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The Bricks of Breaking In: Writer Robert Hewitt Wolfe On Being Ready For Opportunity

January 31, 2023
9 min read time

Looking back on his youth, Robert Hewitt Wolfe (Prodigal Son, Elementary, Star Trek: Deep Space Nine) was always writing. He started his first novel at the age of ten. Started his second in high school and his third in college, although he didn’t finish any of those until much later in his life.

Screenwriting pursuits came to him in college and they quickly brought results. Wolfe recalls, “I won second place in the Goldwyn competition, which was like this UC-wide screenwriting competition. I think I won that from my first or second script I ever wrote.”

This win came with a cash prize, his name in Variety and led to him signing with an agent.

This early success, and the economics of the career paths, pulled Wolfe to focus on writing instead of directing. He relates, “I produced my first student film and it cost me a thousand dollars that I didnt have. I could make a lot more money maybe as a writer than as a director and I dont have to spend my own money. Its a lot cheaper to create a script.”

Five years after UCLA Wolfe got his first writing job. It was a near miss in selling a feature that then brought about an unexpected opportunity, a chance to pitch to Star Trek: The Next Generation.

Wolfe details, "I had written this science fiction sort of epic action script. I was actually negotiating a deal with this company, this independent, mini-major at the time and they went bankrupt in the middle of the negotiation.”

With that deal off the table, Wolfe’s agency, who also represented one of the writers on Star Trek: The Next Generation, sent that same script as a sample and got Wolfe a chance to come in and pitch on the show.

Wolfe adds, “This is back in the day when they had an open door writing policy that essentially you could get invited to pitch either via an agent or if youd sent in a spec sample of Next Generation and they liked it enough to invite you in.”

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This is where hard work and persistence paid off. According to Wolfe, “I pitched to them once and failed miserably, but they seemed to like me. They invited me back again. I tried a second time, I pitched them a couple stories. They again didnt bite on either one of them, but they invited me back a third time. I figured that was kind of it. If I didnt do it this time, I wasnt going to do it.”

Wolfe’s third try was shot down as Next Generation was already shooting a time travel story which is the type of story Wolfe pitched, but he didn’t give up.

He explains, “I was sitting on this couch and it was Ron and René and I think Brannon was there and Joe Menosky. I banged my head on the arm of the couch because I was so frustrated. And then I was like well okay, I got another one. Worf goes into the holodeck with his son, Alexander, to do a Western fantasy and meanwhile, Data is trying to figure out a way to link his consciousness directly to the ships computer and something goes wrong and suddenly everybody in the holodeck becomes Data.”

This pitch became the Star Trek: The Next Generation episode “A Fistful of Datas” and began a creative path that took Wolfe to five years as part of the Star Trek: Deep Space Nine staff.

The industry has changed a lot since Wolfe got his start. These open writing assignments for shows are no longer there, so writers aren’t getting these chances to go in and pitch anymore.

Wolfe recognizes that while the paths in may be different than when he started, the difficulty of breaking through remains. He remarks, “The biggest challenge was really just getting the access to someone who actually can hire you. Getting that access is really, really hard. It was back then and it is now.”

While access is difficult to get, there’s one thing you can control and that’s effort. This is what Wolfe credits for building and growing his writing career. He states, “Honestly, I work really, really hard. Its not a very sexy answer.”

Wolfe elaborates, “I was always writing a new sample. I was always writing a new spec. Then when when they gave me the opportunity on Next Generation, I studied my ass off. I timed the acts with a freaking stopwatch. I just really made myself understand how the show worked.”

When it comes to the business of writing for television Wolfe passes on tips that have helped him though the years and the different shows he’s worked on. He advises, “When youre hired onto a television show, your job is to make the showrunners job easier. Thats it. Everything you do should be with that in mind. That means figuring out how they like to work, what they need to make their life better.”

As for the craft of writing, Wolfe shares, “Every scene should be a result of the previous scene or refutation of it.“

His career Army officer father also provided helpful guidance when it came to navigating a career. Wolfe conveys, “When the bullets start to fly, it doesnt almost matter if you say, charge, retreat, flank right or flank left, as long as you say something. If you freeze, thats the worst case scenario. Make a decision.”

So when it’s time to choose your next project to write, a spec episode of a current show or an original pilot, Wolfe recommends, “You should be doing both.”

On the importance of specs, Wolfe continues, “There are writers who want to see a spec episode of a current show and all the writing programs for people who are looking for access. Nowadays one of the best ways to get access is to get into one of those writing programs.”

In addition to putting in the work on the page, writers should also be putting in the effort when it comes to preparing for meetings. Wolfe stresses, “You should study the people that youre going to see. You should know what shows they supervise. What is the network that theyre working for looking for or whats their sweet spot. Do your homework. Dont just walk in there. Prepare.”

For a staffing meeting Wolfe suggests, “You should know the names of all the characters without looking at a cheat sheet. You want to feel prepared. You want to tell them youre ready to go. You want to project an air, not of cockiness and not of arrogance, but of preparedness, but you still need to feel fun and spontaneous, but underlying that fun and spontaneity there should be a level of professionalism.”

Beyond the preparation that you do, what is it that a showrunner is looking for when it comes to picking someone to join a writing staff? There are a lot of elements that contribute to making this decision and Wolfe asserts, “I want to know that I can spend 50 to 60 hours in the same room with this person. That is not a small consideration.”

What else do showrunners prioritize in lower level writer? Wolfe offers, “I want to know that they are quick on their feet. I want to know that they understand story and that they understand what Im trying to do, or if its not my show, what were trying to do on the show. And also that theyre willing to learn, that theyre not showing up thinking that they know everything.”

For newer writers who get that opportunity to be on a staff, there are things to do, and not do, that can help set you up for success. Wolfe observes, “The biggie one is the team sport of it all. Its hard for a lot of people to figure that out and I think its really, really important.”

He expands, “Dont be the person who just says no. Pitch solutions. Yes, and. Or even no, but heres an idea. First of all, if youre a low level you dont get to say no. But you can say, I have a concern, and then, but I also have a solution. You should always be pitching solutions. Thats a big part of it.”

Another key to a positive experience in the room is to stay on focus for where the story is heading. Wolfe conveys something an experienced showrunner once told him, “I want you to pitch within like fifteen degrees of where were headed. Dont pull the whole thing apart. You can nudge it one direction or another, but dont try to reverse and go all the way back to the teaser.”

What can up-and-coming writers be doing to help keep their career moving forward? Wolfe declares, “My biggest advice always is you should always be writing something. Get to work. Write some more stuff.”

Wolfe reminds writers that this is not an easy career path. He emphasizes, “You better love it. If you dont love it, go to law school. Its a really hard way to make a living. Its long hours. No job security. Really hard work.”

He concludes, “You have to love writing and you have to love storytelling and you have to love television or movies and be passionate about creating them because thats the only thing to get you through it.”

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