Taylor K. Phillips (AB ’15) came to Harvard from Kansas City, Missouri. She was, in her words, “not a first-generation college student,” but she definitely felt the effects of being a “first-generation elite private college on the coast student.” As a result of that, she tried to dive into everything available. However, some things on campus were inaccessible: namely, joining Hasty Pudding Theatricals as an actress. The group had not yet changed their rules to allow women to perform, which wouldn’t happen until 2018. 

So, Taylor performed in musical theater shows with the Harvard Radcliffe Dramatic Club, and then joined On Thin Ice improv her junior year. “They were wonderful. My junior year, during the senior show, I had a granuloma removed on my vocal folds. So I couldn't speak, but I did the show. And then we had a guy who came to audition the next year who said, ‘I almost didn’t audition because I came to your final show last year, you didn’t let the girl talk’,” Taylor laughs. As the standing President of OTI at the time, she confirmed that yes, everyone in the group was definitely allowed to talk.

Facing graduation, Taylor found an internship in account management at an advertising agency in Chicago. She became involved with Second City and Annoyance, and before she knew it, she received a full-time offer from her company. “I said, ‘Sure, but I don't want to be in this department’,” Taylor grins. “They said, ‘That's fine, you can be a creative strategist… Do you want to be in Chicago or New York?’” And thus, she moved to New York with a job. 

“My paychecks came to me and went straight to the Upright Citizens Brigade. That was where you got your education… I moved to New York on September 5th. On September 8th, I started my week-long improv intensive from 9 to 5, and then I started my job the next week,” Taylor recalls. She worked as a strategist for a year and then decided to commit to writing “whole hog.” Her day job became the typical freelance comedian lifestyle: copywriting, tutoring, and helping prepare college applications. “I was helping with general college applications and essays, which I really enjoyed, to give kids creative license and… it was a great training ground for listening to a lot of content and filtering it through,” she grins. 

Taylor started throwing everything at the wall comedically: online humor pieces, stand-up sets, and then about two and a half years into that journey, she started getting packets to write for television. “About two years after that, I started doing a good job at the packets,” Taylor laughs. How she actually landed her job is a very specific and serendipitous story: she wasn’t afraid of the rain, and then somebody’s husband got sick.

“February of 2018, there were a bunch of comedy girls, and we were going to a meetup, but it rained, and so only 8 of us showed up. We've all been friends to this day,” Taylor explains. “One of those women was in the late night scene, and her husband had been a writer at THE LATE SHOW with Stephen Colbert, and she sent a packet for a different show to all of us, which I shared with my then-boyfriend, that led to him getting an interview for a different job that didn't work out. But that eventually led to him getting invited to submit to THE LATE SHOW.” Which he did, and he landed the job!

Taylor’s boyfriend (now husband) Felipe was invited to attend the WGAs that year, but he wasn't nominated yet because he was so new, so he didn't get a plus one in his invitation. “But,” Taylor exclaims,  “one of the writers' husbands got sick, so she didn't go either. So then, the two new writers got plus ones.” Through that lucky turn (though unlucky for the writer’s sick husband), Taylor attended the WGAs and spent the evening chatting with the writer’s assistant on THE LATE SHOW. A few months later, that woman was hired on LAST WEEK TONIGHT with John Oliver. Taylor asked her two years later for a packet for the show, and then she was hired to write there, where she’s been ever since. 

Now, writing political comedy can be tonally different from “silly goose comedy”, which is, of course, an industry standard term. For Taylor, that works out well. “I have always been self-conscious about my silly goose abilities,” she says. “I relate most to stuff that is really grounded and justified, and yet still somehow surprising.” For Taylor, “political comedy, to me, is my natural reaction, I just get to parlay that into a work product. If I were presented with the videos, or clips, or information that I receive while doing my work, my unfiltered emotional reaction, for the most part, would be what ends up getting kind of translated into jokes. I just have to fine-tune it.”

That thread of “grounded, justified, and surprising” is how Taylor approaches teaching comedy as well as practicing it. “When I teach comedy classes, what makes people laugh, I think, is, ‘I recognize that, and that doesn't go there’.” The element of surprise. Taylor grew up influenced by great comedians like Tina Fey, Amy Poehler, Amber Ruffin, Lena Dunham, and Mindy Kaling, who also captured this sort of humor, and many of whom were creating their own work for themselves. That has been partially what has shifted in the industry, is that there’s more space for comedians to create their own work on social media platforms. However, there are also fewer jobs, in general. That is something Taylor is clear on: “A little bit before I first started, you break into late night because you can break in without managers or agents. And then from there, you can transition into scripted or ride the ranks of late night. And I don't think that either of those paths are viable in that way anymore. That's just the shifting nature of the industry.”

But social media isn’t a necessity. It’s more of an opportunity, in Taylor’s eyes. “There are always gonna be new ways to be seen, and when you have the ambition and the hunger… you're looking for ways to get seen and how to optimize where you spend your time and energy.” But above all, Taylor says, “You have to be good first…. you can't be just thinking about marketing yourself. You have to also think about building your skills and your voice.” 

This goes hand in hand with Taylor’s biggest piece of advice, which is something her mom told her on her very first job, way back when she was interning at the advertising agency. “I would call [my mom], and I would say, ‘I don't feel like anything's moving. I'm bored.’ And she said, ‘Well, I think the reason that you're bored is because you're not trying to impress anyone. You're not striving to deliver something to people that you respect.’ And she was so right, that's something I've always kept with me,” Taylor reflects. “I always want to be writing jokes and making things with a certain level of reverence and appreciation for the people the work is for. Whether it's our audience at the show, or my family group chat, or my own notes app, I never want to be in a position where I'm just churning stuff out without caring.”