Confessions of a Failed Screenwriter

A chewed pen sits on a wooden desk
Photo by orangeacid.

Editor’s note: Our friend Randy Steinberg sent along an essay he originally wrote for Scriptshadow and we asked if we could re-publish. He said yes.

Author’s note: Throughout this essay, when I refer to screenwriting it should be meant to understand I am discussing theatrical film writing as opposed to television writing.

I received a Master’s degree in Film in 1998. My concentration was screenwriting, and from that point forward I set out to write movie scripts with the goal of finding an agent, getting produced, and building a career. In 2011, I ceased trying. I threw in the towel. Tapped out. I had failed. I made very little money during all those years, had a virtual rolodex of contacts who probably wouldn’t remember my name in six months, and a bunch of old scripts that only myself and the universe knew existed.

How had this come to pass? It’s not as if I didn’t try. I had diligently written scripts for more than a decade. I knew people both in and out of the Hollywood system liked my writing. I had the chops, the drive, and the ideas to succeed. Why didn’t I?

No one will tell you success in screenwriting is easy, but few impart just how high the odds are. You may secure an agent or a manager, but that is only one step. Once you have representation, your script may be circulated. You may even get an actor or director attached. A small paid option will seem like a giant leap forward. If you are extremely fortunate, your script may sell and even be produced. This may mean some solid income, but don’t quit your day job because you could go dry for years after that. To actually live off screenwriting and that alone (and hope to support a family if that’s part of the equation) is an achievement few realize.

It’s not as if I was unaware of the long odds, but I didn’t play the game correctly. The age old saw “if I had only known then what I know now” applies, but even armed with better knowledge the odds of success increase only slightly. Still, if one hopes to achieve a dream it is best to embark on the journey with the proper tools and information.

What was it I didn’t know? What should I have done differently? Why did I fail where others succeeded? What can I pass on so new writers avoid the mistakes I made?


As with most failures, you have to look at yourself (though many are wont to do that). First, however, let me indulge in a bit of self-pity. When I emerged from film school, I was ill prepared to commence a career in screenwriting. It was the classic dichotomy of theory and practice, and many film school grads face this: no matter how well-schooled they might be, they are not prepared for what lies beyond the halls of the academy. For me, at the time of my graduation I did not hit the ground running: I just hit the ground.

It took me a few years to get over this poor start, but that amount of finger pointing aside, I have no one but myself to blame about the subsequent mistakes I made.

One of the appeals of screenwriting is the lottery-like nature of it. You can go from rags to riches overnight. One day you are the struggling writer in the garret, the next the toast of Hollywood. There is an entire industry built around tips, strategies, formulas, etc. that can help a writer achieve that big payoff. The allure is hard to resist.

That is probably one of the reasons I stayed at it as long as I did. Every time you begin a new script, you have hope. This could be the one. All the disappointments of the past are washed away, like so much sin after a sprinkling of holy water. Writers of all stripes have to deal with constant rejection and self-doubt, but they are the ultimate optimists. No aspiring writer would ever begin a new project if he or she didn’t think it would be the one that was going to make a big splash.

But here is the first and greatest mistake I ever made: I never moved to Los Angeles (I am from the Boston area). I had the opportunity when I was younger—before family and work made it an impossible decision—but I didn’t seize it. I labored under the impression I could write from afar, and, perhaps after a sale or another big development, then move to Hollywood—or maybe never have to live there permanently.

It’s not that this can’t happen. There are writers who don’t live in LA, who write scripts and visit frequently but don’t call the town their home. Some can make noise, but if you are going to make screenwriting your career (especially television writing) you simply have to live in Los Angeles—or at least reside there for some amount of time.

This is truer now more than ever, as reps eschew some clients simply because of out of town status. It’s harder to build the career of a young writer (and sustain the career of an established writer) if he or she isn’t known around town and can’t meet with industry players on a day in and day out basis.

Some writers may be content with one sale or maybe writing material for independent films. Maybe they want to write and produce their own scripts, in which case Hollywood matters less. But if you want to work in the Hollywood system and make a true living from it, you’ve got to be in the mix. There are always exceptions, but personally, in retrospect, it was a very large error not to move to Los Angeles—at least for a time if not permanently.

But let’s put that decision aside. Could I have achieved more, even removed from the center of the American movie industry? Yes, but again I made some poor decisions. If you want to succeed in screenwriting you have to be focused—like a laser. You are only as good as your last script. Everyone wants to know what you are working on next, and if you get sidetracked with other pursuits you fall behind. Reps and producers forget you. Tastes change and new trends form. To succeed in screenwriting you have to stay relevant, and to be on the forefront of people’s minds that means new material all the time.

Life intercedes, so it’s easier said than done, but for a time I wrote a few novels (lousy ones) and then I tried representing other writers for a bit. Both were worthy endeavors, but they forced me to put down my own screenwriting, and this was time I could have been writing newer and better scripts and perhaps breaking through.

And speaking of the wasted time department, I fell into the writing trap that is almost impossible for people to avoid, but bears mentioning because, undoubtedly, it will be asked of you if you attempt to make screenwriting your career: writing for free or writing “on spec.”

Every script that a writer begins without compensation is essentially that. Unless commissioned or written with an eye on raising money for your own film, every screenplay is penned on speculation that it can be sold or at least a manager or agent gained by it.

Some years back, times were a little easier for writers (not much but some). An unknown could procure a rep based on solid writing samples and then work his or her way into the system with small paid assignments. Money for the development of screenplays was freer and studios and production companies were more likely to take a chance on an unknown writer. Those days are gone and writers are being exploited.

More than ever, writers (both new and established) are working for free. These are not their own projects, which they then try to sell or pitch to reps. These are the ideas of producers, managers, and executives. Writers are asked to work on these for months, maybe even years with no pay, hanging only on the promise of a big score when the script is finally sold.

It is often hard for the writer to turn down these opportunities. There could be the chance to work with someone who has clout or access, and passing that up feels like starting at square one. It’s better to cling to something than have nothing, so writers take the chance and work this way, putting aside their own original material to spend time on ideas they might not even have full intellectual control of.

This, as with not living in LA, can occasionally work out, and that one out of one thousand success story fuels the notion that “it can happen to me, too.”

I don’t believe most of those asking writers to work on spec are bad eggs, looking to fool writers or get something for nothing. I do think it’s an unfortunate practice, on both sides of the equation. If you want good work, you pay for it, and there seems to be a belief that writers will still give their best effort even if not getting paid.

On the other side, writers naively believe because someone is offering to get their scripts to higher ups these assurances will be followed through on. But I’m a firm believer that if there is no skin in the game on the producer or managerial side, even if the intentions are noble, you are unlikely to gain traction working on spec.

Of course, there are some looking to exploit writers, but whatever the motivations of those asking for free work, the writer should avoid it. I made this mistake several times. With limited time in this life, a writer should look askance at these situations and try to stay with his or her own original material.

But, if you must do it, do it when you are younger. Trial and error should happen when you have time and freedom on your side. You don’t want to be 20 scripts into your career, maybe with a spouse, children, and other responsibilities, putting down your own work to take free passes at someone else’s idea.

This happened to me toward the end of my screenwriting efforts, and it was not without appeal. It was a situation about a well known true crime story, one which I had a lot of background in. The producers could not afford to (or just didn’t want to) pay me up front, but as it was a front page story (and still is) there was some mojo for the project and the belief that it could be sold. In my younger days, I probably would have bit. But having learned the lessons of a failed screenwriter, I passed.


It’s not just with producers that writers can fall into this trap. Finding representation can also be a time suck and lead to failure.

In theory, the rep is supposed to work for the writer, and this may be true at the higher echelons where a well-known writer can fire an agent or manager and easily sign up with a new rep. But at the beginning stages the writer has little negotiating power. Your only leverage is to walk away, but many writers feel it’s better to hang on to something rather than beginning the search for a rep again.

Part of the reason for my failure is that, in several instances, I did just this. I should have headed for the exit far sooner, but I played the part of the ingénue too long hoping against hope that reps who took interest in my work would actually advance my career.

For example, I had once been introduced to a strong management team. They liked my writing and asked what else I was interested in doing. After discussing some ideas, we settled on something to script. Nine months and four or five drafts later, we were basically nowhere, and these reps didn’t seem interested in trying to work on something else. Furthermore, they did very little to put me forward to the industry as a writer with ideas and skills worth hearing about.

The emotional screws are similar to writing on spec for a producer and go down just as deeply. You have a legitimate rep, an industry player, interested in you and your work. They have the access and the contacts to get you where you want to be, so you are shy about asking questions or pressing the rep too much. They have all the power. The time I spent working on a script the reps never really showed to anyone was time I could have used writing other material and making more—and possibly better—contacts.

The small advantage to these situations is you have control over the material (unless you sign something to the contrary). You are working on your own ideas, with the rep helping to develop but not legally entitled to them. Still, unless you ask specific questions and “manage your manager” you can easily wind up in the same situation you would working on spec for a producer. You labor on a script for months and possibly years with the expectation that your rep will eventually get you and the work out there, but in the end they do neither.

There are many variations on this kind of relationship. A writer can spend much time working on different things for the same rep, but when push comes to shove the rep doesn’t feel it’s right for the market and asks his or her client to begin again on something new. Or the rep is only half-interested in the writer and strings him or her along hoping he or she will produce something amazing, but, short of that, won’t lift a finger to help the writer’s career.

Indeed, a few years after my failed efforts with Management Company A, I was introduced to Management Company B. Company B had an even better track record in the business than A, with big sales and an impressive client list. I showed them some scripts, and they thought I was a skilled writer but stated they could not sell those particular screenplays (more indy, character-driven pieces). Nevertheless, they wanted to discuss other ideas I might have. It quickly became apparent they were only looking for concept-driven scripts –action, big-comedy, horror and sci-fi—and their interest in me was of the “hip-pocket” variety.

This is a situation where a client is not formally signed with the manager, but he or she will agree to look at material the writer submits even though providing no guidance. When the script is complete, if the rep sees possibility in it, he or she will then sign the writer.

Had I been younger, I might have attempted to play ball, but I had learned my lessons by then and realized I would probably spend several months writing on a wing and a prayer—and in a genre that I had little passion for. In the end, I told Management Company B we didn’t have much common ground. They did not seem surprised and made no attempt to convince me we should try to work together.


The experience with Management Company B came in 2009-10. Even then, nearing 40 years of age and with much experience, I let the situation play out for too long. I was still holding out hope this one could be different. I did not want to admit failure. But when I did walk away I actually felt relieved.

After a few months of reflection, I realized I should start to move away from screenwriting entirely. I also realized the irony of it all. My final failure (the reality that I no longer aspired to practice the art of screenwriting professionally) came about because I was not afraid to fail. All those years, I was afraid to walk away from dodgy opportunities, afraid to ask for more commitment from potential reps, afraid to move to LA. Once I stopped fearing those things, I could be realistic with myself and summoned the courage to let it all go.

It was about this time, after more than a decade of trying, that I really and truly started to understand the system and could see why I had failed to make headway.

I began to realize that writing scripts was not the hard part, because if you want to succeed in the Hollywood system you have to be more than a good writer. There’s no question you need skill to make it; one can’t bumble his or her way into a successful writing career. But once you get past some of the first hurdles, success in screenwriting becomes more about market savvy, how you position and develop yourself, and saying the right things to the right people.

You’ll hear Hollywood insiders frequently tell new writers to just “write a great story” and you will get noticed. I think this is terrible advice. If there are two writers of equal skill, one who loves writing period dramas with female leads over 50 years of age and the other who scripts action pieces with 30-year old male leads, it’s not hard to see who is going to get more traction.

Screenwriting is, far more than any of the other writing forms, business-based. No one is going to shell out millions of dollars to make a movie without expecting (misplaced as this often is) millions more in return. Writers need to realize this.

I’ve read enough screenplays (at different levels of development) and seen enough movies by career-professional writers to know the gap between them and the talented aspirational class of writers is not as large as we are led to believe. It’s true that being in the right place at the right time is something no one can predict or prepare for, but I think a certain class of writers separate themselves from the pack by doing the little things that others can’t or won’t do.

No story about how a writer broke in to the system and succeeded is ever the same. There is no magic formula. The best advice I ever heard about success in screenwriting is “be pleasantly persistent.” But some succeed while others fail because they learned to do the little things. The little things evaded me for a long time, and when I did finally understand them I didn’t want to put them into practice.

I found the ideas that spoke to me as a writer were not commercial enough for Hollywood. I was not interested in moving to LA, ever. And I was unwilling to talk the kind of eager-beaver talk that producers and reps in the system want to hear. Perhaps some of this was due to the fact that I was nearing 40 and at a different place in life, but there are plenty of writers, no matter what age, who succeed because they play the game correctly (in addition to possessing great storytelling skill).

Perhaps I was never truly cut out to be a Hollywood-style screenwriter, but all those years of trying would have been less of a letdown if I had not made some of the mistakes I did. Then I could have chalked up lack of success to poor timing as opposed to some of the other missteps I made.


Even though I harbor little ambition for screenwriting any more, I still have people approach me and exclaim “I’ve got a great idea for a movie.” It’s difficult to even hear this because there is so much beyond having a great idea. I used to respond, “Sounds good. Write it up.” Now, I feel I should be a little tougher or at least ask, “What’s your goal?” You need a great idea to begin, but that’s one piece out of a 1,000 item jigsaw puzzle.

It’s hard to be entirely negative. A prominent screenwriter I’ve known for years has always counseled me not to bother with the craft. Naturally, I never liked that advice, but he knew what I was up against. You don’t want to lead on aspiring writers by telling them just to try hard and believe in themselves. You want to encourage someone to pursue their dreams, but at the same time you want them to know exactly how steep the climb is.

As I noted earlier, there are a million books, articles, and blogs about screenwriting that will tell you all the things you need to do in order to sell a script or land an agent. The point of this essay is not to follow suit. I don’t want to tell anyone reading this article what they must do in order to succeed at screenwriting: I’m here to tell readers what I did wrong and why I failed.

A screenwriter who did succeed once told me something about the business when I asked him what I should expect out of a situation with an agent. He said, “It’s all a mystery until it isn’t a mystery.” If this article can take just a small slice out of the mystery by highlighting my missteps, I will take solace in helping someone else succeed where I did not.

About :

Randy Steinberg has taught screenwriting at Boston University.