Jessica Walsh: Frooti, Mango Submarine
Frooti, Mango Submarine

All games have rules, limitations that reign in, and cultivate, imagination. The more defined, the better.

If life is a game, ripe for the playing, what are the rules? If you’re Jessica Walsh, New York-based art director, designer and one-half of the duo behind the 40 Days of Dating blog, book and, soon, movie, you make your own.

Walsh, 28, who calls herself a “gut instinct” person, turned down a six-figure job as a recent college graduate (during a recession, no less) to pursue an internship. Four years later, she made partner at a design studio that, two years prior, wasn’t even hiring. She’s gotten so good at breaking (and making) the rules, in fact, that she now lectures on the value of play as a creative tool.

“We learn to be more results-driven and as a result there is less emphasis on exploration and process.”

In 2008, after graduating with a BFA from the Rhode Island School of Design, Walsh opted for an apartment she could “barely” afford and an internship under Paula Scher at the design firm Pentagram over a cushy design job at Apple. Two years later, after an entry-level art director stint at Print magazine, Walsh contacted Stefan Sagmeister, a high-profile designer known for his album covers for The Rolling Stones, Lou Reed and David Byrne, among others. “I reached out to him for advice on my work and my portfolio,” Walsh said in a short documentary produced by design blog Swiss Miss. “I didn’t think I’d ever get an email back from him.”

Jessica Walsh: Mango Hike
Frooti, Mango Hike
Jessica Walsh: Mango Dive 2
Frooti, Mango Dive 2
Jessica Walsh: Frooti, Mango Dive
Frooti, Mango Dive
Jessica Walsh: Creative/art Direction, Design
Stefan Sagmeister: Creative Direction
Nadia Chauhan, Vaibhav Bhargava: Client
Sagmeister & Walsh/special Guest/1st Ave Machine: Tvc Spot
Marion Luttenberger: Photography/design
Briony Crane: Design/retouching
Scott Carthy: Photography, Behind The Scenes Video
Zipeng Zhu: Website Design & Animation
Henry Hargreaves: Photography
Lutz & Schmidt: Retouching

Instead, Sagmeister offered her a job immediately. Walsh worked in his studio for two years before making partner in 2012. She was 25 years old. Sagmeister & Walsh announced their new partnership by releasing a now-notorious nude portrait—a tribute to Sagmeister’s own naked debut 19 years earlier.

Many women would chafe at the idea of such exposure, not to mention the kind of criticism incited by publishing one’s dating and sex life for public consumption, as Walsh did with friend Timothy Goodman for the 40 Days of Dating project. ( deemed the couple “very annoying” and commenters had a field day proclaiming that Walsh’s social experiment “reeked of fame-whoring.”) But Walsh accepts this susceptibility as par for the course: “Anyone can read into something I say in an interview, or something I do, and put their own spin on it. People tend to see what they want to see. If someone decides to not like me, for whatever reason, I am sure they can find plenty of reasons why. That goes for anyone who puts their personal life out there on the internet. It makes you vulnerable to people’s assumptions.”

Adults are prone to fixating on the practical, she believes, an obstacle in the way of exploring beauty, emotion, imagination and love.

A native New Yorker who grew up in the New York City bedroom community of Ridgefield, Connecticut, Walsh seems to have a never-ending supply of imagination. She always has a few of her own projects in the hopper, in addition to the ad campaigns, typographic installations, illustrations and more she creates for clients. These personal pursuits are an important counterweight to client work, Walsh explains, as they allow her time to play and explore. The discoveries that result often feed back into her client work. Some of Walsh’s best ideas have come from spontaneous play: a mindset that she says allows her to experiment, take risks and suspend what is arguably the greatest source of creative paralysis—the fear of failure.

The state of mind doesn’t come so easily for others. As a teacher of design and typography at The School of Visual Arts and frequent speaker at universities and conferences, she has been surprised by how difficult it is for many of her students to think conceptually. She steers them toward idea generation and authorship, focusing on artistic talent as a means of effective, public self-expression and not just design as a tool to package other people’s content.

Antoine de Saint-Exupéry’s iconic French children’s book The Little Prince—with its fundamental message to adults to cling to the inquisitive and open-minded perspective of a child—resonates with Walsh. Adults are prone to fixating on the practical, she believes, an obstacle in the way of exploring beauty, emotion, imagination and love. “As we grow up we learn things are ‘wrong’ and are taught certain ‘life realities’ that make us less playful and close the imagination down to all the possibilities,” Walsh says. “We learn to be more results-driven and as a result there is less emphasis on exploration and process.”

The good news: playfulness may be innate in us all. Walsh looks to children for proof. “In their minds anything and everything is possible … they are smarter creatively than most adults.” For us creatively dormant grownups, Walsh recommends “plenty of time and space to fail in what you are doing,” adding that a “completely open” mind and a sense of humor help.

Jessica Walsh: Aizone 5
Aizone 5
Jessica Walsh: Aizone 4
Aizone 4
Creative Director: Stefan Sagmeister
Art Director / Designer: Jessica Walsh
Photographer: Henry Hargreaves
Body Painter: Anastasia Durasova
Creative Retoucher: Erik Johansson
Hair Stylist: Gregory Alan
Producer: Ben Nabors, Group Theory
Production Designers: John Furgason, Andy Eklund