7 Freelancing Challenges and How to Overcome Them

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7 challenges freelancers face and how to overcome them

Freelancing can make a very good income but it has its own fair share of challenges. Some of the freelancing challenges such as difficulty in finding new clients, low seasons, stubborn clients, burnout, are cross-cutting issues that affect both beginners and professional freelancers. Just when you think you have it figured out, you encounter a new challenge that must be resolved.

We have therefore compiled seven freelancing challenges that have affected at least everyone in their freelancing journey.

Landing new jobs/ finding new clients

There are various ways of pitching ideas to a client. Freelancing platforms such as Upwork allows you to write a short proposal explaining to a client why they should consider you for their job.

One of the biggest challenges is to write a good proposal to prospecting clients, especially when you’re just starting out with no reviews to your account. Even so, experienced freelancers will also face difficulties in finding projects if clients are not willing to pay the rate experienced freelancers are asking for. This means they get ignored as soon as the client sees their charge rates.

How to land new clients as a freelancer

It may take months before you land your first job. The most important thing is to be consistent and continue pitching to prospecting clients even if you don’t land an interview.

Also, do not limit yourself to a particular platform. There are many freelancer platforms available and you should your cast your net as wide as possible to magnify your prospect base.

Some freelancers look to social networking platforms like Linkedin. This is not only a good way for you to reach potential clients, but also an opportunity to establish your personal branding. There are also transcription websites such as Auris AI that partner with freelancers for translation jobs.

Another effective method is cold pitching. Identify a client whom you feel your services will impact their business positively, then inbox them your proposal to see if they will like it. If you get accepted; bravo! If you get rejected, at least you tried.

Unpredictable job seasons and pay

There are months when your pay as a freelancer is beyond your projected outcome. Gigs keep coming through and clients pay on time as they should. Then there are months that are just the exact opposite.

The solution to unpredictable job seasons

Do not go beyond your spending limits simply because the season is favorable, instead, invest or save the extra pay to prepare you for the less vibrant season.


Burnout is a common experience when a job has demanding timelines and a lot of quality input needed.

One mistake freelancers do is to ask for more work from clients when they know too well that they already have a lot on their plate. This means they may be unable to deliver quality work on time.

How to overcome burnout

Communicate. Being honest with your client about your schedules will not take away gigs from you. Communication helps a client know when you will be undertaking his/her assignment, delivery timelines, and how much he/she will be paying for quality work. This way, you will not receive pressurizing messages such as “ how far are you?”

Outsource. As you grow in freelancing, you start landing more jobs than when you first began. Before this happens, mentor someone on how to undertake such tasks and keep them on standby just in case you need help with overwhelming work.

Time management. Sometimes burnout is just a result of poor programming. You want to wake up at 2 pm to start a job whose deadline is 12pm-midnight. Allocate time for each activity such that no one activity clashes with the other.

Optimize your workflow with artificial intelligence tools. If you are a transcriber or a translator with multiple translation jobs awaiting, use Free transcription websites such as Auris AI for automatic translation. These make your work easier and all you are left with is to polish up on the transcripts or content; a less than an hour’s task.

Clients Who do not pay

Every business has encountered that one customer who tries to be cunning at every negotiation table. This client keeps changing the payment agreement or goes incommunicado for days.

The best strategy is to be alert. Work with clients who have been recommended by certified platforms such as Fiverr or Upwork. In fact, Upwork will sometimes send you an alert when they feel the client is reluctant at approving some crucial details of a contract and even ask you not to make any agreements outside the platform.

Also, follow your instinct. When a client keeps ignoring/dodging crucial details in a work agreement, it is just a tip of a bigger underlying problem you are yet to face.


Working as a remote freelancer can keep you away from your social life. Because of the different time zones of the clients, freelancers will keep awake to work on assignments in line with a client’s time zone hence no time to socialize.

One way to overcome this is to go to a co-working space. This way, you are still able to meet other people as you go about your business.

You can also set aside days such as Sundays or Saturdays where you prioritize your social life 

Negotiating for Pay

Let’s assume you have come across a gig that fits your specialty and you know that you can meet the required deadline. The only problem is; the client is paying way below your minimum rate card. What will you do?

To be honest, I have come across such gigs before and did not send a proposal because I thought the client would be rigid, but I was wrong. Of course, there are clients who do not see how much value quality work will bring to their business, so they think working on a marketing project is not “that difficult”. 

So, write that proposal anyway. However, within the proposal, give a breakdown of why the project will cost more than the client had projected. Prove to them how impactful the deliverables are to their business, leaving room for them to see the consequences of undervaluing the task. If they see your proposal and decide to reach out, it clearly means they are willing to pay your worth.

Maintaining quality work

Freelancing and research go hand in hand. There are times you will not be 100% conversant with what the client wants but that does not mean that you should decline the offer. Instead, look for books, articles, tutorials, etc that give more details on the assigned project. Also, if you had underestimated the scope of work only to realize that it is too technical for you, let the client know in time. Do not wait till the deadline to give excuses.  

Final Thoughts on How to Overcome Freelancing challenges

Just like any other job, freelancing also has its own ups and downs. Do not procrastinate starting out as a freelancer simply because of the downsides. The fun fact is; you will learn to tackle the freelancing challenges as time goes by. If you need ideas on the kind of freelancing work you can take on, check out our list of freelancing jobs you can explore!