To Make It In Hollywood, Your Life Must Become A Cautionary Tale

Self-confidence isn't enough to break into Hollywood; you need to be self-delusional.
To Make It In Hollywood, Your Life Must Become A Cautionary Tale

Welcome to Cracked's final essay on the dark secrets of breaking into Hollywood. Today's topic: to win the Tinseltown game, you must become deluded, daily.

We’ve been through a lot these past four days, haven’t we? We’ve laughed, we’ve cried. Well, I cried. We’re practically family now – that means I can borrow some money, right? 

No? That’s okay, I still love you. As a gesture of goodwill, I still have one more dubious nugget of wisdom to share with you. This is one you likely already either knew intrinsically or deeply suspected, but, like the previous columns, you may not appreciate the extent to which it’s true.

Here’s the truth: if you want to pursue a career in writing for film or television, you have to be insane. Absolutely loony, bonkers, hitting-yourself-on-the-head-with-a-big-wooden-mallet kooky. I hate to make a liar out of middle management’s favorite cubicle poster, but you actually do, in fact, have to be crazy to work here: it doesn’t just help, it’s a prerequisite.

Sneaking Onto the Hindenburg

Like I said, you probably already guessed that it takes a certain type of, shall we say, reality-skeptical personality to willingly subject yourself to all this. There are simply far fewer jobs than there are prospective writers, so simply statistically the odds are stacked against you. You’re honestly probably better off playing the lottery or scouring thrift store blazer pockets for original drafts of the Constitution.

Well, it doesn’t happen for most people… but it’ll still probably work out for me is the absolute foundational fantasy of trying to break into Hollywood. There’s a wide variety of other delusions to choose from, like nah, these talkies are just a fad or the payment is definitely coming, it’s just been deferred! or if a script is good enough it’ll get made eventually, but a belief that you will eventually break in, a faith in one’s self, is absolutely necessary.

man trying on fedora


We’re talking “I think I can pull off a fedora” grade confidence.

Even if you internalize that particular delusion, there’s something else to consider: this is probably the worst time in the industry’s nearly century-long history to try and break in. It’s moving and changing so fast nobody knows what’s going where or what’s going on or what to do. It’s like an orgy that’s been sucked up into a tornado. Maybe you remember a few days back when I mentioned the writer’s-assistant-to-staff-writer pipeline is probably no longer as reliably viable as it once was? Well, it might also be true that a career as a dedicated television- or film-writer isn’t really viable in most cases anymore, either. 

There was a time when getting staffed on a TV show meant you could probably count on a few years’ worth of stability. Looking at Wikipedia, of the top ten longest-running scripted primetime American television series, the most recent started in 2005. The most recent show on the list as a whole started in 2016. While of course there’s no way of knowing what currently-airing show will become a megahit that lasts for decades – my money’s on Fboy Island – there’s also the ever-decreasing episode count of individual seasons. I already addressed streamers focusing on fewer seasons, but the episodes that constitute a season have been slowly shrinking, too. Time was, a season of TV could be nearly forty episodes. Then it was somewhere in the low twenties. Now you’re lucky if you get ten episodes in – damn you, shrinkflation! Isn’t it enough that my Doritos™ X-Treme Spicy Cheez-Blasted Calzone Flavored® Party Sack now contains enough air to be used as a pontoon? 

The Incredible Shrinking Season ultimately means more budget can be spent per episode and makes working TV more palatable for movie stars since it takes less time to shoot, but it also means less paid work for writers. While you do get a relatively slight pay bump if you’re only working a few weeks, more episodes is generally preferable because it both offers more money in the long run and more chances to get an episode you can get a “written by” credit on: these both increase your prestige and, depending on how the room is set up, net you additional payment. The dream of syndication is now all but dead outside of network television, which has long since been eclipsed by streamers and cable as the platform where most writers get employment. 

As I was writing this piece, a new development happened: HBO was purchased by Discovery, and several HBO Max original shows just vanished in the night like a hitchhiker outside of Pete Buttigieg’s house. They’ve laid off 70% of their development staff, and many in the TV writing sphere are taking this as a sign that the streaming bubble is finally bursting. And not only that, but many are rightfully shocked that the shows they worked incredibly hard on are now simply gone without a trace. What this means for the future of streaming is unclear, but it’s probably a fair bet that it’s not going to be super great.

I know I’ve mentioned this before, but it bears repeating that there are now more people than ever trying to squeeze through an ever-narrowing door into a party that’s getting progressively shittier. More and more people fight over scraps that always seem to be a little smaller – it’s an odd state of affairs when there are now record-setting amounts of scripted television shows airing. “Working for a decade on a show and then retiring to live off of residuals once it syndicates” is now essentially an unattainable Boomer dream like “becoming a millionaire from your line of All-Lead Children’s Toys" or “homeownership.” It seems that the future of TV writing is going to be more like freelance writing – you might get a season here and there, but in between you’re going to have to write for video games and comic books and websites and radio dramas and erotic ASMR channels. Trying to break in right now kind of feels like spending your life fighting desperately for a ticket to the Titanic.

This is all to say, a little self-delusion is necessary, and not just for all the reasons I’ve just said. A capacity to lie to one’s self is also vitally important because:

We’re All Mad Here

You are going to fail. You are. I’m not saying it’s a guarantee you won’t get a job writing for film and TV; I’m just saying you’re gonna get your dick knocked in the dirt at least a couple times on the way there. You’re gonna fail, and it’s gonna hurt. Writing a script is like spending hours and hours painstakingly crafting a perfect, beautiful fabergé egg, sealing an irreplaceable little splinter of your soul inside of it, then shooting it out of a cannon at a brick wall. The brick wall here represents indifference – that’s what we in the biz call a “metaphor,” and it’s just one of the many writing techniques I will teach you in my masterclass (only $750!). 

Do you think you’re capable of continuing to lie to yourself after you put so much of yourself out there, only to get a resounding nothing in return? You do? Then what about putting up with people actively rooting for your failure? Because that happens, too. I used to have a bunch of my scripts publicly available to download, and I’ve gotten quite a bit of anonymous hatemail over the years. My script that finished in the Nicholl Top 50 has been called both “woke” for dealing with toxic masculinity and also “relentlessly sexist” for not really featuring any female characters (it’s about a man’s relationship with his father, and 90% of the script is him slowly losing his mind alone in a cabin). Several anonymous internet randos have called it “the worst script ever read.” Someone on a screenwriting forum once told me that I should give up because if it hadn’t happened by my tenth script, it was never gonna happen – which is obviously an insane thing to believe, like the flat earth or that the McFlurry machine is actually broken. 

I’ve never read a single comment on anything I’ve ever written here on Cracked, but I assume you’re all being very supportive and normal down there, telling me how insightful and funny I am and how it’s actually kind of hot and endearing for a man to be struggling with acne in his thirties. The point is, being vulnerable is an important part of being a (decent) screenwriter, and vulnerability on the Internet is like blood in piranha-infested waters (something the video games of my youth made me fearful I’d be encountering much more often in my daily life than I actually do). People will try to pull you down. I don’t know if it’s due to a #hustle #grindset mentality of “thinning out the competition” or just plain old garden variety “their dads were jerkoffs,” but it’s something you need to be prepared for.

You need to be able to lie to yourself in such a convincing way that all the people making their shitty little comments won’t get under your skin. You need to be thinking, “This is but one crystalline moment in time that will pass in a gossamer instant,” instead of the much more alluring, “Well, if all of these people say I suck, maybe I actually suck? I wouldn’t want to disrespect democracy.” 

And if all that doesn’t get to you, there’s the constant deluge of self-doubt. You’ll meet other writers and you’ll ask them “so how’d you get your first paid writing job?” and they’ll say “Oh, I decided to become a screenwriter eight months ago and my first script placed in a fellowship and now I’m repped at CAA” and you’ll smile and say “oh wow that’s so cool haha” but inside you’ll be thinking I’ve been doing this for a goddamn decade, how are you so much better at this than me and clench your teeth so hard your molars are crushed into powder. You can’t compare yourself to others, no matter how tempting it may be. It’s natural to see others having successes where you aren’t and wonder what they have that you don’t, and the obvious answer is that maybe they’re just better at writing than I am. You have to ignore that, even if it’s true. (Especially if it’s true.)

You’ll see people you don’t think are particularly good writers land incredible opportunities while your friends who write wonderful, funny, incisive, devastating scripts wallow in minimum-wage day jobs at the Email Factory. These things take time, and exceptional people will always be the most open about their success. A friend of mine told me he got his first support staff job – not his first staff writer job, his first job as support in a writer’s room – when he was thirty-five. He’s now a hugely successful showrunner, producer, and writer. 

There’s no justice in it. You have to keep that in mind. There’s always a little luck involved in breaking in, so you have to resist that human nature impulse to wonder if the reason you’re struggling so much is because you simply aren’t good enough. That might even be a logical conclusion to reach, which is why lying to yourself is so important. Doubts will crop up like little fires, and you have to extinguish them with the waters of self-delusion or be consumed by them. Trying to become a professional writer is difficult, confidence-shattering, and you’ll almost certainly be absolutely miserable and poor for years before you become successful – which, again, you statistically probably won’t. 

I’m not painting a very flattering picture of myself, I know. I’m probably coming off as a narcissistic, envious, insecure jackass, which is probably fair. I don’t think that I’m such an amazing writer that the only possible explanation for my lack of success is that The System is simply incapable of recognizing my incredible greatness. On my Writing Report Card I’d give myself an A- in Concepts, a C+ in Characters, a B- in dialogue, a D in Structure, a D- in Pacing, and an F- in Having Parents With Their Own Wikipedia Pages.

My point is that by the time you’re reading this I’ll be 31, and it’s really difficult not to wonder if I’m aging out of an industry, no matter how not-based-in-reality that belief might be. It’s hard to fight the urge to lay awake at night and wonder if it’s too late to go back to college, or just get a decent blue-collar union job, or eat an entire LEGO set and then frivolous lawsuit one's way to retirement. You have to be insane, because denying material reality and your own (probably justified) insecurity is part of the game. 

So Is There a Lesson in All This?

Keep in mind the only way to truly lose is to quit playing. You’ve never truly lost out on your opportunity to break in as a writer until the day you write your last script. It’s grueling, it’s arduous, and you’ll fight voices saying you can’t do it both within and without. If you can see yourself happily doing anything else, do that. If you’re like me and are hilariously inept at literally everything else, routinely managing to injure yourself in even the most anodyne daily tasks, maybe you’ve got the right mindset to forge ahead while completely ignoring every sign that this isn’t likely to work out. Because you’ve got a dream, goddammit, and the only person who can take that away from you is you. 

Charles Bukowski once called the urge to write the Itch from Hell, and I think he was on to something there. You should write because you have to write, not because you think it’s an avenue to get an easy job that pays well. It’s an absolute necessity to have that particular neurosis in your pocket, pushing you on. If your brain doesn’t feel like an Instant Pot that’s about to become a spaghetti-scented bomb unless you release the pressure by writing that next script, become an accountant or a professional groin-trauma tester: I promise, you’ll be much happier.

Charles Bukowski drinking

I normally wouldn’t advocate for taking this guy’s advice, but when he’s right he’s right.

And that’s about it! I’ve given you nearly all of my advice. My my, look at you. My little chickadee, all grown up, ready to fly on your own. I hope I didn’t dissuade anyone from pursuing their dreams, but if I did, I probably saved them from quite a bit of heartache since if my dumb ass can make them quit they probably didn’t have the right temperament needed for Tinseltown (the “right temperament” here being “an ability to persist far beyond the limits of common sense or even self-preservation”). If I could sum up everything I’ve learned in one sentence, it’d be this: don’t let the bastards get you down – and remember that your own mind can be a real bastard, too. 

If you’ve my litanies of woe and still want to try your hand, my power to you. I sincerely, sincerely hope you make it big. And someday, after you’ve accepted your Oscar and you go to the coatroom and see a hirsute, disheveled man who obviously snuck in to steal giftbags and stuff as many hors d'oeuvres as he can carry into his pockets, come over and say hi to your pal Ol’ Sweet William. 

William Kuechenberg is a repped screenwriter, a Nicholl Top 50 Finalist, and an award-winning filmmaker. He’s currently looking to be a writer’s assistant, a showrunner’s assistant, or even to be staffed on a television show: tell your friends, and if you don’t have any friends, tell your enemies! You can also view his mind-diarrhea on Twitter.

Top image: Nikolay Litov/Shutterstock

Check out the rest of the series below:

First Rule Of Hollywood: Nobody In Charge Knows What They Want

The Brutal Truth Of Getting Hired By Hollywood To Write

The Unspoken Path To Hollywood Success: Betray, Crush, Destroy Your Peers

The Truth About Nepotism in Hollywood: It's The Whole System


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