When do I stop writing scripts for free?

when do you want to stop building bridges for your career?

“The next great spec script is just over yonder, brother”

When you're breaking in, you've got no choice but to write scripts for free. But once you start getting meetings and hopefully start getting hired to either adapt intellectual properties or to staff on someone's show, the question lingers: should I still write scripts for free? Or should I only chase gigs where I'll be paid up front to write?

It's an open question. I'm pals with established writers who've told me that they'll never write something for free. "This isn't a hobby," they'll say. "This is a job." And I think a good number of reps do encourage their writers to focus on going after paying gigs rather than spending valuable time writing original material for nothing. Depending on who you are, that might be decent advice since the market for original material has all but dried up in Hollywood.

Here's my two cents: I will happily write a script for free if I think that script is going to be the direct necessary bridge linking where I am now to where I want to immediately go next in my career.

That is, at each step in my career, I'll look honestly at where I currently stand and ask myself: what's the next leap in my career I can realistically make with just one great script?

I'll try to figure out what that leap is, then I’ll try to write the one great script that I think will help me make exactly that leap. And for me, that pretty much always means writing that script for free in my own voice.

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At the start of my career, I wrote 15 episodes over five seasons for a show called LONGMIRE. If I may say so, it was quite a good show, a throwback detective series set in rural Wyoming featuring a mature widowed cowboy sheriff coping with personal loss and a rapidly changing American West. The show started life on A&E. It got strong ratings but was canceled after three seasons anyway (the network wanted a younger demographic audience). But then LONGMIRE got picked up by Netflix and ran on streaming for several more years.

And somehow, it's getting watched more now in its afterlife than ever before: LONGMIRE's sixth and final season aired back in 2017, yet the last time I checked a couple of months ago, it was still in the Nielsen ratings' top ten most watched original streaming shows. Four years after it finished. That's kind of crazy. It's a bit of a cozy, hangout-with-the-characters throwback show that seems to play particularly well in "flyover" states and in rural homes.

Good for LONGMIRE and good for me. What am I getting at here? This: as far as I'm aware, in my ten years as a working screenwriter, I've never gotten an industry meeting because of my work on LONGMIRE. I'm talking, not even one meeting or phone call.

I had one stuntman-turned-director note that he enjoyed the show when I met with him, and a bunch of industry people say that their dad liked the show (it seems like everyone's dad likes the show), but working for five seasons as a key writer and then a producer on a successful, fairly long-running TV show has never actually led me to more job opportunities. I mean, it helped bolster my resume and it taught me pretty much everything I know about making TV and writing scripts. But LONGMIRE didn't lead to any industry people seeking me out.

Some of that may've simply been that LONGMIRE was never a hip, buzzy show. I remember one time I met with the president of a TV studio and he asked me what show I was working on. I told him and his response was, "I'm sorry." After the meeting, I checked online: LONGMIRE at that time had higher ratings than any cable show his studio had on the air. But, it wasn't a cool show that you could name drop during a dinner party. It was merely a meat and potatoes type of show that millions and millions of mostly blue collar people were devoted to.

My point here is less to lament the uncool status of the sort of blue collar type stories I'm most drawn to telling than to point out: even produced work doesn't necessarily beget more industry work. There's a lot of produced screenwriters floating around LA with real credits on imdb. Unless you're a name screenwriter — and I am not one — you have to figure out a way to get people to seek you out in particular among this mass of respectable and promising and beginning careers. In my career so far, my spec scripts have been that way.

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Most folks know what a spec script is, but to clarify in case you don't: a spec script is simply a script that someone writes for free, on their own. The hope is that you will then sell it or set it up somewhere after writing it, getting paid afterwards. In that way, it's a speculative business venture.

By and large, my projects tend to fall into three camps:

1. Spec scripts that I write on my own for free, then try to sell or get set-up somewhere.

2. Open writing assignments where I'm among a handful of writers angling to get hired for a gig, usually to adapt some intellectual property or to do a new pass on an existing project.

3. Hybrid projects where I team with producers and develop a pitch or outline with them and then try to set that up somewhere so I can get paid to write the script.

Each camp has its pluses and minuses.

For scripts written on spec, here are my pluses: I get to write what I want. I also control the property. I don't have to compromise my voice or sensibility. Also, these scripts often become a way of introducing me to talented people I want to work with. So, if I get my script to a really cool actor or actresses, most likely they won't decide to attach to my spec script. But sometimes they do. And also, sometimes if they pass they'll still dig the writing enough to want to meet with me generally. And sometimes future collaborations will come out of this.

The minuses: there's a minimal market for original scripts, and if the script doesn't sell, that means months or even years of work for no money.

For open writing assignments, these are my pluses: if I get hired based on my pitch, I know I'll get paid to write the script; a project with a preexisting intellectual property and/or value-add producer or star attached from the get-go has a better shot of getting made; it's a chance to build a strong relationship with whoever hires me.

The minuses: it can take weeks to build up a good pitch — often figuring out the entire story ahead of time — and if they end up hiring someone else, all that work was for nought; it can be tricky balancing your own vision with your partners' vision, especially in the early stages; you often have to manage multiple expectations while also writing for yourself.

For camp #3 — partnering with producers and/or talent first, then pitching the project before writing it — here are my pluses: often there's less competition from other writers because there isn't an immediate payday (that is, partners often seek me out in particular and propose a project); instead of writing an entire script, you're just developing a pitch or outline.

Also in these sorts of projects, I find there's often more room for me to assert my vision because my partners aren't paying me: instead, we're teaming up to try and get someone else to pay me to write whatever I'm pitching. I find that these packaged pitches sometimes gain more traction because they're defined around an intellectual property or talent package, but aren't completed scripts, so potential buyers can still have a creative voice. These types of projects are also a chance to develop strong relationships.

The minuses: if no one buys the pitch, it's a lot of work for no money. And even if you do sell, there's now multiple camps with POVs and expectations you need to account for while also trying to write something you are intimately personally invested in (a prerequisite for me — I'm not good enough to successfully write something dispassionately).

At this point of my career, I try to have one or two projects going in each of these camps. I'm usually juggling writing multiple scripts at a time, but when I do have a down spell for a week or even a day, I'm usually trying to break ground on future spec projects. Mostly, that means writing out initial ideas and character sketches and even listing actors and actresses I want to have in mind for the lead roles. Plus watching a bunch of films in whatever mode that I want to work in.

Eventually, one of these potential script ideas will emerge as the most exciting to me. I’ll start writing some early scenes. And if I get really excited about these scenes, I try to make sure I make enough money to pay the bills so I can clear my calendar for a month or two and just focus on writing my new passion project.

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All things even, my unproduced scripts have done a lot more for my career than my produced ones. Tons and tons more, actually.

As far as I can tell, just about all of my meetings and job opportunities have arisen because people responded to one of my spec scripts. And in ten years, I've only had four of them.

Actually, I've written about twice that many. But I haven't bothered sharing half of them with my reps or other industry people because I ultimately decided they weren't strong enough to circulate. (Or more accurately, my wife told me that they weren’t good enough and I eventually sadly came around to recognizing she was right once again.)

I'm only as good as the last script someone has read by me. So the last thing I want is to have some just pretty good script of mine land on the desk of someone I really want to work with and have it underwhelm them. I’d rather impress someone two years from now than underwhelm them today. And if I am going to swing and miss — and I swing and miss a lot — I want it to be with the tip-top best shit I most believe in.

I also don't want to spam my reps with a bunch of just pretty good spec scripts. I'd much rather be very judicious but have my reps know that when I do send them a new spec script, it's most likely going to be special and it could kickstart a new phase of my career.

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Practically speaking, my career has been built on four spec scripts. Each written for free, on my own. And each functioning as a bridge from one phase of my career to the next. I'll quickly tally those four spec scripts: the bridge I wanted to build with it, what materials I had at the time to build it, what I ended up writing, and what it did for my career.

First bridge: to go from being a Hollywood outsider to becoming a working screenwriter.

Materials I had to work with: an interesting blue collar personal story from growing up in rural America; a love of westerns and mythic American figures like Clint Eastwood and Johnny Cash; a track record as a published poet and academic.

The bridge I built on spec: an original TV pilot for a show called TANGLE EYE. Basically, a Man With No Name Clint Eastwood type of revenge western story set in the modern blue collar small town I grew up in, written with some poetic flourishes.

What it accomplished: TANGLE EYE got me representation; got me a bunch of Hollywood meetings that led to me getting hired as a freelancer for LONGMIRE (set in a similar world as my pilot) and getting hired for three separate pilot deals at three different studios.

Second bridge: to go from being a staff writer on LONGMIRE to creating and showrunning my own show.

Materials I had to work with: several seasons experience writing and producing episodes for LONGMIRE, a modern day cowboy show that reinvented certain elements of the western while still embracing the genre; several years spent developing and writing pilots with studios and producers.

The bridge I built on spec: I wrote the first two episodes of DAMNATION on spec. It's a Cain-and-Abel sort of mythic American dustbowl western set in Iowa in the 1930s that reinvents certain elements of the western while still embracing the genre.

What it accomplished: DAMNATION eventually got ordered to series and ran for one season on USA Network; I made the jump from staff writer to showrunner, hiring my own writer's room and department heads and casting the show and learning whole new acres of the craft in the process; I worked very very closely with talented directors (including James Mangold and David Mackenzie) throughout the process; I learned post-production for the first time, overseeing the editing and mixing and fine-tuning of every episode. Though it ran for just one season, DAMNATION elevated me to a new level in my TV career: instead of looking to staff on other people's shows, from this point forward just about all of my TV work has been about people seeking me out to either create or showrun my own show with them. For my one staffing job since then — on the second season of THE TERROR on AMC — I was sought out specifically to support that show's first time showrunner because of my experience in showrunning DAMNATION.

Third bridge: to go from only working in TV to also working in features.

Materials I had to work with: about five years of experience writing many many TV scripts, both produced and unproduced; a love of 1970s-style blue collar storytelling; a chip on my shoulder as a blue collar screenwriter trying to make his way in an industry dominated by Ivy Leaguers with elite backgrounds; a manager who had a passion project he'd been wanting to pursue for years.

The bridge I built on spec: a throwback gritty sports biopic script called THE OLYMPIAN, about Brad Alan Lewis' quest to go from blue collar outsider to Olympic medalist in the sport of rowing, a sport dominated by Ivy Leaguers with elite backgrounds. I partnered with my manager, who rowed in college and had been wanting to tell Brad Lewis’ story for years.

What it accomplished: THE OLYMPIAN got passed around the industry like crazy, to the degree that it tied for second most votes for that year's Black List (the annual survey of the industry's favorite new unproduced scripts). The script led to countless new meetings, which kickstarted my new side-career writing features, which has been going pretty steady ever since. THE OLYMPIAN hasn't been made yet, but it's gotten close numerous times, with various actors (including an Oscar winner) and directors (with Oscar-nominated films) and financiers attached. And with each attachment or near-attachment resulting in a new industry relationship.

Fourth bridge: to go from working screenwriter whose scripts are directed by others to becoming a writer-director who directs his own scripts.

Materials I had to work with: about ten years of experience as a screenwriter. Years of experience in working closely with both feature and TV directors and in prepping episodes and working on set and working in post-production. A large network of industry contacts and collaborators and fans. Years of experience working in the neo-western storytelling space.

The bridge I built on spec: a feature script called NATIONAL ANTHEM, an ensemble neo-western set in modern day blue collar South Dakota that I wrote as a directing project for myself, partnering with a producer who became a fan of my writing after THE OLYMPIAN.

What it accomplished: we'll see.

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Some possible takeaways from these four bridges:

Each spec script connects in some way to my personal blue collar background. This has been helpful because it gives me a uniquely personal POV on the characters and the story I'm telling and gives me emotional skin in the game, resulting in my best work. Additionally, this personal connection positions me to others in the industry as being authentically qualified to tell this story in particular.

One bridge at a time. I didn't try to create all these bridges at once. Once I broke in, it took me several years of writing on LONGMIRE and largely unsuccessfully developing pilots with others until I was really properly equipped to create my own show on my own. And it was only after I'd really established myself after five years in TV that I tried to make a leap into also having a career in features. And it was only after about ten years of writing both TV and features, and building up a big network of contacts, and building up my skillset in prepping, producing, and editing TV, that I decided to try and make a leap into writing-directing.

I don't try to jump levels while also switching genres. When I wanted to create and run my own show, I wrote a pilot in the same neo-western genre I'd used to break-in with, and that I'd been working in on LONGMIRE. When I wanted to jump from writer to writer-director, I stayed in that neo-western genre that I know so well from LONGMIRE and DAMNATION. That means, even when my role ends up being a new one, at least I'm still working in a storytelling space that I feel incredibly comfortable in. I don't know if I could try to make the leap to directing with this much confidence if I was also suddenly trying to learn how to tell a psychological thriller or romantic comedy type story. (If I wanted to jump into writing horror movies, or romantic-comedies, I’d maybe write that script on spec but I wouldn’t also try to direct it as a first-time director. I know myself well enough to know that I can leap roles or I can leap genres, but I can’t leap both at once.)

Each landing spot is a chance to gather materials for the next leap. I loved working on LONGMIRE, but after several seasons, I started to get ambitious to take the next step in my career. But in that interim, if I ever found myself on the verge of burnout or impatience during the season, I'd remind myself that each LONGMIRE episode I worked on was a golden opportunity to get better at all of the skills I needed to develop in order to capably one day run my own show. Similarly, when I was working on THE TERROR and found myself a little frustrated at not having creative control (it wasn't my job to have creative control), I focused on developing the on-set production techniques and the post-production skills that I knew would eventually come in handy if/when I ever directed my own scripts.

It could've all been luck. But that doesn't matter. Telling myself that I'm either constantly building a bridge to the next phase of my career or gathering materials to build that bridge has given me a sense of ownership over my career, gives me a sense of agency, and allows me to focus on what's in front of me and to determine what next steps I want to take.

I didn’t ask permission. No one tapped me on the shoulder to tell me it was time to create my own show, or to jump into features, or to try and make the leap into directing. I decided when it was time. In fact, my reps weren't always on board with my spec ideas or my timing. One of my agents did a spit take when I told her my idea for DAMNATION ("That's the least commercial pitch I've ever heard"). Another rep thought NATIONAL ANTHEM was probably too ambitious an undertaking for where I was in my career. I take my reps' perspectives seriously and I love that they're honest with their opinions. But ultimately, it's my career. I don't want or need someone else's permission to get into the ring. If I get my ass kicked and/or make a fool of myself with my overweening ambition, so be it. I'll dust myself off and come back tougher and hungrier and wiser and probably with some good stories to tell my buddies over drinks.

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“So let’s all gather ‘round and see if Tony can get to the point”

I'm pretty happy with how my career is going. But I'm not there yet. I'm not at a spot where I'm thinking, "okay, I just want to stay in this place for the next ten, twenty years." I've done some cool shit. Written and published three books. I've created and run my own TV show, written and produced plenty of other TV, and I've written some feature scripts that I think would make great movies. Maybe, one day they will.

I'm proud of all of that. But it's not enough for me. I want more. If my career ended today, I'd publicly say that I was grateful for it. And maybe at some point, I would be. But to be honest, I'd mostly be bitter for a good long while. Because I know I can do bigger and better.

I’ll admit that I'd like to have something more like Taylor Sheridan's career. That doesn't necessarily mean that I want to have the biggest show on cable, like YELLOWSTONE. Though I certainly wouldn't mind.

What I mean is: I want to write and direct my own material for both TV and film, ideally with the sorts of budgets and casts that Taylor Sheridan now works with. And I'm not there yet. I'm still gathering materials to build that bridge.

No one gave Taylor Sheridan those casts and budgets. He wrote his way to them. Which is why I admire what he's done so much. As far as I know, he wrote SICARIO and HELL OR HIGH WATER on spec. His first two feature scripts. And they made two fantastic fucking films.

Those two films made him a name screenwriter. He parlayed that status into WIND RIVER, which he wrote and directed himself on a modest budget. And that established him as someone who could reliably and capably direct his own scripts. One bridge leads to another.

Next, Sheridan parlayed that status into writing and directing YELLOWSTONE. Which doesn’t feel like most 2021 Hollywood product: it’s very much in this dude’s voice. And based solely on the massive success of that show, Taylor Sheridan should be able to command the budgets and talent to write and direct at least some version of whatever he wants for the next 20 years. Right now, he’s a one-man franchise generator at Paramount Network, with a whole bunch of his shows in the pipeline. And I’m very curious what that’s going to lead to.

Taylor Sheridan makes flyover state stories that are artful and populist and make money. Unless he does something to actively implode, he'll be the go-to for those sorts of stories for a good long while. To be blunt, I want to do some version of that. In my own quiet way, I've kinda been making my case as the plan b Taylor Sheridan already. I mean, what is WIND RIVER but a film length LONGMIRE episode with a bigger budget and bigger names?

But I still need to build the rest of the bridge from where I am now — a working screenwriter without name recognition but with I think a good rep as a blue collar writer in some Hollywood circles — to where I want to be: someone who can credibly write and direct his own muscular blue collar flyover state stories and gain access to the sorts of budgets and collaborators that'll help get those stories to a large enough audience so that I can keep writing and directing this sorta material for another 20 years.

And that brings me back to this whole bridge-and-materials metaphor. I think I know exactly where I am right now, and where I want to get to. I think that gives me a huge advantage in an industry full of confusion and misdirection and desperation.

For me, career-wise, I now divide my projects into two camps:

1) projects that can be direct bridges to my desired writer-director status

2) projects that can help me gather materials to build that bridge

If a project doesn't fall into one of those two camps, I'm not interested in it. Not right now. At this point of my career, a potential big paycheck wouldn't lure me to try and pitch on a Marvel movie. Nothing wrong with them, but I'm not in this for the payday. I'm in this to fill the big yawning void inside of me by becoming a blue collar storytelling auteur. Getting rich on an MCU movie won't help me do that.

But writing and directing my own HELL OR HIGH WATER or A PERFECT WORLD or THREE BILLBOARDS OUTSIDE OF EBBING, MISSOURI, or creating, running and directing my own JUSTIFIED or YELLOWSTONE? Maybe that would.

So at this point of my career, I won't write a TV pilot script for someone else for free, because I already established myself as a showrunner with DAMNATION. I don't need that bridge, at least not right now. Same reason why I'll no longer write a feature script on spec for someone else to direct. I don't need that bridge right now either. THE OLYMPIAN was that bridge.

So what will I write on spec, for free, right now? A feature script for me to direct. Or an original pilot for a show I would create and showrun (while also directing key episodes), based on my own original idea. Those are the places I'd like to be right now. And I'm 100% willing to write a script for free if I passionately believe it's the bridge most likely get me from here to there.

So, when will I stop writing scripts for free? I don't know if I ever will. Even if I do establish myself as a writer-director, I really doubt I'll be chasing franchise type projects or prestige pictures. I'll still want to write and direct my 1970s throwback type blue collar stories. And I'll probably need cool actors and actresses attached to my films in order to get financing. And to attract those cool actors and actresses, I'll need to create great characters that they otherwise wouldn't get a chance to play. Which means writing scripts on my own, in my own voice, for free.

But that's my career and my sensibility and my unique package of strengths and weaknesses. Everyone's got their own bag to carry. But in terms of writing specs, I do think it's worth really thinking about where you are right now, what materials you currently possess, and where you can realistically get to with just one great script.

Once you’ve determined those things, then try to write the best script you possibly can — not just to tell a good story, not just to feel like a writer, not just to have a fun writing experience — but to do all of those things while building a bridge designed to carry you from where you are right now to the next phase of your career. And then when you do get to that next phase, you can start gathering up a bunch of new materials to start building your next bridge.

That's what I did. It's also what Taylor Sheridan did — he just did it better and faster and bigger than I did. Each bridge leads to the next one.

First, figure out where you want to be next in your career. Not years and years from now in some far off dream world. No, figure out where you can get to next with just one great script, here in this imperfect world. Then throw everything you've got into writing that script. Just know, chances are, no one’s going to pay you ahead of time to write it. Or give you permission to do so. Or chase you down the street to read it. But that doesn’t mean shit. You gotta write it anyway.