Kim Cross is in her second round of freelancing as a career. But the former editor for Southern Living and Cooking Light says this time she’s feeling much more prepared.
“My first job out of college I worked for a business magazine in San Francisco called Business 2.0 and it was a wonderful job,” Cross said. “At some point, the new economy that we were writing about, the dot-com boom, went bust—and with it, many of the magazines that covered it. ”
Cross said she was thrown inadvertently into the freelance market way before she was ready. She says she only made it work by layering it on top of a day job fitting backpacks at an REI and then by rushing to a hostess assistant gig at a high-end sushi restaurant at night. Fortunately, things are much different for her now.
“Coming back into freelance after bouncing between newspapers and magazines for 10 or 15 years, it was a different story because by then, I had the network and I understood from being on the inside what an assignment editor was dealing with, and so I knew how to make an assigning editor’s job a little bit easier. So, coming in the second time it was a different story and I knew more of what I needed to know to be successful.”
Cross shared with us some of what she’s learned about making it as a freelance writer.
Be an expert
Specialize in something says Cross, then leverage it and make it part of your personal branding. “I know we don’t like to be pigeonholed, but it’s very helpful for an editor to know that you’re an expert on XYZ. Using myself as an example, I woke up one day and realized that I had been an athlete for almost my entire life and I had never written about sports,” Cross said. “I also had a lot of experience as a cyclist. I was a trained mountain bike coach. I coached women’s clinics and I had been around the sport for a number of years and so I thought, I should be pitching to Bicycling Magazine and Bike Magazine, and so I kind of created a little niche for myself in covering cycling for Bicycling, Bike and Outside Magazine.”
Of course, you can continue to build on and expand your areas of expertise, too. Right now, Cross is leveraging what she’s learned about fly fishing into another writing path.
Perfect your pitch
Cross says success often starts with understanding the publications that you’ll be pitching. “You have to have read them. You have to know what kind of story makes it a story for that magazine. It also helps to know what columns are assigned out to freelance and which are done in-house. I haven’t looked at this site in a while but Mediabistro is a great site that I think you have to pay a subscription fee to access some of their content, but they do a lot of classes that are taught by working journalists and freelancers, and they’re a great resource if you’re trying to get out there and freelance.”
Cross says every outlet she’s ever worked for has had its own preferences. “Like some magazines say don’t ever send me an attachment; send me everything in the body of an email. Others say don’t ever follow up with phone calls.”
If you’re pitching a long-form feature, Cross said you’re most likely going to have to make a real investment in time and effort before you ever even make the first contact. “I think it pays to have pre-reported the story to the point where you know you have access to whatever sources you need to get in touch with to make the story happen.”
And don’t discount the need for timeliness says Cross. “You should, ideally, have a news hook. Some magazines are really really strict about wanting some sort of news peg.”
For example, a pitch for a feature about a chef may get a better reception if the chef will soon open a new restaurant — but not too soon. “It’s really helpful to know the lead time of the magazine,” Cross said. “Most magazines have a lead time of at least four months, so it doesn’t do you any good to pitch a story that is relevant two months from now, because that issue might already have shipped to the printer. I’m always trying to think like six months out.”
Multitask for money
Freelancing will be easier if you have built up a cash reserve before you dive in, according to Cross.
“You have to be prepared not to get paid for some months. That can be a scary thing. And sometimes the checks don’t come in a predictable way. If normally you get paid four months later, it doesn’t always happen that way. Things get delayed and that’s when it gets kind of dicey,” Cross said. “Right now, I’m dealing with a magazine that hasn’t paid me for stories that ran six and twelve months ago. They’re a regular client, so it’s really frustrating.”
Her solution is to have a number of stories going at every given moment. “Usually I have about eight things going at once. One of them might be a book project. One of them might be a regularly occurring piece for a regular client, where I just know that once a month I’m going to have to turn in this piece. That really kind of helps smooth out the natural feasts and famines, ups and downs of the freelancing because you might get one big feature a year or a couple of big features a year, but they might land on the same month like they did last year, which was kind of crazy.”
Having a stockpile of money also helps pay for the expenses of reporting, if you have to travel, for example. Cross also offered a bit of guidance on the size of a freelancer’s paycheck. “You might get $75 to $100 for a blog post, but if you can do a blog post a week, that’s $5200 for the year. If you’re working for a big national glossy, it’s usually between one dollar and three dollars a word, which sounds awesome until you factor in all the things we just talked about and the fact that those stories can be the hardest to get.”
Cross recommends a book she used early on in her career called Writer’s Market, which comes out in a new edition every year and offers insights into the current state of freelance writing. Cross does see the freelance market as changing, with fewer opportunities available within traditional print publications.
“So, I think that there’s just kind of a shift happening where entities that assign stories are figuring out how to do this online thing. There’s always going to be a market for stories and storytelling. It’s just that how we tell stories is changing and so we have to adapt for that. But I do think there’s always going to be a hunger for stories whether those are told in long-form, narrative online or in movie form, it’s just changing.”