The Time My "Fun and Easy" Side Gig Completely Backfired on Me
Several years ago, I reached out to one of my contacts and asked her for her candid thoughts on being a full-time freelance writer and editor. Claudine, who had at least a decade’s worth of experience on me, did not have encouraging things to say about the career path: “Unless you have a giant bank account balance (or can handle being super broke), I would not recommend it just yet,” she said.
She was right; it was too soon. I needed more experience, and I needed a steady paycheck. But I could start doing some work on the side in addition to my full-time salary-plus-benefits gig. And so I started pitching and writing.
I found that I really loved the pieces I was working on, and why shouldn’t I? They weren’t so much assignments as things I longed to write. They were my stories, many of them personal. You might say there was even a certain cathartic process to the practice. Nothing felt better to me than when I wrapped up a piece with just the right conclusion. I never missed a deadline (something that gave me great satisfaction), and I got to work with some super talented editors, who made my work the best it could be. I’d heard that the rejection part of pitching was a bear, but rarely did an idea I ever presented get rebuked. That, in and of itself, was a cool feeling—maybe more so than sitting down to write, at least during especially busy weeks.
Then came the rude awakening.
As I learned, being a freelancer means jumping through hoops. Lots and lots of hoops. Almost always, it involves stalking, or if you prefer, following up again, and again, and then again. You have to really, really want to get paid because, trust me, no one is going to fall over himself to make sure you are.
I came face-to-face with this reality this past fall. Previous experiences hadn’t been so brutal, typically involving just one or two “Where’s my money?” emails. And because I count on my salary to pay my bills and buy groceries, I was, fortunately, not likely to bounce any checks on account of past-due payments. But that’s not nearly the same thing as saying I don’t care if I get paid. I signed a contract, I completed an assignment, and I deserved the paycheck.
And I recently discovered how far I was willing to go to make that point. That $100 point.
It started when I followed up on payment for a piece I’d invoiced over a month prior. Per an automated reply from the editor I’d been working with, I emailed the organization’s billing department and was told that, as I may know, “The business is currently experiencing some challenges that have limited our available cash flow. We are exploring options to address these limitations and appreciate your patience and cooperation while we work through this period.”
It was a pleasant enough email, and I’m a compassionate person, but, frankly, I don’t give a fig about its cash-flow issues. Not my problem. I responded a bit more politely than that, however, hoping to keep the conversation going and my payment coming.
When I followed up a week later, I was told to check in the following week.
Once a week for the next several weeks, I did just that. Nobody responded. That’s when I took to LinkedIn. In a bold but not, I don’t think, wildly out-of-line move, I reached out to the editor. Apologizing profusely for bothering her and wishing her well wherever she was working now, I asked her if she could point me in the right direction. Did she know of anyone I could reach out to to help me resolve the matter?
To her credit (and my surprise), she responded with her own apologies, shocked at the situation that had transpired following major layoffs at the organization. At her suggestion, I emailed the sales department. I almost yelped with delight when someone emailed me back immediately, offering another apology and a firm promise: “If you send me the invoice I will personally make sure this is attended to ASAP. In the meantime, please let me know if there is anything additional I can do and/or provide.”
I was so relieved! I was going to get paid for this piece, at long last! That $100 was mine!
But, go figure, I never heard from anyone, and I never received a check or confirmation that my invoice was being processed.
“Hi Stacey,” the woman I’d been corresponding with wrote, “Happy Friday. As promised, I passed your info and invoice on to accounting as well as my management to be handled. I was told they would be reaching out ASAP so please keep me posted and I will follow up again if necessary to help get this resolved for you. In the meantime, have a great weekend!”
I let 10 days go by, busy at work and in life, before reaching out again. My email was met with another round of apologies and yet another promise that it would be looked into. I often felt like I was on the phone with a customer service agent, complaining about something and feeling the anger rise in my voice while trying to remember that it wasn’t the representative’s fault that my flight had gotten cancelled.
Eventually, I tried a different tactic and sent the following: “I'm wondering if it wouldn't be more effective to file a claim with small claims court? I have yet to hear from anyone in accounting, and, frankly, this is unacceptable. I signed a contract, had my piece published, and I deserve to be compensated accordingly.”
It got someone’s attention because about a half hour later, I received an email from the site’s in-house counsel, informing me that my payment would be processed this week. Less than 10 business days later, the check arrived.
At this time, I’m not waiting for any other invoices to be filled, and I don’t owe any editors anything. While it wasn’t nearly entirely about the money, it was an undeniable factor for me as I’m at a point in my life where I just don’t have the time to work for free. That's not to say that you shouldn't explore your options if they don't entail big bucks (especially if you're doing this in an effort to build out your skill set), but rather that when you embark up on your side gig you should check in with yourself as to why you want to do it. For me, it was a fun outlet that gave me a little extra spending money each month. And when it was suddenly no longer that, it was no longer worth it.
We say it a lot, but it’s worth repeating: The bottom line is that you have to do what’s right for you. If your side gig becomes annoying or beyond stressful, you might want to reevaluate why you’re doing it. Yes, there will be challenges, but they shouldn't be so insurmountable that you end up like me, threatening legal action. That's the great thing about taking one of these projects on—unlike your full-time job, you have complete control over how it plays out.
Stacey Lastoe is the Senior Editor/Writer of The Muse. She started writing short stories in the second grade and is immensely grateful to have the opportunity to write and edit professionally. Her work has appeared in YouBeauty, Refinery29, A Practical Wedding, Runner's World online, and The Billfold among other publications. She enjoys running and eating in equal measure and lives with her husband and dog in Brooklyn. All three of them are avid New York Mets fans. Say hello on @stacespeaks.More from this Author