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11 Freelancing Challenges and Solutions

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Recent days have seen the number of people seeking freelancing jobs increase tremendously.

Many people seeking freelancing visualize a free life where they can make decisions autonomously without having a boss breathing over their shoulders. Even better is the flexibility, with people working from home and requiring no dressing up for work or early long morning commutes.

However, while all these might make freelancing a dream job for many, there are a myriad of challenges that come with the freedom of work in freelancing.

Keep reading to learn 11 common challenges freelancers face alongside solutions to help you overcome these challenges.

11 Freelancing Challenges and Solutions



1. Freelancing Can Be Lonely

Loneliness is by far the most prevalent freelancing challenge that most freelancers have reported facing.

This follows findings from a survey conducted by Epson that at least forty-eight percent of freelancers admit to having felt lonely from time to time in their work. The impact of loneliness can even be higher for people who are extroverted or used to working in an open office. Unlike in a corporate setting, freelancing lacks constant work and community meetings. In some instances, one can even go days without meeting other people other than his or her housemates if any. Notably, the challenge of loneliness is most prevalent during the first days of freelancing.


While the distinction between work life and home life can be blurred, an optimal solution can be found in finding some designated work station away from home.

Like some of the successful freelancers, you might opt-in for spending many working hours in public areas such as a coffee shop and a public library. This productivity hack will help you simulate a sense of community and eradicate loneliness during freelancing. You might also opt-in for a shared workplace with other people of similar interests. Here, you can foster a sense of community and enhance networking too.

2. Your Family and Friends Might Want Freebies

You would rarely expect having your inner circle cause problems for your career, especially freelancing.

However, more often than not, your family and friends might not internalize how hard you work in your freelancing occupation. To some extent, they might want you to do their project for them for a low fee or even free of charge.


Such a scenario requires an assertive mind where you have to stand your ground on some work ethics. After all, you wish not to have your loved ones take advantage of your skills have you work hard for that earning that you cannot afford to work for free. Like other clients, you must treat your family and friends to ensure you don’t toil for no gain.

3. Unrealistic Expectations from Some Clients

It’s almost guaranteed that every freelancer will experience a horrific moment after interacting with some clients.

From time to time, you might encounter clients who might have unrealistic expectations from you as a freelancer. Don’t be shocked also to know that these terrific clients are the same who will offer poor pay rates for your services in most of the cases.


To avoid this, it is important that you vet your freelance clients before you start working with them. The number one way to vet any client is to check on the reviews made by other freelancers concerning the client. A series of negative or low score reviews from other freelancers should act as a red flag to signify a terrible client. Opt for clients who have positive and high score reviews from other freelancers.

4. Expect No Pay for Time Off Work

People working at normal corporate jobs will from time to time get holiday time, or be offered sick leaves in their contract.

Astonishing is a HoneyBook Survey whose findings were that at least 92 percent of freelancers don’t get non-working vacations at any moment of their jobs.


Having some time off your work or normal work schedule is important since it helps you recharge. While freelancing won’t have that time off from work, the best thing you can do is plan your vacation in advance. Through this, you can save some money and time and give yourself that break at the right time.

We cannot control how our bodies respond to illnesses. However, we can do some preventative measures to increase the chances of being healthier and away from illnesses. Opt-in for regular exercising and maintaining a healthy diet for a healthy lifestyle. While we are not fully immune from sickness, having a medical insurance cover and some emergency fund is essential to help you cover your medical needs.

5. Less or No Work During Some Seasons

Like most of the ventures, there is a boom and recession in freelancing.

At recession, or rather the low season, freelancers should expect less or no work at times. So, you might need to maximize your productivity during times of work overload to ensure you get the maximum out of your time and toil.


However, during the recession time, there is much that you can do to ensure some productivity. Use this time to work on your skillset and increase your credibility as a freelancer.

You might not be the best in what you do but if you are, know other freelancers are working hard to be more competent. Therefore, commit yourself to some continuous learning especially during the recession period. Use learning platforms such as Skillshare to enhance your skills, learn a new skill, or even both.

6. Maintaining Work-Life Balance Can be Demanding

Once you begin your freelancing venture, you will realize that there exists a blurred line between work and rest time.

Based on a survey by FreelancerMap, about one in six freelancers struggle to maintain a healthy work-life balance. The result of all suffering from burnout and depression is all born of overworking. Even worse in some situations is the negative impact freelancing can have in your relationships, both marriage and friendships. With overworking expected especially during the high season, relationships end up being strained.


The rule of thumb in every venture is to always remember why you started it. In this case, avoid being like most of the freelancers who try out seeking freedom and end up losing it altogether.

Cut out a clear work schedule and rest hours for your freelancing. For example, make 8 am to 5 pm your designated working hours unless it’s an emergency you’re tending to. Use weekends as your free time to rest and do personal things. With such a schedule you can plan your life around your work schedule without having to jeopardize any of the two.

7. Procrastination is More than Easy

There is a reason why corporate jobs will have that tough HR manager, production manager, or supervisor.

Without a boss breathing down your neck, wasting your time is quite possible. Unless you adhere to the cut out working hours and discipline yourself in a habitual followup of your time, you will procrastinate till deadlines hit you.


One of the most resourceful productivity hacks is maintaining accountability levels with a person you can trust. With this done, it’s hard that you will slack off for the better part of your day.

Have a person that will hold you accountable in that you have to reveal your work schedule and assessment of goal achievement would be done after the day is ended. Choosing a close accountability partner such as a spouse, fellow freelancer or friend is the way to go. Ensure you avoid a partner that will let you off the hook for failing to reach the stated productivity levels. Having an accountability partner might be the best productivity hack of your life.

8. Increasing Your Hourly Rate Might Take Time

One of the motivating factors in freelancing is how much you can earn after you climb the skill levels.

However, while many wish for a high hourly rate, this might be out of reach especially during the early days of freelancing. Due to competitiveness in some platforms such as Upwork, some freelancers might bid on similar jobs for less to land the deal. According to a survey by FreelancerMap, almost twenty percent of freelancers have reported their biggest challenge in freelancing is increasing their hourly rate.


Sadly, clients might also choose freelancers who have more credibility than you might possess, especially as a beginner. Well, you have to embrace the fact that nothing great was ever reached upon without hard work and time invested.

Think of freelancing as a hill where you have to invest both effort and time to reach the top. Maintain your diligence and stay focused and you might get your patience and efforts to reward you with a higher hourly rate.

9. Freelancers Have to Wear a Myriad of Hats

When entering the freelancing enterprise, be aware that you’re going to venture into some things you probably haven’t gained the perfect courage to try out.

For example, working as a web designer, you will in most cases not only be doing web design. You will likely also have to take in roles in accounting, marketing, or even administrator in order to run your freelance web design business. This can be quite daunting, especially at first. Unlike a normal corporate job, you won’t get paid for these extra tasks. You’re just going to have to do them, or pay someone who will do them for you.


The best solution, at least while you’re a beginning freelancer and may not be making that much money, is to do these tasks yourself. A productivity hack or two can help you get through such needs. If you really can’t get through some of the extra tasks, think about asking a friend or family member to offer a hand in doing something you’re struggling with that they might find easy.

10. Finding new clients can be difficult

If finding that first client was easy, well, everyone would possibly be a freelancer.

Finding clients, however, is more often than not a big freelancing challenge, with freelance marketplace becoming highly competitive and continuously growing. In the United States alone, Fast Company reveals that the freelance population has grown to about 57 million.


Be persistent and patient. Persistence and patience are the key tools an enthusiastic freelancer might need to possess. Without them, the challenge of finding new clients in the industry will lead to quitting.

Like other businesses, freelancing has the first few years as the years of hardships in finding that new client, customer, etc. Here most of the businesses tend to collapse, and so does the entire freelancing venture for some. If you fail to seek new clients consistently, you will struggle to land any jobs for yourself. It is said that if you don’t have your line in the water, you will catch no fish. In a similar way, keep looking for clients and you will land one if not many.

11. You Might Experience Technical Difficulties

While technical difficulties are not as common as other challenges, the issue is worth mentioning.

At some point in the freelancing venture, freelancers have and will experience technical difficulties either with hardware or software. Internet connectivity issues and unexpected power outages are other common technical difficulties that will plague freelancers from time to time.


You might need to bank on maintaining a great relationship fostered between you and your client so that if any of this happens they will understand if you’re late to submit your work. Opt-in to over-communicate your issues rather than under-communicate them to your client. This will create trust and transparency with them.

Final thoughts on freelancing challenges and solutions

Like any other business, there is no shortcut to success in freelancing.

The fact remains that you likely will face one or more of the freelancing challenges listed above before and even after tasting success. Notably, the ability to adapt to the challenges stated above and finding an optimal way to handle them will tell of how good you are at freelancing. With zeal, patience, and hard work invested in freelancing, you will power through the challenges and have your share of success at this venture.

Want to learn more about freelancing? Take my free 7-lesson mini-course here.



Images by Kenny Eliason and Einfach-Eve

Georgi Todorov of Thrive My Way
Georgi Todorov

Georgi Todorov is the founder of ThriveMyWay, a place for online entrepreneurs, bloggers, SEO specialists, and freelancers to find success in their own way.


LinkedIn: Georgi Todorov

Twitter: @GeorgiTodorovBG

This Post Has 2 Comments

  1. #3 is a biggie Georgi. I recall writing for a highly prominent blogger who simply did not vibe with my first, then carefully thought out, highly tailored, second draft. He refused to pay me. I did an excellent, detailed, in-depth job but we both lived in different universes as far as perspective.

    I quickly moved on with a smile but of course learned the valuable lesson: when a client asks you to bend over backwards, stop working for them before you break your back. 🙂 Fire them before their delusion gives you the mildest headache. Reasonable clients await. I also learned how wealthy people are sometimes the cheapest people around LOL.


    1. Wow, that’s quite an experience, Ryan. You’ve got such a great attitude, and I love your advice about stop working for a difficult client before you break your back. Reasonable clients definitely await!

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