The Creative Independent

New here?

A small plant seedling

Subscribe

Daily

Each weekday morning, spend a few moments exploring the emotional and practical facets of creating with a different working artist. Here’s a preview.

Subscribe

Working on It

Kickstarter’s creator-focused newsletter. Each month, we’ll share stories and advice for your projects and beyond.

On persistence as praxis

Prelude

Tommy Siegel is a singer and guitarist in the long-running indie-pop trio Jukebox the Ghost, as well as solo albums under his name. In addition to his musical life, he is also a cartoonist for the New Yorker, as well as his own webcomics, which have spawned several books: I Hope This Helps (2020), Candy Hearts (2021), and The Secret Lives of Candy Hearts (2025). In 2025, he launched the Extremely Accurate Bird Songs Podcast, in which he and his cohost Billy Libby strive to write a song to represent the essence of every bird species. He currently lives in Los Angeles, California.

Conversation

On persistence as praxis

Cartoonist Tommy Siegel on setting yourself a challenge, balancing new obsessions and current deadlines, and the complications of making art in the attention economy

October 30, 2025 -

As told to Jun Chou, 2246 words.

Tags: Illustration, Music, Process, Production, Collaboration, Politics, Promotion, Focus.

What was your journey from being a musician and cartooning on the side to being better known for your cartoons?

When I was a kid, all I wanted to be was a cartoonist. When I was 13, I dropped it hot potato. I started playing music and stopped drawing completely unless I was bored and drawing things in the margins of notebooks.

On the road, I started doing a shtick on social media called Van Doodles where I would take drawing requests from Jukebox the Ghost fans on Twitter. It became a fun tour thing of promoting we were on the road and a way to keep me occupied in the van.

We were touring less in 2018 and I was doing side music but everything was feeling really difficult. I was like, “Maybe I should try taking cartoon seriously,” but I didn’t know what my own voice was as a cartoonist. In 2018, this cartoonist Branson Reese did a challenge to draw a comic every day for a year. I expected him to flame out at some point but his work just kept getting funnier and funnier. So from 2018 through 2019, I did a cartoon every day for 500 days. It sounds crazy but I am pretty sure that’s what a syndicated cartoonist used to do for their entire lives.

From there, it’s taken over my life in the most wonderful way. I came up with this series of cartoons about Valentine’s Day conversation hearts called Candy Hearts and that’s now become two books. There was another book, I Hope This Helps, that’s a summary of the 500 days of Comics and what I learned about being a creator in the social media zeitgeist through that experience.

As you can probably tell, I am a sucker for challenges. My other challenge has been to submit comics to the New Yorker every week, to keep me active and thinking of ideas. Now I’ve become a semi-regular New Yorker contributor, which has been really fun.

Do you have the same process when it comes to all these different media—animation, cartooning, music, writing?

I can get tunnel vision for something I’m excited about. That may not the most practical thing to be doing in the moment. For example, I had a bunch of book deadlines this spring. I’ve got an entire field guide to North American Extremely Accurate Birds coming out next year. Even with those deadlines, I was a lot more obsessed with my bird podcast and that should not have been a priority. But in my mind, I was like, “I got to finish this song about the rose-breasted grosbeak. The world needs it.” I fall into a new rabbit hole when I think I’m done with something and often I’m not actually done.

How do you get yourself out of those rabbit holes—to fulfill the creative fixations while maintaining the professional deadlines?

I am lucky to have these creative pursuits be my job. My main problem is less falling into a new creative rabbit hole and more making sure I’m actually present and focused. If I’m actually present and focused, not looking at social media or playing video games, it’s amazing how much I can get done. If I let those things in the door, which I often do, it’s a lot less output. Social media is just an incredible energy and creativity vampire.

Social media is such a time suck but then you have to participate in it and in many ways be grateful for it too. How do you balance that?

It’s super complicated. People definitely rightfully accuse me of being a hypocrite because my career is fundamentally because of social media. But you can hold those two truths, right? I’ve been lucky enough to build this platform that I can put my art out and I hate it. The most confusing thing is how to engage with it without letting it also steer your creativity. If we go back to the idea that the medium is the message, what’s complicated about social media is the medium has certain incentive structures and I’m always trying to figure out how can I play within that without getting sucked into making attention bait. The fundamental purpose of social media is to show you ads. Engagement is just sort of another word for an extreme titillating emotion—whether it’s seeing an adorable pet that’s beyond adorable or something that makes you enraged or something that makes you feel like smug and you’re smarter than everybody else.

Those are the emotions that work really well on social media. The danger is: how do I make something that gets the point across that’s not just rage bait to keep us moving into a cultural civil war? It is really easy to make that kind of stuff. People do it. All the political content you see out there is designed to make you feel like “I’m so smart and they’re so dumb.” Which these days is pretty tempting.

I miss the early days of the internet when it was just entertaining. Do you feel like that is something that propels you forward? To make stuff that is just fun?

At this point, yeah. During the first Trump era, I felt more need to draw attention to political things. And to some extent I think that is still useful. But I have been disturbed by realizing the limits of awareness activism.

It feels like a lot of the things we’ve tried to raise awareness about, whether it’s corruption or genocide or whatever, it ends up having some cultural reaction to the awareness activism that is bigger and worse. Because social media is always going to show the other side the most enraging and condescending version of any message because that’s what drives engagement.

What do you see as the role of the artist in this day and age?

I do find that first term / second term juxtaposition really interesting. I think about how much action and protest there was in the first year or two of the first Trump administration compared to now. And it’s so much worse now than it was back then. There is this feeling now where it’s like the dog caught the car and maybe everyone’s just waiting for it to drive into a tree.

The role of the artist, I don’t know. The problem is we’ve gotten sucked into the artist being subsumed into the phone, the rectangle of depression. It’s a thing to sell ads for Mark Zuckerberg, and if you’re playing in Mark Zuckerberg’s casino, the house is going to win. So figuring out how to engage with it’s going to be a different answer for everybody.

There are still effective ways to do some awareness activism or raise money for causes, but fundamentally, people are in such a dark place that even making stuff that makes people laugh has some utility in this moment. People are feeling a deep sense of despair and hopelessness, so making people laugh isn’t nothing, I don’t think that’s superficial at this point, culturally.

It’s really not superficial. When you feel burnt out, how do you deal with it?

Like a lot of social media based creators, I’m always looking for ways to escape.

I’m like a shark; if I stop swimming, it’s not good. Sometimes I do it too much and I have to go camping for five days to remember that I’m a human being. I feel like the combo of being a workaholic who also likes birding every day is a good combo. They can be in really good relationship with each other because birding is very slow. It’s a very slow, peaceful activity.

It plays into your work too. You do the podcast, you write songs about birds, you draw comics about birds. In that journey of finding your voice, was there a moment that you were like, oh, there it is! I like birding. I’m going to draw bird cartoons. I am anxious about social media. I’m going to do that.

I’m trying to embrace the fact that the visual world I’m playing in doesn’t actually have any limitations and I can do whatever I want and say whatever I want. I try to keep that freedom there and not hammer things too hard to the ground. I go through periods where I think of a bunch and then I get bored of it, and I don’t want to do it for a year. I try to respect that part of myself.

I’m trying to let that steer the boat for a minute and see how far I can take it. I stay in touch with whatever is feeling good to me. The internet definitely wants you to just hammer one joke over and over and over again. Especially TikTok. It’s brutal how TikTok silos one joke off and then nothing does well except for variations on that one joke. I’ve seen so many creators out there who are just stuck making the same joke over and over and over again.

That also translates into the music world where you have one song that does really well on TikTok. Then at live shows, I’m there with an audience who only knows that one song, and they’re all there to hear that one song and—

Maybe even 15 seconds of that one song, right?

That’s another interesting thing I feel like gets lost in today’s day and age. I discovered your band through Let Live & Let Ghosts, and it’s such an album where every track bleeds into the next. I wonder how much gets lost when it just becomes a song, or 15 seconds of a song.

I’m like you, I love an album. I love an album experience. Back to the medium is the message: If the medium is Spotify, then the album is not the medium, unfortunately. But I’m still into making art units that are obsolete.

In college I had written a concept album parodying the Book of Revelations and I hadn’t finished it. One of my pie in the sky ideas for the last 20 years has been, what if I made the whole apocalypse record? So it’s like 95 percent done. It’s been really fun to come collaborate with my college self and actually finish it.

You’re in conversation with your college self but you’ve been in the music industry for a decade plus at this point. What is the difference between the Tommy in college and then now doing this decades later?

It’s really fun. My college self was really dumb in some ways and didn’t know how to do anything but there’s an unhinged creativity at that age that is un-jaded and naive in a really fun way. So it’s been awesome to collaborate with my former self. You have this “anything can happen” mentality.

I feel like I’m mentoring my college self creatively. I can admire his wacky creativity and also be like, “That verse should be half as long,” and he’s not around to tell me no. That’s really nice growth. I know a lot more about how to produce music and I didn’t know how to record anything back then. I really can’t wait to have that finished. That feels like an important record for me and I’m glad that it’s actually happened.

When you’re just starting out, there’s so much play involved because you don’t know the rules, but once you know the rules, you’re shackled by them. I’ve talked to a lot of people who say this across media, like “I miss when I didn’t know anything. I could just make up my own rules.”

Those first couple of years when you’re learning a new medium are super pivotal. I still find myself riding off the coattails of ideas that I had in those first couple of years of drawing comics. There’s an innocence. You don’t know what the guardrails are, and so you’re going past them more than you would when you actually know what’s successful in your medium and are overthinking it. It is awesome when I look at my cartoons from 2018 to 2019 and I go, “I hate how these look, I hate it, but there’s a lot of good ideas in there.” I feel the same way when I listened to the first Jukebox the Ghost record. I hear my songs and I go, “I hate how you’re singing them. Your voice sounds terrible. But there’s a good idea in there, and I’d like to re-record it.”

Taylor Swift had the right idea when she re-recorded all her songs. Maybe we should all do that.

We joked about at one point when we were disputing the rights of Let Live. We debated doing a Let Live & Let Ghosts (Taylor’s Version).

Tommy Siegel recommends:

Trick Mirror by Jia Tolentino

Songs in the Key of Life - Stevie Wonder

Dick’s Picks Vol. 3 - Grateful Dead

Eddington

World of Tomorrow, parts 1-3 by Don Hertzfeldt

Some Things

Related to Cartoonist Tommy Siegel on persistence as praxis:

Cartoonist Denis Kitchen on coming full circle in your work Cartoonist Conor Stechschulte on repetition as revelation Cartoonist Daryl Seitchik on sustaining your practice

Pagination

Previous
Michael Biello
Random
...