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The Challenges of Freelance Writing

I’ve been freelance writing for magazines like Woman’s Day, Men’s Health, and Parents (and their accompanying websites) for a couple of years now. Until last October, I was freelancing because I love to write. The extra cash went straight into our wedding fund, but it wasn’t something I needed to survive. (Although, it’s worth noting here that I began freelance writing about non-sports subjects on purpose when I realized I wanted a long-term career as a writer so that I would have a broader portfolio.)

In October, everything changed when my full-time position at ESPN as a sports business reporter ended. Now I’m earning the bulk of my money from freelance opportunities. Since I’m no longer exclusive to ESPN for sports, I’ve had the opportunity to write about sports business in a wide variety of places, from sports sites like SB Nation, to investment blogs The Motley Fool, and even political web magazine The Federalist. I’ve also been approached with editorial opportunities, like this one I wrote for SAP, a technology company transforming sports as we know it.

In addition, I’ve continued to write about everything from career advice to online dating for national magazines and their websites. I’ve also started writing for Bustle.com, a website for women that covers lifestyle, entertainment and fashion. Recently, I was asked to write press releases and blogs for a dating website. The same day I pitched myself for a piece on cloud computing in a home remodeling magazine.

While my personal expertise is in sports business, specifically college athletics, my research and writing skills allow me to write about anything. Which, has its advantages and disadvantages….

There are some amazing things about being a freelance writer. I make my own schedule. I propose or handpick every assignment I add to my workload. I get to meet interesting people in every imaginable industry as I write about a wide variety of topics. In one piece I get to be snarky, and in the next I’m explaining complex legal issues.

It’s not all sunshine and rainbows, however. If you’re considering trying to make a go at being a freelance writer, consider whether you’re ready to tackle these challenges:

  • Different voices. Every publication/website has a distinct voice. You’ll have to adapt yours daily, and sometimes hourly, as you juggle assignments from different places. Last week I worked on two pieces in one day for two very different outlets: one required a hip/fun sort of vibe and one required a serious legal tone. I caught myself getting snarky in the legal piece and had to go back and edit it out before I sent it to my editor. 
  • Different styles. You’ll also need to keep up with style guidelines for each website. Maybe one prefers you spell out “percent” and another wants you to use the “%” symbol. Editors will get annoyed if you repeatedly make the same mistakes, so you can’t just count on them to adjust it to their style. You’ll need to keep track somehow.
  • Bookkeeping. Last week, I worked on pieces for five different outlets. Each handles paying me differently; some require invoices and some automatically deposit into an account I can access online and withdraw funds into my bank account. Those that require invoices all have a very specific way I have to submit my invoice. Some pay within a week or two. Others routinely take two to three months. I have one company that hasn’t paid me from an invoice I sent in October and I’ve now had to follow up twice.
  • Organization. To deal with that last issue you have to be ultra organized. I keep track of jobs in two places, tracking pieces I’ve been assigned, whether I’ve completed the assignment, if I’ve sent an invoice for the job and when/if I was paid. As if that’s not enough to keep track of, I also keep a spreadsheet with every pitch I make to an editor. I list the date, publication, editor and pitch. If the editor turns down the assignment, I keep track of the reason they gave to improve future pitches. For example, if the editor tells me they never use freelancers for relationship pieces, that’s important for me to note. I also leave a column for a follow-up date in case I don’t hear from the editor. Generally speaking, you don’t want to pitch the same idea to more than one editor at a time. For most of my non-sports work I give editors two weeks to respond. I always state in the follow-up email that I need an answer because I want to pitch to another outlet, which usually elicits a response. I include a date by which I’ll move on (usually a couple of weeks, unless it’s time sensitive) if I don’t hear from them.
  • Time Management. This one won’t be as tough if you’ve worked at home previously, but if this is your first foray into working from home, you should ask yourself if you really have the discipline to do so. There are days I have to force myself to walk past a full kitchen sink or avoid the laundry room, because I know if I start doing chores around the house I’ll never complete my work on time. It’s easy to feel like you should be doing household chores simply because you’re at home. While I do have days when I can stop and do a load of laundry or clean the kitchen, I also have to avoid the distraction when I have an impending deadline. In addition, you have to avoid the urge to procrastinate when you’re given a deadline that’s weeks or months away. Trust me, it’ll sneak up on you.
  • Patience. When I have a great idea, I can’t wait to write about it. Unfortunately, it can take editors days or weeks to get back to you with the go-ahead, depending on the publication and your relationship with the editor. To make matters worse, as I already explained, you generally aren’t supposed to pitch an idea to more than one outlet at a time…which means you have to wait for one outlet to pass before you move to the next. This was a tough pill to swallow when I was only freelancing on non-sports topics, but now that I pitch sports pieces it’s even more difficult. More often than not, my sports pitches are based on current events. There’s nothing more frustrating than sending a time-sensitive idea to an editor only to have him (interesting note: I’ve never once had a female editor on a sports piece) never respond. Then you have to decide how long to wait to follow up before you move on to the next outlet. It’s tough to freelance a truly time-sensitive piece.
  • Unpredictability. One week you might have 10 assignments and the next week none. An outlet might pay in two days or they might take two months. If you’re used to having a salaried job, this one is going to be a tough adjustment.
  • Variable workweek. This one isn’t unique to freelancing – I didn’t have normal work weeks when I was writing full-time for ESPN either. It can be a blessing or a curse. I rarely go an entire weekend without working. In fact, the only reason I can remember a weekend when I didn’t work was because I had my bachelorette party over an entire weekend recently. Otherwise, I can’t remember the last weekend I didn’t work. It might only be a couple of hours here or there, but I always seem to find something to work on over the weekend, especially if I have a Monday or Tuesday deadline hanging over my head.
  • Valuing your services. This one might be the toughest. I’ve been offered everything from $20 to $2,400 for freelance pieces (and there wasn’t that big of a difference between the length of those pieces). I’ve had one magazine offer me half what another routinely pays me for nearly the exact same blog. There is no real industry standard, especially when it comes to work that lives on the web. I have a hard time saying no, but I’ve had to learn to value my services in a way that allows me to make a living at this. No doubt, the worst is writing for a new outlet or client and having them ask you to quote a price. It’s incredibly difficult, because similar outlets often have vastly different budgets. If an editor agrees to my price without negotiating, I worry I undersold myself. If I price myself too high, I might lose the job to another freelancer with lower rates.
  • Finding work. Ok, maybe this one is the toughest. As a freelancer, you’ll probably spend a great deal of time figuring out who to pitch. The majority of places I’ve wanted to pitch didn’t list the editors or their email addresses, so I had to do some investigative work to track them down. Then, after you spend all that time determining who to pitch, they might turn down your idea in less time than it took you to find them. Now you have to go find somewhere else to pitch your idea or come up with a new idea for that editor. Some days, I feel like I spend as much time pitching as I do actually writing – and probably 75 percent of those pitches don’t turn into paying jobs. (Once I write for a publication several times and get to know the editor my success rate is around 90 percent, but I’m constantly looking for new opportunities and pitching new outlets, so my overall success rate is much lower.)

Any questions about freelance writing? Leave a comment, and I’ll answer anything I can.

One Response to "The Challenges of Freelance Writing"

  • ifeanyi egede
    Monday, June 23, 2014 - 4:17 pm Reply

    Nice piece yo wrote up there. I’m a freelance football/sports writer. How do I get more clients? Can you outsource some of your football/sports writing gigs to me?

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