21 Common Challenges Freelance Writers Face (How to Deal with Them)

There are over 57 million freelancers in the US alone. And that number will increase to 86.5 million by 2027. That means more competition, opportunities, and challenges for freelance writers.

For instance, do you find balancing multiple projects challenging, dealing with inconsistent income, and handling rejection and criticism? Do you yearn for a healthy work-life balance? You are not alone.

In this blog post, you will learn how to prioritize tasks, negotiate rates confidently, and learn from constructive feedback for personal and professional growth. So, let\’s get started with overcoming 21 common challenges freelance writers face.

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1 Key Challenges in Freelance Writing and How to Overcome Them

Key Challenges in Freelance Writing and How to Overcome Them

Freelance writing can be a challenging but rewarding career. Here are some critical challenges you will likely face and how to overcome them.

1. Balancing multiple projects effectively


An independent freelance writer has several complementary projects that must be accomplished. You could simultaneously be your company\’s CEO, Managing Director, Marketing Director, Sales Manager, and Chief Financial Officer. Let alone your projects.

For example, I write and design my marketing copies, submit Upwork proposals, communicate with clients, and write their work. Failing to balance multiple projects effectively could be catastrophic to a freelance writer\’s finances, relationships, and health.

Tips to balance multiple projects effectively

  • Set priorities because not all projects are equally valuable.
  •  Set deadlines for each task to avoid procrastination and stay on track.
  •  Delegate tasks to free up some of your time for essential projects.
  •  Take a few-minute breaks between longer tasks to keep refreshed and focused.
  •  Use project management tools for freelancers such as Asana, Click-up, or Notion.
  •  Don\’t be afraid to turn down projects when you are already overloaded.
  •  Be flexible enough to adjust your schedule as needed.
  •  Communicate with clients to update them on your progress or potential delays.

2. Inconsistent income and financial uncertainty


Source: realinvestmentadvice

Another common challenge freelance writers face is inconsistent income and financial uncertainty. Freelance writing does not guarantee a regular paycheck like a regular job. There are off-peak seasons when you can barely make ends meet.

Inconsistent income and financial uncertainty also occur due to client budget changes. Some clients spend more money at the beginning of the year and gradually reduce their spending towards the end of their budget period.

However, utilizing peak seasons can guarantee a summer break and buffer you against potential financial uncertainties.

Tips to avoid or overcome slow months

  • Diversify your income streams in terms of clients and projects.
  •  Anticipate your client\’s declining workload and prepare accordingly.
  •  Market yourself. Showcase your skills, portfolio, and value proposition to clients.
  •  Create a budget to track your income and expenses.
  •  Build up a savings cushion to buffer your finances in case of unexpected expenses.
  •  Network with other freelance writers to find potential clients, advice, and motivation.

3. Finding and retaining clients in the competitive freelance market

Many freelance writers also need help finding and retaining clients. It can be challenging for newbies to navigate the competitive freelance market. Whether it is Upwork, Problogger, or Freelancer, the barriers to entry and client acquisition are significant.

Established freelancers and digital marketing experts recommend a client acquisition strategy that involves blogging and email marketing. Beginners who do not know where to find clients should start with Facebook Search, using keywords such as \”freelance writing jobs\” or \”content writing jobs.\”

On the other hand, client retention refers to how long you can work with a client. How often do your clients leave? What approaches do you take to persuade and negotiate with them to stay longer? Client retention generally relies on delivering quality work and ensuring client satisfaction.

4. Staying motivated and productive in a self-driven environment


Freelancers must also contend with staying motivated in a self-driven environment. Note that freelance writers sit in their workspaces for extended periods. For instance, I work about 10 to 12 hours from Monday to Friday. Sometimes I might be \”busy\” but not productive.

Freelance writing requires significant self-drive because you are your own boss. You will need to be told what to do and what not to do. It is up to you to ensure that your personal and professional tasks are up to date and that your balance sheet is satisfactory, which could be challenging.

Here are some tips to stay motivated and productive in a self-driven freelance writing environment:

  • Create a comfortable, organized, and conducive work environment.
  •  Personalize your workspace with items that inspire creativity and motivation, such as background ambient sounds, aromatherapy, books, natural lighting, and inspirational quotes.
  •  Use freelance tools to track your time, productivity, and income.
  •  Avoid physical discomfort by taking regular breaks, stretching, moving around, and changing your posture.
  •  Seek feedback and support from your clients, peers, and mentors.
  •  Set rewards and incentives for achieving your writing milestones.
  •  Find an accountability partner and join writing groups to share your goals, progress, and insights.

5. Handling rejection and criticism

Although rejection and criticism hurt, they are essential for personal and professional growth. It is important to distinguish yourself from your work to avoid taking your client\’s comments personally. Here are some instances when my work was rejected and criticized.


Rejection and criticism can affect your self-esteem, confidence, and motivation to the extent of doubting your abilities and skills. Some freelancers have even lost interest in writing altogether. It could also impact your income and reputation, like I lost hundreds of dollars in the projects above.

How can freelance writers deal with client rejection and criticism?

  • Maintain professionalism and manage your emotional response without being defensive
  •  Have a growth mindset. Seek clarification as to why your work was rejected and ask the critic what areas to improve
  •  Use AI productivity tools diligently to increase your writing quality
  •  Use the rejection or criticism as a motivation to grow and develop your craft
  •  Build a support system and a network with other writers for advice, tips, referrals, and encouragement
  •  Build a portfolio of positive feedback

6. Staying organized and managing time efficiently


Source: Google Calendar

Another critical challenge most freelancers report is difficulty staying organized and managing time efficiently. As noted earlier, freelance writers handle various projects, clients, deadlines, and financial and administrative tasks. You might feel overwhelmed, overloaded, and stagnant if you are not careful.

A dusty and unkept workplace is psychologically draining. A workspace that is not smelling great can lower your attention and focus. Staying organized includes keeping your desk clean and your workplace polished to avoid distractions. However, the most challenging part is time management.

Follow these steps to stay organized and manage your time efficiently

  • Create a routine that works for you and your clients, set a schedule, and stick with it.
  •  Prioritize your tasks and break them into manageable chunks.
  •  Use tools and apps to help you plan, organize, write, edit, and manage your projects.
  •  Delegate non-writing tasks or outsource specific responsibilities to free up more time for your core writing work.
  •  Keep your physical and digital workspace clutter-free and well-organized using folders, labels, and file management systems to store and retrieve documents efficiently.

7. Marketing and promoting your freelance writing services


When you tell someone you are a writer, they must understand that you are also responsible for marketing and promoting your services. Usually, newbie freelance writers think that article writing training is the end. They need to understand that marketing your writing services is also essential.

It is usually challenging due to limited marketing knowledge and difficulty in choosing the right marketing channel. Besides, building a personal brand takes work in the competitive freelance writing realm. Finding and retaining long-term clients also requires strategic marketing efforts.

This challenge requires you to establish a robust online presence. That could mean having a professional website, being proactive on freelance writing social media groups and creating a solid online portfolio. Another strategy is to network with industry professionals and attend freelancing events to get advice from those who have been where you are before.

You can also market your freelance writing services by offering discounts and promotions to attract new clients and get your name out there. Be persistent. Keep writing, networking, and promoting your services.

8. Setting and sticking to competitive rates


Source: completecleaningcontracts

When I started writing, I found it so challenging to set my charges. Whenever a client asked, \”how much?\” I would rush to various freelance writing Facebook groups to ask the experts.

My peers and mentees have also approached me countless times, asking whether they should charge their clients based on word count or pages written. It is understandable because of the difficulties in estimating some writing projects\’ time, effort, and value.

You should know the average market rates or client budget when starting. You may also feel insecure about your writing skills and experience.

Besides, there is enormous competition with other writers who may charge lower rates. Setting and sticking to competitive rates is difficult because you need to balance the quality of work with the quantity of work. Due to project type, complexity, and writing niche differences, you cannot stick to the same rates.

Therefore, there is no specific answer to what rates you can set for your freelance writing services. According to Upwork, beginners can charge between $0.05 and $0.10 per word. Intermediate and advanced freelance writers charge between $0.30 and $1.50 per word.

However, it would be best to calculate your rates based on your expenses, goals, desired income, and the value you give your clients. In other words, your freelance writing rates should increase as you gain more experience and reputation.

9. Writing without a portfolio


This is the most significant challenge beginner freelance writers face. Your writing portfolio is a collection of your past writing projects. It is what you show to potential clients to introduce yourself, your work samples, expertise, and skills. However, most freelance writers still need a portfolio.

Writing without a portfolio brings is a challenge that brings other challenges. Critical issues like finding and securing clients, entering a new niche or field, and landing better projects become increasingly difficult. An influential writer\’s portfolio should be professional and friendly and have a clear and catchy headline highlighting your value proposition and area of specialization.

There are several tools you can use to create your writing portfolio. But they will depend on your preferences, budget, and goals. Other factors to consider are the maintenance cost, ease of use and update, level of customization and design, and your target audience and clients. A portfolio is crucial for advertising your writing services and building your brand.

Where to create your freelance writing portfolio

  • Use website-building platforms like Wix, WordPress, or Weebly to create and customize your writing portfolio
  •  Host your portfolio online with platforms such as Clippings, WriterFolio, JournoPortfolio, or Contently
  •  Compile your best work samples into a PDF or Word document and attach them to client\’s emails and your applications

10. Not having enough work or clients



Freelance writing has peak and off-peak seasons. This is particularly true with academic writing, where there will be more jobs when students are in school and fewer jobs during the holidays. Sometimes the off-peak season can be so severe academic freelance writers might not have enough work or clients for months.

In contrast, article writing gigs could be available throughout the year because various industries need writers. An article writer may experience off-peak seasons when specializing in one industry. For instance, the writing demand for travel and tourism could be seasonal.

In addition, economic and technological factors like recessions, budget cuts, market changes, artificial intelligence, and large language models (LLMs) can affect all your income streams. A freelance writer must understand these changes and take appropriate measures to ensure enough work and clients.

Tips for freelance writers without adequate work or clients

  • Save money during the high seasons
  •  Develop a reputation for quality work and meeting deadlines
  •  Learn a new skill and expand into other niches
  •  Craft irresistible pitches highlighting your value proposition and expertise
  •  Apply for many jobs and seek work from your previous clients
  •  Gather testimonials from your satisfied clients and use them to attract new clients and referrals
  •  Study negotiation, communication, and persuasion skills to stay agile and competitive
  •  Improve and showcase your portfolio through a website and social media platforms
  •  Stay up to date with the industry\’s technological advancements like artificial intelligence and LLMs

11. Isolation and loneliness


Isolation and loneliness are challenges that writers face in their freelance journey. Note that writing is a solitary activity requiring concentration and focus, which cannot be achieved in a noisy or crowded space. As such, freelance writers need more social interactions and connections which you must learn to cope with.

Remote work can also blur the boundary between your personal and work life, impacting your emotional and mental well-being. Going many days without support and feedback from colleagues, mentors, and peers can also be devastating professionally and psychologically.

In other words, isolation and loneliness could result in anxiety, depression, low-self esteem, and reduced creativity and productivity in your freelance career.

Here are some tips that have worked for me that I am confident will help you too

  • Create and stick to a schedule that balances your work and personal life
  •  Set aside time for social activities
  •  Exercise regularly to stay physically and mentally healthy
  •  Join online and offline freelance writing communities for support and feedback
  •  Take breaks from social media to avoid comparing yourself to others and the negativity associated with it
  •  Write in a way that expresses your feelings to connect with others
  •  Share your writing for validation and recognition

12. Setting boundaries with clients for a healthy work-life balance


Source: Psychology Today

Some clients assume that you are available 24/7. If you develop such a rapport with them, setting boundaries might be seen as unpleasant and could compromise your relationship. While your values might be around customer satisfaction, being available to clients around the clock could weigh heavily on your loved ones.

Playing with your kids, spending time with your spouse, and attending to your projects depends on the boundaries you set with your clients. Otherwise, you might not have adequate time for personal development, let alone eating with your family.

However, work-life balance looks different for every freelance writer. Some people are okay with working longer hours than others. I recommend that you understand your preferences, circumstances, and priorities and manage your responsibilities in a way that promotes your well-being and satisfaction.

How to set boundaries with freelance clients for a healthy work-life balance

  • Set office hours, lines of communication, and communicate them to your client(s)
  •  Establish and agree with the client on the project scope, timeline, and expectations, and stick to them
  •  Say no to unreasonable client requests and demands outside the project scope
  •  Use a contract for every writing job to protect your rights and interests
  •  Seek client feedback and validation but don\’t allow them to dictate your confidence and self-worth
  •  Be direct and honest without beating around the bush or trying to sugarcoat things
  •  Focus on jobs in your core strengths and outsource or delegate those outside your expertise
  •  Be flexible to bend or break your boundaries as long as it is not a regular occurrence.

13. Managing finances and taxes independently


Managing finances and taxes independently can be a significant challenge for freelance writers. First, freelance writers often have irregular and unpredictable income streams, making predicting and planning for future earnings difficult.

The inconsistency makes budgeting and planning for personal and business needs even more complex.
Additionally, freelancers are responsible for paying their taxes, including self-employment taxes. These taxes are usually higher than the regular income taxes.

You may also need to handle your retirement savings, health insurance, and other benefits employers would otherwise provide.

Follow these tips to effectively manage your finances and taxes

  • Separate business and personal finances: Open a dedicated business bank account to keep track of income and expenses related to freelance work.
  •  Track income and expenses: Utilize accounting software or spreadsheets to organize and categorize financial transactions.
  •  Budget and save for taxes: Consult a tax professional to estimate and understand your tax obligations.
  •  Plan for retirement and insurance: Research options such as individual retirement accounts (IRAs) and freelance-specific insurance plans.
  •  Seek professional advice: If managing finances and taxes become overwhelming, consult with a financial advisor or tax professional who specializes in working with freelancers.
  •  Stay updated on tax regulations.

14. Burnout and stress


Source: Pexels

Burnout and stress pose significant challenges for freelance writers due to the unique nature of their work. The freelance writing industry is often characterized by tight deadlines, demanding clients, and the pressure to produce high-quality content consistently.

The absence of a traditional work structure, such as fixed working hours or set breaks, can blur the boundaries between work and personal life, exacerbating the risk of burnout. Freelance writers must constantly balance multiple projects, juggle client expectations, and manage their time effectively.

The fear of losing clients or missing out on opportunities can also lead to overcommitment and working long hours, resulting in mental and physical exhaustion. The isolation that comes with working alone for extended periods can also contribute to feelings of stress and burnout.

Adopt the following strategies to manage freelancing stress and prevent burnout

  • Incorporate regular breaks, exercise, healthy eating, and sufficient sleep into your routine. Taking care of your physical and mental well-being is crucial to maintaining productivity and preventing burnout.
  •  Avoid overloading yourself with excessive work, and communicate clearly with clients about achievable deadlines.
  •  Practice effective time management: Plan your workdays, allocate specific time slots for different tasks, and avoid multitasking. Utilize productivity tools and techniques to stay organized and focused.
  •  Connect with other freelance writers through online communities or networking events.
  •  Schedule time off to recharge and rejuvenate, even if it means temporarily pausing client work.
  •  Incorporate stress-reducing activities into your routine, such as meditation, deep breathing exercises, or engaging in hobbies.

15. Impostor syndrome


Source: CNN

Freelance writers are familiar with the impostor syndrome. It is the feeling that you must be better, smart, or talented enough for your work. You may doubt your writing abilities and achievements and fear others will expose you as a fraud.

Impostor syndrome can be challenging for freelance writers because it can make you undervalue your work and charge low service rates. It can make you avoid applying for high-paying or prestigious writing gigs that you are qualified for.

Impostor syndrome also results in procrastination. You may procrastinate on your projects or spend too much time revising and editing your work. It also makes freelance writers reject positive feedback or compliments from clients or peers and compare their \”inferiority\” to other writers\’ \”superiority.\”

Tips for freelance writers to overcome impostor syndrome

  • Recognize and acknowledge your impostor\’s feelings and thoughts, and challenge them with facts and evidence of your accomplishments.
  •  Celebrate your successes and achievements, no matter how small or big they are
  •  Seek constructive feedback and support from other writers or mentors who can help you improve your skills and confidence.
  •  Focus on providing value to your clients and readers rather than impressing them or meeting unrealistic expectations.
  •  Embrace your uniqueness and authenticity, and don\’t try to copy or imitate other writers.

16. The writer\’s block


Impostor syndrome and writer\’s block are two different things. There are days when your creative juices are flowing and days when you can write with enthusiasm.

Then, there are those days when your creativity slows down to a standstill, days you can\’t create new work and can stare at a blank page for hours. That experience is what we call writer\’s block.

It can be caused by apathy, anxiety, anger, and problems with other people. Other factors that can trigger it are fear, procrastination, overthinking, distractions, perfectionism, skill deficiency, insufficient research, confusion, bad timing, lack of inspiration, insufficient time, and unprocessed emotion.

Writer\’s block can stay with you for a few minutes to days, weeks, or months. It is a significant challenge to freelance writers because, during that time, they can\’t create new work or move forward with their projects.
Note that writer\’s block does not care how much work you have.

Even if you had a whole truckload of client work, writer\’s block would not allow you to dot an ink. However, there are several ways to overcome this challenge.

Tips for overcoming writer\’s block

  • Take a break from your writing and do something else to relax and gain a new perspective
  •  Don\’t worry about perfectionism. You can always revise and edit your work later
  •  Write in blocks of 25-minutes with short breaks in between, also known as the Pomodoro Technique
  •  Get a good night\’s sleep to feel refreshed and energized
  •  Avoid distractions when you are writing
  •  Use a mind map, an outline, or a checklist to map your thoughts
  •  Use artificial intelligence tools with prompts to spark your imagination and get started

17. Finding a profitable niche and specializing



When I started freelance writing, this was the most challenging thing: finding a profitable niche and specializing in writing. For many years, I was a Jack of all trades.

Most expert freelance writers advise that I write on anything I come across – technology, travel, pets, houseplants – name it. They said it would slowly dawn on me what I could write best and that only then was I supposed to specialize in a niche that resonated with me.

Although that advice was crucial to my specialization, please don\’t use it. I agree that niching down is profitable, but I\’m afraid I have to disagree that it should take you so long. Besides, they will not tell you that finding a profitable niche only makes sense if you want your website or blog.

If you are yet to create a blog, determine what things you can write easily, and don\’t be choosy. Focus on doing good research and producing quality work on various niches. These will come in handy when pitching for jobs from various industries. It will enhance your flexibility significantly.

When specializing in a profitable niche, consider food and nutrition, personal finance, education, health and wellness, or business and marketing. Don\’t worry about whether you have the passion in those areas. The interest will develop along the way. Just dig in deeper.

18. Maintaining consistent output


A freelance writer can write between 500 to thousands of words per day. However, remaining consistent from Monday to Saturday and January to December is a significant challenge. Maintaining consistency is particularly difficult not only in terms of output but also in terms of quality.

Sometimes you can have a lot of work on one day, so much that you cannot produce the same quantity and quality the following day. Besides, you might feel unmotivated on some days and slack off more than on other days. The discipline and work ethic required to produce quality articles can also fluctuate.

While this is understandable, the inconsistent output can significantly impact your finances. Some possible ways to overcome the challenge include creating a running list of ideas organized by topic or category. It pays off to plan your days and weeks in advance.

In addition, you can stick to a writing schedule that distributes your creative energy evenly throughout the week and take the weekends off. Most importantly, track your writing output every month and set improvement goals. It will help you monitor your output and get back on track whenever you slack off.

19. Avoiding false self-employment pitfalls and legal issues


Most freelance writers have found themselves in situations where clients treat them as employees. However, with false self-employment, no benefits and protections are associated with an employment contract. False self-employment can have severe social and legal consequences, including paying back taxes, social security contributions, fines, or even imprisonment.

False self-employment is difficult to avoid if you work for one client, follow their instructions and content strategy, and use the client\’s equipment and resources. It is easier if a freelance writer has alternative income sources. You don\’t have to worry if that sounds like you.

Ways to prevent false self-employment in freelance writing

  • Ensure there is a written contract defining the freelance project scope, duration, and terms of engagement
  •  Seek multiple clients
  •  Diversify your income streams
  •  Take control of the project processes, such as setting work hours, rates, and working methods
  •  Create a professional identity such as a website, portfolio, or business name

20. Affording health insurance


As a freelance writer with no formal employment benefits, you may need to pay for your own health insurance. Freelancer insurance costs vary depending on the plan, your income, location, and eligibility for subsidies. However, the average monthly premium could be about $495.

Note also that freelancer health insurance may have high deductibles and limited coverage. The networks could also be restricted, making access to quality care more difficult.

Some possible ways for freelance writers to cope with this challenge include;

  • Shop for health insurance in the Health Insurance Marketplace, established by the 2010 Affordable Care Act.
  •  Join your spouse\’s health insurance policy if they are employed and have one
  •  Explore health insurance options through Freelancers Union and get group plans and discounts
  •  Set up a health savings account to save for your medical expenses and reduce your taxable income

21. Late payments


The most frustrating and sometimes irritating challenge freelance writers deal with is late payments. It has been so commonplace since I started freelancing about five years ago. Nearly every client you work for will sometimes pay you late and cause significant cash flow problems. If you delegate and outsource some of their work to your colleagues and writers as I do, you might be forced to pay your writers from your pocket.

Some clients may not respect the deadlines or payment terms, which can be stressful and unreliable. You might be in trouble if you have to cover urgent expenses and bills by relying on such clients.

Besides, some clients ignore your reminders, make excuses, and dispute the quality of your work at the moment of payment. You might wonder why they had to wait to tell you at the last minute.

Here are some possible ways to deal with this challenge

  • Research client\’s reputation with other writers and avoid those with a history of late payments
  •  Maintain a good correspondence with the client and send them invoices promptly and professionally
  •  Negotiate a fixed payment date and charge interest or late fees on overdue invoices
  •  Contact the publication\’s finance department, editor-in-chief, or managing director when the client becomes unresponsive
  •  Send consistent reminders until the payment is processed

Achieve Freelance Writing Success with Professional Content Writing Training Services

The list of challenges that freelance writers face is long. From impostor syndrome to writer\’s block to handling rejection and criticism, we have discussed 21 of them. Other common challenges include keeping up with the latest industry technologies and procrastination. Overcome these challenges by delegating duties, exercising, using the Pomodoro Technique, and networking.

Don\’t hesitate to contact us for professional assistance in your freelance writing career. We offer a high-quality content writing course that will equip you with the skills to leverage the most recent AI writing tools to increase productivity and avoid some common freelance writing challenges.

Fill out the form below to get started.

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