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" Anna Holmes was the founding editor of Jezebel, Gawker Media&amp;#039;s &amp;quot;girly&amp;quot; website that transformed the female-centered Internet with humor, critique of traditional women&amp;#039;s media, and a hefty dose of feminism. Now a freelance writer and a columnist at  The New York Times Book Review, Anna is one of the most recognizable names in media. Her career journey hasn&amp;#039;t been a straightforward one, but she&amp;#039;s continually found the nerve to jump headfirst into new and terrifying ventures. Still, at 40, she&amp;#039;s not sure what she wants to do when she grows up. I studied journalism at NYU, which was a fucking waste of money. The school is incredibly expensive, it took 16 years to pay off my student loans, and I don&amp;#039;t recall that I learned that much about journalism. I&amp;#039;m not convinced that the six-figure sum I graduated owing was worth it. You don&amp;#039;t have to study journalism to be a journalist, but at the time I felt like you needed to be in New York to get into publishing. I wanted to write what back then you would have called literary nonfiction, the kinds of things being published in Harpers and The Atlantic and The New Yorker. My first internship was in my second year of college at the New York Press, an alt weekly. I vaguely remember helping with listings of cultural events, mostly administrative stuff. That was unpaid. My second internship was at The New Yorker, on the business side. It was 20 hours a week, paid, and very exciting. I interned at Entertainment Weekly my last year of college. They made a space for the interns to pitch small stories. It was paid too. I worked at the computer lab at NYU as well, and those two things are what allowed me to survive. When I left college, I left New York for about six months because I was very upset about a boyfriend I had prior. When I came back, there was an editorial assistant position open at Entertainment Weekly. I wish I could say the woman I worked for was a mentor, but she was not. Her work as an editor certainly taught me things, but she was either too distracted by her own job or contemptuous of the fact that I had a lot of energy or ideas. I remember telling myself I would never do that if I were someone&amp;#039;s boss. It was very disappointing when some of the other assistants were getting promoted and I wasn&amp;#039;t. I felt like I had failed somehow. [In retrospect] I wouldn&amp;#039;t have let my feeling ignored and undervalued get to me. I wish I had known then that everything would be OK, and my worth did not rest on getting promoted to this higher position.  I moved over to HBO to work as an assistant to one of the producers in the documentary film department. I decided to leave after a year and a half because I realized the path upward was to become like my boss. I admired her, but I didn&amp;#039;t want to be an executive behind a desk looking at other people&amp;#039;s unfinished documentaries. I got a job at Glamour as a staff writer. At this point I&amp;#039;d been out of college for almost five years, and this was the first time it was my job to write all the time. I had this idea that I would supplement the more bread-and-butter sex and relationship stuff with serious content, but that was not the case. I was interviewing sex and relationship experts over and over again. It was soul-destroying. I felt increasingly disgusted and bored and contemptuous of the sorts of stories I had to write, many of which felt made up by top editors. There was one in particular that I believe the headline was, &amp;quot;What Is Your Secret Sex Personality?&amp;quot; I didn&amp;#039;t know what that meant and I don&amp;#039;t even know what it&amp;#039;s supposed to mean now, but I successfully pulled something out of my ass to make them happy. I was also working at Cond\u00E9 Nast. Even if Glamour isn&amp;#039;t fancy the way Vogue is, a lot of the company is about portraying a lifestyle that people aspire to, which is very much about materialism and wealth. I didn&amp;#039;t like that. The company seemed to be populated only by white people, and the only people who were black were the mailroom and cafeteria workers. I really did not like that. Which might explain why when Jezebel launched we went after Cond\u00E9 Nast more than other companies. I had a chip on my shoulder, which I don&amp;#039;t apologize for.  While I was at Glamour, I had a breakup with a boyfriend who stood me up twice \u2014 I&amp;#039;d been dating him for months, and he just disappeared. So I sent him an angry email basically telling him to get lost, and then I forwarded the email to all my girlfriends, and they were cheering me on. I thought about how these sorts of letters were an actual genre. No one had written about it, but these letters existed and historical figures had written them. I thought it would make an interesting book. There was an agent I knew socially, and she thought the book idea was great, so she helped me craft a proposal. It wasn&amp;#039;t that hard to sell, but that said, it wasn&amp;#039;t like I got a lot of money for it. After the book was sold, I had a reason to leave Glamour. The book involved tons of research. I got to spend a lot of time at the library, in online archives, talking to historians. I did the book in about nine months, and it was all-consuming. I hadn&amp;#039;t spent that much time by myself in a long time, and I realized I like hanging out with myself. It felt like when I was a kid getting to play by myself. The book came out in the fall of 2002, and it got some good press. I had worked very hard and I was proud of myself, but it wasn&amp;#039;t like it led to people calling and offering me better jobs. Throughout my 20s, a lot of the people I was friends with worked in magazine publishing, and we were all freaked out and didn&amp;#039;t know what we were doing. I felt very alone, even though, in retrospect, people were all feeling afraid. It seemed too vulnerable to admit to weakness. I freelanced a bit after the book came out, but I didn&amp;#039;t know what I wanted to do. Then a friend I worked with at Glamour asked if I would do some freelance editing at Star magazine for a month or so. I really couldn&amp;#039;t have cared less about celebrity gossip, but I liked my coworkers. I think some of us felt like we were slumming it, so there was a certain camaraderie. At this point 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. For example, Harpers had an internship program, but it was half the year and unpaid. There was no way I could have done that. By my early 30s, I was like, &amp;quot;I don&amp;#039;t know what I&amp;#039;m doing, but I also have to pay my bills.&amp;quot; I didn&amp;#039;t have time to think about my career strategically because I had to pay my rent.  I went to go work with a start-up magazine within the same company as Star. I was on vacation in Australia, and I got a call that they shut the magazine down \u2014 it had been less than a year. I was crying not because I really believed in the vision of the magazine, but because I was like, &amp;quot;How am I going to make money?&amp;quot; On my way back to New York, I ran into a woman who used to work at Entertainment Weekly. She said she was working at InStyle and they needed a freelance editor. They hired me on a six-month contract, which was then extended. At InStyle, I had an office. I was working among grown-ups who appreciated my competence. I didn&amp;#039;t hate the content because it was very straightforward: It wasn&amp;#039;t sexist, it wasn&amp;#039;t gossipy, and it wasn&amp;#039;t as materialistic as some magazines. About eight months into working there, they asked if I would be interested in being the editor of an InStyle website. This was 2006, and no one I knew in print media had gone to work on the web. There were bloggers, there was Gawker.com, but those were kids and they got paid $12 a post. It was not something that was tenable for a 33-year-old. At the same time a friend I had worked with at Star said that she was going to start a women&amp;#039;s site for Gawker Media, and did I want to help her? I initially said no, because it was the web. But I was being offered two new things, both online. I realized that I would hate working as the editor of InStyle online because it would primarily be assigning reporters to cover fashion shows and celebrities. I could do that, or I could work on this new venture, which I was informed would pay competitively. So I said yes. A few weeks later the woman said she wasn&amp;#039;t going to do it anymore. I was on my own. That was Jezebel. Starting Jezebel was terrifying. I didn&amp;#039;t know whether what I wanted to read would be shared by anybody else. I didn&amp;#039;t see anything like it in terms of commercial web property. And working on the Internet was not something that a lot of my friends were doing. Print seemed like a much safer space. So it was terrifying but also exciting. I was terrified for a good year after we started. I never felt like I could relax and enjoy its success \u2014 and it never got to that point, but that&amp;#039;s OK. The harder I worked and the more seriously I took it, the better it was. I couldn&amp;#039;t have been half-assed about it. After three and a half years, I left because I was very burned out. I just didn&amp;#039;t have a very healthy life, emotionally or physically. I was very sedentary, I worked every single hour I was awake. I had been concerned that the owner of the company would fire me because he seemed a bit mercurial about most of his staff. I think he also wanted it to be more commercial. I put so much of myself into Jezebel that I wasn&amp;#039;t going to try to change the site in any way that didn&amp;#039;t feel right to me. I felt that more than three years in, it was a successful, influential site, and I could leave and feel good about it. After I left, I took some time off. Jezebel was talking about doing a branded TV property, so I helped out with that, and I was working on two Jezebel-related books. So I wasn&amp;#039;t lounging around, but I wasn&amp;#039;t getting up at 6 a.m. to run a blog for 12 hours.  We sold the two books later that fall, in 2010, one of which was The Book of Jezebel and one of which was branded to our feature called Pot Psychology. In 2011, I wrote a column for the Washington Post. But I wasn&amp;#039;t fully freelancing, because I had to work on the book and I was primarily living off the advance. I could be a little picky about what I chose to write about, because I wasn&amp;#039;t dependent on it for money. Now, I&amp;#039;m writing a column for The New York Times Book Review. Pamela Paul, the editor of the Book Review and someone I greatly admire, called me last summer and asked me if I&amp;#039;d be interested in coming on board as a columnist for the section, and I said yes immediately.  I know many people freelance successfully, but I have no interest in making that my primary source of income. It&amp;#039;s too stressful, constantly having to try to think of stuff to pitch editors. The older I get, the less I want to write stuff that I&amp;#039;m meh about. I have a lot of opinions, but I&amp;#039;m not sure they all need to be preserved in prose. If I were to do anything differently, I would believe in myself more in my 20s than I did. Maybe it&amp;#039;s part of being in your 20s. Maybe it was the fact that I&amp;#039;m female \u2014 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&amp;#039;t have, and who seemed to have an innate confidence that I never felt. The best things are to be persistent \u2014 not annoying, but persistent; believe in yourself, but not to the point of over-entitlement or arrogance \u2014 and be patient. A lot of people want things to happen for them very quickly. But if when I was 25, someone was like, &amp;quot;OK, Anna, you can write a cover story for Harpers. Go!&amp;quot; I don&amp;#039;t know that I would have been in the right position to do that. Someone else once said to me, &amp;quot;Everyone else I admire has written a book by the time they&amp;#039;re 30.&amp;quot; So what? You shouldn&amp;#039;t write a book because it&amp;#039;s something you check off on a list. You write a book because you have something to say. This idea that you&amp;#039;re a failure if you haven&amp;#039;t done X, Y, or Z by X, Y, or Z time is silly.  Media is changing so rapidly that, although it can be destabilizing or unnerving, it&amp;#039;s exciting. I didn&amp;#039;t know at 19 that the web would become a thing. But in a way, the web is what saved me. If you told me at 16 that I&amp;#039;d be bored by magazines 20 years later, I&amp;#039;d be like, &amp;quot;What are you talking about?&amp;quot; There are not these traditional pathways that there used to be. Where you went to school isn&amp;#039;t as important. Who you know isn&amp;#039;t as important. In publishing, at least, you can make a name for yourself if you do good, honest work. A lot of times not-so-good, not-so-honest work gets noticed because the people are very loud. But I don&amp;#039;t think that has a lot of staying power. I don&amp;#039;t know what my next job will be, but it will probably be in media. A lot of times I&amp;#039;m just like, &amp;quot;I&amp;#039;m going to move to Namibia and work with orphaned elephants. Fuck this stuff.&amp;quot; I don&amp;#039;t have a five-year plan. Maybe that&amp;#039;s dumb, but it is who I am. I can&amp;#039;t pretend otherwise. Get That Life is a weekly series that reveals how successful, talented, creative women got to where they are now. Check back each Monday for the latest interview. RELATED:  Get That Life: How I Became a Professional Cheese Eater Follow Jill on Twitter. Photo credit: Kathleen Kamphausen for Cosmopolitan.com; Anna Holmes. "^^<http://www.w3.org/2001/XMLSchema#string>
<http://www.cosmopolitan.com/career/advice/a6858/get-that-life-anna-holmes-jezebel/>