10 Freelance Writing Challenges You’ll Face And To Can Overcome Them

How to overcome freelance writing challenges

A career in freelance writing is an art and a form of self-expression where creativity makes your mind wonder.

How to overcome freelance writing challenges
Mastering how to overcome freelance writing challenges is key to a successful career. – Photo Credit: Freepik

However, when writing is your full-time job, you can’t rely on creativity or wait for a lightning bolt of inspiration. In the freelance writing industry, your work must always be high-quality. But how can you do that with so many obstacles in your way?

In this article, I’ll show you the most common freelance writing challenges every freelance writer must handle and how you can overcome them.

1. Inconsistent income

Why did I start with such a topic? Usually, this is the first thing that comes to mind when you start your freelance writing career. “What if I don’t get paid?”

Unfortunately, this is probably one of the most common challenges every freelancer must handle. There are many reasons behind an inconsistent income. Whether it’s because you worked on fewer projects or because of your client’s late payment, the fact is that you won’t get the same amount every month.

Not knowing how much and when you’ll get paid can be very stressful when you need to put food on the table. However, there are a few strategies to cope with it.

Building an emergency fund will definitely take the pressure off. You’ll know you’ll cover most expenses even if you don’t get paid for a few months. Also, you’ll be relieved to know that you can face unexpected expenses, such as a car fix or a hospital bill.

Writing a contract with clearly defined payment terms will protect you, if you ever need to hire a lawyer to get paid for your work.

Additionally, you can diversify your freelance income sources. Don’t depend on just one client or project. Do your best to acquire new skills and find new clients. These strategies will be fundamental to keeping the money flowing.

2. Setting rates

Putting a price tag on your work is never easy, especially as a beginner. You’re proud of your work and want to be fairly paid, but you’re afraid of setting rates too high that’ll push your customers away.

Finding the perfect balance is challenging but not impossible. Freelance writing rates depend on the project scope. Before determining a rate, ask your client who’s the target audience, what’s the niche, where it’ll be published, how long the text should be and so on.

These questions will help you understand how complex and lengthy the project will be. You can also research your competition and find out what rates they apply for similar projects.

Alternatively, you can also set your rates based on your expenses. How much do you need to make a decent living? Consider your housing and utility bills, health insurance, transportation, food, clothing and other fixed expenses. This will help you define a minimum wage, meaning you can never charge lower than that.

3. Finding and keeping new clients

Finding clients is challenging when you’re a beginner. Regardless of how good a writer you are, no one knows your work. So, how can you get your first client?

Building strong client relationships is key to retain satisfied clients. – Photo Credit: Freepik

Freelancing platforms are a great way to get started. Platforms such as Upwork, Fiverr or Freelancer post new jobs daily. Many of these jobs focus on beginners looking to build their portfolios. While pitching, aim for projects that are an exact match to your skills. This way, you improve your chances of getting hired.

Online job boards are excellent for finding prospective clients. Indeed, Glassdoor or even LinkedIn offer excellent opportunities to freelance writers.

Moreover, building a content marketing strategy is the answer to putting yourself out there. Start a blog about what you do and be active on social media. The more you show your writing skills, the more likely you’ll get potential clients soon.

Once you get your first client, there’s a new task: keeping them! How?

For me, there are two basic rules for client retention: Always delivering high-quality content and meeting all deadlines! If you guide your work through these two rules, I guarantee you’ll have satisfied clients.

However, competition is fierce, so you need more than that. So, put yourself in your customer’s shoes… How would you like to be treated?

Building strong client relationships will require you to be responsive and professional and use a friendly tone regardless of client expectations. They don’t need to know how much work you have if you’re overwhelmed or tired. These will sound like excuses and make potential clients doubt your work capacity.

4. Learn about marketing

Many freelance writers aren’t aware of how important digital marketing is to their craft. Having a portfolio, applying to writing gigs and being present on social media will help your freelance business, but you need something more.

Learning the basics of digital marketing will help you identify your potential clients and their needs, outline a content strategy and monitor your strategy performance.

Marketing will also help you build a personal brand. Unlike what you might think, this goes beyond creating a logo or writing the perfect catchphrase. Your personal brand is who you are as a writer and how you present yourself to others. Once you get the hang of it, clients will know you for more than your high-quality work.

5. Set your priorities

One of the biggest challenges of working as a freelance writer is juggling multiple projects simultaneously. That’s why you must define what’s more urgent!


Check each project deadline and start with the one you must deliver soon. If you have one complex project and another a bit simpler, attack that one first. That way, you’ll have your mind (and schedule) free to dedicate all your attention to more complicated work.

Building a task calendar and having a regular writing routine might help you define your priorities. This is especially useful if you want to take a few days off. If you write down where you should start next, it’ll be easier when you get back to work.

A focused writing environment and eliminating distractions will help you keep on track. And if your mind starts to wander, unplug all social media and try the Pomodoro Technique (work for 25 minutes and then rest for another 5).

Once you become a successful freelance writer, you can always hire someone and delegate tasks that’ll consume the time you should be focused on your writing process. Hiring an accountant, a marketer or a web designer will free you from those tasks, and you’ll have more time for your clients.

6. Keeping a healthy work-life balance

You might think a freelance career will help you find the perfect work-life balance easily. I regret to inform you couldn’t far from the truth.

Working in the freelance writing business allows you to define your own schedule. However, there’s a catch most people don’t know about. If you work anytime and anywhere, you’ll get sucked into workaholism and not even realize it.

To avoid falling down the rabbit hole, you must define boundaries!

  • Define a regular writing routine and a work schedule and inform your clients. You don’t want them contacting you in the middle of the night!
  • Reply to your work emails only during your working hours.
  • Avoid cutting off time with your friends and family to work.
  • Establish work-free days.
  • Take time for your hobbies.

Having some time off work and enjoying quality time with your friends and family will avoid loneliness feelings! Besides, your creative juices will flow, and you’ll be more productive and engaged.

7. Battle the Impostor Syndrome

I don’t have any statistics on this matter, but I can almost guarantee all freelancer writers, at some point, have dealt with Impostor Syndrome.

The Impostor Syndrome holds back many aspiring freelance writers from doing what they enjoy the most. – Photo Credit: Freepik.

You know what it is… that intense sensation of feeling like a fraud when compared to other high-quality writers and that nothing you do is ever good enough.

I don’t know about you, but I sure had my fair share of Impostor Syndrome, usually when I’m about to deliver a project and waiting for the client’s reply. If they take too long to answer, I always assume the worst!

Fortunately, I’ve found a few strategies to avoid such a feeling. Here’s what I do that’ll help you too:

  • Acknowledge how you feel. Usually, talking with others is an excellent first step.
  • Write down your accomplishments. After reading it, you might not feel like such a fraud.
  • Stop focusing on perfectionism! No one knows everything, nor do they do everything right. Do your best, and everything will be fine!
  • Avoid comparing your work with others! Every writer has a unique writing style, so comparing yourself to others is just a waste of time.
  • Don’t dwell on social media! Although you’re using it professionally, you might put yourself down instead of finding sources of inspiration from other people’s work.
  • Don’t let it hold you back! Write about whatever you want. Your passion will fuel your work, and your readers will notice it!

8. Coping with writer’s block

The dreaded blank page! This a challenge for freelance writers everywhere!

Sometimes you only need a few minutes before getting started. While at other times, you take weeks or months before finding the right words. However, working in the freelance writing business means you must write if you want to put food on the table! You can not afford to spend weeks on end without writing.

How can you turn this around?

Don’t overthink it, and start writing! Your first draft will be sloppy, but the beginning of something remarkable. If this doesn’t work, take a break and do something completely unrelated. It’ll help you be more creative and productive.

Building a creative writing prompt will help you get to the point faster. This way, your writing style will be more concise.

Finally, edit and revise only after the writing project is done. Avoid feeling trapped in the same paragraph or trying to aim for perfection. Who knows… after reading your first draft, it might not be that bad!

9. Dealing with rejection

This is the most frustrating part about providing freelance writing services. You put your heart and soul into your work, and it’s rejected. Unfortunately, hearing a big and round “No” is much more frequent than you might think.

So, how can you deal with rejection and keep your motivation high?

First of all, always reply in a professional and friendly tone. Your work might have been rejected at this time, but who knows… maybe there are new freelance writing opportunities around the corner! And second, try to understand what went wrong. Use your business mindset and learn from your mistakes. It’ll help you improve your writing skills.

Also, accept you’ll hear several “No’s” before hearing your first “Yes”.

10. Not having enough work

This is another freelance writing challenge every freelancer faces now and then. Even with excellent client feedback and a solid client base, there’ll be times when you’ll be almost out of work.

  • Use these strategies to avoid not having enough work:
  • Don’t rely on just one client. Find more clients from different businesses and build strong client relationships.
  • Broaden your skills. It’ll help you find new clients and new projects.
  • Gather constructive feedback and testimonials from satisfied customers and post them on your online portfolio and social media.

Your best strategy to avoid the feast and famine cycle is consistency. Find dedicated writing time daily by sending an irresistible pitch and applying to new creative projects. Also, remember to post on social media regularly.

Are you ready to face your own obstacles?

You’ll find many more challenges along your freelance writing journey. Each writer, in their own writing niche, will battle to overcome obstacles.

This will happen to you too! What you must do is preserve!

Build a focused writing environment and create a regular writing routine! This way, common freelance writing challenges like these will be peanuts!

However, from time to time, you’ll struggle to find motivation. Regardless of your motives, remember why you decided to become a freelance writer. Focus on your passion for writing and write as if no one is watching!

Writing engaging content: how to connect with your readers

Anyone can write content. Yet, only a few can write engaging content.

To connect with your readers requires more than incredible writing skills. – Photo credit: Freepik

Whether you’re a content writer, copywriter, blogger or marketer, I’m sure you’ve struggled with the content creation process at some point.

Now, more than ever, content creation has become much more than writing. We want to attract readers, and we want them engaged.

When your audience interacts and shares your original content, they’ll be helping spread the word about what you’re writing. Also, it´s the perfect way to present yourself to your customers.

But what is “engaging content”?

In this article, I’ll show you how you can write compelling content for your audience.

What is engaging content and why it matters

Engaging content refers to any text that draws people’s attention and draws them to keep reading.

Regardless if you’re writing for your own website or a client’s, all you want is to allure your audience into reading all through to the end.

Why is this important?

The longer you keep your readers engaged, the more likely they will buy whatever services you’re promoting.

Today, we know engaging content helps boost conversions, promotes brand awareness and generates high organic traffic. In the world of marketing, this is the holy grail. This is why having striking writing skills is essential. Yet, as a writer, there are other abilities you must learn to succeed.

The content pillars

Writing any type of content is far from boring. With each new project, you must adjust your writing style to your client’s needs, tone and voice. Even so, there are a few ground rules you should always consider.

Know the audience

You may have the topic, but you must know to whom you’ll be writing. As a skilled writer, you know there are many ways to approach the subject. So, knowing your target audience will help you decide what’s the best writing style and format for your message to be understood.

To write engaging content you must know who is your audience and their goals. – Photo Credit: Freepik

Know your audience goal

The keywords you use to build your content marketing strategy are the best way to learn your audience’s intention. Why are they googling such terms? Once you have your answer, it’s time to help them get theirs. Structure your pieces of content around your audience’s goal. This way, you’ll get straight to your reader’s needs.

Know your business goal

Before starting writing, you must ask yourself a few questions:

  • Why you’re writing about this theme?
  • What’s the purpose?
  • What are you looking to achieve?

These simple questions will help you structure your original content. In the end, you’ll achieve your readers and your business goals.

How to make your writing more engaging

Regardless of what you’re writing about or which format you use, your articles must be fascinating and drive your reader’s curiosity. Here I’ll leave you some tips I use daily to guarantee my audience is engaged:

Enjoy what you’re writing about

I know, it sounds obvious! But writing about what you enjoy will help get your reader’s attention. They will feel your enthusiasm and be eager to read your next piece.

However, sometimes you must write about the most boring topic. Whenever you find yourself in this situation, try to understand why this subject sparks people’s attention. Maybe you’ll find some common ground, and it’ll be easier to please your loyal customers and their readers.

Structure your content

When writing long-form content, such as a blog post or a case study, be sure to structure your text before writing. It’ll help you organize your thoughts and how you present your argument. Also, it helps cover all topics about that specific subject.

Building your content structure helps organizeyour thoughts. – Photo Credit: Freepik

Invest time in headings and subheadings

These are responsible for your content’s first impression. And we know it only takes a few seconds to build first impressions and a lifetime to change them.

Headlines and subheadings are the first words your audience will read. It’s your chance to capture their attention. Your remarkable content will do the rest.

So, spending more time finding the right words to create bullet-proof headlines it’s crucial. To guarantee original content meets readers’ needs, some writers use long-tail keywords as titles. It’ll make our content more appealing and easier to find.

Write as if you’re speaking to your audience

Not all your readers are experienced academics used to formal and complex words. So, if you write similarly to the way we speak, your piece of content will be more accessible to more potential customers.

Additionally, the reader will feel you know their mind and that you’re speaking directly to them. They will feel heard and unique, persuading them to keep reading.

With the Hemmingway App, ou can check your text’s readability level. Besides, this incredible tool provides plenty of suggestions to help you improve content for websites according to your goals.

Write in the active voice

One rule of writing, whether it’s on or offline, is to use the active voice. Besides sounding more vibrant, it gives your readers the feeling something is happening right now. It’ll keep them engaged long enough to read everything you wrote. Also, your writing will sound more concise and elegant.

No fluff

Our attention spans are getting shorter day by day, especially when it comes to online content. We know what we need, and we want it fast. Most readers online skim the articles only to read a few words instead of complete sentences.

Writing Job
Writing only what’s essential is key to engage your audience. – Photo Credit: Freepik

So, avoid writing content for websites that doesn’t enrich the reader’s experience. Be direct and get to the point as quickly as possible.

Be original

In today’s world, it’s hard to be completely original. Everything is invented, and nothing is truly new. Yet, as an online writer, you can bring a fresh perspective to a highly discussed subject.

On the other hand, if you must write about something that was already written, use your own words. You don’t want to become known as the writer who copies other people’s work. Besides, regarding SEO, Google Search will penalize your content if it shows unoriginal sentences or paragraphs.

In-depth research

The web is full of made-up facts and fake news. The last thing you want is to make it even worse.

Providing accurate data is one step to building a reputation as an online writer. Regardless of the information your ideal customer is looking for, in the end, all they want is to know what’s true.

So, when you’re writing, confirm your sources before including them in your content. This way, you’ll capture your reader’s attention and become a reliable source as well.

Share your personal stories

Using your experiences to connect with your readers will make your original article more relatable and captivating. They will feel compelled to read what you have to say, and you’ll leave them with a positive impression.

Sharing personal experiences is a good way to connect with your audience. – Photo Credit: Freepik

Sharing how you overcame the same problem they’re having now is one way to go. Another is to share other people’s experiences (with their consent, obviously!). This will invite your readers to comment and share their own experiences.

Use visual content

Reading online is much different than reading on paper. Adding to people’s shorter attention span, reading on screen is harder on the eyes, information is processed too quickly, and it drains mental resources faster. The result: your readers will get somewhere else before reading everything you wrote.

This is why you must avoid big pieces of text. Mix it with a few visual elements, such as photos, vectors or infographics. It’ll enrich your content and make it more skimmable. This way, your readers will get the main message, even if they don’t read every sentence.

Write shorter sentences

Your killer headline is attracting new readers every day. Yet, only a few read everything you wrote. Perhaps, your original article is too dense!

Even the most avid reader will feel discouraged in front of pilled sentences and paragraphs. So, breaking your text into smaller pieces makes it easier on the eye. Besides, it’s more attractive and feels effortless.

Always spell check

Regardless, if you’re writing a blog post or a book, avoiding spelling and grammar mistakes is fundamental knowledge. Some would say it’s the first rule of writing.

Spelling mistakes makes your writing look sloppy. – Photo Credit: Freepik

So, another tip for writing compelling content is to avoid these mistakes at all costs. If you’re like me, once I see a spelling mistake, I can’t barely get past it. Even if you’re an incredible writer, these mistakes will leave a lousy impression on your readers.

AI-powered tools will help you on this mission. One that I use the most when writing in English is Grammarly. Its interface is user-friendly, and its remarks are spot on. Unfortunately, they don’t have other languages. So, when I’m writing in Portuguese, I use LanguageTool. Although it’s not as developed as Grammarly, it sure helps quite a bit.

Another piece of advice: even if you are confident about your writing skills, always spell check. You’ll be surprised to see there’s more to improve than you thought.

Use power words

Power words are embedded with a strong meaning, which usually triggers a psychological or emotional reaction in audiences. Usually, copywriters use power words to make their content more interesting and call people to action.

Choosing which power words suit your article will depend on your goal. Here’s a list of the seven types of power words you can use. You’re welcome!

Bring variety to your content

People enjoy novelty and tend to ignore repetition. So, to keep your readers engaged, you must mix up your content.

Yes, you can still write. However, you must find new ways to present your content to people. Video content has become a growing trend in content marketing. Younger generations prefer watching videos in search of information rather than reading. Other alternatives might include podcasts, streaming, social media posts or user-generated content.

Regardless of your decision, always keep your audience in mind. Posting on the wrong platform will keep your target audience from reading your captivating content!

Avoid repeating words

The beauty of writing lies in the variety of words we have at our disposal, regardless of the language we’re writing.

The pros and cons of freelance writing
Online tools will help you find the right words for your content. – Photo Credit: Freepik

However, when you’re writing for quite some time, it’s common to fall for the same terms over and over. Avoid this by checking a dictionary once in a while. Finding synonyms will enrich your high-quality content, making it more engaging. Also, by expanding your vocabulary, you’ll sound more experienced and educated.

When writing in English, I often use the Cambridge Dictionary and WordHippo. For Portuguese, my go-to tools are Priberam and Reverso. Without them, writing valuable content would be much more complicated!


Usually, this is the last item on any piece of persuasive content. By using a call to action, you’re engaging your audience, asking them to take action. As a result, with a single word or sentence, you can convert potential clients into real customers.

Using a call to action helps boost your conversions. – Photo Credit: Freepik

However, you shouldn’t overdo it. It’ll make you sound like you’re forcing people into something, which usually has the opposite effect of what you want. People want to know they have a choice, so use a call to action with moderation and make it feel like it’s a natural step to take.

Summing up

Creating engaging content is more than writing. Although you’re writing skills are crucial, there are plenty of other abilities you must keep in mind.

Keeping your audience engaged daily, requires you to be on top of your content’s performance, as well as growing trends. Therefore, you must check and update your older content, while creating new.

Hopefully, with these simple strategies, you’ll make your content more engaging. Let me know how it went!