Top 11 Toughest Writing Challenges And How To Overcome Them

This article contains everything you need to know about writing challenges, what causes them, and how to overcome them.

Writing is a lonely, mentally challenging, and sometimes grinding profession. Most of your time is spent in front of a screen, trying to put words together, while your brain is telling you, “Nobody would read this.”

On top of that, you’re expected to create a schedule, set rates, and find time for family and friends. Like Ernest Hemingway famously said,

“Writing, at its best, is a lonely life.”

Ernest Hemingway

How do you overcome countless writing challenges and keep your sanity at the same time? Well, there is an art to it, but in this post, you’ll learn:

  • What writing challenges every writer faces
  • What causes these obstacles
  • How to overcome them

Let’s dive in!

1. Online Distractions

Top 10 toughest writing challenges and how to overcome them

The biggest writing challenge for me is eliminating distractions for a few hours so I can get into a flow state and cultivate a habit of daily writing.

In this modern world, distractions are everywhere. I like separating them into two categories, offline and online distractions.

Offline distractions are easy to eliminate. Establish boundaries, and tell everyone in your house not to disturb you for the next few hours. Most people are reasonable and will respect your request.

Writing with kids in the house may be a challenge, but it comes down to timing. Aim to complete your deep work when they’re asleep, playing with their friends, or at school. Focus on the creative work while the house is quiet. Then, you can do any non-creative tasks, like answering emails, when they’re home and awake. Being a writer with children might mean early starts, late nights, or both.

The real challenge is removing online distractions. With so many social media platforms, you can’t keep track of them all. They draw your attention all over the place, and when it comes time to work, you find getting into that flow state impossible. A good web blocker like Freedom app can help.

How To Eliminate Online Distractions

Getting rid of online distractions requires a combination of discipline and tools to keep your core creative time distraction-free.

My ritual for eliminating online distractions is to close all the tabs I’m not using, like Instagram, Facebook, Twitter, and even email. I put my phone in a drawer in the next room. However, even after taking these steps, I still feel tempted to open Facebook or YouTube, and this is where distraction-blocking tools, like Freedom App, come in.

It blocks the news feed of any social media platform. That stops users from getting into that zombie-like trance where you’re scrolling Facebook for what feels like five minutes, then you realize an hour went by.

Simply head over to the Chrome store, and you’ll find distraction-free extensions for YouTube, Facebook, and any other social media platform.

I highly recommend installing the distraction-free YouTube extension since writers need to do a lot of research and this sometimes requires this search tool. YouTube shows videos you might like on the right sidebar, and if you get distracted, you can easily waste hours watching videos.

Distraction-free YouTube blocks the sidebar on the right so you can watch what you need for research purposes then head to your favorite place to write. You will still need a modicum of self-control but all it takes is one looming deadline for you to see the error of your ways.

Read our guide to the best distraction-free writing apps.

2. The Feast And Famine Writing Cycle

The infamous feast and famine cycle is another major challenge to those making their living as a freelance writer.

A feast and famine cycle refers to balancing the act of writing with finding your next writing job. One month you might get a lot of work and beat your monthly income target, and another you won’t even come close. Consider this an opportunity rather than a challenge. 

How To Overcome The Feast And Famine Cycle

Think of yourself as an employee of your company. Pay yourself a set salary that covers your expenses, and the money left over you either put into an emergency fund or invest back into your business.

This prevents you from going overboard with spending when times are good. Then when a famine rolls around, you have some money to fall back on while you get more clients.

This doesn’t tackle the root of the problem, however; it only treats the symptom. The other reason this poses such a challenge is during the feast period, many writers stop marketing and landing clients. When the inevitable famine comes, they have a lot of time to market their services, and this brings in a new flow of clients that leads to another feast.

Now that we know what causes a feast and famine challenge, the solution is obvious. Never stop marketing! Some ideal forms of marketing for writers include:

  • Pitching
  • Paid ads
  • Cold email
  • Social media outreach
  • Content marketing

Don’t stop once you’re busy because your lack of marketing might not show itself immediately, but in a few weeks or months, you’ll start to feel it. 

Set an hour or two aside every day and pitch your service to potential clients. Make it a habit, and if you don’t have time to pitch because you’re too busy, hire a virtual assistant to do it for you.

By constantly pitching your writing services to potential clients, you’ll never experience a feast and famine cycle again. Your workflow becomes predictable and reliable.

Check out our guide to the best writing jobs and also our list of side hustle ideas for writers.

3. No Time To Write

You’re a full-time writer. You spend your days tapping away at the keyboard while sipping piping hot coffee, right? For most writers, finding time to write is a chore since life has a habit of getting in the way. But that’s where budgeting your time comes in. When you want to get better at money management, you budget your money. So why not do the same with your time?

How To Find Time To Write

Once you’ve structured your day, look for times where you can improve or eliminate as this allows you to get some extra writing done. The first time I planned my week in advance was difficult, but I quickly got into a creative groove.

Another mindset shift you must make is that you don’t need a laptop or computer to start writing. You carry a smartphone, so if you don’t have access to your computer, whip out your phone and blog away. You can always send the file to your computer later.

4. Writer’s Block

Ernest Hemingway once said writer’s block is the most terrifying challenge he ever faced. You know the terror. You open a Google Doc or Microsoft Word document, then you stare at a blank screen having no idea where to start. It can be very daunting for many writers. For those just starting out, it can feel insurmountable.

You don’t have to go through that dreaded challenge every time you start working on a new project. The most common reason people experience writer’s block is that they judge their work before it’s time.

How To Overcome Writer’s Block

Many new writers working across different genres expect to write pure magic as soon as they touch a keyboard. Instead of writing then editing, they judge and throw out their first drafts. With this practice, you’ll obviously feel stuck because writing a perfect first draft of a new story is impossible. Your first draft will be terrible regardless of your writing skills. and that’s fine. You can always edit your draft later.

Once you understand and accept that your first draft will be poorly written, you won’t experience writer’s block anymore. Daily writing becomes a piece of cake.

When you start writing, don’t judge your work. Just write. No matter how horrible you think your writing is, don’t delete or edit it right away. That comes later.

YouTube video

5. Productivity Lulls

Some days, you feel tired and unproductive. The words will refuse to flow. You will find a voice in your head questioning every word you write. All writers experience this, and it’s a good thing. Slow days allow you to appreciate productive days when you can write a few thousand words in a blink of an eye.

Here are a few tricks you can use to make your unproductive days a bit more productive.

How I Overcome A Productivity Slump

My three go-to techniques for increasing productivity are:

Multiple studies show the benefits exercise provides your brain. It improves thinking power, sharpness, and motivation. In simple terms, exercise promotes the growth of a protein called BDNF, which is found to increase mood, improve learning and even protect your brain against Alzheimer’s and Parkinson’s diseases.

After running around the neighborhood a few times, hop in the shower.

Do you notice that when you’re showering, unique and creative thoughts magically pop into your head? This is because you’re relaxed and stress-free. These creative opportunities are essential to being productive.

Last, avoid eating until you’ve reached a required word count. For example, have lunch only after you’ve written 2,000 words. This technique encourages you to give yourself a reward for completing a difficult task. You’ll also be more inspired because hunger is a strong motivator.

Read our guide to productivity for writers.

6. Self-Editing Your Work

One of the biggest fears most freelance writers face is posting or sending an article to a client that includes typos and other mistakes. After you’ve written a post without judging it, you can bet you’ll find typos and structural problems. You also need to decide which subheadings are relevant, entertaining, and eye-catching for readers versus knowing what to cut. That’s key whether you’re writing a short story, article, or a soon-to-be Amazon best-seller.

Editing is harder and more draining than writing itself because when you’re writing, you enter a flow state after a few minutes. Editing is a drag on mental energy, but love it or loathe it, it’s still an important part of the writing process.

How To Structure Your Articles

Outlines can make your life ten times easier. When creating an outline, visualize yourself holding your reader’s hand and walking them through everything they need to know to fix whatever problem your article solves. 

After you’ve completed your outline, the rest is easy. You’ll feel like you’re just filling in the blanks since the structure of the post is already complete.

You can use index cards. A good outlining app can also help.

How To Edit While Feeling Drained And Bored

After you finish writing an article, put it into a good grammar checker first and fix any basic issues. Next, change the font and print the article. Why?

If you write in Arial and edit in a different font, the change tricks your brain into thinking you’re reading a different piece. You’ll be more likely to catch small errors. And printing your post on a sheet of paper prevents you from writing while you’re reading, which can interrupt the flow. Editing and writing are two very different processes and should be kept separate at all times. Instead, make a line under the mistake, then edit the document on your computer later.

I started doing this for my writing and have greatly reduced the number of mistakes in my articles, as did working with a professional editor.

Check out our self-editing guide.

7. Managing Deadlines

Many creatives dislike deadlines as they feel stifling and stressful. However, deadlines mean your clients want a piece of work by a set time. Missing them can result in a client terminating a contact. The potential for lost income can be a powerful motivator for the freelance writer.

It’s also important to realize that deadlines are should not just be imposed by clients. Deadlines are also important if you write for yourself. This is because shipping quality work consistently is key to earning a good living as a writer. You can’t earn from something you endlessly rewrite! While it may be difficult to start with, try setting yourself a deadline for every piece you work on, regardless of whether there is a client-imposed deadline also.

How To Set Attainable Deadlines

The first step in setting attainable deadlines is to break down your project into smaller chunks. For example, research,  outline, writing the first 1000 words, then the last 1000 words, and finally editing. Breaking things down not only makes tasks less daunting, but the consistency of regularly hitting smaller deadlines will increase your motivation and your productivity.

Next, review previous projects and notice past delays. Maybe your piece required more research or editing took longer than anticipated. Factor this into the time it takes to complete your next writing project. Never stop evaluating and updating your processes.

After you’ve written blog posts for a while, you’ll gain a feel for how long you take to research, write and edit a post. When you receive a writing project, instead of trying to finish it as soon as possible, give yourself enough time to complete your project.

Even if your client hasn’t given you a deadline for a post, set a deadline for scheduling, submitting, or publishing. This ensures you don’t rush your post because of a deadline and hand in mediocre work. We recommend using personal Kanban to manage writing projects.

Setting writing goals is a great way to get into a routine and change the way you think about deadlines. You could set goals around:

  • Deadlines
  • Money
  • Submissions
  • Publications
  • Projects e.g. NanoWriMo
  • A daily word-count

8. Researching Your Work

You need a system for capturing ideas and reviewing them. Many new researchers like Evernote. That’s ok for clipping story ideas. The commonplace book as popularized by Ryan Holiday is popular too. However, I recommend using the Zettelkasten method for capturing ideas and reviewing them regularly. Essentially, summarise ideas as you happen upon them, interlink them using software or index cards and turn the results into work you publish.

Researching and structuring blog posts, articles, and book chapters is sometimes a struggle for writers. After all, how can sit down to write if you suddenly have to stop to research a location, fact, figure, or story idea? This challenge is particularly stressful if you’re writing non-fiction or freelancing.

How to Research Your Work

Read our guide to the Zettelkasten Method or check out my interview with Sacha Fast about this method

9. Isolation and Loneliness

Creative writing is a lonely profession, after all writers spend a lot of time alone with their ideas and words. However, this doesn’t mean you shouldn’t make time to socialize with friends and family and meet new people.

Socializing is a skill. Like any other skill, you can improve it or lose it. If you’re spending all day indoors working on creative writing projects and you don’t emphasize socializing, don’t expect to maintain your social skills. An argument could even be made that strong social skills will help you write more engaging content.

How To Overcome Feeling Socially Isolated

As a writer, you must prioritize what’s important to you. Since we’re social creatures, socializing should be up there with food and water. But few writers prioritize it.

So instead of watching Netflix or browsing the internet after you’ve completed your work for the day, try something new. Go to a networking event for writers, take up a new hobby like dancing, surfing, or martial arts. These are all interesting ways of making friends with people who share your interests.

By getting out and about and talking to different people, you will also get a broader understanding of what other people are interested in. How they talk and interact with each other, etc.. All of this will help you become a better writer, whether you are creating fiction or writing freelance.

Check out our guide for lonely writers.

10. Feeling Like Your Work Isn’t Good Enough

It’s common for many new writers to work on a story or article, then get it ready to publish only to decide, “I need to improve it a little.” That’s fine for a bit, but too much revising and self-editing can rapidly degenerate into procrastination and perfectionism. You need to finish and submit your work if only to get feedback. Sometimes rejection and criticism are what we need to grow as a writer, not another round shadow boxing with our own self-doubt.

How To Overcome This Writing Challenge

Commit to submitting and publishing a set amount of creative work each week, month, or year. Get feedback from a professional editor if you find yourself reworking the same pieces endlessly. As Stephen King famously said:

Write the the door closed, rewrite with the door open.

Stephen King

Read our guide to conquering these types of writing fears.

11. Stifled Creativity 

It’s normal to sometimes feel unproductive Similarly, feeling creatively dry is a common writing challenge. It’s particularly pertinent if you’re engaged in creative writing, like a short story or a novel. But you can take a few steps to get your creative juices for story ideas flowing again.

How To Get Your Creative Juices Flowing

There are several ways of getting into a creative headspace. Some include;

  1. Watching a new movie
  2. Reading a great writing book
  3. Listening to a podcast about writing
  4. Socializing with old friends or make new ones

The activities above all do one thing. They take your mind off your writing challenge and let your subconscious do the work.

Did you ever notice you never get an amazing idea while you’re actively thinking about how to solve a problem? Great ideas come when you’re doing something totally unrelated like watching TV or talking to a friend or family member.

Use this knowledge to your advantage. Next time you face a creative writing challenge, take your conscious mind off the problem and allow your subconscious to find a solution.

If you still need help, read our guide to self-care for writers.

Final Word On Writing Challenges

If you face challenges while writing, don’t worry. The blank page is sometimes intimidating. So, spend more time creating than consuming, particularly across genres. That’ll get your creative juices flowing.

Then, get into the habit of working on story ideas until they’re ready to publish. When in doubt, set an hour or two aside each day to focus on your work without interruption. The journey towards writing a 50,000-word novel starts with 500 words a day. Those writing sessions quickly stack up on top of each other.

If you’ve time left at the end of the day, take an online writing course. Thanks to the internet, you can easily learn from top-tier writers without spending thousands of dollars or traveling. That’ll help you improve your writing skills. With a few simple tricks and techniques, you can kiss all these common writing challenges goodbye.

FAQs About The Toughest Writing Challenges

What is a creative writing prompt?

A creative writing prompt is a project like a short story or poetry challenge. Prior to tackling the challenge,  know the purpose of the writing challenge, which writing style to use, and who the audience is.

What is creative writing and what are some examples?

Creative writing is any form of writing that goes outside the bounds of academic, journalistic, and technical writing. NaNoWriMo is an organization that promotes creative writing by holding short story and poetry challenges around the world. Other examples of creative writing include flash fiction and poetry.

Writing Challenges Infographic

Writing is a tough gig.

Perhaps you’re working on that difficult first draft, but you’re struggling with self-belief?

Maybe you’ve been playing with an idea for months, but deep down you know it’s not good enough.

Or perhaps you want to turn a hobby into a professional career that pays the bills, but you’re not sure how to do it?

Even if you’re a more accomplished writer or someone who’s finished a book or works with paying clients, it can take years to gain the confidence needed to become a professional writer.

These are common challenges, which anyone who wants to become a writer faces.

I wanted to learn more about these common writing challenges so last year, I asked 22 top authors and writers one question:

What was your greatest writing or creative challenge and how did you overcome it?

Now, I’ve put together the best answers in this writing infographic.

Save it, Pin it, share it!

Writing Challenge infographic
Right click and hit save as to download and read