Relative Success in Hollywood

On defining what success means to you in this town.

In mid-2015 I was suffering from a crisis of success…rather, a crisis of lacking success. I had been in Hollywood for nine years working to achieve success in the industry and I felt like I had finally made it. I made a well-received first feature film for $6000 and been hired to direct my first real professional project: a series for Hulu. It had a real (though still small) budget, the project already had distribution on a major digital network and I was sure this was going to help launch me into the next phase of my career. I threw myself into it. I moved to Miami for seven months, I sacrificed more than I will publicly admit, and I wrapped the project feeling satisfied that I had met its demands and would be rewarded for it.

To be clear, I didn’t think I would suddenly become the next big thing, but I did think it would lead to more work and better projects and that, surely, I would be propelled upward. After all, sizable digital series with distribution on Hulu should mean something and I was confident the project, with so much invested in it, would be backed by solid marketing.

But in the summer of 2015, the show was released to so little fanfare or attention that it was as if it had never been released at all. Zero marketing was invested in it. No one reviewed it (which turned out to be a blessing in disguise), no one was talking about it, no one watched it and I found myself in pretty much the exact same position I was before I made the series. I had spent seven months away from my wife and son, from my home in LA, from working on other projects and the response was worse than bad, it was non-existent.

It felt like another failure after a string of so many. So many projects that I felt would lead to something, anything! and were instead DOA and never got much beyond me sharing them on YouTube and hoping someone would watch it. As a result, I was in a place of really questioning what the hell it was I was doing.

Following the show’s release in July, my family and I headed up to Seattle for three weeks to visit my parents and vacation. I also planned to use it for some soul searching on my part. It was around this time I started listening to a lot of Marc Maron’s WTF podcast and I heard an interview with Jason Segel about his newest film THE END OF THE TOUR where he plays David Foster Wallace. In the interview, he spoke about the idea of success, both his own and how Wallace saw it. I can’t quote it here, but this bit is from another interview he did around the same time:

“You put your heart and soul [into something], and it comes out, and it does as well as it can possibly do,” Segel told Baron. “And then you realize that you feel the same. Like, ‘Oh, shouldn’t this 10 years of incredibly hard work and achievement have made me feel different?’”

I’m paraphrasing here but with Maron he discussed the idea, shared by Wallace, that if you define success by how much money you have, you’ll never have enough of it. If you define it by how famous you are, you’ll never be famous enough. This was something I really needed to hear and it started me on a journey, on a path, that I’m still on to this day. It was from this that I stumbled onto Stoicism and its application towards everyday life (“what is up to us, what is not up to us”), the writings of Ryan Holiday, meditation and more.

This is normally the point in articles like this where I say “Here are five steps to determining what success looks like for you” but the truth of the matter is that I haven’t figured it out myself. Two years later, I’m still trying to define what success means for me. I’ve taken small steps: moving out of LA so that my life doesn’t revolve around Hollywood, to a house surrounded by woods and nature, continued to meditate, focused much more on my family, cultivated hobbies and interests beyond film, put more emphasis on reading more so than watching (which was easy because I was a voracious reader to begin with), all of these things I’ve done in an effort to combat feelings around career related success, both negative and positive.

The closest thing I can imagine at the moment as to what a successful career would look like for me is the ability to make the movies I want to make and supported by budgets appropriate to the needs of the project (i.e. I can’t make every movie for $6000 no matter how much creative freedom I have) and supporting my family as a result. And that’s about it. That’s where I’m at.

On Other People’s Success

As I write this, the sun has just reached the point in its morning arc where it can cut through the loose foliage of the trees around our house and ignite the window in front of me, creating a pattern of sunlight and shadow that sweeps across the top of my desk. I have a candle burning, it’s quiet and my dog, Hadley, is laying at my feet. I have been writing this since 9am with my plan to publish at 10am and move on to one of the two screenplays I’m currently writing. From my office I can look out on the four acres around my property.

Despite this rather peaceful scene, I struggle everyday against ‘The Resistance’ as Steven Pressfield calls it in ‘The War of Art.’ One particularly toxic form of The Resistance is envy of my peers. It’s so difficult to see others meeting with success, to see others selling scripts, directing films, on set, taking meetings, etc. It’s bad. I’m jealous of all of you out there getting to make things. It doesn’t matter whether its a self-funded series or a studio funded feature, it hits me and I wish I was that person. I can’t help it and I know its dangerous and unhealthy. As a result, my definition of success ends up being defined by what others are doing and how I’m matching up to them.

When that happens I try to remember this entry from a newsletter I get called The Daily Stoic:

“In the entertainment business, it’s common to hear the announcements for big new projects by colleagues and competitors. It’s true in sports and in Silicon Valley and many other industries too: So and so just raised _______. So and so just sold their next book for ______. So and so just negotiated a package worth ____. Which inevitably prompts concerned writers, athletes and executives to rush to their agents or representatives and complain: How did they get that?!?! Why didn’t I get that?!?!

“A good agent will remind them of this simple fact: We don’t know the actual terms. The deal could have impossible earnouts. There could be almost no upfront money. The contract terms could be incredibly onerous. The sale might look compelling but the person might actually be losing money on it.

“This is a truth that can be applied to all walks of life: We really have no idea about the terms of other people’s deals. We don’t know what went into them. We don’t know the conditions they’re on. We don’t even know if they are happy with what they got or if it was a bitter defeat.

“So we shouldn’t judge — positive or negative. The Stoics would remind us that what other people get or earn is not in our control and therefore none of our business. They would remind us, as Seneca did, that “slavery often resides beneath marble and gold.” (that is, success and money isn’t always the gift it appears to be). Try to live your life with this in mind: What other people are getting — or what the media is claiming they got — is misleading and distracting. Don’t focus on it. You don’t know the terms of anyone else’s deal. You only know yours — and that’s all that should matter.”

And it’s true. Often, if you ask someone, they’ll tell you the truth about it in person. On Twitter it looks like a huge deal but when you bring it up to them in person they’ll tell you “Oh, it was a horrible deal for us but it was our only option” or “its cool that these people are involved but it could turn out really bad, we have no control over it.” It’s fascinating. Much like the project I discussed in the beginning of this post, on paper it looks great, but as you now know, it wasn’t that great.

This happens all the time.

You realize what a waste it is to have been jealous of what other people are doing. You feel embarrassed. For one, other people’s successes and/or failures have nothing to do with your own. Hollywood is not a zero sum game. And you realize that success in Hollywood can be relative.

On Success in its Many Forms

I feel like my peer group is reaching that point in their time in Hollywood where they’re having to shit or get off the pot. They’ve been in LA for 10 years, haven’t reached whatever their definition of success is (this isn’t a judgement) and are realizing maybe they should do something else. But that doesn’t mean they have to move back home and become an insurance agent. I know a number of people that have made changes (mostly away from writing, oddly enough) and found something in Hollywood that they really enjoy doing.

A friend of mine, while not giving up on writing, started PA’ing on reality shows. He told me that in doing so he realized how much he loves being on set and being a part of the action. “I’ve always thought I could be that guy who would write things and send them off to be made and move on to the next script but I don’t think that’s true. I love the mechanics of production too much. And even if that means only being a PA, I’m okay with that.” He seems happier than I’ve seen him in a long time. Another writer I know started working as a Script Supervisor and by all accounts loves it. Another person I know left a development job to go work at a news station in the midwest. He recently won a Regional Emmy for his work. I can tell that they all seem happier than they had been.

Maybe ‘success’ in Hollywood is finding that thing that you really enjoy doing and that’s all it should be. Why be miserable as a writer if you can be happy as a grip? Why continue to fail as a DP when you can continue to get work as a prop master? Is it that you really have a deep seated desire and talent to be a DP or is it just the picture you’ve always had for yourself?

Maybe success is finding a way to realign what we want for ourselves with who we really are. Not everyone is a director, not everyone is a writer. Maybe if you stopped worrying and fretting and beating yourself down for not being a DP and instead threw yourself into props you’d find success and, as a result, some kind of happiness. That seems to be the case for a lot of people I know. And they seem genuinely happy with the new path they’ve found.

I feel fortunate that what I want for myself is aligned with who I am. I know, and have known for a long time, that I both want to write and direct and can make a career out of it. I’ve met forms of success with it that support that idea (despite my opening example). I continue to work, to be hired, to find homes for the projects I want to make. It hasn’t been easy like having a breakout-Sundance-hit-sell-for-$20-million-and-make-$100-million-at-the-box-office easy, but I’ve managed to find a way. I guess, in one form or another, that’s success.

So what does Hollywood success look like for you? Is it an Oscar? Is it your film making $1 billion at the box office? Is it having millions in the bank? A huge house? A Ferrari? Is it being famous? Marrying a rich beautiful actress or actor?

Hollywood makes you think that’s what success looks like but the truth is that most of us, even if we have a good career and get to spend our lives working in Hollywood, won’t have any of those things. So what then? Is everything short of those things a failure? It can’t be and I can’t imagine living a life in which anything less than giving an Oscar speech is failing (what a miserable person I would be).

A Possible Definition of Success (In Any Field)

In ‘Tribe’ Sebastian Junger writes about the self-determination theory, “which holds that human beings need three basic things in order to be content: they need to feel competent at what they do; they need to feel authentic in their lives; and they need to feel connected to others. These values are considered “intrinsic” to human happiness and far outweigh “extrinsic” values such as beauty, money and status. Bluntly put, modern society seems to emphasize extrinsic values over intrinsic ones, and as a result, mental health issues refuse to decline with growing wealth.” Hollywood emphasizes these as well, doesn’t it? With award shows, million dollar spec sales, houses and cars and expensive offices. We buy into it but don’t seem to feel successful and happy when we get those things, when we have money in the bank, when we buy our beauty and achieve our status.

Instead, perhaps we should be pursuing the three pillars of self-determination: autonomy, competence, and community.

Yesterday, I really struggled with my writing. I woke up late because I forgot to set my alarm, and the whole day felt off. I spent most of my writing period fucking around on Twitter, Facebook and staring off into space, but not good staring off into space. Finally, I gave up and closed the computer. I felt the trees and the sunlight and the air calling to me. So, I went outside with my chainsaw and axe and started chopping firewood. In front of me was a pile of logs that needed to be split and behind me an empty wheel barrow. I chopped and filled the wheelbarrow until it was full and then walked it over to where all the firewood is stacked. I came back, filled it again, walked it over. And then a third time. And now, the pile of wood was gone and the firewood was split and stacked and drying. And a day that started out shitty ended with a small pile of success made with my own two hands. I was tired, sweaty, my hands were blistering and yet I felt better than I had all day.

I suspect that struggles around success is something EVERYONE in EVERY creative field deals with, whether they know it or not, and maybe this post will help provide some focus and clarity.

I wish I had something more concrete to tell you. But the answers to something like this are often personal and unique.

It’s really up to you.

If you enjoyed this story, please recommend and share to help others find it! Feel free to leave a comment below!

Joshua Caldwell is a director, writer, producer, and MTV Movie Award Winner. His debut feature film LAYOVER was made for $6000 and had its World Premiere to sold out crowds at the 2014 Seattle International Film Festival where it was nominated for the prestigious FIPRESCI New American Cinema Award. In 2015, he directed the first season of Hulu’s SOUTH BEACH and the Paramount Pictures feature film BE SOMEBODY. In 2017 his latest film, the action-thriller NEGATIVE, had its World Premiere at the Newport Beach Film Festival and will be released in the fall.

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Director, Producer, Writer, INFAMOUS, NEGATIVE, LAYOVER. MTV Movie Award Winner. Reel:

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