1. Never say no.

I can count on one hand the number of times I’ve turned down an article offer or failed to submit something in a call for pitches. Just the other day, I received a call for submissions from an up-and-coming travel website for which I really want to write. Despite having my hands full, I’ve just about got my pitch together. Why? Because I rarely turn down paid work. The more you write, the more capable of a writer you become and, duh, the more money you make.

Here’s a top-of-mind list of some of the work I’ve written for pay and what I learned:

  • Ghostwriting health-related columns about probiotics — I don’t even recall what probiotics are other than they’re in yogurt and I love yogurt, but I learned how to research an unknown-to-me topic and match a previous ghostwriter’s voice. Also, ghostwriting pays hella good.
  • Non-bylined SEO copy — I learned a ton about SEO writing at this gig, stuff I still apply to articles and headlines to this day. I also learned how to naturally incorporate robotic SEO-friendly phrases into something a human could read, understand, and perhaps even enjoy. This headline is a decent example — can you spot the SEO juice?
  • Non-bylined website copy — As the low man on the editorial totem pole, I wrote damn-near every non-article word for a now-defunct travel magazine’s website. Know what’s not fun? Finding 15 different ways to describe 15 different backpacks that are all essentially the same. But that paled in comparison to…
  • Multi-source community news reporting — Being a newspaper reporter is perhaps the hardest job in all of media. The pay is crap, someone’s always pissed at you, and the churn and burn is unbelievable. (Take some time today and go thank your local newspaper’s reporting team. Hint: they like pizza.) I learned how to complete multi-sourced news articles on a daily deadline, which roughly equated to finishing two byline pieces a day that required interviewing five-to-seven people, attending a meeting, sifting through multiple press releases, answering multiple angry phone calls, posting a brief or two, following up with something on the police scanner — all by about 5pm every day. Oh, and don’t forget “maintaining my social media presence.”
2. Learn the art of editing.

I remember receiving my first four-figure payday for an article like it was yesterday. Instead of feeling a sense of accomplishment, I suddenly felt overwhelmingly insecure. It took me months of writing and rewriting, pitching, querying, groveling, and then waiting…90 days after publication to receive my check. It dawned on me that to live even a basic middle-class lifestyle, I’d need to publish about 10 four-figure features every year. That seemed impossible, and it damn-near is, as only a handful of freelance writers earn a five-figure income from article writing alone.

I realized that I had to get on staff, and to do that, I had to become not just a writer, but an editor. So, I took more technical writing classes, brushed up on different journalistic styles, and offered to work with anyone who needed an editor. My first editing gig was editing a monthly newsletter for a small, nonprofit environmental organization for $25 a month. I worked with volunteer writers who were all awful writers, but I worked my butt off (way too hard for $25) and learned how to squeeze the most out of every writer.

Learning to edit also makes you a better writer. I spent two years on a newspaper copy desk editing thousands of words of copy every night doing the most banal kind of editing — line edits, proofreading, fact-checking, AP styling. But you know what? My copy is cleaner than it’s ever been and my editors appreciate that.

3. Surround yourself with awesome writers and learn from them.

I’ve been blessed to work with a myriad of accomplished writers and editors — men and women with Pulitzers, Lowells, NMAs, and all sorts of financial and critical successes. Through our interactions and direct mentoring, I learned what makes them successful and applied those lessons to my career.

If you’re not already in the game or you’re working with people below your level, then this may take joining a writing group, doing an internship, freelancing for free or cheap, or taking a writing class. Whatever it takes, surrounding yourself — be it physically or virtually — with awesome writers will put you in a position to learn from more experienced and more knowledgeable scribes. But it doesn’t happen through osmosis — you’ve got to pick their brains, read everything they write, study how they write it, note their work habits, seek their counsel, solicit their feedback, and proactively extract their skills and advice.

4. Be disciplined.

If you want to be a writer, write every day. Make it your full-time job even if you already have a full-time job. Between Matador, another major client, and a few small clients, I regularly bill 70-hour weeks. Five-to-six days a week and about 46 weeks a year, I’m at my laptop from 7am to 7pm (minus the occasional powder day), if not longer. My editors know and value the commitment I make to my work.

It’s a matter of discipline — are you disciplined enough to sit and write for hours and hours at a time about subjects you may or may not feel passionate about? If not, quit now and don’t waste your time because you’re not a professional writer.

Writing is not something I do to unleash my creativity or exorcise my inner demons — it’s how I put food on my family’s table. It’s how I live, son! But I love it, and having been around the world and worked many shitty non-writing jobs, I know how privileged I am to write and edit for a living.

5. Treat writing as a trade, not a craft.

I don’t give a hoot what your writing instructors or professors have told you about “honing your craft,” because it’s a bunch of bullshit. Writing, like carpentry or plumbing, is a trade, something that is learned, applied, and constantly relearned. Sure, it’s sexier than installing a toilet and more creative than hanging crown moulding, but, at its essence, writing is a trade and the best writers began their careers with that understanding. If you’ve got it, truly got IT, then your writing can blossom into an art. Stripped to its core though, a trade — a skill learned and applied — it will always remain.

Since childhood, my father taught me the importance of being able to build things with my bare hands and how to work hard outside. We dug ditches, put up drywall, framed rooms, graded driveways, hung trim, replaced siding, cleaned gutters — like the post office, rain or shine. I hated every minute of it, and my upper-class-white-bread-suburban friends (most of whom’s fathers didn’t own a hammer, let alone know how to lay out a stud wall 16” OC) thought we were some sort of freaks for doing it. “Why don’t you pay someone to do it?” they’d ask. I shrugged, “I dunno, pops is cheap,” (which he is).

But it wasn’t just that my dad didn’t want to pay a tradesman, even if he could afford the best around. It was about him imparting the value of hard work, teaching what it takes to accomplish a difficult task, and making me realize that you’ve got to work hard for everything in this life — nothing is given to you. Learn how to work hard at the hardest of jobs, apply that ethic to whatever you want to do in life, and you’ll be successful.

In my 20s it all clicked and I applied those lessons to my work. I treated writing and editing like a trade, got up early every morning, packed my lunch pail, and busted my ass all day writing and learning how to become a better writer.

You’ve got to work hard, but you’ve also got to know when…

6. It’s okay to step away from the laptop.

Some of my best ideas come to me when I’m out on the trail or slopes. When my back aches, my carpal tunnel is acting up, I’m frustrated, and my eyes are blurry from so much screentime, I turn everything off and go outside. It may just be to putter in my workshop for an hour, walk my dog, or go for a quick hike, but realizing when it’s more productive to stop working has made me a better writer. I find that an hour of play equals many more hours of productive writing, and is, therefore, a lucrative trade.

7. Be brave.

Early in my career, I actively avoided injecting opinions into my work, probably as a result of my journalism training. I diluted my thoughts, hoping to cast a wide net, but that hamstrung my voice and left my writing feeling hollow. It had no guts; it incited no emotion. My writing was straight-up boring.

I was working with my editor on a piece and I just couldn’t bring myself to state the obvious about a certain group of people for fear I’d offend them. I finally admitted that I didn’t want to offend them, and the editor looked at me like I’d just jumped out the window. He said something like, “You’re a writer Rory! You’re supposed to be hated and loved, but, my god man, you don’t want them indifferent to you! If they don’t care, then you won’t make it. Do you want this piece published or not?”

I wanted it published, got it published, and have never been afraid since.

8. Clarity, honesty, and brevity trump all.

Even though I grew up on a steady diet of Hemingway, somewhere in my development as a writer I lost touch with how the majority of people read and how to write for them. It’s all about clarity, honesty, and brevity.

  • Clarity. Don’t dance around a statement. Come right out and say it. Even if that means your first draft isn’t exquisitely written, you can always go back and rewrite once you have the main idea spilled onto the page. All those great writers and editors I’ve worked with share one thing in common, despite their diverse writing styles: they don’t beat around the bush. They go for it, kill shot every time. That’s what I strive for.
  • Honesty. Don’t stretch the truth. Don’t lie to your audience. Don’t feign authenticity — your audience is a pack of lurking hyenas who can smell deceit and fraud a mile away (ironic coming from a former ghostwriter, amirite?). Don’t fill holes in your story. Keep ample, detailed notes. I’m working on a story now about a trip I took 10 years ago and that wouldn’t be possible if I hadn’t taken copious notes with times, dates, names, location descriptions, and verbatim quotes. While my laptop is my cooking implement, my moleskines (and, increasingly, my iphone) are my hunting and gathering tools.
  • Brevity. Numerous studies have shown that most readers don’t actually read, they scan. Successful publications — be they online or on dead trees — know this and publish thusly. That habit is only increasing as the web feeds readers a firehose of information in their social streams, RSS readers, Google News headlines, etc. Hook your readers in the first paragraph, tell them why they should give a shit in the second, and don’t waste a goddamn word the rest of the piece. Every single word must have a justification, a raison d’être. If not, cut it and don’t look back. Now more than ever, you’ve got to be mercenary about every single word because your audience is a simple click from leaving forever and without an audience, you’re not a writer.