That response to my concerns that leaving a well-paying, full-time job to freelance write was completely bonkers was all the support I needed to hear. Within a month, I had officially put in my notice and decided to freelance write full-time, a term that I would soon learn is the ultimate oxymoron.
Nine months later, I'm successfully supporting myself on a salary procured by freelance writing for multiple publications and feeling like my father was right — despite what mainstream society, school counselors, and most parents (aka, those who aren't eccentric artists, like mine) tell us.
Finding the footing to sustain a career of freelance writing isn't easy, but it's also not impossible. Or insane. And if you're going to take the leap, these keys to success will help you land on your feet.
While I do recommend freelance writing as a career, I would definitely not recommend waking up one day and quitting your job without a plan. Two important reasons that I was able to take this risk without dissolving into a complete stress head is that I had a significant amount of money saved up beforehand, and I had previous connections to the freelance world. Having at least a couple months' rent in your bank account will ensure that you have a buffer period to lock in your client base and get into the groove of such a huge adjustment. Additionally, start reaching out to publications you currently — or hope to — work with, and let them know that you're planning to make this change. This way, you’ll have an idea of your workload and client roster before you actually dive in.
The key to getting freelance writing jobs is, simply, writing. Whether this is for a blog you haven’t even shared with a lot of people, a school newspaper, or another online publication, there is no sample too small or insignificant. Just write. And write some more. And keep track of what you're writing. Cultivate a portfolio of samples you can be proud of, on topics you care about, and you will instantly have an edge up on much of your competition.
Is there a publication you've been dying to write for but never seems to be hiring? Craft an engaging email, and send it off to the closest applicable email(s) you can find online. Be strategic about who you’re reaching out to — the editor in chief's email may be listed online, but there's a good chance you won’t ever hear back. Instead, target editors that work specifically in the vertical or verticals you’re looking to write for. If their emails aren’t listed online, find one that is and use the email structure (i.e. first initial, last name) to reach out to the appropriate person. Even if they're not looking to expand their freelance portfolio right now, it never hurts to put yourself on their radar for the future.
Searching for freelance jobs can pretty much be a full-time career and in and of itself. Instead of navigating the deep, dark well of large job sites alone, be strategic and find newsletters and websites that cater specifically to editorial careers. I'm personally a fan of the Brian Scott Morning Coffee Newsletter from FreelanceWriting.com, Ed2010.com and its accompanying Twitter feed, and the All Indie Writers job board, which breaks down listings in clear terms. If you are more comfortable using more general job board sites, try setting keyword searches for "writing" or "freelance writing" jobs, which will then be emailed to you on whichever schedule you choose.
Whether it's with your editors, PR agencies, or other freelancers, make friends! It can be hard to develop personal connections with people when both sides are communicating from behind a computer screen, so put in some extra effort to get to know the people you're crossing e-paths with. The more people in the freelance world like you and like your work, the more jobs and assignments you’re likely to get in the future.
Most people who make a living as a freelance writer have some sort of contract position. This type of position usually lasts anywhere from four to six months, but can often be continued longer and is generally fairly noncommittal. The terms vary greatly between publications — some contract positions are for a single vertical, while others may require working in a more general category, like lifestyle. Some require a certain number of hours or schedule per week, while others are more flexible and allow you to work on your own terms. Either way, contract positions are a great way to have a certain amount of reliable income that you know you’ll be receiving monthly, weekly, or even daily — relieving some of the pressure that can come with hustling 24/7 for your next paycheck.
Though the whole not-having-a-set-schedule part of freelance writing would definitely be on most people's "pros" list, it also means that you won't have your standard evenings and weekends free. This, combined with the fact that you likely are obsessed with what you do (you kind of have to be to take this risk), can sometimes lead to unintentionally overworking yourself . . . and not realizing it until it’s 3 a.m. on a Friday night in front of your computer and you realize you haven’t taken a day off in as long as you can remember. It happens, guys. Make sure to set aside some time a week to get away from your screen and put work aside — nobody wants to hire a worker that’s a burned-out space case.
One of the most common questions I get is, "how do you get anything done?" Between school and more typical full-time jobs, we're all pretty used to being told what to do, as well as how and when to do it. With freelancing, this all goes out the window — you'll need to be completely self-motivated, something that can seem daunting for those who haven’t done this type of work before. But motivating and regulating yourself is far easier when it's work that you want to do and feels different when it's according to your own system of organization and scheduling. Don't work well in the mornings? Sleep in and work late. More auditory than visual? Leave yourself voice notes. Sick? Take a day off and work extra hard when you're better. Find a system that suits you, and you won't feel like it's a burden.
People often ask me what my average day looks like, assuming that not having a desk job means I don't have any type of schedule. While I don't have a schedule imposed upon me by an employer, I’ve found that it's helpful to settle into a general ebb-and-flow of your day-to-day. Whether that means trying to wake up around the same time, working the same chunk of hours, or heading to a coffee shop every morning, find something that feels comfortable and work it into your routine. While this may sound counterintuitive, it will feel comfortable rather than stifling, since it's both self-imposed and flexible. Your job isn't at risk if you oversleep or change things up, but maintaining even a loose sense of stability will help you stay on track.
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10Find Your Perfect Workspace
Image Source: Orion Pictures
Don't worry, a freelance writer's workspace looks quite different than that which you're likely used to. When you first start, I suggest trying out a variety of spots: different coffee shops, libraries, co-working spaces, and/or your own home, depending on your desk setup. Whichever one (or two) you like the best — those that feel the most comfortable, have the best WiFi, and most caffeinated drinks, obviously — should be your go-to. This doesn't necessarily have to be the only place you work, but having a plan can relieve unnecessary stress and time wasted driving around or contemplating your next move.
Above all, you need to love what you do. Freelance writing may sound like a dream job — and, in many ways, it is — but it will feel like a struggle if it's not where your heart is. You will need to self-regulate, hustle, chase jobs, make connections, and, at the end of it all, continue to work your butt off. If you love writing and are passionate about it, there’s a good chance you'll often ask yourself how you could possibly get paid to have so much fun.
