The Editor Who Became a Song and Dance Man

People leave journalism all the time, taking jobs in public relations and advertising or on the content teams for tech platforms, streaming services, or purveyors of razor blades. And sometimes, very, very occasionally, they depart for show business. In a LinkedIn post last month, Wired features editor Mark Robinson announced that he was leaving his position at the magazine “to pursue my interests in performing as an actor and singer.” A graduate of Stanford’s journalism school, Robinson, 58, spent most of his editing career at Wired, joining in 2000 in San Francisco and before Condé Nast acquired it in 2006. In 2005, he coined the verb “crowdsource” with fellow Wired editor Jeff Howe. His first job was editing its front of the book section, which won a National Magazine Award in 2009, and he rose to be the magazine’s executive editor in 2015. He left Wired in 2016 for a short stint as the editor-in-chief of Epic but returned the following year as a features editor focusing on longform stories. But alongside his career as a magazine editor, he began singing jazz standards at nightclubs. “Sometimes I would have like, three gigs a week. I’d be finishing an edit and then like running out the door to go to a performance,” Robinson told The Fine Print. “And I loved that because it was two pursuits that I was really, really into.”

Alas, this is not a tale of a karaoke session after an office party inspiring someone to turn pro. “People will make jokes like, oh, we should have Robinson sing,” he said. “When they would go do karaoke, I would always say, ‘Oh, sorry, I only sing with a live band.’” There were exceptions. He recalled performing a memorable karaoke duet of “The Wind Beneath My Wings” at a company retreat with the copy chief. “We were pretty well in our cups,” he said, “which maybe explains why I was willing to do karaoke. I don’t know.”

Robinson said he has always been “a singer of some sort or another.” He took voice lessons in high school and college and sang in a professional choir in his twenties. But it was on stage in the clubs of San Francisco where he began to feel a connection. “When I started my nightclub act that was like a new thing,” Robinson said, “it was at a much higher level. I was leading a band, I was getting paid. I was doing it, basically, as a professional. I mean, it wasn’t exactly touring the country — don’t get the idea that it was anything other than small time. But that’s where I kind of mark my return to performance from when I was a kid. I started feeling like, ‘Oh, okay, I’m a professional singer now.’” In 2006, he released Some Small Dive, an album of crooner tunes like “I’ve Got the World on a String” and “East of the Sun.”

But the impulse to perform full-time came much later in 2018 when he sang in a local production of My Way: A Musical Tribute to Frank Sinatra. “I got bitten by the theater bug at age 53,” he said. “At that point, I started really putting a lot of time and effort into auditioning and studying acting, and started taking voice lessons again because I was doing musical theater.” Then came 2020. When the pandemic arrived, “it just led me to a reassessment of what I was doing in my life, how I was spending my time, what was important to me.” Robinson loved editing and loved Wired, but “it wasn’t as interesting to me as trying something that I wasn’t good at or hadn’t mastered in the way that I had magazine editing, and that seemed attractive.” His wife, Leslie Winick, was also going through a career transition; after working at Stanford’s office for alumni relations for 25 years, she retired last year and is now offering executive coaching. They were both at a place where his leaving journalism was financially feasible. “He is the definition of ‘deep dive.’ I mean, it shouldn’t surprise me that this is his approach to acting,” Winick told The Fine Print. “Mark is one of those people who swims in the Bay.” She means the San Francisco Bay, where water temperatures rarely rise into the sixties, and the currents are swift.

So far, Robinson’s acting career is off to an auspicious start. Alongside numerous roles in theater productions around the Bay Area, he has five independent film credits on his performance resume and was cast in another film last month. He starred in his first commercial (for a coffee brand) at the start of the year and was on his way to a callback for another commercial on the afternoon of our interview. That said, finding work as an actor isn’t easy. “I think I probably auditioned for, I don’t know, 40 commercials in the last two years,” he said, “And I booked one.”

Like his journalism career, Robinson noted that it helps to be driven by a passion rather than fixate on landing one big break. “I’m in this fortunate position where I can at least try and see what happens,” he said, “So, I don’t really have any goals, as far as singing and acting are concerned. And I didn’t really have any goals as far as journalism was concerned. It was something that I was drawn to, and I didn’t do it for the money. I never really considered a career in the performing arts. I think it seemed unrealistic. And to this day, I don’t know how realistic it is.” But, in some ways, learning to embrace uncertainty was a hard-won lesson from magazines. “I see now, in ways that I didn’t see when I was in my twenties pursuing journalism, that you kind of never know,” he said. “The most important thing is just to put in the work and to try, and the rest is out of your control.”

Branching out from singing jazz standards has, so far, included putting in hours of training. Robinson joined a weekly acting studio and enrolled in a ballet class to improve his dance fundamentals. “The biggest reason I’m taking dance classes is when you go to audition for musical theater, there will often be a dance audition,” Robinson said, “And I have had so many horrible, humiliating experiences in those dance auditions where there’s all these dancers, and they know all the moves and all the terminology and everything. And then there’s me, and I’m just like, a parody of somebody who has no idea what they’re doing.”

Though he now considers acting and singing his full-time job, Robinson hopes to moonlight as an editor through the occasional freelance gig. The way he sees it, both journalism and the performing arts are creative, collaborative pursuits. “The best work that you do as a magazine maker is tapping into your creativity and other people’s creativity,” Robinson said, “The same thing is true when you’re making a piece of theater or making a film, or even making a TV commercial. That experience with a TV commercial, I found to be, surprisingly, creatively satisfying. It was great. It was just like a great day on the set [with] cool people who were intent on doing something that was gonna be fun and interesting.”

When asked which song is his favorite to perform, Robinson had to think for a moment. “I will often say that my favorite song is the one that I’ve learned most recently,” he said. “There’s a song called ‘Everything Happens to Me’ by Matthew Dennis. It’s a very funny, somewhat cynical lament told by a character complaining that nothing goes right for him. And it’s just a great song.” He was quick to add, “I’m probably the opposite of the character in that song. I feel like I’ve been so lucky, so it’s not like I share the character’s point of view or anything, but I just love that song.”