Anna Holmes On How Unconventional Career Moves Can Save You

Doing everything by the book wasn’t working for digital pioneer and Jezebel founder Anna Holmes, so she wrote a new one. Here’s what she learned about taking big bets on yourself.

Anna Holmes On How Unconventional Career Moves Can Save You
[Newsstand Image: Bibiphoto via Shutterstock]

Beyond studying journalism at NYU, Anna Holmes didn’t take a traditional path to her current gig as a columnist for The New York Times Book Review. Holmes, who founded the feminist blog Jezebel in 2007, spent her first few years out of school working for gossip magazines and women’s publications she grew to hate, feeling “ignored,” “undervalued,” and “very alone.”

Anna Holmes

Today, Holmes is a model of success for digital journalists–and she continues to make unconventional career choices that feel ahead of the times. After turning “girly Gawker” into a leading voice among a new wave of feminist voices, she took time off to publish The Book of Jezebel. (I also worked with Holmes when she edited The Atlantic Wire for a few weeks last summer.) She will soon leave freelance life to guide digital efforts at cable TV channel Fusion, where she will be editor of Digital Voices and Storytelling.

The life of a digital writer has come a long way since Holmes took a risk on Jezebel. “No one I knew in print media had gone to work on the web,” she said of her decision. “There were bloggers, there was, but those were kids and they got paid $12 a post. It was not something that was tenable for a 33-year-old. It can still be a scary, uncertain world out there for aspiring journalists.” Though even “kid bloggers” make more than $12 a post now, it can still feel scary and uncertain–which is why Holmes shared some wisdom on navigating it all with Cosmo.

1. Don’t go to journalism school.

“I studied journalism at NYU, which was a fucking waste of money,” she told Cosmopolitan‘s Jill Filipovic. “You don’t have to study journalism to be a journalist.”

It sounds harsh, but it took Holmes 16 years to pay off her debts. At the same time, she didn’t feel like she had gained access to the jobs she wanted. “I felt very far away from what I wanted to do when I was in college. It seemed like those jobs only went to people who were Ivy League grads,” she added. And because of her debts she couldn’t afford to apply for things like Harper’s six-month unpaid internship.

In a separate interview she clarifies that she got an undergrad degree in journalism. But still: “I did not feel that I learned that much in the program, and by the time I realized I wasn’t learning that much, it was too late for me to switch majors.”

2. Know that everyone–not just you–is freaking out

“Throughout my 20s, a lot of the people I was friends with worked in magazine publishing, and we were all freaked out and didn’t know what we were doing,” she said. “I felt very alone, even though, in retrospect, people were all feeling afraid. It seemed too vulnerable to admit to weakness.” Knowing other people feel just as terrified and horrible as you do doesn’t necessarily change the state of media, but at least you might not feel so alone.


3. Believe in yourself, but not to the point of arrogance.

Young journalists are too hard on themselves:

If I were to do anything differently, I would believe in myself more in my 20s than I did. Maybe it’s part of being in your 20s. Maybe it was the fact that I’m female — I worked with a lot of women, but it was not lost on me that the most powerful people in publishing tend to be guys. The writers who were respected the most at EW were the dudes. Sometimes I felt like I was a bit of an impostor, because I was surrounded by people who went to Harvard or Princeton, and had these privileges I didn’t have, and who seemed to have an innate confidence that I never felt.

The best things are to be persistent–not annoying, but persistent; believe in yourself, but not to the point of over-entitlement or arrogance–and be patient. A lot of people want things to happen for them very quickly. But if when I was 25, someone was like, “OK, Anna, you can write a cover story for Harpers. Go!” I don’t know that I would have been in the right position to do that. Someone else once said to me, “Everyone else I admire has written a book by the time they’re 30.” So what? You shouldn’t write a book because it’s something you check off on a list. You write a book because you have something to say. This idea that you’re a failure if you haven’t done X, Y, or Z by X, Y, or Z time is silly.

For more career advice from Holmes and news about her latest move, check out Cosmopolitan and Re/Code.

About the author

Rebecca Greenfield is a former Fast Company staff writer. She was previously a staff writer at The Atlantic Wire, where she focused on technology news.