“If You Have To Put Out 17 Listicles A Day, Who Has Time To Edit?” Lean In’s Jessica Bennett Talks Journalism Lessons For The Brand World

For Jessica Bennett, making the jump from journalism to branded content has meant new opportunities for creative storytelling.

She was a senior editor at Newsweek before joining Tumblr (which recently sold to Yahoo) as executive editor, and now is editorial director at Sheryl Sandberg’s non-profit, Lean In.

Jessica Bennett

The Strategist spoke with Bennett about the transition from journalism to branded content, her new gig at Lean In and how women in media can succeed in leadership.

At Lean In, you’re building an editorial strategy from the ground up. How did you get started?

Well, you could say I leaned in. I was abruptly laid off from Tumblr, along with our entire editorial team. We didn’t know at the time that Tumblr was about to be acquired by Yahoo — which helped explain the insanity of it all.  I knew Sheryl a bit from writing about women’s issues for years, and had interviewed her a few times. I was seated next to her publicist once at a dinner in New York. So, when I was suddenly jobless, I emailed them both.

I don’t think Lean In was looking for a journalist to join them — that wasn’t really part of the plan — but the reality was that they had this incredibly engaged community, and there was a huge space for them to start providing content to them. So, I pitched the idea, and I guess they liked it!

What are the goals for editorial at Lean In, and how is it different than a regular publication? How do you measure success?

The ultimate goal is the cause: helping women Lean In to their ambitions. It’s a non-profit, so we don’t operate like a regular news organization, but we do provide content — whether that be essays or multimedia or PSAs or video. It’s fun to be part of a place where the goal is the mission, not simply clicks. It’s really about sparking compelling, smart conversation around these issues more so than going over our traffic numbers with a fine-tooth comb.

Does creating content for a brand hold the same stigma to journalists as switching to PR?

I think it can — but it doesn’t have to. Producing content around women’s issues, or content around social trends coming out of Tumblr, is pretty much your standard editorial. A big part of my job is securing partnerships. So, for example, we produced a big package with Time Magazine for Father’s Day, where famous dads wrote letters to their daughters about how to lean in. At Tumblr, the stories we were producing were appearing in places like WNYC and New York Magazine, so it felt almost like throwback, super traditional journalism in a lot of ways.

I think content funded by brands is this sort of not-so-secret middle ground where journalists can still produce good work, but actually have the funding to do it. We’ll see how long that lasts, but for now it’s where the jobs are.

In general though, I think content funded by brands is this sort of not-so-secret middle ground where journalists can still produce good work, but actually have the funding to do it. We’ll see how long that lasts, but for now it’s where the jobs are. For what it’s worth, I still have the “PR is a sellout” journalist mindset. I would never do PR.

Is the bar for success is lower in online media than print?

I think it varies wildly based on publication. But the reality is that legacy print media had weeks — and oftentimes months — to refine prose and report on a topic. Online media moves quickly, so inherently there is not time to make the quality as good. That’s not to say there isn’t opportunity for really great and innovative online journalism — and there are tons of places where that exists. There’s a lot of crap too — but both can exist.

I was probably one of the last journalists of the younger generation to have a super traditional training. I worked the night cops beat at The Boston Globe after college as part of a fellowship program — like literally knocking on doors in my parka in the middle of the night, chasing down cops, carrying a police scanner around with me. That didn’t last long — thank God — and then I got my first staff job at Newsweek, doing features. Experience like that doesn’t exist a lot of places any more. I was literally working with the best editors in the business. Just amazing, amazing writers and editors who were rewriting the shit out of your copy, but you loved it. I think today, it’s a different story. If you have to put out 17 listicles and four photo galleries and 5 reported pieces a day, who has time to edit?

What’s one lesson from Lean In that applies to women in media pursuing leadership?

For me, the novelty of Lean In is that it put words to what I believe many women of my generation struggle with: that paralyzing sense of self-doubt, that insecurity, that fear of being perceived as too harsh (or, god forbid, bitchy), that subtle fear of speaking up that causes us to keep our hands down instead of raising them. Institutional sexism definitely still exists, but ask any woman in her 20s or 30s – I guarantee you, she’s felt this. I would find myself in editorial meetings, having a really good idea but being afraid to voice it, or — when I did voice it — stumbling over my words. For women in media in particular, where so much of the rise at a news organization is about not just having the good ideas, but voicing them and delivering them — that confidence is so important. So for me, reading Lean In for the first time — long before I worked for the organization — and hearing that even Sheryl Sandberg felt all of those things, well, it was validating. It somehow made it OK, and it made me conscious of it — which is the first step toward overcoming it.

What’s a recent project you are proud of?

Sheryl gave this great commencement speech at Barnard a couple of years ago where she ended by asking the women, “What would you do if you weren’t afraid?” — and challenging them to go and do it. That phrase has always resonated with me, and so around graduation this past year we wanted to produce a campaign that highlighted it. So we went out in New York City and asked young women what they’d do if they weren’t afraid, produced a video out of it, and launched a Tumblr. We knew to some extent that we would hear a lot of things that women would do differently could they just overcome their fears — but it was actually pretty sobering to hear it all out loud in one sitting. Women are holding themselves back. Because they are afraid. We need to learn how to overcome our fears.  That’s been a really great thing to be a part of.

What are some editorial pet peeves?

I love this question. Here are three:

1) An email interview is not the same as a real interview. I can’t tell you how many times I’ve been submitted a piece, as an editor, and had to go back and ask the writer, did you actually talk — like with your voice — to this person?

2) Headlines that force you to click and then tell you nothing. See Huffington Post Spoilers for everything you need to know about this.

3) People (and this is usually a female thing) who sign their professional emails with “xo.” Or worse, people I’ve never actually met or spoken to who sign their emails with “xo.” In pitches! Like, that’s weird. I don’t know you. You can read my full rant about this in The Atlantic.