’s so exciting.
It’s not an easy skill to master, especially if you don’t innately have it! But I would highly highly highly recommend doing everything you can to improve.
How? Well… Practice. Putting yourself out there.
Writing this weekly newsletter has been great practice for me. Doing direct to camera social media has been another huge step in getting over another “ick.” I don’t think I’d feel comfortable doing that if I hadn’t spent the last decade pitching movies (now mostly over zoom, so it’s really not that different!).
Go meet new people! Whether via Hollyweird’s monthly Hollyweird Hangs (for paid subscribers, which are online so you can join from anywhere), or
’s monthly FilmStack meetups (if you’re in LA), or ’s incredible community of writers practicing pitching together (which is hands down the thing you most need to know how to do as a writer)!But really, however you do it, and wherever you do it, getting better at taking chances, at risking falling on your face, at being vulnerable with other people… simply TRYING TO DO IT is the thing that will in fact make it easier. Eventually.
I believe in you.
You can do it.
I did.
Well… I’m working on it.
You get the idea!
Previously on… Hollyweird!
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