How to Make It as a Freelance Writer

Mark Twain wouldn’t have lasted one minute in this place.

By Raf Miastkowski /// @RafFoSho

When talking with writers about writing, one will invariably hear them complain about it. Clearly writing isn’t brain surgery or teaching an ostrich how to ride a tandem bike, but there’s something about it that just reeks of tedium. Whether it’s the actual task, the administrative side of the work, the deadlines, or the fact that it feels like you’ve signed on to do homework for the rest of your life — it’s just a prime job to gripe about.

It can also be a tough career to get into. Chances are not a single one of the English or creative-lit courses that you took in college ever taught you anything about how to actually use writing to make a damn dollar. (Thanks, college.) That’s why over the years, I’ve had several friends, and friends of friends, ask me for tips on how to turn writing into a job. Posed with this question, here’s an excerpt from an email that I wrote sometime in 2014:

Writing in the Internet age is a crucible; it is a trying road marked by beautiful, reassuring successes and relentless rejection.
It took me years to figure out that I wanted to write, and then it took some more time to figure out that writing books or stories or poetry was not the way to go for me. After determining that I wanted to write for magazines, I started interning — first at The Onion and then at Time Out Chicago. I was optimistic, but at both publications it was clear that there would be no positions opening up. Both had massive layoffs around 2009. Both shuttered their print operations in the past few years. I had to adjust my expectations.
Shortly after, when I was a freelance writer for a local publication — one that had my contact information in their database so that they could send me checks with a modicum of efficiency — I couldn’t get editors to respond to my pitch emails. I still can’t get editors to respond to my pitch emails. It can be maddening, and sometimes I still feel like I’m trapped in a Sisyphean daydream. Voltaire wrote something about God being a comedian, performing for an audience too afraid to laugh. I try to laugh.
I’m being a bit dramatic, but as a job, writing is dying. It’s going to be hard. It may also be worth it.
Seeing your name on a piece that you edited and re-edited and was finally satisfied with is a fantastic feeling. Getting a paycheck for visiting a place and crafting a story is a fantastic feeling. I’m sure you’ve figured this part out, or you wouldn’t have emailed me.
I wish someone would have given me real, practical advice when I started out. Nothing complex. Just simple tips that would have helped me get started. So, here are some of those:
-Do you know what kind of writing you’d like to do? Writing is not just magazines and books. It sure as hell isn’t writing for newspapers, because most of those will probably be dead within ten years. People also write for companies and ad agencies and Twitter accounts. I know for a fact that bloggers with around 1500 Twitter followers charge companies at least $50–$75 per post to feature products. It’s a smart idea to consider those gigs. During my time as a copywriter at a startup, I made a decent salary. In general, writing for companies is more profitable than writing for publications. You’ll probably make more money for work that’s more boring, such as writing for B2B medical-supplies journals.
-You’ll need to score a gig first, and then build experience and clips. Starting an online portfolio is probably a good idea. Take screengrabs for your portfolio, because online links tend to go dead after a few years, and you could lose your work in the graveyard of cyberspace.
-If you’re applying for jobs and you don’t have a lot of experience, focus on job applications that require you to perform writing exercises. These companies are more likely to hire someone with skills, rather than someone with a fancy resume. It’s an easier way to get your foot in the door.
-Another way to get your foot in the door is to write for free to build up that portfolio. You could contribute to a website, or try an internship. It’s nice to write for a site that matches your interests. It’s not about followers or likes, it’s about getting some good writing on a page, and then later sharing it with potential employers.
-I think you have to write for yourself, at least on the side. Write about things you want to. It’ll help keep you sane, and keep your writing sharp. I like to write about alleys. It’s dumb, but I don’t care. I like to do it.
Hope this helps.

Of course, there’s no manual on how to get started making money in this field, but it’s also surprising just how difficult it is to find practical advice on the topic. It seems that just a few actionable tips can lead to the avoidance of a lot of assfuckery. And that’s what I’d like to help with, which is why I gleaned some helpful advice from people who actually know what the hell they’re doing. So, pour two fingers of scotch, soak it all in, and disregard the paroxysms of self-doubt. Things are going to be fine.

“You’ll set yourself apart quickly if you a) get your work in on time, b) make sure it’s clean and factually accurate, and c) are a nice, respectful human being. Seems obvious, but it’s not always the case.”

Rachel Handler, News Editor at The Dissolve

“Find good editors who make your copy better and do anything they ask. Flatter them. Ask them to coffee for career advice even if you don’t want it. Pitch, offer, and beg to work for them. Then study their edits closely. Think hard about what they did to make your stories better. Until you start doing it yourself. Also, make your deadlines. You’d be surprised how many people don’t.”

Brandon Copple, Managing Editor at FitchInk

“Focus on getting in to a short list of publications, maybe even start with five. Read the publications, even if it’s just for a month and when you apply pitch the editor some dynamite stories with language and concepts that will fit right into what they’re doing. I am very relieved when I see a writer ‘gets us’ and doesn’t need much of an initiation process. If I know you can go on autopilot when I need you to, and you bring a fresh set of eyes and style to a piece that’s well-conceived and written, then I’m happy.”

Sean Cooley, Senior Editor at Thrillist

“As you work your way up, your first few paid gigs are likely to be short, and not show your range as a writer. So, paid or unpaid, write the pieces you want to have in your application to show your ability. Having great published work is awesome, but it can’t hurt to also include a wonderfully written unpublished piece. If you’re not getting your ideal paid assignments yet, then writing something a little longer or creatively demanding is good practice for you anyway, and will show employers that you’re ambitious, and if you’re capable of more demanding assignments. Plus, when employers are reviewing clips from a publication, they may wonder how much of it was the publication’s editorial voice, or an editor’s intervention, but with an unpublished piece there is no mistaking where the credit is due. However, notable turnoffs with this approach include when a piece was obviously an assignment from a college course, or of course, if it sucks, so don’t entirely forego an editorial process on unpublished material you apply with…get feedback.”

Aaron With, former Editor-in-Chief at Groupon

“Consider social media accounts, especially Twitter and Instagram, your new resume. Assigning editors will quickly do a scan of your accounts to see if you already have a loyal following and to gauge your creative style and expertise. Post regularly and always remember that your account, for better or for worse, could sway a hiring decision.”

Chris Aung-Thwin, News Editor at AskMen

“Be comfortable in the trenches. Write even if it’s for free. Write because you enjoy the craft. Take odd jobs. Experiment freely. Only when you keep at it is when writing pays dividends.”

Michael Nolledo, Chicago Editor at Insidehook

“Don’t be afraid to cold-pitch editors you’ve never met before if you have a great idea. The worst thing they can do is delete your email. Just remember to have a thick skin and never take being ignored personally.”

Amber Gibson, writer for Four Seasons Magazine, Hemispheres, Plate, and many others

“Make connections. Write to editors (pitch to them regularly), write to other writers (throw around ideas with them), contact publicists and ask for more information. If you want people hire you, you need to get your name out there.”

David Hammond, Dining & Drinking Editor at Newcity

“Write as many jokes as possible all the time. Don’t get discouraged when someone tells you that your joke is bad. Fear = paralysis. Never stop moving, LIKE A SHARK!”

Jennifer Jackson, headline contributor for The Onion

“Continue to practice while you wait. Writing ability atrophies like a neglected muscle group. Even if it’s not for something that involves a paycheck, keep after it, even if it’s just a 5–10 minute writing exercise. When it comes time to produce, you’ll thank yourself.”

Andy Carpenter, one-time owner of the second-best humor column in South Carolina with a circulation under 30,000