Courtney M. McSwain, Writer

Anatomy of a Freelance Writer’s Life: Q&A with Hillary Crosley

Hillary Crosley Image

Photo Courtesy of Hillary Crosley

Hillary Crosley is a freelance entertainment news journalist who has worked for the biggest outlets in the business: MTV News, Billboard, The Source, Vibe, XXL and Trace magazine in the UK among others. Crosley currently acts as the New York bureau chief and weekend editor for and is the host and producer of “After Hours” for Additionally, Crosley is the editorial director at, which she co-founded with two other women in order to open up conversations relevant to women of color across the globe.

Also, she’s hilarious.

Crosley was gracious enough to give me some of her time recently and share how she began working as a journalist, manages multiple jobs as a freelancer and stays motivated. Taking in her humorous outlook on the freelance life, I was comforted to know that even a 10-year industry vet experiences emotional highs and lows. Still, somehow, being able to work every day in stretchy pants makes it all worth it.

CM: How did you start in the journalism industry?

HC: I started in journalism while I was in England at the University of Warwick. I didn’t quite know what I wanted to do in terms of a career choice, but I always knew I was good at writing. While I was going to school there, I figured—and it sounds really stupid when I think about it—but I literally was watching someone interview Lenny Kravitz and I was like, “I could totally do that.”

I looked around at the different magazines that I liked—and I’ve always been a proponent of: try it; if you like it great and if you don’t then you know not to do that again. Don’t assume that something is going to be terrible before you even give it a chance. So I reached out to several different magazines including Touch, which was an urban magazine in the UK at the time. I reached out [and] offered my services as an intern and they shunned me. They were like, “No, we don’t need any help. The person you want to talk to is always in a meeting…” blah, blah, blah. I was like, okay, that’s ridiculous because everybody wants free help. But that’s fine. I’m not going to let this stop my progress. Let me see if I go to a show and write it up if I like it or not, you know just for my own experience.

I ended up going to a show for this artist, who is long gone now, but the first show was sold out.  The next show, which I ended up getting a ticket for, was actually an industry show. I ended up at this concert with all of these different editors and different writers. Because I had been paying attention, I realized who was who in the crowd. I approached this young lady who had a column in the back of Touch. I asked her if she had any advice in terms of getting started. She said, “You don’t have an album you want me to play? You don’t have a demo?” I was like, “Yeah I don’t sing outside of the shower.”

[Crosley managed to convince the writer that she was only seeking advice, not a record deal. As it turns out, that same columnist also happened to work for MTV News. Crosley then met another writer who worked for Touch, the magazine that had just rejected her internship offer. He told Crosley the magazine could definitely use her help. Unfortunately, the magazine folded before she was able to start work. Crosley went back to the columnist she met and landed an internship with MTV News. At age 20, Crosley had found her first entry into the entertainment news business.]

CM: Have you been writing all your life?

HC: I have, actually. I’ve always kept a journal. Whenever we had writing assignments, I did quite well. It’s one of those things that you’re just naturally good at. I’m naturally good at talking to people. I can strike up conversations with complete strangers. So that works for journalism.

CM: When you were in college, did you get a journalism degree or was all of your training on the job?

HC: All of my training, well not all but most of it, was on the job. I didn’t have a journalism degree as an option in college. We had English and that was it. I did an English and African American studies double major with a minor in film. Because we didn’t have a journalism degree, when I got out of school—the way that you would write an academic paper and the way that you write a piece for a magazine are completely different, so I just kind of felt robbed. I was annoyed. You have to re-learn how to write essentially.

For journalism pieces, you’re trying to be sparse. You’re not trying to be verbose because, at the end of the day, this is someone’s free time that they’re using to read your piece. Don’t waste it with a lot of superfluous words. A lot of my talents were sharpened thanks to great editors at places like MTV News and Billboard and The Source—all those different places where people took my work and handed it back to me drenched in red ink. Fortunately, I always had a good feel of being a natural reporter and a natural writer, so if my writing sucked at least they knew I was comfortable with a great story.

Journalists need to be aware that you’re going to hit a point where you might need to get a tutor. If you’re not in the place where someone has the time to really flush out that skill—because it is a skill, it’s not something that is going to come naturally to everyone. I got a tutor. No shame. She was a professor at NYU. She just really helped me figure out how to write those words and structure my pieces. I guarantee that if I went to journalism grad school or had a journalism undergrad I would not have had those issues. But I didn’t go that way, so you’ve got to be realistic with yourself. I was raised that if you can’t figure it out for yourself, find someone who can.

CM: Have you always been a freelancer or were you ever on staff at a publication?

HC: I became a full-time freelancer in 2009, but I had always been writing here and writing there. When I started at The Source I was writing for Trace in England. After I left The Source, I went to MTV News and I was a full-time freelancer there. Then I went to Trace and I would write for them, but I would write for other people too. Then I went back to MTV News and I kind of was giving them news. Then I went to Billboard full-time, and there I freelanced for other people as well. I worked for XXL, I worked for Vibe. In the entertainment news industry, you always want to keep your contacts fresh. You always want to be able to freelance here and there because you never know when you’re full-time gig will come to an end. That’s what I learned in that first lesson in England. The woman that I met at the concert—she had like 14 different jobs. I realized then that it’s always good to have several pots on the fire. Thinking that way, a lot of times when the bottom dropped out of one job, I always had something else to fall back on.

CM: What’s been the most challenging part of that concept of always staying active and always having multiple “pots on the fire.”

HC: You never feel like you can sit down. There’s always something else that you could be doing. There’s always something else that you could be writing. There’s always something else that you could be checking out. Sometimes that’s the luxury of having one full-time job that is substantial, because then you don’t have to worry about the deadlines that are always kind of hanging over your head.

Other people have said this, and I agree—being a journalist is like never getting out of college. You always have a paper due, always. Sometimes it’s nice to just have one job where you have multiple papers due as opposed to the multiple papers due for your main job, the side job deadline and then the other job deadline.

CM: What’s the most fun part of being a freelancer?

HC: Not having to commute when it’s 27 degrees outside. I can be ridiculous and say, if it’s raining, “Oh, I think Wednesday is going to be bad for me, how about Thursday?” I can actually do that. I can schedule my life, and I love that freedom. I really enjoy being able to work in a tank top and some stretchy pants all the time. I like to be able to eat food that is not take-out in my kitchen. I like being able to get my work done without a lot of unnecessary meetings where people are talking, and it’s great, but then you look up and half the day is gone and you still have a full day’s worth of work to do. Those are the things I don’t miss.

CM: I’m interested in what you were saying about never being done. As I’m learning my way through my first year of doing this, I constantly have this feeling that I haven’t done enough. I think you probably hit the nail on the head—there’s always something due, so you never have that sense of completion. How do you manage that—or deal with that internally?

HC: You just have to do what you can. I have an Evernote things-to-do list that I have on my laptop as well as my phone and I’m constantly checking things off. When I think of things when I’m not at my laptop, I can put that into my things-to-do list and then erase it from my mind because I know it’s written down. That helps with being able to turn off.

Ultimately, you really have to take time to turn off and you have to protect it. There’s an Audre Lord quote where she says self-care is political warfare. As ridiculous as it sounds, it kind of is. People become very upset when you say, “This is my off day, I’m not responding.” But you have to take that time for yourself, or else you’re going to melt. Some people can really work nonstop and that’s how they succeed. I’m not one of those people. I have to work, work, work and then I have to have a day where I just don’t think.

Restructure your schedule so that you have time for you, and then everything else will be better. If you don’t allow your brain to replenish, you’re going to suck at everything and then no one’s happy.

CM: I wanted to ask you about Why did you decide to branch out and co-create your own magazine?

HC: I decided to co-found Parlour Magazine because I was at Billboard and I was tired of writing about nothing but hip-hop. I really wanted to be able to expand my voice to women’s issues, feminist issues, talk about politics, talk about clothes, dresses—when you’re the only woman in a room full of hip-hop dudes, it’s really not the space for that. So I was tired. I was bored. I was like, “I’m over this.” That’s really what started Parlour.

The ultimate goal is to make it a global conversation where women of color can have that space to communicate ideas. The more traveling I’ve done, the more I realize that while we might be in different spaces around the world, we’re going through very similar issues…It’s the diasporic experience, really. That’s what I love about it.

CM: I feel like in this day and age, a lot of people are trying to figure out ways to create their own thing. Even if they’re employed by someone else, they are still trying to create their own innovation. What do you think about that in terms of being a freelance writer—how important is having that entrepreneurial spirit to surviving as a freelancer?

HC: If you’re freelancing, you are your own business. So if you don’t have that spirit, you might want to pick another job.

CM: What is your ultimate dream?

HC: My ultimate dream is partly being fulfilled right now, being able to pay my bills and work from home. Because I’ve spent so many years working in an office and thinking to myself, “I can really do this in my bed. It’s cold and I don’t know why I need to work at this computer as opposed to my computer. This is dumb.” I do see the point of working in an office in terms of building community and loyalty and in terms of being able to get together and share ideas…at the same time, I really enjoy being able to work from home and not having to leave my house. Everything is here. I have my printer. I have my phone. I have my Internet. All I need, really, is a paper shredder and life is going to be grand.

It’s not an easy thing to do, by any means. Sometimes it’s terrifying. Sometimes I’m really angry. Sometimes I’m really happy. Sometimes I think to myself, “What are you doing?” Sometimes I’m just like, “This is the most amazing thing you’ve every done.” It really, vacillates. But I’d feel the same way if I were in a day job.

CM: Is there anything else that you’d like to add?

HC: If you’re going to be a freelancer, make sure you keep your money right. There’s a book called “The Money Book for Freelancers, Part-Timers, and the Self-Employed.” It’s really about how to manage your funds so that, even though your check comes sporadically or not necessarily on a specific schedule, you can still have financial freedom and not feel like you’re hanging over a cliff all the time.

Other than that, stack yourself with encouraging sayings [for] when you’re staring at your computer thinking, “This sucks.” You can go to that little bookmark [and say], “Oh, look at this bounty of information that tells me that I can do it and that I’m great.”

CM: I’m actually staring at my wall and all of the post-its I have with little quotes on them.

HC: Yep, it matters.


You can learn more about Hillary Crosley by visiting her website or following her on Twitter. Also, be sure and check out


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