The Most Common Fears Freelancers Have — and How to Overcome Them

Sam Woolfe
5 min readNov 4, 2019

Many people go freelance because of the freedom and flexibility it offers them. As a freelancer, you can choose your own hours, where you work, and what kind of work you do (within certain parameters, of course). But as many freelancers will tell you, the promise of improved work-life balance doesn’t always materialise as easily as you think it would. You have to be highly disciplined in order to develop a healthy routine.

Moreover, a lot of freelancers find the nature of their work extremely stressful, spending their days worrying about job insecurity and financial instability. Indeed, while office life may feel miserable and motivate people to consider freelancing, the latter can sometimes take a bigger toll on your mental health, if you’re not careful.

Some freelancers eventually decide that this way of working is not for them. For others, however, they may feel that the benefits of freelancing are too good to give up, but are unsure of how to minimise or cope with the different stresses involved. In this article, we will look at common fears freelancers face and how they can be overcome. It’s crucial to be aware of the reality of freelancing and to be prepared for some challenges. If you can make it work, freelancing can give you the autonomy and work-life balance that you are craving.

Not Earning Enough

One of the biggest fears for freelancers is that they’re not earning enough. And sometimes as a freelancer, you may not be earning enough — or as much as you could be earning. Simply scraping by to survive, dipping into savings, or getting into debt can obviously be a major source of stress as a freelancer.

However, you can avoid this situation (as best you can, anyway) by refusing to undersell yourself. Many freelancers get trapped in low paid work because they don’t assert themselves in terms of asking for pay that is worth their time, experience, skills, and output. When you start out as a freelancer, it’s normal to start with low paid work while you build up your portfolio and make a name for yourself. Nonetheless, over time, your skills will improve. This is why every freelancer needs to know when and how to raise their rates.

Not Getting Paid on Time

One common anxiety that freelancers share is not getting paid on time. This can be particularly stressful when a specific client is a particularly big source of your income, or multiple clients don’t pay you on time.

As a rule of thumb, all clients should pay you within a month of you submitting your invoice. It’s not fun to chase late payment, but sometimes it’s absolutely necessary if you want to get paid on time in order to pay your bills and expenses. One way to avoid this situation is to state on your invoice that you expect to be paid within the time frame agreed by the client, and inform that that you will charge interest for late payment.

Also, while chasing late payments may be a cause of anxiety, especially when you have bills to pay, you can reduce this stress by having a clear-cut procedure for dealing with the situation. When payment is a day late, send a reminder email. If payment is still late after assurances from the client, follow-up with a phone call. As a freelancer, you are entitled to be paid on time. You don’t have to feel embarrassed or desperate by chasing payment. As a freelancer, it’s important to recognise that your reliability in delivering work deserves to be met with reliability in payment.

Losing Clients

If you’re freelancing, the prospect of losing clients may be on your mind. Unfortunately, freelancing can be unstable and is less secure than working as a permanent employee for a single company. Clients could drop you anytime or they could suddenly disappear. That’s not unheard of. Freelancers often have anxious thoughts about losing a big client or multiple clients. This would leave them in a situation where they’re suddenly not making enough to pay their bills.

You can deal with the fear of losing clients in a variety of ways. Firstly, as a freelancer, your goal should be to secure reliable, long-standing clients. So make sure you look for long-term projects. Also, check out employees’ reviews of companies, as you don’t want to work for a company you end up wanting to leave. Seek out clients you want to keep in the long run. Later in your freelancing career, it may be wise to minimise the work you do for start-ups since a high percentage (90%) of start-ups ends up failing. Keep your eyes set on reputable, well-established, and successful businesses.

A lot of the fear freelancers have about losing clients tends not to be based in reality. You may imagine the worst based on a mistake you made or because of a delayed response from a client. However, it’s unlikely you’re actually going to lose a client in these situations. You can ensure a long-term relationship by becoming indispensable to your client. This means consistently producing high-quality work and always being reliable. If you regularly get positive feedback from a client, then make sure you remind yourself that you’re a valuable asset that the client won’t want to lose.


When you work as a permanent employee for a company, you may feel confident about your ability to progress in the role. There may be various training opportunities available, promotions, and other options for career development. In contrast, as a freelancer, you are pretty much in control of your career progression. It’s up to you to build skills, apply for more senior roles, and push yourself to achieve the best of your abilities. You don’t have a team or a boss encouraging you to improve.

Indeed, stagnation is a common fear for freelancers. You may have been working for the same clients for years, yet feel, deep down, that you can provide more valuable work to companies you hold in higher regard. Having unfulfilled potential as a freelancer can make your current work situation feel meaningless and zap motivation out of your working days.

In order to avoid stagnation, it’s vital to devise ambitious long-term goals and keep them in mind. Every day, do something that will edge you closer to those goals, however small those steps may be. Build skills and networks. Constantly challenge yourself. And always be on the look for your ideal role, as well as companies that align with your values and aspirations.

Originally published at on November 4, 2019.



Sam Woolfe

I'm a freelance writer, journalist, and author with interests in philosophy, ethics, psychology, and mental health. Website: