• 2019-2020
Advice to My Middle School Self: Interview with Bess Kalb


Advice to my Middle School Self


We are excited to announce the launch of a new speaker series for the MTS Community. This speaker series titled, “Advice to My Middle School Self” is the first element of a new Distance Learning Program (DLP+) initiative. Through a range of DLP+ events, we hope to bring our community together in new ways in the weeks ahead.


On Thursday, April 30, Andrew Davis, Head of School, interviewed Bess Kalb, an Emmy-nominated writer for Jimmy Kimmel Live and the author of the recent best-seller Nobody Will Tell You This But Me, which is now being turned into a movie. Bess talked to our students and parents about how she went from Brown University graduate to comedy writer for Kimmel, Hilary Clinton, and her 225,000 followers on Twitter. She also reflected on her advice to her middle school self and our students. Read excerpt, and watch the entire stream below.


Andrew: We have a whole bunch of things that we’re going to talk about, but one of the first things is, part of your audience are elementary and middle school students. Paint a little picture about how you went from elementary school to writer for TV show, turned writer of a book, soon to be movie. 

“I would say [to my middle school self]... don’t worry so much about being cool, don’t worry so much about being popular or being a nerd, because guess what, Bess, you are a nerd, a huge nerd, and everybody knows it. And everybody will throughout your life. And that’s the point. Be exactly who you are. Because who you are is definitely good enough for a lot of things."

Bess: …the short answer to your question is, I’ve always been the same person. I went from elementary school writer and author to adult author and writer, and I think that really says something special about elementary and middle school teachers, which is that they kind of see who you are right away. I can say now I am the same person I was that I was in elementary and middle school that I am now. Now I just have a drivers license, I have a baby, I have a husband who is putting a chicken in the oven right now that I brined all day. These are things that I didn’t do in elementary and middle school, but the writer part of me was always the same, as was the jokester, the comedy person. I wasn’t the class clown, I wasn’t a funny person, I worked really hard in elementary and middle school. I was really serious about my homework. I read a lot of historical fiction books. I was really into playing elaborate Mayflower themed historical games with my few friends. I wasn’t like an outgoing person, but I was really funny at home, at least my parents made me think I was, to my face, but as a kid, I really loved telling jokes and making my parents laugh and having the freedom to sort of goof around and be myself, and so that part of me really was something that in my adult professional life I was able to tap back into. 

"I would also tell elementary school Bess that I got to high five Tom Cruise and really cool stuff that, I would say sit down, sit down, you’re not going to believe this – listen to me – George Clooney will look at something you wrote and say that’s pretty good, and it will be the best moment of your life."

Andrew: Something that I really got to see first hand during the time you lives in San Francisco was the discipline in rigor that you brought to writing. Even though it was completely self imposed deadlines. Can you talk about that and why you did that? 

Bess: Yeah, that’s a good question. It’s sort of how do you train yourself to be the type of person who when there is a job open you can do it. You basically have to do it as if it’s your job before it is. So I was making very little money when I moved out here…. I was making $12.50 an hour. It was the only job I could get writing. But I wrote every day. I wrote very different types of things. I would write on my personal blog, and I would write jokes on Twitter. Now that’s what opened up a whole new world for me. I would write – I had something like 50-100 people following me – all my friends just people who knew me, and I would write jokes about politics, jokes about observations of San Francisco and the Bay Area, and just jokes. I did it to amuse myself, my job was boring (I’m always the one that laughs the most at my own jokes), so oddly, the way I see it, if I’m amusing myself, then it’s good. So I would write these jokes on Twitter every day, and I did it in this disciplined way as if I was this professional comedy writer, and eventually, crazily, luckily, a real comedian, a real comedy writer - his name is Rob Delaney - he now has a show on Amazon called Catastrophe - which is very inappropriate, but maybe your parents can watch it - he’s a very funny man, I encourage you to check him out on Twitter. He’s very funny. He retweeted a joke of mine and then wrote underneath it “super funny person alert and then had my handle @BessBell (that’s a little plug) - “always be hustling kids” … he retweeted me and suddenly all these Letterman and SNL and Family Guy writers started following me and that was crazy because I was nobody. I was a 23 year old who just graduated from college crashing at various cousin’s houses, who had real comedy writers really thinking that I was a real comedy writer.

"And it took that, just born out of a discipline to write every day and take myself seriously, that other people did. I’m so glad I did, that I was writing jokes for no-one because I got noticed."

Andrew Davis: You also recently announced via instagram that your book is now being turned into a movie and you are writing a screenplay. So you’re going from fact checking to Twitter joking to Kimmel writing to Twitter joking to book and now writing a screenplay. How are you thinking the difference there or is it kind of like the book on the shelf – “I’ve seen movies, I can figure this out.”

Bess: A little bit, yeah, I think everybody kind of feels like they’re faking it a little bit. Like you can’t believe that people are trusting you with the thing that you’re in charge of or the thing you’re doing, is at least my experience, until you realize you do it, people respond to it, they’re happy with it, do more and improve and research and look to other people who are doing it well and constantly learn about what it is you’re supposed to be doing and get better. And so I see this not as something as “sure I can do this,” I see it as a big challenge. I’ve seen every phase of my career as a big challenge that I have to rise to meet. It’s not just, well I lucked into this, and here I am. 

…I’m not saying I’m particularly good or better off or more talented than people who make it, certainly not, there are people far funnier than I am, far better joke writers who are writing for the show, people who have much more original ideas for books. I just kept plugging at it. I just worked really, really hard. It’s not glamorous.

"I worked really, really hard until I was good at the thing that people gave me a chance to do."

Watch the MTS YouTube LiveStream from April 30.

A few highlights of Bess's work for Kimmel as well as some of her more recent writing.

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