Leaving Work Behind

3 Rookie Freelancing Mistakes I’ve Made as a Writer

Written by Anne Dorko on April 25, 2017. 5 Comments

Fingers typing on a laptop

There’s no getting around the fact that being a freelance writer is difficult. However, it can be a lot easier when you learn from the mistakes of those who have gone before you.

While I still consider myself a freelance writing rookie in many areas, I do have a small amount of experience under my belt to share with you. Some of the most difficult struggles come from a fundamental misunderstanding of yourself, and the only way to push through is to acknowledge those issues early on so you can find ways to adapt.

In this article, I’ll share three crucial mistakes I’ve made as a rookie freelance writer. There may be no silver bullet solution, but I hope that self-awareness and some experienced advice will help point you in the right direction.

Let’s get started!

Mistake 1: Ineffectively Balancing My Workload

I’ve lived an alternative lifestyle for five years now, using freelance work as one of my income sources. Creatively problem solving life’s ordeals so I could fly around the world, go scuba diving, and take a solo bicycle tour has given me a lot of confidence. However, this kind of overconfidence can backfire.

I have a tendency to overestimate what I can do well in one day, because I believe I can overcome any and all challenges. While this approach works wonders most of the time, it butts heads with the freelance writing sphere. Well-written words simply take time, energy, and creativity to put together.

Without factoring in elements such as your energy level and any unexpected events, you’ll quickly feel overbooked and overwhelmed. This ultimately leads to underperformance and late work.

How to Balance Your Workload

Quality writing takes a certain amount of mental presence and creativity. These can vary greatly day-to-day depending on the person, and as such, it can be nearly impossible to predict what you can handle from one day to the next.

Here are a few things that help me retain a semblance of control:

  1. Don’t take on a dramatic amount of new work all at once.
  2. Follow a consistent sleeping schedule. This may be the most important advice for anyone about anything.
  3. Find your most productive time of day and focus on those hours. I hate waking up early, but my most productive hours are between 6am and 10am.
  4. Avoid tasks that drain your energy. Dealing with emails makes me feel like a deflated balloon so I try to wait until after my initial work spurt to check my inbox.

What will work for you depends on your personality and motivation. Try these out first, and see how they go. Then, evaluate and experiment to figure out what works best for you.

Mistake 2: Developing ‘Negative Habituation’

If you’ve ever followed a regular routine, you’ll likely be familiar with the concept of habituation. For example, if you take the same route to work every day, eventually you’ll stop consciously thinking about the steps to get there. You know your freeway exits, how to time that tricky red light, and where you can snag the best parking spot. After a while it becomes second nature, and you stop noticing the little details along the way.

However, there’s something else I like to call ‘negative habituation’. This is when you develop blindness to the things you see over and over, and your brain fills in the gaps when something is missing (or slightly different). Of course, this is problematic when you need to be detail-oriented!

In my primary writing gig, we keep checklists with editing rules for each client. This is a great resource – until my brain starts assuming it knows what is or isn’t on that checklist because of how often I’ve reviewed it. If a small detail gets changed, I don’t always notice because my brain assumed it already knew.

Of course, this can lead to missed deadlines or revisions, and can cause hassle for others along the chain who are trying to ensure the client’s needs are met.

How to Combat Negative Habituation

One way to trick your brain into remaining alert to old elements is to change up any visual formatting every so often (if possible). Font sizes, colors, and the text’s formatting (i.e bold and italics) are all fair game here. This mixes things up enough to force your brain to see new changes.

You can also automate some of your work by letting your computer handle basic editing. One simplified example might be to use the Find tool in your editor to find comment problem phrases, typos, or grammar issues. You might even use macros, which completely automates this for you.

Finally, my last tip here is a simple one: take breaks between writing and editing if you have the time. Of course, this is hard to do if you’re still dealing with the first mistake and have an imbalanced workload!

Mistake 3: Searching for Jobs Without External Help

For most of my freelance career, I’ve relied on word of mouth and generally making sure people knew I existed. However, I encountered problems when turning my side gig into my full-time career.

It turns out that finding freelance clients is difficult, and the necessary promotion and pitching was a lot harder than I originally thought! I’ll admit, most of my success today has been from good fortune and a lot of manual effort to dig up viable candidates.

However, this level of effort meant I failed to pursue freelance writing for a long time. Eventually, I discovered that there are services available to help writers find high-quality gigs. Of course, knowing about this earlier could have had a huge impact in my freelance career, and they can make a world of difference to yours.

How to Search for Jobs More Effectively

Simply put, you’ll need to find those who aggregate quality job offers. Though there are services such as Upwork and Freelancer, it can be challenging to find good opportunities because anyone can join and post. Instead, I prefer to find professionals I trust and follow their lead.

Free options, such as the Morning Coffee newsletter, do their best to point you to solid opportunities. However, since it is a free service they aren’t always able (or willing) to vet for quality gigs. Premium options (such as Paid to Blog Jobs) are often the way to go. They have more resources to track down and vet potential work, and in addition will often provide tools and resources to help you apply for (and win) gigs.


Freelance writing is one of the most challenging pursuits I’ve ever taken on. I’m not a natural, but I stick with it because of how rewarding the experience is. What’s more, it’s a good ‘sandbox’ for learning to recognize your mistakes and adjusting for them.

You may not be able to correct all of your freelancing mistakes overnight, but here are three key examples to watch out for:

  1. An unbalanced workload, possibly because you have miscalculated how much you can handle on any given day.
  2. Negative habituation, which could degrade the quality of your work.
  3. Searching for jobs without help, which will waste a lot of your time without necessarily landing you many quality gigs.

What mistakes have you made as a rookie freelance writer? Feel free to share your own experiences and advice in the comments section below!

Image Credits: Oliver Thomas Klein

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5 Responses to “3 Rookie Freelancing Mistakes I’ve Made as a Writer”

  1. Lisa
    April 25, 2017 at 2:31 pm

    Really like #2! I hadn’t really ever thought about all the things I might be missing because my brain is filling in the details, but it makes sense. That’s like how editing without reading aloud can prove troublesome because our brains read what it should say not what it does.

    Thanks so much for sharing, and giving actual tips on how to overcome these problems.

    • Tom Ewer
      April 26, 2017 at 2:10 pm

      You’re welcome, Lisa! Thanks for your input. 🙂

    • Anne Dorko
      April 29, 2017 at 7:47 am

      Hi Lisa, thanks for your feedback! I’m glad you found this helpful. #2 is a tough one. Actually, reading these lists aloud would probably help, too, because it forces you to hear each word 🙂

  2. Freelance writing jobs
    August 18, 2017 at 9:58 am

    Great advice to the three mistakes given.

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