Freelance Writing: Five Major Challenges and How to Overcome Them

Freelance Writing: Five Challanges of Freelance Writers and How to Solve Them
Image by rawpixel from Pixabay

Freelance writing is a great way to earn money, develop one’s writing and proofreading skills, and establish one’s reputation as a writer. This occupation is becoming increasingly popular because of the perks one can get from it.

Becoming a freelance writer enables you to have a schedule that fits your lifestyle. This means you’ll have some slack by having the ability to work at your own pace and time, with only your client’s deadline as your limitation. You can work from home or anywhere too!

As freelance writer, you don’t have to go to a workplace or report to a boss or superior. You are considered as an independent contractor, who has control on the means by which you’ll write assignments, with few specifications along the way. So long as you give what your client wants, you’re good.

Freelance writing can also help you earn decent amount of income so long as you keep your client base and assignments flowing. And since you have the prerogative to get as much work as you can handle, you determine the fate of your pay check.

These commonly known perks of freelance writing are what got me into doing it as my current job. But I have to admit, it was not easy starting out on this job AGAIN.

It just feels weird that after four years of working with the government, I am back to my old freelance writing days.

Five Major Freelance Writing Challenges

Becoming a freelance writer isn’t as glamorous as it seems. Just like any job out there, it comes with its fair share of challenges.

Freelance writers have their own set of roadblocks. Here are some of the major ones that I have identified ever since I started doing freelance writing:

Writer’s Block

Writer's block
Image by Lukas Bieri from Pixabay
Have you ever came to a point when you’re staring at your blank screen for like thirty minutes or so and still not a single word pops out to start your article with?

Yeah, I know it sucks big time!

If you haven’t heard of it yet, this is called writer’s block and this is by far the most difficult situation a freelance writer must hurdle.

Time Mismanagement, Procrastination

Time Management Procrastination
Image by Free-Photos from Pixabay

When I was still working in the government, I don’t have even the slightest opportunity to slack off. How could I if I have shift and tasks to complete each day?

Apart from being in the defense community, I am also also a [struggling] law student, who gotta do what she had to just to make both ends meet and rock law school. So, I don’t have time to be complacent and lazy.

On the other hand, things become a little different when you work from home as a freelance writer. Sure, you have more time for yourself; to pursue hobbies or endeavors that were otherwise not practicable when you work as a government employee. But with less control and more freedom, you’ll have the tendency to procrastinate and delay things, knowing that you have so much extra time in your hands.

Boredom, Lack of Enthusiasm

Boredom, Lack of Enthusiasm
Image by Pitsch from Pixabay

Don’t get me wrong, I love writing. And honestly, not many people in my family and cliques know about this. My love for writing started when I did freelance writing work in 2010 and it grew as a passion during my work as defense research writer.

I love writing about health and wellness, territorial disputes and defense, law, and lifestyle. Accomplishing writing tasks along these lines didn’t feel like work at all. But as I was getting article writing jobs about furniture, VPN, garage doors, etc., I noticed that I was losing my enthusiasm.

Writing assignments eventually became a pain in the ass. Back then, all I wanted was to ditch opening emails from clients.

What I Did to Overcome My Freelance Writing Challenges

# 1 — Writer’s Block

Writer’s block is my problem ever since. I still struggle against it even now that I am in law school. Whether it is article writing or answering a law school essay exam, I always have a problem getting out that first sentence.

Fortunately, I got help from a prolific writer I know and love, my boyfriend, Jumel. As a defense analyst and researcher, his bread and butter is writing.

According to him, the solution to ward off writer’s block is to just start writing and keep doing it until all your creative juices come out. Then, proofread after.

So, I did exactly as he told and it made a lot of difference in my freelance writing.

For instance, whenever I’d have even the shallowest idea at any given time, I’d go straight to my laptop to write them, caring less about my sentences’ and paragraphs’ coherence and unmindful of any grammatical errors. The next thing I knew, I was picking up the momentum I need to finish the article.

As soon as I’m happy with my draft, I’d review and proofread it and incorporate my information sources for attribution. I’d dedicate the next hour refining my draft to make it succinct and tailor-fit for what my client needs.

# 2 — Time Mismanagement, Procrastination

One thing I learned from being a freelance writer is that time is STILL of the essence. Admittedly, the term “freelance” has mislead me quite a bit into thinking that I’ll have all the time in the world to study while working, and still do fun things on the side. I realized that freelancers live a happy and balance life because of time management.

One way I devised to manage my time is to keep a planner. It helped me plot all my article deadlines and law school tasks. It’s nice to write a list of to-dos and be able to tick off each item you accomplish throughout the day. Somehow, it keeps me always on check.

Next, I try to keep my to-do as practicable and realistic as possible by prioritizing things that need to be completed first. I’d highlight in my planner the most urgent and important ones so I’ll finish them first. Then, I’ll proceed completing the other less urgent (but still important) ones in my list. By doing this, I feel a sense of accomplishment and I don’t get frustrated because I have all my tasks done before my working day ends.

As for procrastination, I use my very own get-up-and-start-method. Unfortunately, you can’t find this term anywhere else but I am sure you get a picture of what I do with this. It is so simple that people often underrate and take it for granted.

The problem with procrastinators is that they are brilliant in setting out a great plan but they are suckers for unnecessary delays. Through this method, you wire your brain to just start and get things going. You do it by mustering enough determination to just begin whatever task that you are bound to accomplish on that day.

J.P. Morgan’s famous quote inspired me to figure out and adopt this method. His quote says:

“The first step towards getting somewhere is to decide that you are not going to stay where you are.” 

So, I thought that the only way not to be stagnated from where I am is to act and act timely.

This is the reason why whenever I feel lazy or feel like procrastinating, I get up, do some stretching, and I go to my keyboard and write.

# 3 — Boredom, Lack of Enthusiasm

Freelance writing is not all party and fairy tale. Often times, you don’t get the topics that interest you.

But should I complain?

As a freelance writer who makes a living out of it, you shouldn’t be too picky. I know there are other ways to it, like writing and selling your own e-book or audio-book, but I am not exactly that type. I am one that works with clients and does her best to give them the solution or innovation they need in their business through content creation. Declining projects, which are often good-paying ones, is the least that I should do.

So, how do I remedy the boredom or lack of enthusiasm? Simple, I indulge and spark my own interest!

When you open your mind and see through the topics that you are assigned to work on, you will see the assignment in a whole new level.

Personally, when I did this, I eventually became more interested and excited with each assignment because I know that I’ll be learning a new thing every time. Then, I realized that freelance writing doesn’t just make ends meet or put food on the table; it enriches your soul and mind too.


So, there you have it — my major freelance writing challenges and my remedies to overcoming them.

How about you?

Do you experience these problems too?

What did you do to overcome them?

Feel free to let me know in the comment section below.




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5 thoughts on “Freelance Writing: Five Major Challenges and How to Overcome Them

  1. Hi, Tina! This post taught me a lot about freelance writing. Just like you, I also do freelance writing although very limited. I only write 2-3 articles for a specific client and the workload comes in season only. I can relate to the procrastination and time management part. It is really a pain in the ass to add those factors in our existing daily grind, but completing our tasks each day turns every side hustle into fulfillment.

    By the way, since you shared that you are freelance writing these days, if you do not mind me asking, may i know from which portal did you apply or how were you able to get a client? I am looking for a steady alternative source of income from freelance writing. Your response would help a lot. Thanks a lpt and keep writing, Tina! 😊

    Liked by 1 person

    1. I couldn’t agree more. Perhaps, we just have to find our way through these. Like in my case, I am still beating that menacing writer’s block! Lol.

      I actually don’t work specifically for clients or get jobs from portals. I am a nurse-turned defense analyst who once worked with the government. Most of my work come from my old network. But for national security reasons, I’m afraid I can’t disclose details any further, my friend.

      Nonetheless, if I may suggest, I’d like you to check Facebook jobs. I have some friends who got their home-based work from there. When I checked it myself, a handful of companies were looking for writers. If you search for “writing jobs”, a number of listings will surely pop up.

      With your good and engaging writing, I am sure you won’t have a hard time finding writing jobs. 🙂


  2. Pingback: 19 Things to Celebrate From My 2019 – The Open Concavity

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