By day, you’ll find Matt Dorfman in the New York Times office, art directing for the prestigious Book Review. By night, he’s often working on freelance illustrations and book cover designs himself—you’ve likely sees his work on many Penguin titles and you probably spent much of 2014 tapping the iPhone logo he designed for the hit podcast Serial . What makes Dorfman’s work such a joy to look at? It has a lot to do with the seamless way that he marries the worlds of illustration and graphic design.

Even before the Times, Dorfman has always managed to fit in freelance work alongside his design day jobs; it’s a balancing he learned early on in his career. Over the phone, Dorfman told me the story of his first freelance commission—one that would pave the way for his prolific career in the world of book publishing.

“I spent 11 years working for a record company. It was into my third or fourth year and I was doing a lot of pick-up design stuff where I’d reformat someone else’s files (like taking a CD cover and shoving it into cassette packaging). I was regarded more as a production manager than a designer and I was roundly unsuccessful at altering that impression in-house.

“I was out one night to see my friend Will Leitch, a writer, give a reading. I met his editor that evening, Kristen Pettit (who has since become a close friend). When I heard she was an editor for a young adult subdivision of Penguin called Razorbill, I told her if she ever needed someone to work on book jackets, I volunteered myself. Mind you, I’d never worked on them before.

“Kristen—in a remarkably trusting mood—actually called me. She gave me a jacket to work on, which in retrospect is completely outside of my wheelhouse. It was a young adult title called True Confessions of a Hollywood Starlet. It was written from the perspective of a teenage girl who has fallen off the wagon in a pretty hard way—she’s borderline alcoholic, and she hides out in this Indiana town as a high school student. It’s told through the form of her diary, and she relearns how to be human despite being this incredibly successful actress. They’ve since made it into a movie.

“Working on the book cover was a welcome change of pace from the music business business. I didn’t associate as a big YA reader,but I liked movies like Mean Girls well enough and moreover, Kristen was actually asking my opinion on matters related to design! There was an actual back-and-forth dialogue as to the narrative intent of the story. In a professional work capacity, this was at this juncture a relatively rare experience for me. It was tiring though because I was working on it primarily at night. I guess it was a precursor to the way I work now—being at the New York Times during the day and working freelance during the evening.

“I sent Kristen a lot of sketches before she gave me the go-ahead. My source points were for books that didn’t make sense for that audience—I was drawn to a lot of crazy conceptual stuff. She was always very nice about the things I sent her that weren’t working, and would just explain, ‘This isn’t that kind of party.’

“We ended up with a cover that looks fairly antithetical to the rest of my portfolio. It is the genuine outliner. It was based on the Hollywood walk of fame and I had to tap into my feminine side for it—the hardback cover is still closest to my heart.

If memory serves, the stars were printed with a transparent glitter gloss, which made the whole package particularly bejeweled.

“Looking at it now (and admittedly, it’s been years since I really gave it a hard stare) the jacket has some ornamental detailing that the modern day version of me would probably hesitate from indulging; but if you follow the logic that everything you make paves the way for everything else that comes afterward (which I do), why would I change anything? At its root the book has very little to do with my experiences as a person or as a designer, so approach notwithstanding, I’m relieved that I can look back on it and see that it still makes a coherent statement about what the story actually is.

“The hardest thing that I discovered—and which I still find about working on books—is the difficulty of finding the point of entry that’s both germane to the book and reflective of the spirit of the audience that the publisher is trying to capture. That tension between reconciling the goals of the publisher with my own sense of what is narratively true is something I haven’t stopped struggling with.

“Though the end product isn’t representative of what I work on now, the experience was a net win every which way. Kristen and her family have since become some of our best friends.We’re friends with her husband, her sister and brother-in-law, and husband as well as a handful of yet more friends who we’ve met through them. Our kids play periodically. The whole experience was a powerful demonstration of your freelance clients becoming incredibly meaningful people in your life outside of work. We’ve been rafting together—during which an essential set of car keys was misplaced— and we (or at least I) can still laugh about it.

“I like to think that I’m friendly with all of my clients but I’ve only ever been locked out of one client’s car while stuck in a rented wetsuit, and Kristen is that client. Broader friendships notwithstanding, the whole experience gave me enough of the sense of the pace, the demands, and the questions that come with a freelance exchange like that to give me what little confidence I had at the time to reach out to others and keep working.”