When did you get the idea of writing “Read This When You’re Sad”?

As all great ideas start, I got the idea while lying in bed one night feeling sad. I wanted something lighthearted that would make me laugh. I still think it’s weird when people on Zoom calls are like “Doing anything fun this weekend?!” and how people act like everything is OK and that we should be OK during a pandemic. I wanted to write something that addressed the notion that it’s fine to not feel like yourself right now. It’s OK to be sad and you’re not alone. At the same time, I believe in the power of humor and think it’s necessary right now. We need to find ways to laugh and get through the day. This project deals with the complexities of laughing during a time that, well, sucks.

I laughed at the “Never feel dumb for ordering a piano at a piano bar” line. The book reminded me of Jack Handey. Is he an influence? Who are comedy writers you love?

First off, thank you. I really appreciate that! And that’s a really kind comparison. Not that I’m near that talented, but I do often gravitate toward that style. Especially as someone with copywriting experience, I have an appreciation for short, punchy jokes that say a lot in just a few words. I also knew I wanted to create something that someone could find value in immediately — no matter where they are or what they’re doing. So the idea of being able to open this up to any page and laugh, or not necessarily have to read each page in order. The last piece of why that approach felt right is that I wanted this book to feel more like a two-way dialogue. So much of creating during Covid feels one-way — I really miss performing in a room with other people. I was hoping that these one-liners, mixed with things like trivia and word search puzzles, would form something more interactive and experiential, versus just a string of my long-form thoughts which I’m certain would put people to sleep. So that’s just a long way of saying thanks for comparing me to Jack Handey. As far as comedy writers who inspire me, it’s a list that grows every day. Everyone who wrote for The Good Place. Also, Emmy Blotnick has probably been one of my favorite comedians. There’s a lot of different types of comedy writing and a lot you can learn from the different forms, so I definitely draw inspiration from all kinds of places, whether it’s stand-up comics or screenwriters or authors or sketch writers. Plus, social media — as much as it overwhelms me — has sort of democratized comedy. I feel like I see something new that really makes me laugh every day. It’s a conversation for a different time but there’s so much gatekeeping in comedy I just like to see people making jokes and building their own audiences. The world needs more laughter.

You make the ebook available for free on your site but encouraged readers to make a donation to the Child Mind Institute, which helps families struggling with mental health and learning disorders. Why did you choose this as your publishing approach?

 I mean, the simple answer is that I’m a hero. No, obviously kidding. I think there were a few factors here. I wanted to release something sooner than later because I wanted this to be a pick-me-up during a tough time. Traditional publishing takes far longer than that timeline, not to mention how difficult it is to even get a book picked up in the first place. As far as offering it for free, I just didn’t think people needed to be paying for my dumb jokes about Zoey 101 during a global pandemic. And I say that from a place of privilege. I know a lot of people wouldn’t be fortunate enough to even have that choice to make. I’ve asked people to donate to organizations for some of my other shows and it’s worked out well. It’s something I try to do when I can — come hear me tell fart jokes for a good cause. Beyond that, I thought a digital approach made sense because of the nature of creating stuff right now. I liked the idea of throwing up a landing page, being able to donate somewhere with one click, putting my book in a form that replicated the experience of actually reading — being able to digitally turn the pages, etc. I think people will continue to get creative with digital projects as COVID continues. To answer the point about why CMI: Child Mind Institute is a great organization doing some really important research-driven work regarding mental health. And being open, being vulnerable, being able to create a path forward is ultimately what this book is about. It was a perfect match and it’s been really nice to see people donating. 

You’ve spoken about the importance of persistence in carving out a career as a writer. How do you keep your attitude positive when editors don’t accept pitches?

That’s a great question. In my opinion, resilience is one of the most important traits for anyone in a creative field. Rejection is like Daylight Saving Time: you have to try to get used to it or you’ll be sad. It can absolutely be discouraging. For me, a few things help my perspective. First, everything is so subjective. What’s right for one editor or publication might be wrong for another. Maybe the timing is off. Maybe they already have a similar piece planned. Second, you have to really like writing, or designing, or insert whatever your creative interest is here. Like really, really like it. Because you’re going to get rejected. It happens to everyone! But if you truly love what you do, you aren’t doing it for external validation. I’m going to keep writing until I don’t want to anymore, not for any reason besides the fact that I really enjoy doing it. Sure, I’d prefer that people see my work and that I can make a living from it, but creating is so ingrained in who I am that I’m not going to stop just because the New York Times has rejected me 1,322 times (but who’s counting?). And lastly, I often remind myself that writing/comedy isn’t the most important thing in life. I don’t know if I’m allowed to say that but it’s not. I work really hard, but if I get rejected from something, oh well, I’m just grateful that I’m alive and that potato chips exist. All that said, rejection should also lead to reflection. It’s always important to learn and improve, no matter where you are in life. So I try to hold myself accountable and do the work needed to get better.

You also do stand-up comedy. Have you been doing virtual shows during the pandemic? How are you keeping sharp?

I have! I even did a virtual comedy festival based in Texas back in October which was really cool. It’s great that people have found new ways to bring audiences together. Unfortunately, nothing really replaces the energy of being in the same room. I try to stay sharp by writing in some capacity every day. Whether that’s stand up, a TV pilot, sketch videos, or anything else. I’ve also been writing on an animated comedy web series which has been a fun outlet. I’ve definitely been keeping busy while at the same time trying to be forgiving of myself if I don’t feel like being productive — I hope we’re all being kind to ourselves right now. There are some days where I’m just like “Actually, I’m going to watch Broad City for six hours” and then I do that.

You worked for many years as a program director and counselor at a camp in Minnesota. How did that experience help form your comedic sensibilities?

I’m happy you mentioned this! Anyone who knows me knows how important camp is to me, and how instrumental it’s been in terms of my creative career. I’m definitely a lifelong camp person. I went there (Herzl Camp) as a kid, became a counselor, and then ended up leading the Counselors in Training program. In general, camp is a place where you can take risks and fail in a controlled, comfortable environment — I can’t explain how crucial that is for kids. The absence of phones and other technology forces you to use your surroundings and get creative for entertainment. There’s a lot of thinking on the fly, especially when you need to keep the attention of a bunch of kids who just had dessert. I’d even go so far as to say that my first “writing gig” was in high school being part of the writing team for a weekly SNL-style show that happened at camp. Camp is just such a goofy place where everyone is fully accepted as their true selves, and when you have that unconditional support you can do whatever you set your mind to.

You once wrote a letter to Anna Kendrick and read it on TV. Did you ever hear from her?

No! I’ve told myself she’s just waiting for the perfect time to reach out to me. Maybe her phone has been out of battery for several years.

What’s next for you?

I would like to be able to see my friends and family safely by 2022. That would be cool. In terms of comedy, I just want to keep challenging myself and getting better at what I do. I’d ultimately love to write on a TV show. I’d like to be on stage again without people having to wear masks. I want to write the jokes on the Laffy Taffy wrappers. If Seth Rogen is reading this I’d like to have Shabbat dinner with him sometime. I’d really like to mentor more creatives and help them navigate their career however I can — what can I say, once a camp counselor always a camp counselor.