A Decade in Coaching: A Look Back
On October 20, 2022, I will be celebrating 10 years since I officially launched my coaching business. In some ways, it feels like forever ago. After all, this business has changed not only me, but my entire life and the life of my family. It brought so many new, remarkable people into my life who have become my closest of friends, and helped me write my future path. It reinvigorated me. It changed my day-to-day. After all, stepping into this was when I really found my lane. So in many ways it feels like I’ve been doing this forever. But in others, it feels like it only just happened; I only just got started, only just figured out how this whole thing is going to work.
Before 2012, I had worked with writers one-on-one for a few years, but in a wholly unofficial, cobbled-together capacity. It wasn’t a job. It was a thing I fell into through the job, if anyone asked. Once a writer myself, I’d spent the better part of my 20’s working in development, then much of my 30’s running a coverage service and what was a fairly prominent screenwriting contests back then. I always had writer friends. They cared for what I thought enough to call me for advice on more than one occasion. So this thing… it was a conversation I always had. The child of a filmmaker, a person who never worked in a different business sector, the business, and the business of writing specifically, was always present in my world.
The first time someone I didn’t know, who wasn’t a friend of a friend, or a writer I’d come across during my days in development, reached out to see if she could book time with me for a consult, I was completely stumped.
“Time for what?” Was the first thing that came out of my mouth.
We had met some weeks before, when I taught a Business of Screenwriting weekend workshop on the east coast.
I had no idea what to tell her when she asked me what I charged.
But somehow, that’s how it began.
In a way, this was a natural continuation of the things I’ve always done: Listening. Discussing. Supporting. Providing insight and advice. It helped that I was running a coverage service. That I had friends who were writers on their way up. Friends in development. Friends on the producing and representation fronts. And, in my rearview, years upon years in development.
In those early days, I didn’t have a word for what I was doing. I tried on different job titles when I thought of what this could one day become, but none stuck. Years later, it was my friend, literary manager Marc Manus, who described me as a screenwriting career guidance counselor when he recorded a podcast with Scripts & Scribes. To this day, it feels like the best way to describe what I do. Even though you can’t exactly put that on a business card.
The truth is that, now almost fifteen years ago, I didn’t start working with writers in a wholly unofficial capacity with the goal of turning our work together into a business. In fact, as I had insisted to my husband and any of my friends who dared inquire if I wanted to turn it into a full time thing, there was no “there” there as far as I was concerned. There was no one doing career coaching or screenwriting career guidance counseling, or whatever you wanted to call it the way I had envisioned it because there was no formula. There was no uniform path that would guarantee screenwriting success. You couldn’t prescribe a path to success and send writers along their way. There was no one offering up this sort of ongoing writerly support that focused on ongoing-basis coaching entirely tailored to each unique writer because, I ventured a guess, no one out there was looking for that.
But 2008 had come and gone, taking us through a recession and a writers strike, a point in time that had served as a turning point in representation, and specifically as far as management was concerned. As my friend, manager Dallas Sonnier, who at the time ran Caliber Media, told me, things were changing. Managers who, in the heyday of the spec market, pre-strike and pre-recession, used to manage no more than 15-20 writers, suddenly found themselves having to represent “twice as many writers to make half as much money,” which consequently meant, for most managers, loading their client list in order to maintain their income standards and keep their businesses afloat. Writers, in return, found themselves seeking additional support via less traditional avenues.
Don’t get me wrong: Premiere clients, those writers who had built and maintained successful screenwriting careers, continued to receive time and attention from their representatives, agents and managers who were eager to keep their business. I remember a manager friend telling me, using Simon Kinberg, a darling of the industry at the time following such successes as Mr. & Mrs. Smith and Sherlock Holmes, as an example: “If you represent Simon Kinberg, your entire job is to service and keep Simon Kinberg, and maybe one or two like him. Everyone else on your list is way, way down.” Emerging writers found themselves eager for more guidance and attention that their newly secured representatives didn’t always have the bandwidth to give, as every dollar of secured income for their clients required double the amount of work it previously had. Working writers who were well on their way but still no Simon Kinbergs sometimes found themselves looking for a more agnostic sounding board to help them on their path. Which is, as it turned out, where I seemed to come in.
At some point, one of my private writer clients – of which, by 2010, I had about 10 or 12 of – came into town. We got together for dinner with another client and… before I knew it, instead talking about the business, their careers, their challenges or their writing, they were both on me, eagerly advocating that I should take this thing I was doing public and make it my job, full time.
I wasn’t kidding when I mentioned earlier that I didn’t think there was a “there” there. Yes, I always loved supporting my writer friends through their challenges and struggles. I could listen to them and talk about their careers for hours. Even when I was working in development, I found myself more deeply invested in the writers themselves than I did any one particular projects. It didn’t help that the production company I was working for didn’t make the sort of content that I passionately loved. And running a coverage service? The highlight, again, was working with writers, finding those writers that I felt incredibly passionate about. I always wished I could help writers avoid the mistakes that I myself was so afraid of making in the 5-minutes when I was lucky enough to have found my own footing as a writer; in development, I always tried to call my writers and prep them for meetings before we sat down with my higher-ups. But that was just… my quirk. This weird thing I was oddly passionate about. There was nothing I loved doing more than listening to, supporting, and sharing whatever insights I had with passionate, hard working, talented writers.
Regret has always been a big thing for me. I just didn’t want to have any. And so, following that dinner in 2010, I found myself wondering whether there could be a “there” there, something I could offer to a larger writing audience. For the record, I didn’t believe there was. If there was, wouldn’t have someone already come up with it? And no one was doing the sort of ongoing, bespoke thing I had in mind. So in 2012, I decided to give it a go. To launch the business. To make it available to writers who did not know me from Adam. Not because I thought it would be a huge success, but rather because I never wanted to regret not having tried. And the thought of it just kept… bothering me. Needling at me. What if there could be something there? What if all the years I’ve spent working in development, aggregating information from friends in representation, screenwriting, development and production could generate useful, actionable information for writers, both emerging and professional? What if the way my brain loved to collect data, religiously observed the turns of the industry, and catalogued what until then I perceived as interesting-to-me but otherwise useless information for anyone not industry minded, could actually be useful to someone?
My husband Tony, always my biggest champion, rolled back his sleeves and built me a website. My good friend Shelly Mellott, currently the president of Final Draft and with whom I launched a Business of Screenwriting workshop years earlier, invited me to speak and moderate a couple of panels (with the incomparable Syd Field RIP and Michael Hauge, no less) at a big screenwriting event she was working on. On October 20, 2012, I launched my business. When someone wrote on facebook: “You guys! Lee Jessup is now offering one-on-one career coaching for screenwriters” I was stunned. Yes, I’ve been teaching workshops, running competitions and working with writers for a million years, but my general outlook had always been… Who the f**k am I? Turns out more people then I’d ever imagined were interested in this thing I wanted to try. My plan was to launch the business, give it a few months, then, when it found no takers, pack it up, go back to something more traditional in production or development. Instead, being a career coach for emerging and professional writers became my full time job within two months.
Over the years, this job has given not only great friends and amazing writers to root for, but it’s also allowed me in on so many amazing, rewarding “firsts”. The moment Greta sold her first pilot, FRANKIE CASH, to HBOMax. My husband and I were downtown celebrating his birthday when she called to tell me. The day when both Eileen and Nora got into the WB TV Writers Workshop. The day Paul followed in their footsteps, after claiming himself the Susan Lucci of TV writing programs. The call I got from Eileen, when I was heading to the NYFA to moderate a manager’s panel, telling me that her pitch for HIGHWAYMAN sold to New Line. I was in Mexico on vacation when Moisés called to tell me he got his first job. And then there were the late night texts from Crosby when his screenplay BRING ME BACK became the subject of a very aggressive bidding war. Kim calling to tell me that 3-months after landing her first rep she got her first staffing gig on CHUCKY, her dream job. And Katie. And Chandus. And Barbara. And Michael. And Moisés And Amadou. And Rose. And John. And Nora. And Pamela. And April. And Michelle. And Scotty. And Robert. And Charmaine. And Josh. And Elad. And Hussain. And Janene. And… And… And… So many writers. Too many to name here but… you know who you are. Every time one of my writers got staffed, landed a writing assignment, had their movie made, produced their episode of television, sold a pitch or a screenplay or a pilot, got signed, got into a fellowship, won a screenwriting competition or killed it at a fellowship interview, they have all given me so much to celebrate, so much to be proud of. Yes, breaking into screenwriting and sustaining a screenwriting career is never easy and sometimes not very joyful. And there are very, very hard moments. But mine is such a happy job.
And it’s only gotten busier and more exciting in the decade since it first launched.
Back in 2012, the majority of writers looking to break into the industry were favoring writing features over writing TV. That same year, 288 original scripted television shows were released in the US. Not too shabby, but nothing like the 559 original scripted adult-driven programs the industry generated in 2021. Today, there are many more writers who are working in and trying to break into TV writing. Not only that, but many writers are working in both features and TV, where back then you were either a TV or feature writer, but rarely both. Netflix launched its first major series, House of Cards in 2013. Amazon Prime did not launch Transparent until a year later, in 2014. Most people were not yet aware of Hulu. HBO wasn’t streaming. Peacock, Paramount+, even Apple TV+, were not a thing. Quibi had not come or gone.
I look back at the decade I’ve been doing this as a public offering and… so much has happened, so much has changed. There was the Sony leak, the CAA/WME wars, writers divorcing their agents as part of the move against the ATA in 2019. The WGA strike that almost happened in 2017. Then the strike that Covid squashed in 2020. And now the potential writers strike in 2023. Zoom rooms. Mini rooms. Writers rooms for features. The big 4 becoming the Big 3 (agencies). Disney buying Fox. Amazon buying MGM. Warner Brothers. Discovery. So many agents shifting to management in recent years, after the WGA and the ATA (Association of Talent Agencies) settled on new agreements which marked the sunsetting of the dreaded packaging fees. It’s never a dull moment in this industry.
And over these many years, I’ve seen writers break in, get working, staff on shows, sell pitches, sell spec scripts. I met some of my best friends who became part of my life way beyond writing, and have had the privilege to root for writers at all levels, from seasoned professionals to just-starting-out as they fought the good fight for the careers that they wanted to build, sustain and actualize. Yes, there are frustrations; breaking into screenwriting, be it for features or TV, has never been easy. And working in the industry is rarely a straight, smooth path, for good or bad. For every writer who’s gotten staffed, who’s landed an open writing assignment, sold a pitch or a spec script, there have been others who didn’t get that coveted spot in a screenwriting fellowship, who had a rep pass on them, who didn’t get the writing assignment that was so close to being theirs. So my job is both gratifying and heartbreaking. The agony and the ecstasy. There are high highs and very low lows on every writers’ journey, at every level of a writers’ career, and I have been privileged to have been allowed in on all of it.
What comes next remains to be seen. There are definitely some things that I am beyond excited about and can’t wait to share with everyone. Coaching has created relationships and opened doors for me that I did not expect to have materialized, and I am excited to walk through them, grateful for the opportunities that they have brought into my life, the possibilities they created moving forward. If one thing is for sure, it’s that there will continue to be more changes in the industry, as this never, ever gets boring. Time will tell, on all fronts, with all things. But for now… I can’t wait to see what this next decade brings.