Forever Employable Stories: Tara Schuster, former VP of Talent and Development at Comedy Central and Author of Buy Yourself the Fucking Lillies

In anticipation of the launch of my new book, Forever Employable, I’ll be sharing a series of interviews and stories from people from all different professions who have created a platform for themselves to make them forever employable. In this episode, I speak with Tara Schuster, former VP of Talent and Development at Comedy Central and author of Buy Yourself the Fucking Lillies.

Be the best at the worst: Why cleaning Jon Stewart’s coffee machine was the fastest way to a forever employable career

“My passion is puppetry, what can I do with that?” That was Tara Schuster’s immediate response when, upon graduating college, she was told to follow her passion. Armed with a playwriting degree she realized there was much more to learn before finding her dream job. Instead of going back to school for another degree she threw herself into a series of entry-level positions, i.e., internships, initially at jokes.com and then at Comedy Central working on The Daily Show with Jon Stewart.

She was one of many interns on staff all trying to get “discovered” for their comedy skills. Instead of vying to be the funniest or wittiest, she took on the jobs that none of the other interns wanted. Her mantra: be the best at the worst. Whether it was transcribing videos, updating the homepage, running for bagels or cleaning the coffee machine Jon Stewart used every day, Tara quickly earned a reputation for reliability and competence. True competence, it turned out, was in short supply at the time. 

Watch my interview with Tara Schuster about being Forever Employable

This competence created opportunity since her ideas got attention from her bosses simply due to the diligence and attention she paid to the jobs that no one else in the office wanted. This was one of the two flags Tara planted — to be an authentic person in the entertainment businesses. Coupled with her other flag, writing — something she dedicated time to every morning — she began to quickly rise in the ranks and landing in the VP of Talent and Development role helping bring Key & Peele to the forefront of pop culture. 

In parallel, Tara was accumulating a ton of writing. Reading and writing every day, she’d paid close to attention to what type of comedy was succeeding in the market and used those same formulas in her own writing. When a friend casually introduced her to a book agent she already had a ton of material to consider. That material consisted of things that she always thought “nobody would read” and that “no one would care about” and yet, here she was on the cusp of her first book deal with this exact material. 

Her first book, Buy Yourself the Fucking Lillies, sold well and attracted tons of attention to her other platforms including Instagram. The growth in her network and audience has pulled in new opportunities to write a second book, turn her book into a tv show and other popular writing options, as well as many inbound speaking requests. 

As you’ll see in the interview, Tara worked daily to build her skills, platform and content foundation so that when opportunity found her she was ready to seize it. That opportunity became a flywheel for other inbound leads that continue to keep Tara busy, writing and entertaining an increasingly larger audience. She has become forever employable. 

Transcript 

JEFF:    Hey folks. Super excited to be back for yet another one of my, as it turns out, accidental podcasts, I supposed. It’s a video-based thing. I don’t know what that’s called. My guest this time is the author of a book called Buy Yourself the Fucking Lilies which I love. I love that title. The former VP of Talent & Development at Comedy Central. I’m so glad to be talking with Tara Schuster all the way from Los Angeles today. Tara, thanks so much for joining me.

TARA:  Thank you for having me. I’m thrilled to be here.

JEFF:    Tell us a little bit about yourself, your career, and how you go to where you are today.

TARA:  When I was graduating college in 2008, I heard at a lot of commencement addresses, “Follow your bliss. Find your passion.” I was like, “Cool, cool, cool. Are you going to pay my student loans?” My passion is currently puppetry. Like what will be done with this? I was very confused about what I wanted to do. The only thing I could think to do was try to learn more. I knew I wanted to be in entertainment in some way. I didn’t know how to get in the door. I took the first available job within entertainment which was a production assistant for Comedy Central’s website called jokes.com. My friends are all working at Goldman Sachs and have all these fancy jobs and I’m with jokes.com. The reason I took the job was because it was just the first open door and I went to Brown for playwriting. I was like, “Wait, I don’t know.” There’s so many things I don’t know that I didn’t get from college and this job was in digital media. I knew nothing about digital media. I lied my way into the job. They’re like, “Do you know HTML?” I’m like, “Yeah, of course, I could do that.” I just assumed I’d figure it out. But what I let lead is I don’t know anything about that. Let me attack it. Like can I look at this as grad school for digital media and my first entry into entertainment.  It worked and from there, I sort of kept doing the same thing which was what don’t I know about? Let me learn and attack this job from a place of curiosity. It really helped me see things that other people didn’t see. I ended up being very good at being able to identify talent and voices, new comedians because I wasn’t so locked in. Everything was new and I really had beginner’s mind and I always tried to approach any job from that point of view of sort of a novice.

JEFF:    I got my first gig very much the same way. Although it was in web development as well and they said, “Do you know HTML?” And I said, “I can spell it.”

TARA:  You told the truth. That’s where we differed. I totally lied.

JEFF:    I got my first gig there too. In New York City as well, my passion as music and music production. I looked at being an intern at a music studio on 21st and Broadway on the overnight shift for a summer. It was a lot of making popcorn for Big Head Todd & the Monsters. You learn a lot there. You attack that kind of stuff.

How do you go from the jokes.com to the VP of Talent and Development?

TARA:  I had one entertainment internship right after college at The Daily Show with Jon Stewart. What I learned at that internship was be the best at the worst. I didn’t really know much about entertainment, at that point, and I didn’t really know much about comedy other than I liked it and I really liked TV. I saw all the other interns were very performative. They would try to do bits to get discovered and I noticed that the adults were like so not pleased with that. They’re so not entertained. It was like, “How can I stand out? I want to do a good job. I love this show. How can I really work rigorously here?” What I realized was there were all these horrible jobs that nobody was taking seriously like transcribing the tapes, making sure that the bagels were always in the bagel bin, and the one that really struck me was that the coffee machine that Jon Stewart used to make coffee after rehearsal often had no water, had an ominous red light blinking, dirty. I was like, “Okay, I’m going to make that coffee machine my bitch. I am going to be the person who can always be relied upon to fix the single most important piece of equipment in any creative space. The coffee machine.” It’s like a lifelong lesson. There are all these weird, little opportunities around us that people perceive to be the worst and there’s no competition for them. Nobody else was trying to clean this coffee machine. Nobody was vying for the job and so, I owned it. I owned the coffee cleaning lane and it really mattered because then when I applied to this jokes.com job, The Daily Show highly recommended me. I took that and at Comedy Central – I’m in this lowly PA position. I would be the best at updating the homepage. Be the best at transcribing standup videos. I really tried my hardest at these things that were not glamorous. I ended up earning this reputation as somebody who was very competent. I think people underestimate how, in short supply, true competence and reliability are. I would then pitch to my bosses, “What if I ran the livestream for this comedy show? What if I did an interview series with Wyatt Cenac or whatever comedian?” Little by little because I had proven myself as somebody who they could trust, they would give me more opportunities to do things. That’s really how I was able to take that and parlay that very lowly position into a promotion pretty quickly by proving my case, by showing them my value. Then I even switched entire departments. I’m glossing over sort of a whole thing where I ended up being the digital producer for Key & Peele, which is sort of what launched my career in a more major way.

The way I got that job was I was best at the worst of all of these digital things. By the time I saw Key & Peele, the pilot, I said to my bosses, “I can be the digital producer for this show. I just graduated college. I understand how people consume sketches. Please give me this opportunity.” It wasn’t that hard for them to say yes because I had already proven myself. I pivoted from this more data entry thing to a more creative job as a producer. Then I proved myself in that arena and then pivoted into development which is a completely different field that at the time, many people said, “Oh, you can’t make that leap. Only people who work in development or an assistant on another development desk. They worked in the agency. They worked for management. Nobody comes from digital into development.” I guess I should say development means we’re the people who find and produce the TV shows. It’s our job to find the ideas.

Basically, everyone said, “You can’t get that job.” But because I had really shown, to the development people, that I was good at digital media through Key & Peele I spoke to them and I said, “Look, I’m going to bring you this skillset that you don’t have. Nobody on your team knows anything about digital media. I just killed it on Key & Peele and understand creative people. Keegan and Jordan trust me. I might be a hybrid of things.” They were willing to take a chance on me because I had really proven myself.

My whole career has been people telling me I can’t do something because I don’t have the skillset and then me showing the value that I do have and kind of working around their expectations.

JEFF:    In the new book Forever Employable, the first step that I recommend people do is to plant a flag. Planting a flag means identifying this expertise or your experience or this domain that you would like to build your platform on and become recognized for and be known for. One of the questions I get all the time from folks is, “How do I decide where to plant my flag? I’m more than one thing. I’m two things or three things.” You said you planted two different flags. Can you tell us a little bit about that?

TARA:  This connects to what we were first talking about too. When I graduated college, there was such a pressure to find your passion. I wasn’t sure what my passion was except that I loved storytelling. I knew storytelling more generally; entertainment more generally. What I did was I planted my flags. I knew I liked writing. So, I planted a writing flag and I knew I wanted something more stable and producorial; like an executive job. What I did was, for the writing, I committed to writing every single day and to pursuing that. I knew it wouldn’t be my income earner but I wasn’t going to spend any less time on it because of that. People always ask, “How did you write a book while you had a full-time job?” The answer is very simple. I woke up early. I wanted to and the only way to do it was to do it in the mornings before work and on the weekends; so, I did it.

On the writing, I took myself seriously. I wrote for an hour every day before work for 10 years. I put plays up. I would write blog articles. Things that seemed stupid at the time but were practice until I got my book deal at Penguin Random House. Simultaneously, I planted my flag as somebody authentic who was on the side of artist in the entertainment industry at a pretty high level; like finding these shows, going out to shows, acting with integrity. I was really lucky early in my career to have a boss who didn’t act with integrity. I saw, “Oh, if you do that, your career will flame out.” I saw all the things not to do and then I basically acted in response to that. “Okay, if he carried himself this way, I’m going to carry myself this way.”

I think we’re all more than one thing. If you’re lucky enough to have one thing, cool. I wasn’t. I had two passions and right now, I’m exploring the writer one as my primary. Now it flipped. The executive thing was my primary for a long time and now I’ve taken a step back to be a writer full-time now that I can financially.

JEFF:    I love that you said you woke up early to write the book. That’s how you do it. You wake up early. You do it on the commutes. You do it on the weekends. You do it at night. How did you get a book deal? How does that come about from this story?

TARA:  All of the stupid writing that I had been doing for 10 years was accumulating. The New Yorker is my favorite publication. I had written down it would be a life dream to be in The New Yorker. I don’t remember exactly why but one day I was like, “Well, let me reverse engineer some Shouts & Murmurs.” They’re short, satirical comedy pieces. In comedy, I have watched so much comedy that I realized it’s like math. Some of it’s not but it is usually like premise plus this equals laugh. I just started reverse engineering in a Google Doc: Satire. Then I was like, okay, they took a premise of something. They took a subject. They added a framework. The two are disparate. That’s why it’s funny. They like butt up against each other. I got really specific about it and then started writing my own. I submitted to the slush pile of The New Yorker. That’s just their random email address. I was expecting nobody to ever read it and sure enough, I got my first piece in there. The New Yorker Online but it was stull huge for me because I wasn’t a “real” writer. I had been writing every single morning and really through college. It’s even more years.

Once I got The New Yorker. I was like, I want to write a book. I had always wanted to write a book. I had wanted to write a book since I read David Sedaris as a little kid. Now I had a little more credibility from when I was going out and talking to people about it. I said this out loud. I talked to somebody who had written some New Yorker things and had gotten a book deal. She got me in touch with her agent. By the time I talked to her agent, I was so prepared because I had a ton of writing. I had written for many, many years plus all these stupid blog articles. I started at Thought Catalog and Hello Giggles but then it was New Yorker and now Forbes. There’s no way to build other than to build. If you sit there worrying about, “Well, this isn’t even going to matter and nobody is going to read it,” that’s such a waste of time. When people think about writing as something magical, I like to very quickly say, “There’s no magic to writing. There’s just practice.” I often get asked, “What if I get writer’s block? How do you get inspired?” I was like, I’ve barely ever been inspired to write. If I needed inspiration to write, I doubt that I would ever write. It’s a commitment. I like to write. I feel worse if I don’t write. I have time every morning where I write. That’s it. Because I practice, I get better. I think it stops people from writing because they think it’s unattainable. I just want to say, “No, it’s a habit and it’s practice and that’s about it.”  

JEFF:    A lot of folks will say, “What am I going to write about? Everything has already been said. I don’t have anything good to share.” With this practice, you start to generate some of these ideas that eventually people do want to listen and do want to read and hear about. You publish this book. What’s happened since then? Has that book helped you attract new opportunities? Has it served to build your platform?

TARA:  It’s been kind of crazy but the book is about self-care. I grew up in a neglected household where things came to die. And sort of how did I pull myself up from that muck and then I give what I hope are practical, non-cheesy tips for building rituals, taking care of yourself. It’s resonated. Knock on wood. It’s been covered by a lot of different places. It’s really kind of gotten out there. Some of the opportunities, some of the small ones, are just to connect with people authentically which is why I wrote the book anyway. It was to make people feel less lonely. Even on Instagram or something, since the publication of the book, I think my Instagram count has gone 8-fold. Things like that. Smaller things, but then there have been opportunities to speak at bigger platforms and speaking gigs and I had a lot more lined up except for the pandemic. The pandemic has presented its own opportunities. Tonight I’m talking to a book club over Zoom which I probably wouldn’t have had time for if I had been on a book tour right now. I get to connect really with the readers. I think it’s given me an opportunity to write a second book which I’m working on the proposal now. Hopefully, it’s given me the opportunity to turn the first book into a TV show like thus, marrying the two things I love more than anything: writing and TV. It’s yet to be seen, some of the opportunities, but all the little seeds are there.

JEFF:    Thank you so much. I really appreciate you making the time and sharing some of that.

TARA:  Thank you so much for having me. It’s lovely to connect. It’s just nice to connect with people in this time.