Embracing the Imposter

Mailchimp and Pop-Up Magazine teamed up to create a powerful animated series about “imposter syndrome.”

No matter how successful we are, there’s always a tiny voice in the back of our minds that whispers, “You’re a fraud.” Imposter syndrome is the psychological term for that feeling that we’re not as great (or even as competent) as people think we are. We all feel like imposters sometimes—even our favorite creators.

With its animated series Outer Monologue, marketing company Mailchimp set out to explore imposter syndrome, in part because many Mailchimp users struggle with feelings of being frauds—they’re artists, musicians, authors, and entrepreneurs who use Mailchimp to connect with their audiences and customers.

“We try to put ourselves in the shoes of people who are striking out on their own and trying to build something,” says Sarita Alami, senior manager of brand marketing at Mailchimp. “Imposter syndrome and ‘faking it till you make it’ are issues that come up a lot among creative entrepreneurs. We wanted to speak to people and hear what their inner monologue was during a pivotal imposter moment in their careers.”

a gif by Katy Wang, showing an animated image of actress Joy Bryant as a young girl.

Animator Katy Wang led a small team of creatives who brought actor Joy Bryant’s story to life for one of the Outer Monologue pieces.

Mailchimp has a long history of producing animated shorts about its users. The site Mailchimp Presents features documentaries, short films, series, and podcasts about creative pros and entrepreneurs. For the Outer Monologue series, Mailchimp teamed up with longtime partner Pop-Up Magazine. Pop-Up Magazine creates live magazine shows—on a wide variety of topics—with writers, radio producers, photographers, filmmakers, and illustrators. Pop-Up Magazine also produces The California Sunday Magazine, a mag that covers cinematic photography from California, the West, Asia, and Latin America.

Pop-Up Magazine has used Mailchimp to promote its own shows and publications since the beginning. “Starting a business is kind of nuts,” says Pop-Up Magazine founder Chas Edwards. “It’s scary a lot of the time. Imposter syndrome is an experience that we, the founders of Pop-Up Magazine have definitely had.”

Chef Flynn McGarry was one of the subjects of the Outer Monologue series. Click on the image above to watch a trailer; all of the animated shorts can be found on the Mailchimp Presents site.

For the Outer Monologue series, Edwards and the team at Pop-Up Magazine Brand Studio scoured their contact lists for well-known creators who would be willing to crack open their polished personas and share the gooey stuff within, and five volunteered to talk about their anxieties: Chef Flynn McGarry, actor and producer Jay Duplass, journalist Molly Bingham, playwright Ngozi Anyanwu, and actor Joy Bryant.

“Imposter syndrome and ‘faking it till you make it’ are issues that come up a lot among creative entrepreneurs. We wanted to speak to people and hear what their inner monologue was during a pivotal imposter moment in their careers.”


Pop-Up Magazine conducted interviews with each of the subjects, asking them to talk about a time in their careers when they felt like frauds. “Even the most successful people in the world have moments where they’re presenting to the world that they’re successful and competent and beautiful and talented, but on the inside they're terrified. We were asking people to share a vulnerability, and that’s what makes this series so powerful,” says Edwards.

Mailchimp and Pop-Up Magazine chose animation to tell the stories. “Animation has played a significant role in how we present ourselves as a brand,” says Alami. “It can be a useful way to convey information with a wink—our mascot, Freddie the Chimp, is winking, and we try to put some of that into everything we do. And we feel strongly about supporting people who are making cool things.”

still from Outer Monologue animation about Jay Duplass.

Actor and producer Jay Duplass was one of the subjects of the Outer Monologue series. Click on the image above to watch a trailer; all of the animated shorts can be found on the Mailchimp Presents site.

After the interviews, the Pop-Up Magazine crew found five animators to bring the stories to life. Each animator or team of animators was matched to a story that suited their style. “We want to bring viewers into the hopes, dreams, and fears of the narrators,” says Edwards. “Our fears often look like crazy nightmares, and our hopes and dreams look like magic. Animation is a format that lets us represent feelings, emotions, dreams, and fears in creative ways.”

Pop-Up Magazine recruited animator Harry Teitelman to bring Duplass’s story to life. Teitelman has been a professional animator for more than a decade and has taught animation at the School of Visual Arts in New York. Teitelman and fellow freelance animator Suejee Lee were given complete creative freedom and animated the Duplass film over the course of about five weeks.

First, Teitelman put the Duplass interview on repeat and started sketching. The animator launches every project in a notebook, drawing basic shapes and scenes. He creates a visual language to use throughout the piece. With these rough guidelines, Teitelman starts crafting art boards in TVPaint and Photoshop using a Wacom tablet. “I always start with pencil and paper because it’s too tempting to hit that undo button when I’m working digitally,” he says.

A selection of sketched storyboards that animator Harry Teitelman drew as he developed his Outer Monologue animation about actor Jay Duplass.

For the Duplass piece, Teitelman strove to preserve the actor’s emotional transparency. “I’m a big fan of Jay Duplass and his work. He comes from a place of emotional truth, so I wanted the animation to reflect that,” he says.

In his interview, Duplass discussing having a set of programmatic responses to social situations, routines guaranteed to get a laugh or some other response. “It’s this overarching mechanism that we have, to get through the world and interact with people,” says Teitelman “We have set up these almost algorithmic processes, and they don’t always coincide with what we're feeling on the inside.”

GIF of a robot walking, from an animation about Jay Duplass, created by Harry Teitelman.

Animator Harry Teitelman brought actor and producer Jay Duplass’s story to life for one of the Outer Monologue pieces.

So in the final piece, Duplass’s imposter syndrome took the form of a robotic mask, a hard, perfectly faceted face that protects the softer stuff within. Teitelman created a series of boards with TVPaint to plot the film and filled in the details using custom brushes in Photoshop. He animates in TVPaint and uses After Effects for compositing scenes. His combination of tools often creates happy accidental visuals. “In this case I used a watercolor-type brush, and then put the layers on different blending modes. I just swing through different modes until I get something that looks cool,” he says. “And if you can get that look in Photoshop, you can just animate it that way in After Effects. You get this fun look that you wouldn’t expect.”

Award-winning animator Katy Wang was recruited to bring actor Joy Bryant’s deepest fears to life. Wang works with London-based animation studio Blinkink and has done work for several brands, including Absolut, Penguin Books, and Girl Effect. For the Outer Monologue piece, Wang led a small team of fellow animators.

Actor Joy Bryant was one of the subjects of the Outer Monologue series—the animation, created by Katy Wang, was a Vimeo Staff Pick (click on the image to watch).  

To start, Wang also put the Joy Bryant tapes on repeat and pulled out a pencil and some paper. “I always start coming up with ideas by listening to the voice recording over and over again and seeing what images appear in my head,” she says. “Then I start drawing small thumbnails in my sketchbook—like a very rough, badly drawn preliminary storyboard. I always try to immediately start storyboarding because it helps to piece together how scenes transition from one to the next. My approach is usually very playful and colorful, so I’m always trying to think of scenes that will be both fun to watch and fun to animate.”

Wang starts on paper and moves to the digital world when her rough sketches are finished. She uses Photoshop to design the film and Animate to put it all together. For Wang, color is key. “When I came up with the color palette for the whole film—seeing all the style frames in a grid and feeling happy with how the colors all worked in harmony—that helped me envision how the final film would feel by the end.”

Examples of animator Katy Wang’s thumbnails and final style frames for her Outer Monologue piece on Joy Bryant.

The Outer Monologue shorts and other Mailchimp Presents films are filled with color, motion, and honesty. They’re a far cry from traditional marketing campaigns. For Mailchimp, storytelling is a more powerful way to reach customers than any online ad. “Outer Monologue is not branded; it doesn’t have anything to do with the Mailchimp product,” says Alami. “We thought that if we made content that resonated with our audience emotionally and spoke to their everyday experience, that it would be enough for them to care and for them to want more. And we found out that we were right.”

“We didn’t set out to build advertising assets,” says Edwards. “We didn’t think of this as an advertising campaign. We thought of it as a marketing effort, but at a different level. If we could create compelling content and stories, we give people a reason to visit the Mailchimp site that isn’t purely transactional.”

“Our fears often look like crazy nightmares, and our hopes and dreams look like magic. Animation is a format that lets us represent feelings, emotions, dreams, and fears in creative ways.”


And those visitors stick around and come back to watch more. “It’s very difficult to ignore a genuinely captivating story,” says Alami. “Engagement is the most important metric. A genuine story doesn’t make people feel like they’re being advertised at. Stories let us spark interesting conversations that don’t have anything to do with Mailchimp. We are putting work out in the world that makes people feel like they can talk about their experiences and maybe like they’re less alone.”

Mailchimp doesn’t have plans to produce more Outer Monologue shorts but has many more stories to tell. “We have some other animated projects in production—one involves puppets that I'm incredibly excited about. It showcases some humorous situations people go through around the world,” says Alami.

Pop-Up Magazine will continue to perform live shows, publish The California Sunday Magazinee, and create content for brands across the globe. Find out more about their live performances and publications at the Pop-Up Magazine website.

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