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Dos and Don&rsuqo;ts on Dipping Your Toe Into the Freelance Writing Pool



onfession: most of my learning experience with freelance writing has been the hard way. It’s been through clients that never contact me again without any good reason at all. It’s been through poor business practices from content writing agencies that don’t seem to appreciate their writers. It’s been through agreeing on projects that I never should’ve said yes to in the first place. So, today, for all the freelancers out there, I put together a few dos and don’ts that will help you stay afloat in the freelance writing pool (without learning everything the hard way).

1) DO: Learn how long it takes for you to write something.

For me, writing about writing, or books, or social media, or entertainment, or food, or health and wellness, comes fairly easy. However, ask me to write about trends for small business IT infrastructure, and I’ll probably spend about 10 hours on the research, trying to comprehend what on earth that means, then another several hours writing something that makes sense.

It isn’t that I am not interested in pushing myself outside of my comfort zone, but I also want to make sure I understand how my time is being valued. I learned this lesson the hard way recently when I accepted the opportunity to write a test article for a website, and I realized how long this test article was taking me. The several hours I spent weren’t worth the $50 I received for payment. In this case, it wasn’t so much that the content was difficult to write, but the research itself sent me down a rabbit hole that resulted in spending many more hours than expected preparing the article.

My best advice for understanding how long it takes for you to write something is get out a timer (or seek out a time tracker app that works best for you), and time yourself for each content piece you write. I realized this is especially important if you tend to work by word or by a flat rate (rather than an hourly rate). If you have taken five hours to write an article that you are being paid $50 for, was it worth the time and money? Understanding how long something takes will help you weigh the decision to continue working with a client or to re-evaluate your rates.

2) DON’T: Be afraid to say no.

It’s funny—the second you start saying no, the better you get at it. When it comes to freelance writing, though, why is it important to say no? First, I don’t know about you, but saying no, or even counter offering an opportunity with a different rate, isn’t easy. I am fully aware there is a risk in losing out on that potential income. However, sometimes it’s necessary in order to maintain your mental health as well as career health.

Here are a few freelance writing circumstances, where I encourage you to consider saying no:

  • When you are really bored (or painfully disinterested) in the subject
  • When the rate is well below what you are accepting
  • When you already have a full plate

Remember my IT infrastructure reference before? Well, that was a lesson learned the hard way. Thinking I could wing it in some way, I suffered through a piece for a media agency and only finished writing an article about this subject because I promised them I would. Let me tell you, it wasn’t worth the weekend that I spent writing it, the money I was paid, or the mental energy it drained out of me.

In addition, two other circumstances when I have said no are when a rate is well below what I’m accepting and if I already have enough projects to sustain me. There are exceptions to those two rules, of course. For one, if I’m already working with a client that pays well in other projects, I may likely be flexible on my rate with something else. Also, if I know a certain project I’m being offered won’t stress me out too much (and it won’t take me too long), I’ll probably say yes, even if I don’t necessarily have the time.

Remember, though, we can only do so much; and if we know something is going to be one project too many or far more trouble than what it’s worth, it’s important we, as writers, learn to say that important word—no. (Consider Fast Company’s tips on how exactly to say no without burning bridges.)

3) DO: Follow your intuition.

I recently discovered that intuition can be an important tool. A few weeks ago, I received an opportunity to write for a new, up-and-coming marketing agency that seemed promising and exciting. I was pretty proud of myself, too, because I had just cold pitched them my writing samples, and it was one of the first times I had tried anything like that.

Once I got started, I realized how suspicious everything seemed. The rate was acceptable; but once I logged into their system to start working on the projects assigned to me, I realized I never figured out exactly how I would get paid. Then, the process of how I would be working with them was mysterious as well. They gave me writing assignments without any context of the client. It wasn’t until I wrote them (several times) about it that they provided clarification.

When I finally did deeper research on the company, I ended up connecting with a fellow writer on LinkedIn who worked for them previously. I asked this writer about their experience with the company. In very few words, this person said that my initial suspicion about the place was right on. This helped me get a clearer perspective as the company didn’t have any reviews about them (from a hired writer’s perspective). Days later, the company took away assignments from me that I had received (without any forewarning or reasoning, as I hadn’t missed any deadlines nor expressed any of my doubts yet). When I followed up about the assignments they took away, all they said was that they had assigned them to me on accident.

I sent them an email that night letting them know this wasn’t a good fit for me. Not surprising, I never heard back from them. I learned that your intuition has a lot to say and is often your best guide for writing jobs. However, if you are new to the game, your intuition may not be sharpened. So, here are a few warning signs:

  • The client doesn’t communicate very well. By not communicating very well, I don’t mean that there is a language barrier that is getting in the way. It could be that the client isn’t responsive, isn’t clear about the expectations, or changes his or her mind about the rate you both initially agreed upon. A client that starts out not communicating very well is going to stay that way.
  • You have to submit a test sample (and you aren’t getting paid for your time). This isn’t always a hard and fast rule of a bad future client; but with a writing gig I had applied to recently, when they replied with instructions on the test sample I would be doing, I opened up a 100-page PowerPoint presentation. I promptly declined the opportunity. I don’t mind the occasional writing sample; but if I’m not getting paid for this test sample, I have to consider whether or not I want to spend my time on it (and risk not getting the job).
  • The client promises to pay...later. I’ve seen many writing jobs where the job offer admits that you probably won’t get paid very well (if at all). However, there is a promise that you, the writer, will be paid later on once the website takes off. That promise to pay later is a huge warning sign that you shouldn’t be taking the writing job.

4) DON’T: Put all your eggs in one basket.

I’ve learned this the hard way. I wish that writing gigs were as permanent in my life as junk mail. However, in one moment I can find out that suddenly a client doesn’t need my writing services or something about the relationship changes, and I’ll need to break it off with the client. Either way, writing jobs come and go.

With this, I’ve learned to continuously look out for and apply to writing jobs. I may not say yes to everyone that writes me back, but keeping my finger on the pulse of writing gigs is an important way for me to stay afloat without struggling so much when a writing job ends. If you are in search for writing jobs, consider this resource, which lists several sites to check out, for finding your next gig.

5) DO: Have quality sample pieces.

While I’m not a supporter of any writer working for free, it’s important to get quality writing samples. In a not so recent past, I submitted my guest post article to popular blogs, such as Men with Pens, The Write Practice, and even a fairly popular health food company called Perfect Bar. You don’t have to get featured on a major website to get quality writing samples, though. I have my own blogs, where I’ve published writing samples, and those get added to my portfolio.

One important tip I’ve learned: if you are contributing to a blog, make sure you save your writing sample as a PDF as well as saving the link to the website. Unfortunately, much like how clients come and go, websites do, too. So, make sure you save your work offline as well as saving the online link. In addition, if you do love a piece of writing and your bio isn’t attached to it, reach out to your client and find out if they wouldn’t mind if you used this piece of writing as a sample for future work.

I currently use JournoPortfolio for my writing portfolio, but consider a few of these other portfolio websites as well.

6) DON’T: Underestimate yourself.

You would be surprised how much you can write outside of your comfort zone. Through Upwork, I had the opportunity to write for a college that needed web content and blog posts. I never thought I’d be able to write about the paralegal career path or talk about the hospitality industry as if I knew what I was talking about, but I did.

This experience has taught me a lot and has inspired me to write outside of my comfort zone. You can’t grow if you aren’t willing to be a little uncomfortable. I’m not saying to spend hours on something that makes your eyeballs bleed, but don’t be afraid to push yourself. Sometimes, I fear what stops a lot of us is the “imposter syndrome”; but if you can get over telling yourself you aren’t qualified to write about that (whatever that is), you will surprise yourself.


Freelance writing feels a bit like you’ve decided to learn to swim by throwing yourself into a pool without any inner tube or floaty wings or lifeguard watching you. There are ways to get over the hurdles that are set before you, and I hope with these tips in mind, you can venture ahead and avoid learning things the hard way—like I did.

freelance writing pool


Nicole Pyles

Nicole Pyles is a writer, blogger, and bookworm living in Oregon. Her articles have been featured with The Write Practice, Ripley’s Believe It or Not, and Perfect Bar. Follow Nicole on her writing journey by following her on Twitter at Being the Writer and on her blog, The World of My Imagination.


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