“What advice do you have for an aspiring writer?” is a question that any person who has been published fields inevitably at some point, not because of any particular success but because the field can seem so nebulous and impenetrable from the outside that those looking to get started are understandably often left grasping for any shred of concrete, useful information. Maybe this person, they imagine, will turn up a first step that is unequivocally right and will open up some imagined self-explanatory path. A path, for instance, that can lead into becoming a successful freelance writer.
As a person who has attempted to respond to this question, I find it hard to feel like my answers are very satisfying. Even more so than in the past, there is no particular path to follow or ladder to climb – a reality that is both liberating and more than a little terrifying. There might have been an easy answer at some point, but there definitely isn’t right now, as media companies launch and fold in the space of months, and ever-evolving media and platforms challenge the written word for consumers’ constantly shrinking attention spans.
Becoming a Successful Freelance Writer
When it comes to offering advice to freelance writers, the answers become still more complex. Most writers are freelance writers, and certainly even more start out that way – yet the current flux of the media landscape makes it tough to full-throatedly recommend the job to anyone, especially those who’d like to make a full-time living at it.
I was thrust back into full-time freelance work in 2020, when I was laid off like so many others due to my company’s financial concerns around the COVID-19 pandemic. Even with the connections I had made and clips I had from years as a staffer, it was still scary. But the combination of what I had built to that point and the skills and ideas that I had developed when I was just starting out has helped me keep finding not just work but new, exciting opportunities that I wouldn’t have had access to as a staffer – as well as a lot more flexibility. What follows are a few of the ideas I keep coming back to even as the industry changes.
1) Keep what you’re passionate about front and center – especially when you’re just starting out.
Whether you’re interested in writing fiction, nonfiction, investigative journalism, criticism, or anything else, your biggest asset as a writer is your specific point of view – the questions that you can ask and the answers you can dig up that no one else would think to pursue.
That’s why I recommend thinking of your work as two interconnected tracks. First, the opportunities that lend you credibility – ones that may not involve writing your dream project but allow you to work with a thoughtful editor or get your words seen by more people or, very importantly, put you in a better position to pay the bills. Second are the ideas that you just can’t get out of your head, that you feel driven to pursue even if everyone thinks they sound stupid.
I know my work has always had these two components from the beginning – honestly, whether I’ve had a staff role or not. But if you have never had anything published, it probably sounds like unusable advice. You want to know how to pitch, how to network with editors, what makes a piece salable. I think always keeping both considerations in mind, though, helps those things fall into place.
On my path to becoming a writer, I was looking for those concrete answers, too. That’s why I enrolled in Columbia Journalism School right after I received my bachelor’s degree. About six weeks later, I dropped out. Not because journalism school is bad or because Columbia’s specifically is bad or anything like that; but it just wasn’t right for me. I didn’t feel as though I was getting those answers that I came for – quite possibly because those answers don’t exist.
The only place I could find that would take me on as a writer was a Caribbean music blog, some distance away from my interest in jazz and American popular music but a chance to write (for free) all the same. My editor there was invested in my work and gave me chances to learn and experiment. This led to my first paid clip, a review of a dancehall album for NPR. I would put my work there in the first category, in that it helped me get my footing as a writer – and yet it was tied to the kind of historically grounded, well-contextualized work I wanted to do in other relatively niche music genres. At the same time, I was able to leverage those clips into chances to write for an affiliated jazz site (also for free), staying grounded in what got me into writing about music in the first place.
If I were starting again, I would tell myself to lean into that even more with a personal blog or newsletter. If you care about telling a story – care in the deepest, most personal way, not because it’s trendy or seems like it will find an audience – other people will care about reading it. It is undoubtedly a hustle trying to tell those stories while you’re working on just getting something published, but that is the part of the hustle that will pay dividends.
2) Get used to constantly reevaluating your personal time/money equation
Talking about “hustling,” of course, leads us to “hustle culture,” which is incredibly easy to fall victim to as a freelancer. Many rates haven’t changed since the ’90s (and in some cases the ’70s), making it harder than ever to rely on freelance work to survive. Ultimately, you have to decide what makes writing worth it for you and, specifically, which gigs are worthwhile. When I was starting out, I wrote a lot for free and worked as a bartender. That’s a lifestyle that can be tenable when you’re 23 (as I was) but may feel a lot less practical at 33 or 43. Writing is real work, and it takes time. Churning out rote blog posts for $20 a pop just so that when you Google your name something comes up may not take long to feel more draining than rewarding.
There’s no shame in enabling your writing with a day job, and unless you’re doing a pretty specific kind of journalism and ignoring direct conflicts of interest, no shame in doing the same with copywriting/marketing/public relations work. For me, the latter is something like my day job, despite the fact that it’s all freelance. The less I’m interested in the project, the more I charge – a necessity, after all, because it’s harder to invest in something you don’t care about as much, and writing, as I mentioned, is deeply personal even when you’re doing something as mechanical as typing up a press release. That work allows me to take on projects I really care about that might pay less.
Of course, you’re always searching for that dream assignment – the pitch you’ve been working on for ages landing at a visible publication that pays you more than you expect. But it’s a lot easier to hold out for that, and to stay energized to keep chasing it, if you don’t constantly feel like you’re pouring your heart out into a black hole.
3) Find your niche (and make it obvious)
One of the reasons that I felt so out of place in journalism school was that my interests lie mostly in what’s considered “soft news” – entertainment writing and criticism, as opposed to the “hard news” of, say, politics, commerce, or systemic inequality. Of course, there’s never been a clean divide between these two things, and the further along I got as a writer, the more I found myself needing some of the basic “hard news” skills to write my “soft news” stories – just as “hard news” journalists sometimes struggle to write about cultural context that might flesh out their stories.
But if I had continued in journalism school and wound up starting my career in a more traditional way – as a cub reporter at a local paper or TV affiliate – I might not have been able to hone in as easily on the things that fascinated me, the passions that now lead plenty of editors to my inbox because they know that I am a reliable voice on, for example, jazz, women’s college basketball, and country music. I didn’t start out as an expert on all those things, and, in fact, have come to the latter two over my years as a writer. But because I jumped into all of them headfirst, often fighting against skeptical editors every step of the way, I’ve been able to give my name a kind of associated shorthand. You just want an editor to have something, anything, where their knee-jerk response is, “Oh, we need [your name] for this.” Maybe it’s because of your location or your style, your in-depth knowledge of a niche industry or your knack for writing short stories with a particular bent.
Don’t limit yourself, but get specific – and advertise your niche, whether on your website or newsletter or on social media. Of course, Twitter and Instagram are double-edged swords and deserve plenty more caveats than recommendations. But I don’t think I would be writing about sports professionally if I hadn’t tweeted about them, a lot. To become a successful freelance writer, it comes back to being true to what you care about; people can suss out clout-chasing a mile away. Post as you write, with the intention of helping people better understand what exactly you’re about.
4) To become a successful freelance writer, don’t forget the basics
If you are not responsive, timely, and professional as a freelancer, you won’t get called again – and that makes it nearly impossible to begin a career in the field. It’s of a piece with the aforementioned advice about becoming an editor’s go-to for a topic. Another way to an editor’s heart is clean copy in by (or before!) a deadline, coupled with responsiveness to edits and emails. Especially if you’re in journalism, you want to be an editor’s first call when a story breaks and they need a time-sensitive follow-up, and the only way to earn that trust is by meeting those bare-minimum standards the first and every time.
I know as well (better?) than anyone what a bugbear procrastination can be, how deep the anxiety that fuels it (especially when writing about a topic you care about) goes. But done, as is so often said, is better than perfect – your editor can’t do their part of helping improve the piece and clarifying your points if they don’t have anything to work with.
The basics bring us back to that initial point, of making the foundation of your work the ideas and projects you care about. Especially as a freelancer, you’ll work way too hard to afford to get cynical about the work. If you can’t find a seed of joy in the process, whether it comes from sating your curiosity through research, speaking to people as a reporter, or the craft of writing itself, it’s just not worth doing. Tapping into your wildest flights of fancy, the most random rabbit holes, and most creative perspectives is the fruit of your labor – the byline is just a nice bonus.
Natalie Weiner is a Dallas-based freelance writer whose work has appeared in the New York Times, the Washington Post, Rolling Stone, Billboard, and NPR, among other publications. A selection of her work can be found at natalieweiner.com.
