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Nobody Told Us About These Freelancing Challenges Before We Started - Freelancers Share Their Experiences

In this article, we’ll highlight key freelancing challenges freelancers face in their line of work and what you can expect if you plan on becoming one.

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In this article, we’ll highlight key freelancing challenges freelancers face in their line of work and what you can expect if you plan on becoming one.


We now live in an era that allows off-site work where we can complete tasks from the comfort of our homes, cafés, or wherever we want. This revolutionary wave is made possible by the sweeping digitalization of work processes and the fact that automation is gradually replacing human input to get work done more efficiently.

Remote work and freelance work are fundamentally intertwined as both entail the practice of working from anywhere and on your own terms; you’ve got the liberty to listen to symphonies as you change the world. 

Below are interviews with freelancers who share with us their freelancing challenges and tips on how to be an effective freelancer:

Freelancer #1 -  John Oladele, Graphic Designer

What attracted you to freelancing?

I got bored and exhausted from the routine 9 to 5 work and felt I needed a break from the rat race. I needed more time to accomplish personal goals and for my family. And after seven years, I felt it was time to make the switch. So I went in headlong, and here we are.

How has your freelancing journey been so far?

So far, so good. It’s come with its ups and downs. I’m very good at what I do, so I already built a reputation before quitting my job, so there’s always a backlog of gigs to sort out. Sometimes I get inundated but just prioritize according to deadlines, that way, I can work on projects and have them completed in time.

Freelancing has also afforded me the latitude to address areas of my private life that in my paid career would have proved impractical unless you’re prepared to get queried or chided by the management.  

What are the freelancing challenges that you face in getting work done?

No manager or coworker is available to ask for assistance when issues arise throughout a project. Clients often request that freelancers utilize a program or app they have never used before. Thus, they frequently have to become accustomed to new software quickly. This takes time, but it's also a terrific investment to learn something new. New freelancers could also invest a lot of time in looking for tools to simplify their jobs and lives.

Also, being a salesperson is a key aspect of freelancing, which can be stressful if sales aren't your strongest suit. I may have to pitch to clients without knowing their budget, so I must balance making as much money as possible with the risk of losing out to a more affordable candidate. We freelancers may need to issue invoices and follow up with clients about payment and serve as our own accounts department. 

Another freelancing challenge is communication. If your client can’t or won’t communicate with you, you’re likely in for a rocky road. This issue is especially common among companies that aren’t used to working with freelancers. Often, these businesses forget that you aren’t present in the office for important meetings and conversations and might not bother to loop you in on developments. For best results, set expectations upfront for the amount and type of feedback you require and stick to them.


Freelancer #2 - Ikenna Ibezim, Ghost Writer

Why did you go into freelancing?
Well, let’s just say I’ve always been fascinated by the idea of becoming my own boss. Freelancing offers such an opportunity where I wouldn’t have to get off bed in the wee hours to prepare for work and then have to face horrific traffic. So yeah, I’m enjoying my experience in freelancing. 

How has your freelancing journey been so far?

So like I said, it’s something I’ve always had in the cards, and it's been great since.

What are the freelancing challenges that you face in getting work done?

A major freelancing challenge is the problem of late payment. It is difficult to deal with a client who pays late or doesn't pay at all, just as it is frustrating to be paid less than you are worth for goods and services. Customers occasionally pay after the due date owing to basic disorganization. Other customers, however, fail to pay because they lack the money to do so. Others anticipate you will become weary of pestering them for cash and leave. 

But my way around this is to keep a record of clients that routinely delay in payment, and when I get contracts from them, I’ll request to be paid upfront. This way, further payment delays are mitigated to the barest minimum. This approach may work for freelancers who demonstrate consistency and competence in delivering projects.

In addition, another freelancing challenge is underpayment. Businesses frequently believe that they may save money by underpaying freelancers for their work. This behaviour not only serves to irritate freelancers but also frequently leads to businesses receiving subpar deliverables. What they say about freelance work is true: you get what you pay for. 


You'll also like:  "Don’t sign on the dotted line!" Client red flags freelancers should watch out for before getting down to work

Written by

Tobey C. Okafor

Internet Entrepreneur and Content Writer based in Lagos, Nigeria.

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