The CV and client list of graphic designer, illustrator, and art director Timothy Goodman will likely inspire yearning, if not outright jealousy, among burgeoning designers and students. He’s worked in-house for Apple and at experiential design firm Collins, received numerous awards, famously dated Jessica Walsh for the celebrated 40 Days of Dating, and now provides his slick design solutions and tumbling, typographic illustrations to the likes of Airbnb, Google, and The New Yorker.

But in the early days of his career, Goodman found himself in a situation many young designers will be familiar with: fixed with a tight brief he was ill-equipped to take on. Fresh out of university, Goodman landed his first job at publishing house Simon & Schuster. The work and the realities of the commercial, client-based world was an abrupt shift from the joys of student experimentation. Today, Timothy tells us the story of his first ever commission.

“I went to work as a book jacket designer at Simon & Schuster a couple weeks after I graduated from the School of Visual Arts in 2007. John Fulbrook was the creative director at an imprint called Scribner. I met him a couple times during my senior year to get advice on my portfolio, and I was a big fan of his thinking and his contagious energy. Upon graduating, I was getting offers for a lot of money at branding agencies, but at the time I really felt like I needed a mentor—someone who would let me find my own voice. In school, I looked up to designers like Paul Sahre and Rodrigo Corral because of their gorgeous book covers and editorial work, and I really got swept up in the novelty of it. So when John offered me a job at Simon & Schuster I jumped at the opportunity.

“Right away he gave me two manuscripts to read, Writing Motherhood and The Lathe of Heaven by Ursala K. Le Guin. I had to do both book jackets at the same time. These were the first two covers I had ever designed in my life. The Lathe of Heaven was a reprint of the 1971 science fiction classic and I was given the green light to be adventurous and creative with it. There were some allusions to flying turtles in the book, so I thought it would be fun to bring that to life. Also, it was the first and last time I ever used Bank Gothic. Weeeeee!

“However, Writing Motherhood had many restrictions from the publisher and editor; there had to be stock photography and it had to have a very modest and conservative design for a specific genre. Just using Gotham on this cover was pushing it. I didn’t know the symbols or iconography of motherhood; I didn’t know where to start. I had to research and understand design from both an editorial and image-based point of view. As a recent graduate who was working on a conceptual thesis all year, I really wanted to come up with ideas and show my chops on Writing Motherhood, I didn’t want to lay out stock photography.

“I didn’t know how to design something for thousands of mothers to read, I was too caught up trying to make something that could win an AIGA 50 Books | 50 Covers award. Boy was I in for a rude awakening.”

“Doing boing both of these simultaneously was both painful and extraordinarily valuable. John kept drilling me on the ability to design a cover for a different audience and for different genres. It couldn’t and shouldn’t be whatever I wanted it to be. John would yell at me, “Your type sucks! You think you’re so good and you can’t even lay out simple Gotham on a cover?!” I didn’t know how to design something simple, and I didn’t know how to design something without some clever idea behind it.

“My ‘bubble’ popped during this process, and I’m glad it happened to me so early on. Like movie stars say, “you do one for them and then you do one for yourself.” I learned the design world can operate in similar ways. Now, I constantly strive to make time to do self-authored projects that stimulate me in ways that client work can’t, and I strive to make my client work as fun and satisfying as my self-authored work. This balance helps me communicate ideas to an audience in fresh and provocative ways while also creating something that’s digestible and simple.”