Obama Sent His Daughters Anna Holmes’ Essay. Her Message? Say ‘No’

After I finished reading Anna Holmes’ new book, The Power of No, I wrote a 3,000-word essay on why it matters so much — especially right now. It’s a book I feel everyone should give to their young people — and young women, in particular — because if there’s one word people should have fluency and comfort with, it is no. 

But rather than reading Anna my prose, it seemed like a great starting point for our conversation on Rushfield Lunch. 

“The book is very gendered in the sense that it’s kind of written for women,” Anna tells me. “Women and girls have a harder time saying no because they’re socialized not to do so. It starts as early as kindergarten when they are expected to be the ones who help in classrooms; teachers often look to girls unknowingly, and girls often offer to help because they know they’re expected to be helpful. As they get older, they learn that boys are encouraged to assert boundaries, while girls are rewarded for being warm. This only increases in volume and intensity as girls become teenagers — at least it did for me.”

Born in California, Anna says she can remember being a child who wasn’t afraid to say no or set boundaries with people. “But as I got older, especially in my preteens and then teenage years, a certain insecurity or self-doubt crept in that made it difficult for me to say no; it made it difficult for me to identify what the things were that I didn’t want to do and then therefore to communicate them to other people. My entire life since then has been in some ways an attempt to get back to that 7-year-old spunky girl who felt that she had the ability and the right to say no.”

A proud fellow member of Gen X, Anna graduated from New York University in the mid-1990s and embarked on a media career that has few comps: She’s been published by the New York Times, The New Yorker and The Washington Post; in 2007, she founded the Gawker Media website Jezebel, which quickly became one of the most essential and oft-imitated brands in the digital media era. The website made Anna a figure of great renown in New York media circles and led to countless opportunities — including the chance to give the 2015 commencement address at Emma Willard, a girls’ boarding school in upstate New York. That’s when Anna conceived of The Power of No, without even realizing it.

“I wanted to do something that was a little counterintuitive,” she says of the speech. “And I thought about what I might have learned — or wanted to learn — when I was younger, when I was their age, and that was the importance of creating boundaries and not always agreeing to encroachments on those boundaries, learning how to say no, to refuse or reject people’s expectations and demands on my time, on my labor, on my body, et cetera. So I decided to do a commencement speech about no.”

Six years later, while writing for The Atlantic, Anna turned the speech into a widely read piece. How widely read? “I’m not gonna tell you this because it’s a total brag — but, anyway. I heard that President Obama had sent it to his daughters. That’s what I heard — which is a brag.”

During our chat, which you can watch in full above, Anna touched on a variety of topics, including how Hollywood executives can learn to embrace no, and her reflections on Jezebel.

“I wonder sometimes: What would a new Jezebel look like? I don’t know,” she tells me. “I don’t know because there was plenty to critique and complain about back in 2007 when that site started. But now the culture is just overwhelming in terms of its misogyny. If someone said, ‘I want you to restart Jezebel,’ I would probably say no. Because I wouldn’t want to do it again, but I also wouldn’t know how.”