Stop Reading Books on Writing! Use These 5 Freelance Writing Tips Instead

By Erin O’Neil

You know all those books you have on freelance writing? Put them away. Now. Stop reading them immediately. I’ve already read them for you.

I’m one of those people who loves research — perhaps a little too much. You might even call me a research evangelist. So when I embarked on a full-time writing career, I pored over every book I could find on the subject.

And there are a lot of books on freelance writing. Like, dozens. Hundreds. Many are highly recommended. Many are totally irrelevant. A large percentage are just plain boring. But sandwiched in between, you’ll find some overarching themes that can put you on the path to a successful and fulfilling writing career.

I don’t even want to know the amount of money I wasted purchasing books on writing freelance to glean information on inside tips and tricks of the trade. I refuse to delve that deeply into my order history. But there’s a silver lining to all of this. Because I spent weeks of my life reading over 100 books on freelancing, you won’t have to.

Derived from the best books on freelancing, use these 5 tips on being a freelance writer — and regain valuable time to do good work and get paid.

1. Jay-Z is a valuable business coach.

Some of the best advice on freelancing is best summed up in the immortal words of Jay-Z: “I’m not a businessman, I’m a business, man.”

You may not be wearing a suit and working a 9 to 5 every day, but as a freelance writer, you are a business. And you’d better start acting like one if you want to pay the bills and avoid living in a cardboard box.

This means organizing projects, invoices and payments effectively. As a business, you’re responsible for all the administrative tasks, the bookkeeping, the marketing — and delivering great work to your clients on deadline. It also means sticking to a daily schedule, showering regularly and banning sweatpants from your wardrobe.

The scariest word in the above paragraph for many freelancers is marketing. And yes, marketing your work may require hustling outside of the internet and your home. It may involve attending some initially awkward networking groups. Them’s the breaks.

Putting yourself out there and letting others know about your work doesn’t have to be fake or insincere. Marketing strategies can be as simple as taking a writer or editor you admire to coffee, or sending an e-mail to an editor you—ve worked with in the past saying “thank you.” Attach a sandwich board ad to your dog when taking her for a walk advertising your services. Whatever. Just market!

Once you get over the initial “awkward” feeling, marketing your business becomes much easier down the road. And if you want to be your own boss, marketing isn’t negotiable. You must do it.

2. Do your homework, then do it again.

One of the things I vastly underestimated when jumping into writing full-time was the amount of research. As a freelancer, your research often has nothing to do with fleshing out a story. Before you even think about hitting “send” on an e-mail query to an editor, you’d better have a good handle on the tone, target audience and subject matter of the magazine.

Essential for writer recon missions:

  • Find the target’s (potential client, company, magazine, etc.) website. Read everything, especially the “About” section or “mission statement” if they have one.
  • Take notes in some form on the tone, style and structure of the market. Download the press kit if available and add details on target readers, the current and future editorial calendars and the masthead. Keep these notes organized and available for future reference. You’ll need them when writing a query letter, or just for a pitch if you don’t query.
  • Click on some of the writer bios, if the site has them. Are they mostly staff writers, or are many articles written by freelancers? What sections would you like to pitch to?
  • Read everything on the website again, and archived articles if possible on magazine websites.

Basics for sending the actual query:

  • Do not ever send something to “ Ever. This is a black hole of death used to decrease the number of pitches editors have to wade through.
  • The website masthead is usually the most current and effective source for editor info.
  • It’s best not to send things to the head editor. Most publications have editors for specific sections of the magazine or site. Sleuth out the e-mail address if it isn’t listed (they usually are, though, except for top tier publications).

3. Use the force to kick negativity and bitterness in the ass.

A recurring theme in many books on writing, from novelists to magazine editors, is how essential it is to be persistent, take things in stride and remain positive. This is a tough industry, but not an impossible one. That being said, it’s easy to get discouraged along the way, which is a perfectly human reaction sometimes.

Just be wary of those negative inner thoughts dominating your brain. If you don’t keep them in check, they can become a self-fulfilling prophecy. If you never accept criticism on your work, it won’t ever get better, and it will limit your career. If you constantly think you aren’t good enough, or that everything is a lost cause, you’ll send out half-baked queries and pitches that never get a response.

Here’s a real life example of how negative thinking can kill your writing (and your career):

Over a year ago, I attended a meeting of a large writer’s organization. The members were primarily fiction authors working on novels. Part of the meeting involved discussing the stress and lack of confidence authors go through after having their manuscripts rejected (or worse yet, ignored).

One participant angrily recounted his ongoing struggle to get his book published. The plot involved a man and his dog. And then the unpublished author was out for blood.

In an extremely unsettling manner, this gentleman proceeded to actually take out hard copies of his rejection notices and dispute each of them on a case by case basis. He finally concluded his tirade, breathing heavily, with this:

“My book clearly wasn’t rejected because of the quality of the writing, but because editors and publishers are idiots and thought a book about a man and his dog wouldn’t sell. Well, look at “Marley and Me”! Look how that did! A bestseller! It’s a movie now! And they think my book isn’t worth publishing! Morons.”

Mr. Bitter-and-rejected didn’t seem to notice that many of us had quietly scooted our chairs away from him and glanced wistfully at the exit doors as he was speaking. And we all made sure not to cut him off as he was leaving the parking lot.

The angry guy at the meeting wasn’t a bad writer, but he wasn’t great, and the rejection letters were right: The book sounded boring. But he’d become so frustrated and bitter that he’d convinced himself the problem wasn’t him, it was everyone else.

If you find yourself doing this, take a step back. Go for a run. Put things in perspective. Don’t become so closed minded and bitter that your work and career suffer. Not to mention that thinking that way will probably make you miserable.

In more practical terms, get out of a negative thinking rut fast for this reason: Budding writers often don’t have great health insurance, and therapy is really expensive.

4. Play games with yourself (in a healthy way).

Rejection sucks, plain and simple. But you know what? Ninety-nine percent of writers get rejected. And I’m not referring to that old anecdote about Dr. Seuss, either. I’m talking about modern authors who went on to write bestselling novels and win awards.

In his book On Writing, Stephen King writes about tacking all of his rejection letters to the wall using a large metal spike (and he notes that he had to replace the spike several times to accommodate the large number of rejections).

David Foster Wallace, one of the most intelligent and talented writers of the past decade, taped all his rejection letters from magazines end on end throughout his office, like a DIY wallpaper project.

King, of course, is a household name. Wallace went on to win a MacArthur Genius Grant, and wrote novels and short stories that many critics consider to be some of the finest in postmodern literature. His books of short stories are largely compilations of essays published by magazines who initially rejected him.

What can humble writers like you and me learn from this? Plenty. Use rejection as inspiration to work harder and harder, like King did. View getting published as winning a game of strategy, as Wallace did. Rejections aren’t a bad thing. They mean you’re trying, and trying is probably more than 75% of the battle.

Jenna Glatzer had some great advice on this in her book Make a Real Living as a Freelance Writer. In a section about creating goals, Glatzer suggested creating a goal of receiving 10 rejections. When I first read this, I thought she was nuts. But then I realized what a brilliant suggestion it was. Getting 10 rejections means you’re playing the game, pitching and getting your work out there.

Don’t take rejections or a lack of response personally. Instead, turn it into a game you can win. Inbox filled with rejections? Send out more pitches. Not getting responses? Look over your old queries and see what you can re-work to fit the magazine.

5. Draw on experience, or just stuff you really like.

Before I became a writer, I worked in finance, pretty much two polar opposites. But through reading books on freelancing and finding a niche for my writing, I realized a way to make it work. There’s a big market for financial journalism, business writers and writers who know about mutual funds and hedge funds and estate planning.

If I can bridge the gap between my professional background (the finance industry) and writing, believe me, so can you.

So right off the bat, think of ways your unique background can help you establish street cred with publications and editors. Build that up first. Once you—ve gotten a few good clips under your belt, branch out. Do you love cooking, sports or travel? Write about them.

Writers who write on subjects they enjoy create articles that are engaging and fun to read. Your passion for your subject will shine through. And believe me, there’s a market for everything. Just crack open your copy of the Writer’s Market and browse through the trade magazines section. And then get to work!

Erin O’Neil is a freelance writer and financial journalist in Atlanta, Georgia, and does not live in a cardboard box. You can find her work sprinkled throughout various financial publications and trade magazines, or just visit her website at

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13 comments… add one
  • My priority is to get 7 rejection letters, then I start again, looking for another seven.

  • Kathy

    Great article. I took away a few tips! One thing I’d like to comment on though is the part about the guy at the conf with the rejections. Perhaps if those agents had told him his WRITING was boring instead of the story, he would have known how to fix it. I think that agents aren’t willing to tell a writer what they can do to improve their writing when really that is all a writer wants to know!

  • Rio H

    Best article I’ve read to date on this site: practical, thorough, succinct, direct and on-point in all directions. Thanks.

  • Christiano, that’s a really good way to look at things. It can help keep you motivated, too, because you’re constantly ramping up and cranking out query letters.

    And Rio, thanks! Practical was the goal. I hope it helps…the world needs more successful writers and less discouraged ones.

  • I have a trick which is a combination of #2 and #4 – when I receive a rejected query I revise it, send it to another editor, and send the editor who rejected it another query on a different article topic–all within 72 hours. This way there are always irons in the fire!

  • This post made me feel better because I AM doing most of these things regularly. I just need to focus on #1 and be consistent with everything. I need to sharpen my focus and my operations.

  • Erin, this piece is just amazing!

    I just can’t get the ten rejection idea out of my head. As some one who tends to get far, far more non-responses than rejections (according to my pitch tracking software), I can really get behind that advice. A rejection is a response. It means you have had the editor’s attention for at least a split second.

    It’s the blending of persistence and having a thick skin: if an editor hasn’t rejected you yet, you should probably reach out again about your pitch. Or send a new one. A high percentage of my assignments come from following up on a pitch or repitching when the first idea was already assigned or not quite right.

    • Gabi: Thank you! I love the ten rejection idea goal too… that tip comes courtesy of Jenna Glatzer. And yeah, exactly. A response means at least they took notice of the pitch (and hopefully your name). I think right now not getting a response is the norm, though.

      So much of it is persistence, and it’s really easy to get discouraged, another reason why sites like this one are so important!

      Tara: That’s smart, especially with a deadline on the turn around- it took me a long time to put that sort of thing into practice. But that way your research for a pitch isn’t ever wasted. Reduce, reuse, recycle, etc.

      Sarah: Just keep doing what you’re doing. It can be so discouraging and takes time, but it’s similar to the idea of starting a small business… slowly building momentum until finally work comes to you (or you aren’t freaking out about the electric bill, which was my goal for awhile).

      Mikeachim: You’re welcome, and thanks! Here’s how I look at the business angle: Being a good writer is a very valuable skill, and a very underestimated one. The media acts as though there are tens of thousands of Columbia J-school grads clawing and hissing to get $10/hour jobs. I really don’t think that’s the case. But starting out can be tough– to be honest, I can see why it would make sense to keep a full or part time job at first, if only for the health insurance.

      • Agreed, the popular media trades on extremes – and all too often, a horror story about how writers are a dying breed and there is no money to be made. This isn’t the case, but it’s true that if you don’t set yourself a base-level hourly rate and stick to it, it’s easy to do work that will slowly bankrupt you. Especially the “10 articles for $2 each” variety. Starting out can be tough, and keeping going tougher, but I don’t see it as any tougher than it’s been for the last few decades – and in many ways (eg. publishing to Kindle and so on) it’s a far more open market and a far more exciting time to throw yourself into commercial wordsmithing.

        The main thing is to be prepared to wear many, many hats as a writer. You need a bigger metaphorical hatstand. (Um. I may be losing control of this metaphor).

  • Regarding point 1, Danielle LaPorte told a friend of mine something that sunk deep into her – in essence, “you can’t do your legacy work if you starved to death last year”. Businesses earn money in order to make a profit, and they’re all about offering the world a service with confidence and integrity. For me, that’s been the hardest thing about going freelance – becoming professional about the business side instead of being the hobbyist I started out as.

    All your other points are bang on. But my fave by far is 4). Writers have minds that want to play (that’s why we’re so easily distracted). If we can fool ourselves into acting in a professional business manner by gamifying what we do, so it feels more like goofing around than a day in a virtual cubicle – then we really start to get somewhere. 😉

    Thanks for the fun & useful read!

  • This was awesome. Although I am still in the fight-your-demons stage, I appreciate this condensed version of all of those many books. The more experience I gain, the more I realize that those experiences out-value a few books here and there.

    Thanks for writing! 🙂

  • Everything a writer needs to know, packaged perfectly in a nut-shell. Plus, a a great read!

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