ESPN Senior Ed.: “It’s Worth Being Poor To Be Able To Do What You Love”

Playboy‘s SVP of digital content Jimmy Jellinek (L) and ESPN senior editor Alison Overholt

Five magazine writers and editors sat between the two huge ornately-topped marble columns in the back of the General Society of Tradesman and Mechanics’ library Tuesday evening for’s “Same Skills, New Career” panel discussion, and they want you to know: yes, you can change careers.

Moderator Alison Overholt, senior editor at ESPN The Magazine, lauded the virtue of persistence. Panelist Jimmy Jellinek, senior vice president of digital content for Playboy, said that all you really need to get started is that good idea and a little bit of leverage. “If you’re a low-level employee,” as he once was at Details, “you automatically have credibility. I would send out pitches on [their] letterhead.” (“Always FedEx pitches,” he added. “People pay attention to FedEx.”)

“Leave yourself open to uncovering the story you pitch,” panelist Danielle Sacks, a former PR agent who’s now a staff writer for Fast Company, suggested. Panelist Will Leitch, founding editor of and contributing editor for New York, advised attendees to treat those who champion their work well. “They will be helpful.” And panelist Rachel Sklar of the Huffington Post, who didn’t break into journalism until after she’d gotten a law degree, advocated being “nice, friendly, and warm.”

Leitch said career success was often a matter of adaptation. “If I’m working on this story and I don’t know what the hell I’m talking about, I need to find out fast,” he said. Jellinek explained — and his co-panelists agreed — that the one of the best ways to learn is to claim ignorance to someone knowledgeable on the subject. “People love to talk, so let them,” he said. “Everybody wants to be an expert.”

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Panelists had divergent takes on whether a journalism degree is necessary, but the ultimate consensus was that real-world experience trumped all, whether starting as a fact-checker for a publication, as Sacks did, or experience at a college newspaper. Leitch, the only panelist with a journalism degree, looked back fondly on lessons learned on a school paper staff. “You and this group of 15 idiots have to make it happen, because not putting out a paper is not an option.”

Amid the generally positive and jovial evening, Jellinek and Overholt each hammered home that sincerity is just as much of a requirement as skill in journalism. “You can teach a person to report — you can’t teach a person to write,” Jellinek observed. Overholt said she didn’t immediately jump into journalism for fear of ending up broke, but after six months of checking spreadsheets, she decided that money shouldn’t have been the issue: “It’s worth being poor to be able to do what you love.”

After the discussion, Leitch had some nuggets of wisdom for one skeptical audience member seeking elaboration on Leitch and Jellinek’s praise of blogs as the best place to break in. “It’s an outdated notion that ‘blog’ means ‘MySpace diary’,” Leitch clarified. “You just need to write something no one else is saying. Online blogs make media a meritocracy.”

Will Leitch, founding editor of and contributing editor for New York

Alison Overholt, senior editor, ESPN The Magazine

Phil Rudich