Jorge Colombo illustration for the New Yorker's Bar Tab. Art direction by Deanna Donegan.

Flipping through the New Yorker’s Goings On About Town is an essential part of the city’s cultural experience, whether you’re a tourist or a bonafide city dweller planning out your weekend.

The section begins with a large photograph boldly setting the mood for what to expect from New York that week, followed by rectangular illustrations representing everything from pop and ballet to Broadway. The illustration and photography feels fresh—as lively and current as the events they communicate. These works are commissioned by senior designer Deanna Donegan, and have become essential pops of color playfully energizing the historic magazine’s three column spreads. The pepper of contemporary flair sits as comfortably in the publication’s pages as its famed black-and-white cartoons.

Goings On About Town opener, the New Yorker. Art direction by Deanna Donegan.

Donegan first entered the magazine’s design department right after graduating from the School of Visual Arts. She designs the New Yorker’s newsstand edition half-cover wraps, art directs the photography and illustration for Goings on About Town and Shouts & Murmurs, and commissions some of those memorable spot illustrations that get artfully tucked into long sections of text. Donegan was also behind the design of that New Yorker tote, which was dubbed 2017’s “it” bag by various fashion editors, and became the subject of endless social media remarks—gushy and snarky alike—as it took on an unprecedented life of its own.

We caught up with Donegan before her commute to One World Trade, and right after she’d taken her cat out for its regular morning wander, to learn more about her daily routine and what she looks out for in new illustration talent.

I’ve never seen a specific tote bag “trend” quite like yours did last year. Even in Berlin, where I’m based, I see it all the time. Did you anticipate that it was going to get so popular? 

That’s amazing to hear that it’s in Berlin, I had no idea! I don’t know anything about its reach outside of the States at all. When I created it, I didn’t even know that it was going to be given to subscribers, and I never thought it would become so popular.

When my creative director at the time asked me to design a tote, I made a bunch of different options. I utilized cartoons and illustrations for some, and this one was the only design that used just the logo. It got chosen, but then I didn’t see it again for around a year or a year-and-a-half. I kind of forgot about it. Then one day, all of a sudden, it was just everywhere. It was really fun for me to see that both teenagers and older men wearing it—all different types of people. I thought that was the best thing: I didn’t make something that was feminine that only women would wear. It seems pretty universal, and it was so fun to see it take on a life of its own.

The New Yorker tote, designed by Deanna Donegan.

How long have you been at the New Yorker?

For over five years now—it’ll be six in November. Time goes by so fast. I first started as an intern when I was in my junior year of college. I was there for a semester, and only two days a week. I didn’t think I made much of an impression at all. I was fixing jammed printers; I didn’t have to get anyone coffee or anything like that, but I wasn’t sure how much of an impact I was making.

When I graduated college, I was working at a gallery on the Lower East Side, not really sure what I was going to do, and not making very much money at all. There was an opening at the New Yorker—an entry-level position in the art department—and my previous internship manager gave me a call and asked if I would be interested, which of course I was. 

What were your first impressions?

I was terrified. Even unjamming the printer I was like, “Am I going to mess this up?” There’s a little bit—even to this day—of a library vibe in the office. Everybody’s working, they’re on their own track, doing the thing that they’re best at. Everyone’s got their head down.

Today, where do you look for new illustrators to commission?

I’m always looking for new people. For Goings on About Town, I try to use at least one new person every week, if I can. That’s usually not too difficult. And I find people absolutely everywhere—on every app that you can imagine. People also send promotional emails and cards. I’ll do class visits and guest critiques. If they’re a student and they’re not quite ready, but there’s a spark there, I often keep track of them on Instagram.

Instagram is a great place for keeping tabs on people’s work, because so many illustrators are posting there all the time. People aren’t updating their website every day—which is understandable—but they’ll put new stuff on their profiles.

Meeting people in person has also been very valuable for me. If I’m at a Society of Illustrators or American Illustration event, or a gallery opening, and I meet new illustrators, just getting a sense of their personality is really helpful. When I read a piece, I can then match personalities. That’s a lot of what art directing illustration is about, I think. If you can match the right illustrator to a story—when the tone matches, and they’re interested in the content—then it makes the whole process fun and enjoyable. And it shows in the work.

When you’re first reading a text that needs an illustration, do you find that you have a library in your head and you immediately think—“oh, that illustrator would be perfect for this”? Or do you comb through your folders and bookmarks to find a match?

The majority of the time, someone will immediately pop into mind. That’s not to say that there aren’t other people that would be great, and sometimes when the initial match doesn’t work out, I end up being surprized in the very best way. 

What do you value most in a relationship with an illustrator?

The best thing is communication. I go back and forth on email, mainly. I’m never opposed to talking to people on the phone, but email tends to work out for everyone. It keeps us moving in a forward direction because we can see what we’ve already discussed, and there is no such thing as over communicating. We’re often two people in two different time zones, and we can’t be expected to read each other’s minds.

If I give some direction and it’s a little bit confusing, please ask. Don’t feel like you can’t. It’s going to benefit both of us to really understand what we’re working towards, and it’ll help us get there faster. Editorial deadlines don’t really allow for us to go around with miscommunication for too long.

I also really value a willingness to try things. An art director doesn’t always have the perfect solution right away, that’s why we’re enlisting an illustrator’s help. We want your mind and your ideas. But also, we like it when you’re open to trying the ideas that we might have, because we might have some insight from the editor or the writer to help infuse what we’re doing.

Goings on About Town. Art direction by Deanna Donegan.

Could you give an example of a particular piece that has been especially memorable for you?

There have been so many memorable illustrations over the years, but one that sticks out in my mind is a piece illustrated by JooHee Yoon. Working with JooHee always feels like working with a magician. Her work is surprising in the best way. You can give her the most straight-forward topic to illustrate and she’ll approach it in a way you never would’ve thought of, but that works wonderfully.

One of those such pieces was when we worked together to illustrate Action Bronson for a story about his new Viceland cooking shows. Even though JooHee doesn’t typically work on portraits, I knew she’d be the perfect person to tackle this and give it the fresh foodie vibe it needed. There was a lot of back and forth about small details toward the end—whether to add or take away some signs, how stoned he should look, so on and so forth. We’d both been staring at the piece for far too long, but what was especially memorable about the whole thing was that we were on the same page in terms of communication, we made compromises, and we trusted each other to do what we were each good at, and that allowed us to make a lot of progress in a short amount of time. I think we ended up with a really great illustration.

The New Yorker spot illustrators are quite a special commission; they’re so unique and specific to the magazine, and they aren’t tied to a particular story so you can be playful with them. What is the most challenging aspect of these from your perspective?

The spot series are so much fun, because they’re so open. It’s a moment we can let an illustrator’s personality shine. Sometimes, we’ll do something timely—if it’s summertime, maybe some beach spots, or athletic ones when the Olympics are happening. In between times, it can get really open, and creative things often come out of that.

The challenge is the size of them. They’re very tiny. So if your illustration style is detailed, you have to pare down and make things more graphic in order for them to read.

What’s been a recent favorite series for you?

There’s a fairly recent one that I really loved, which was done by Rachel Levit Ruiz. I left things pretty open. It wasn’t a special issue. It wasn’t a particular time of year, so she did these wonderful drawings of women leaning on chairs. It felt like yoga or acrobatics, and also just a little bit strange in the best way. I love them, and we got a good response from readers about that series.

Spot illustration series by Rachel Levit Ruiz. Art directed by Deanna Donegan.

I know that you’ve led the art direction of a number of special issues too. How do you divide up the workload of these in the design department?

It was our current creative director Nicholas Blechman’s idea that when special issues come about, one art director would lead the entire issue. I’ve really enjoyed this. The first one I did was a food and travel issue, and then I did the technology issue most recently.

You don’t know until a couple months out that you’re going to take it on. Once I know, I’m talking to whoever the main editor of the issue is, trying to get as much information as possible so that I can begin as early as I can. That might mean getting the spot illustrations finished up because those are more open and we have a theme already, so we have a vague direction.

The special issues become a great place to try things that take a bit longer; the things that we can’t do otherwise. In the tech issue for example, we had a bunch of sidebars illustrated by Nick Little, and he animated them for online. That’s something we may not do in the normal hustle and bustle of things, but with a bit of foresight, we were able to make it happen.

The New Yorker’s 2018 Travel and Food special.

For illustrators who want to pitch themselves to you, what advice would you give?

I can obviously only speak for myself and my personal preferences, though I would imagine that it probably extends to other art directors as well. I really feel that if you want to show me your work, a promotional email is the best way to go.

It’s not that I don’t love getting mail and seeing people’s postcards, but it’s so much easier for me to go back and reference an email. I have a folder that I push all promotional emails into, and I often look back through it. It’s a little bit more cumbersome to go through a pile of postcard promos. I have a giant overflowing basket of them on my desk, which is probably an eyesore to the rest of my department! And postage and print costs money. I sometimes think it can be unnecessary.

If you’re trying to get out there and share some work that you created, you can just email. It doesn’t have to be an elaborate message either. You don’t have to reference something that you saw. You can just introduce yourself very briefly and say “this is my work that I wanted to share with you.”

Cari Vander Yacht illustration for the New Yorker’s 2018 Food and Drink special. Art direction by Deanna Donegan.

It is important when doing that to not be too general about it, though. It’s important to consider the publication that you’re writing to—so you shouldn’t send the exact same message to every single art director. You should ask: “Where do I fit in at the New Yorker?” Most people have an idea, if they’re promoting themselves for the New Yorker, of what it does. So if you send things that aren’t in line with the content we’re producing, then it’s going to be hard for me to see where you fit in. If you like our portraits and want to do that, then send portraits and tell me that’s what you’re interested in.

That being said, I also think it’s important to send your best work, even if it’s personal work—it doesn’t have to be work that was published. People will often put an image on their postcard that might not be their best work, but it got published so they think that’s more important. It’s really not. I’d much rather see something that you really enjoyed making, because that’ll come through, and then you’ll get hired to make more of that thing.

Whatever you send, send what you want to do more of.