Last updated on November 3rd, 2021 at 07:43 am

In 2009, my mother and I were watching some procedural alphabet soup show, CSI or NCIS or one of those lot. A Korean spy wanted to blow up the Pentagon made of duct tape and Kleenex.

“This is awful. I could write something better than this.”

My mother looked at me. “If you think you can do it better, do it better.”

Five years later, I started for working for Dennis Lehane, and took a massive step towards that goal.

Dennis Lehane was one of my favorite authors. He wrote the books Gone Baby Gone, Live By Night, and Shutter Island, to name a few. At the time, he was plunging deeper into the film and TV world, and I became his writer’s assistant. It was my opportunity to learn from someone who was one of the best at the craft.

Some inside baseball here: The title, “writer’s assistant,” doesn’t do the role justice. It sounds like a bitch job — which it is.

But if you want to be a television writer, it’s plum. It’s one of the few types of jobs for writers with a clear path: writer’s assistant is a stepping stone to staff writer, to eventually becoming a showrunner. Plus, the staff writer salary is a dramatic step up for anyone grinding it out as a Hollywood assistant.

Everyone scrambles to land the writer’s assistant job, and openings don’t just pop up on Craigslist.

Aligning myself with Dennis, at this stage of his career with multiple TV deals on the table, was the equivalent of drinking 4 Redbulls then jumping on a rocketship. I was stoked but cautious. I remember writing to my parents:

“This isn’t to say I won’t be doing ‘undignified work,’ like coffee runs, or picking up laundry. I will. It’s not glamorous, I promise. I could lose my job two weeks from now because our personalities clash, or he thinks I’m doing a horrible job. This could run bad, just as easily as it could run good.”

Turned out it was a mixture of both. And while I thought it’d be the launching pad for the rest of my career, I had no idea it’d be my last job in Hollywood.

How to land a writer’s assistant job

Before working for Dennis, I worked at a literary management company. Dennis’s manager was one of my 3 bosses. As a Hollywood assistant, 75% of the job was rolling calls and servicing clients, so over the years, Dennis and I had built a little rapport. He wouldn’t know me from his Starbucks barista, but we chatted about the merits of Breaking Bad and Game of Thrones.

That year his star was on the rise. He was already a successful novelist whose books did incredibly well as films. Ben Affleck was signed on to direct and star in his latest film, Live by Night.

He had written on a season of The Wire, and just joined Boardwalk Empire for season 4. They brought him in to rewrite a script stuck at Fox called Deep Blue Goodbye, and he was also attached to the Silk Road story, days after the story broke.

Like I said. He was the rocketship, and I wanted aboard.

There was only one problem: He wasn’t hiring, and as far as he was concerned, he didn’t need to hire. I knew I’d only get one chance to pitch him, to peak his interest in me, so whatever I said needed to be stellar.

Here’s the email I eventually wrote:

Hi Dennis,

Amy S. said she mentioned her and my discussion to you, and that you said I should feel free to shoot you a note. After spending the last two years reading most of your work (and scripts/treatments based on your books) and observing your transition to Los Angeles, I thought of a few suggestions that could make the process an easier one…_

1) A temporary west coast assistant. Right now, you’re entering the very lucrative re-write market with publishing deadlines in the horizon. You’ve just moved your whole family across coasts. You need someone onsite to help coordinate your LA schedule, get your affairs in order, and get your office running._

What it would take: A short-term West Coast assistant. To get all the trains running back on schedule.

How I could help: I’d work with T. (whom I’ve coordinated with in the past) to manage your schedule, acting as a stop-gap until you were settled. This was part of my regular duties here at IPG: coordinating Amy’s schedule while simultaneously coordinating for J. (agent for James E. and Michael C.).

Benefits to you: With someone on the ground in LA to deal with the minutiae, you could focus on the two most important things in your life: your family and your writing.

2) A research / writer’s assistant. Currently you’re juggling a wide breadth of projects, e.g.,Travis McGee rewrite, Three Month Trilogy, your own imprint, book tour of WORLD GONE BY, LOVE / HATE remake, etc. A researcher / writer’s assistant would sift through any and all material, organize it for you, so you can focus on creating your worlds.

What it would take: A dedicated West Coast researcher / writer’s assistant.

How I could help: I imagine you’ve worked with a stable of excellent researchers and assistants. They are/were likely organized, voracious readers and thoughtful writers (prerequisites for this role). What makes me different is my network. In addition to those traits, I’ve fostered relationships so I can get many books and scripts in the unpublished, unproduced market. For example, last week Paul H. requested an unpublished book represented by a rival agency. Within hours, Amy and I were able to get a copy to him because of my relationships.

What the benefits are to you: You’re a thorough reader, taking on material both wide (across a spectrum of genres) and deep (tracing a genre down its roots, e.g., for literary crime fiction, James Ellroy, James Lee Burke, James Crumley). But you face more projects and stricter time restraints. I can not only process, filter and organize information for you to write more efficiently, but get access to resources that you may want.

Given the above, I hope you can see I’d provide immense value to your work, and you’d consider taking me on as an assistant. I understand there are reasons why you’d be hesitant, which is why I’d suggest several options to make this very low-risk for you: I could start remotely or onsite, whichever is more comfortable for you. We could do a one-month, uncompensated “trial” period. If you didn’t feel the fit was right, we’d part ways, no hard feelings.

That being said, I have a great deal of respect for you and the work you’ve done. I think it’d be brilliant to work for you in some way. Thanks for your time, I hope to talk with you again soon.

– Chris

A bit formal, but pretty good.

This one email took about 3 months to write.

Successful stalkers haven’t performed this level of research.

I read everything he wrote. Not just the books. Every unproduced TV script. Each draft. His short stories. His play adaptation of his own short story. The adaptations by other writers of his short stories.

I stayed late at work and studied every one of his film or television deals. I knew every option price, when every extension payment was due, and the exercise prices. I could tell you what the bestseller bonuses looked like, and to the dollar, what he’d get paid for every draft of his TV pilot script.

I combed through 7 pages of Google results and read every interview after every release of every book and movie, until I could tell you where his love for reading came from (his mother took him to the Boston Public Library when he was a kid) and that he’s allergic to wine (sorry France). Then I watched all his keynote talks on Youtube.

Fortunately, Dennis avoids social media like Hep C. so I didn’t have to dive deep into Facebook, Twitter, or Instagram. But I would have.

One final piece of leg work: Before sending out my email, I listened to an interview that Charlie Hoehn did everyday for a month straight. Charlie is an expert at cold emailing authors and pitching how he can help, so I piped his advice into my ears on my morning bike ride, pumping my legs in time to his voice on Overland Avenue.

Months of work… for one email. But it worked.

Sort of.

He didn’t need a personal assistant in LA, he said. But he was interested in the research help as a writer’s assistant.

“How could you perform research for me and still do your job for Amy?” he asked. “I work fast so I usually need fast responses to my research questions.”

I threw up a hail mary and told him I’d quit and work for free for three months.

“Dude, don’t quit your job, that’s crazy. We’ll try out the research. Work me into your lunch hour,” he said.

Would I have worked for Dennis for free? 100%. But I gambled on the fact he’d appreciate the gusto, and would let me do it on the side. The gamble got my foot into the door.

Researching for Dennis Lehane

Over the next 9 months, I researched. How would a doctor in the 1940’s treat seizures? How about migraines? How does an EMT treat someone who attempted suicide? I looked into military-grade firearms, yachts, playgrounds in Santa Monica (3 different projects, all unrelated).

I wish I could say that I knew my work was excellent. I wish I could say it was only a matter of time before Dennis hired me full-time.

The truth was, the first month of temporary work turned to 3, 3 turned to 6, and I was a nervous wreck the entire time.

Was anything I sent even good? Could he use it? If he didn’t use it, did that mean I screwed up? Or did it just not make the page? I said I’d only email once per day, but what if he wants me to check in more often?

I was like a high school teenager who landed his first girlfriend and had no idea how to talk to her.

Like a crazy person trying to keep themselves sane, I wrote little notes to myself, like this:

Still plenty for me to do with Dennis to help him. Keep your foot in the door. Don’t be desperate. You have to be in this for the long run. Let’s say after this month, he says he’s still not ready to bring me on. Suggest another project. If you want to work with someone badly enough, you make it happen.

In spite of all my insecurity and neurosis, I stayed patient. Landing a writer’s assistant job was a war of attrition: if I overextended, I’d lose. There were so many moving parts, so much competition, that sometimes it’s just right place, right time. If you’re not patient, it won’t happen.

Hollywood lore revolves around the wunderkinds: the Max Landis’s, Lena Dunham’s and Zac Efron’s. You start to think: Why haven’t I reached that level of success yet? Compounded by inflation of happiness and success on social media, you start to wonder why you’re the only one struggling.

You forget about the David Chases’s, the Michelle Ashford’s and the Vince Gilligan’s of the world — extremely talented people, all who took time to build their careers.

So I stayed patient. I found other things to work on, like a chef pushing a pot to the back burner to simmer. I started interviewing elsewhere: Paradigm, Virgin Produced, MTV. Nine months into the research gig, I decided to leave my current role with or without a new gig. Before I left, I threw up one last hail mary, to see if Dennis was still interested in bringing me on:

“Don’t know if you’ve made up your mind about LA versus Boston yet, but I’m planning on turning in my two weeks to IPG next week (I feel I’ve plateaued in terms of my learning and it’s time to move on).

“I’m letting you know because I’d still love to talk about the possibility of working for you, if that’s still an option you’re open to discussing.

“Obviously, no pressure to respond. I understand a lot’s on your plate. Just wanted to let you know the interest was still there.”

The next day I heard back.

Let’s meet, he said.

How to ace a Hollywood assistant interview

You know that dream, where you have to give a presentation in front of an auditorium full of strangers? You spend months preparing for your presentation, but when you get there, you realize you left your notes at home?

My meeting with Dennis went something like that. Minus the dream part.

Let me backup.

How did I prepare for my interview?

I put together a list of questions he could ask me. Then I spent about 2-3 hours recording myself on camera, answering the questions until I was perfect.

Using the briefcase technique, I prepared a batch of notes to show him exactly what I could do. When I got into the office that day, I stuffed those notes into my drawer, which is precisely where they remained during the actual interview.

Fortunately, the meeting itself was pretty simple: First, he told me all the reasons why I shouldn’t take the job.

“Here are all the reasons you shouldn’t take this job. It’s a lot of boring personal assistant work. Laundry. The dogs. The house. Scheduling.”

“You don’t want to do this,” he said. “You’re going to get bored.”

I told him I was happy to eat crow, as long as he looped me in on all the creative projects.

He agreed. Over the next few days, we hammered out the details, negotiated salary, and picked a starting date.

I had landed my Hollywood dream job as a writer’s assistant.

What it’s like to be a writer’s assistant

True to his word, Dennis kept me involved creatively. The next weekend, he invited me to watch him pitch his take on a film about the Winter Hill gang. For the next two weeks, my writer’s assistant duties were watching the first seasons of Mad Men and Deadwood, and breaking out the A, B, and C storylines into their individual beats.

Also true to Dennis’s word, I quickly got sick of the personal assistant work.

But let’s talk about the cool shit first.

Within a few months we had a pilot that seemed 95% greenlight for a straight-to-series show at Hulu. Dennis called me from Germany and told me that in the deal, I was attached to him — in other words, he was going to be the showrunner and I’d be the showrunner’s assistant.

We actually had a long conversation about the best way to proceed with my career. He asked me, if a show went, would I want to be a showrunner’s assistant or a writer’s assistant?

More inside baseball: Showrunner’s assistant reports directly to the showrunner, writer’s assistant is responsible for taking notes in the room. Typically, the showrunner’s assistant’s salary is better than a writer’s assistant salary.

“The writer’s assistant position is terrible,” he said.

“It’ll look good on your resume but you’re better off working for me. You’ll learn more. As the writer’s assistant, you don’t talk. You’re going to meet a lot more people as showrunner’s assistant, too.”

To this day, I appreciate that Dennis took the time to take me under his wing.

United Talent Agency was sending us baby writers to read to staff our writer’s room. I started reading their spec scripts, to have a shortlist ready when Dennis returned.

Two days later, he called me back.”Stop reading. The Hulu board needed a unanimous decision to greenlight the show. We didn’t get it.”

We moved on.

I researched the Cleveland Torso murders for a pilot about Eliot Ness post-Al Capone (“Mad Men with guns,” Dennis called it.) I looked into native Hawaiian fauna and the burgeoning meth industry in O’ahu for the US remake of Love/Hate for Showtime. And I spent a month in and out of the Santa Monica Public Library researching insane asylums and treatments for the mentally insane during the 1940s for a Shutter Island TV series we were pitching to HBO.

There were a bunch of other little projects as well. Doing his social media, creating an email newsletter for his fans, redesigning his website. Mostly I loved the research. I loved morsels of my work coloring the worlds he created — even if it was just a line — that could ultimately appear on the screen.

I brought that detail on the page, I thought. I helped bring it to life.

But more than the research, I fell in love with the status of the role. I loved that people who clamored for Dennis’s attention — publishers, agents, producers, journalists — thought of me as an extension of him. If they wanted to get his ear (or on his calendar or call sheet) they had to go through me.

Before I worked for him, I was another baby writer clawing up the mountain. Afterwards, I was “Dennis’s guy.” That opened a lot more doors.

Unfortunately, the reality of being “Dennis’s guy” was far less glamorous than the idea of it.

How to be an amazing Hollywood assistant

Good Hollywood assistants have an expiry date.

When I first started in Hollywood, I wasn’t just happy to be an amazing assistant… I was thrilled. Run to Hamburger Hamlet and pick up lunch for the office? Sure! Read 2 books over the weekend for Monday morning? Yes, please. Print 6 scripts, hole punch and bind them? Absolutely.

Everything was new and exciting. Just walking down Sunset with the SoCal sunlight beating down on me at 12:45 in the afternoon felt amazing. My bosses wanted their assistants and interns writing “coverage” day and night — they asked if my coverage was any good.

Of course it was, I told them. I write the best coverage.

I went home that night and asked my friend what coverage was (glorified book reports for scripts). I thought it was the coolest thing and started knocking them out.

In the beginning of your assistant career, it’s a privilege to be a part of the Hollywood machine. It doesn’t matter that you’re a cog, or less than a cog — the washer holding the cog in place — you’re still part of it. You play a role in the engine that grinds up stories and plasters them onto screens. It doesn’t matter that you don’t have a life, don’t make money and have no real responsibility… you were in the movie business.

That enthusiasm is enough fuel for the first 2 years. After that, you’re on fumes. You feel like you’ve paid your dues, and you’re ready to see the tiniest upward movement in your career. If it doesn’t come, the “go-get-em” attitude becomes “it’ll-still-be-there-tomorrow.” And the veneer of Hollywood glamour starts to fade.

By the time I worked for Dennis, I was into Year 4 in Hollywood. I didn’t realize it, but I wasn’t that “amazing assistant” anymore. That’s the person I promised Dennis, and I wasn’t delivering.

One day, he called me into his office. “The research is great. But the personal assistant stuff, it feels like you think you’re too good for it.”

He was right. My heart wasn’t into it anymore.

It didn’t matter how good I was at the research stuff. I promised to I was willing to eat crow, and I didn’t live up to my end of the agreement. I resented the personal assistant work: driving back and forth to Santa Monica to schlep his dogs to the vet, one drooling all over my windows in the back seat, the other crawling into my lap while I’m trying to drive. I hated going to the DMV to register a car, or doing the smog inspection. I hated combing through flights to book international travel only to change it at the last minute, or coordinating with the cable guy who promises to show up at the house somewhere in the window of 8am to 4pm.

Let’s be perfectly clear: This isn’t some Hollywood assistant horror story. I’m not some mistreated celebrity assistant. This was 100% my fault.

Dennis was upfront about what the job entailed. He was fair, and simply asked me to honor the agreement we made. I always got the job done, but I was never great. I couldn’t be that amazing Hollywood assistant anymore. My expiry date passed.

When we first interviewed, Dennis promised that I’d get bored, and this wasn’t the right job for me. His instincts were right, as they often were.

Leaving Hollywood for the startup world

For five years, the only thing I wanted was to get into a writer’s room on a television show. My job as Dennis’s writer’s assistant was the closest I got during those years in Hollywood, and I’ll always be grateful he gave me the opportunity.

At the end of 2014, I got offered an opportunity to work at a startup. On one hand, it was completely outside of entertainment, and it took me far, far away from my goal of ever writing for television.

On the other hand, there was still a lot of impact — my work would get put in front of a million readers on a regular basis. There were no assistant duties. I could work remotely, on my own hours, which I’ve since learned is a gamechanger. And after years of watching people grind it out in the Hollywood machine, I realized you could be wildly successful in your career and still be completely unhappy.

I stayed with Dennis until I found him another assistant. I wanted to find him the right person, and avoid the mistake we made with me. At the time of this writing, my successor is still there and by all accounts doing amazing. I like to think I got that part right.

Perhaps that’s how my Hollywood career ends, with a whimper instead of a roar, a cautionary tale for those not quite ready to sacrifice it all for a shot at the silver screen. But part of me thinks, perhaps not.

The dream is at some date undetermined, to give it another go. I have no idea how or when or why. There’s just this seed of the desire to finish what I started. My time working for Dennis may be over, but I like to think I’ve just stuck a pin it that Hollywood dream for now, and as the entertainment and technology world continue to merge, I’ll get the chance to go back and pick it up again.

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Photo Credit: Mark Fugarino, Andrew Imanak