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The Risks And Rewards Of Freelance Journalism

Sally Mauk and Gwen Florio, hosts of Parsing The Press

After being laid-off, more and more journalists are turning to freelancing. But it's a tough field. Missoula-based freelancer Ann-Derrick Gaillot talks about the pros and cons of freelance journalism, and the diversity and freedom it can offer. It helps, she says, to have a side gig.

Listen now on Parsing the Press, a weekly look at how the news is reported, with Sally Mauk and Gwen Florio.

Sally Mauk As the online world expands and as traditional media shrink, there is growing opportunity for freelance writers and journalists. Ann-Derrick Gaillot is a freelance culture journalist and critic based in Missoula and is profiled everyone from Congresswoman Ilhan Omar to Piano Pat from the Great Falls Sip and Dip to tennis champion Naomi Osaka. She's written for Rolling Stone, The Nation, BuzzFeed and the International Network of Street Newspapers, among others. Ann is our guest today.

And my first question is, what appeals to you about being a freelance journalist.

Ann-Derrick Gaillot I think what appeals to me most about being a freelancer is just getting to work with different editors and getting to work on stories that I'm really passionate about and really care about, rather than trying to appeal to like one website's audience all the time, or just always being limited by what people at one website think is interesting versus being able to talk to people from a bunch of different websites or publications that have a bunch of different interests.

Sally Mauk So there's a lot more freedom, right?

Ann-Derrick Gaillot Yeah, absolutely, a lot more freedom. I was a staff writer at The Outline for a couple of years and I really enjoyed that. But it was definitely, I always had to kind of write to what the website's audience was. So being a freelancer, I can do, for the most part, things that I am most interested in.

Sally Mauk Gwen I'm just guessing here, but it seems like there are more and more journalists who are freelancing because they lost their regular journalism gig.

Gwen Florio Yeah, that's something I was really curious about, was that as traditional news organizations cut and cut and cut their staffs, does that create more opportunity for freelance journalist, more competition? Both?

Ann-Derrick Gaillot I think that there's definitely more competition, as far as editors have more emails in their inboxes than ever from more and more people. I think what I've noticed more is just rates going down. So like places that used to offer a dollar word or more are just not there anymore or they've cut their budgets. Or I'm also noticing, in the past where I've kind of had more wiggle room to negotiate a rate, places are just kind of not willing to do that as much anymore because they have had their budgets cut.

Gwen Florio That leads to something I wanted to ask you when you talked about the freedom, you have freelancing to choose the subjects you like. I'm wondering about the security or lack thereof, both in terms of income and things like health insurance.

Ann-Derrick Gaillot Freelancing is definitely super precarious. For one year after I was a staff writer I did strictly freelancing all the time, and I definitely got burnt out on it because while I did get to write those stories that I'm most passionate about and interested in, I also took on a lot of assignments, you know, a fair number of assignments just for the money so I can pay my bills. Not like anything I really hated or anything, but kind of trying to fill that extra income is really, really hard. And I think it does burn you out, which is why, I think, I don't know how people freelance without having a side gig, honestly. Because the one year that I didn't have a side gig, I completely worked myself to death, I felt like. So that's really the key for me being able to pursue the stories that I want is having a side gig.

Sally Mauk Well, Ann your beat is pop culture, which is a big umbrella. But what does your approach have in common with, and what is different than, someone who's reporting, say, hard news versus pop culture?

Ann-Derrick Gaillot I think that there's like a misconception in some circles that like cultural journalism, it's not like as strict as other news traditions. But in cultural journalism, you always still have to research, get the facts, get comment from people involved. Basically just get your facts straight and do your reporting and research.

I think the biggest difference is when people look to cultural journalism, I think they look to it for analysis of a trend or a phenomenon more than they look to hard news for analysis.

Sally Mauk Gwen, journalism is, Ann just said, it's still journalism. It comes down to good writing and getting your facts and quotes straight and being accountable for what you're reporting. I think she's absolutely spot on about that.

Gwen Florio That and being able to write about a wide variety of subjects. And I think, again, in both traditional and freelance journalism, again, as resources are cut, you've got to be willing to jump in on anything. And your website has stories about everything. Everything. I was just impressed with your range. But given that, within that, do you have a particular kind of story you most like to do? If you could just do one kind, what would it be? Or do you like the variety?

Ann-Derrick Gaillot I like the variety. I think that, like, comes a lot from just me not knowing exactly what I want to buckle down on. But also just, I don't know, I, my attention goes everywhere. I think if I had to do one kind; that's so hard. Maybe, more and more I'm writing about things from a historical perspective and I think I'm really enjoying that. So, if I could do more pop culture criticism and reporting, just talking about how things from the past affect us now or have taken us to here, I would love to do that more. But then again, I love doing interviews and profiles, so I'm not sure.

Sally Mauk Ann, mainstream journalism strives to add diversity, but it still has a long ways to go. Do you think freelancing offers more opportunity, maybe, for journalists who aren't white?

Ann-Derrick Gaillot Yeah, that's a tough question. I think that it does to the extent that you have the choice to pursue stories for different audiences. But to a certain extent, no, because no matter how good of a story idea you have, if the person up top doesn't think it's worthwhile or doesn't think it has a readership, then it doesn't really matter. So I think that it will be easier for freelance journalists of all kinds — like racial diversity, gender diversity and economic diversity too — to get their foot in the door as freelancers when more editors and, like, people up top are also diverse.

Sally Mauk That's an excellent point.

What's your best advice for someone who wants to pursue freelancing, besides having a side gig?

Ann-Derrick Gaillot That was definitely my advice. I think just try to have a community of other writers and journalists around you, because one thing that's great that I loved about working — not in a newsroom, because I was remote — but on a staff, was just having, like, other people to bounce my ideas off of and have conversations with and learn from. So I think that is probably the most important thing is just make sure you're not isolated or in a silo.

Gwen Florio I was just curious. We've touched a little bit on this, but the greatest risk and the greatest rewards of freelancing.

Ann-Derrick Gaillot The greatest risk is going broke. And also, at times, the greatest risk can be not having, just, that institution behind you if you got something wrong, or just not having the institutional backing. But the greatest reward is just getting to guide your own path in your career and getting to be your own boss, I guess.

Sally Mauk One final question for you Ann: how on earth did you get an interview with Naomi Osaka who just won The Australian Open, may be the best women's tennis player currently playing and had to have had thousands of interview requests? And you nailed one of those.

Ann-Derrick Gaillot Yeah. Oh my God, I have no idea. I think that one thing that made my request stand out is that I was pitching for the International Network of Street Newspapers. So I think assuming that she wanted to prioritize a nonprofit paper, maybe. I have no idea. But I'm so happy that she did. Maybe because I'm also Haitian, that, like, sealed the deal. I'm not sure. But yeah, that was definitely a huge win for those street newspapers.

Sally Mauk Ann, Gwen, we're out of time I'm afraid. But thank you so much.

You've been listening to Parsing the Press, a weekly look at how the news is reported featuring journalist and novelist Gwen Florio and Sally Mauk.

Do you have a comment or suggestion for a future show? Contact Sally Mauk at

Parsing the Press is a weekly look at how the news is reported, featuring journalist and novelist Gwen Florio and Montana Public Radio's Sally Mauk. Listen on MTPR Fridays at 7:50 a.m., or find it wherever you get your podcasts.

Retired in 2014 but still a presence at MTPR, Sally Mauk is a University of Kansas graduate and former wilderness ranger who has reported on everything from the Legislature to forest fires.
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