3 of the Biggest Challenges You’ll Face as a Freelancer

Joanne Poh



Paint a picture in your mind of the typical Singaporean employee, and chances are you’ll come up with a Raffles Place office worker, choping his seat at lunchtime with a packet of tissue.

Well guess what, Singapore’s actually getting a bit more diverse in terms of the types of work people engage in. Notably, the number of people who work as freelancers or sole proprietors is steadily increasing as more young people decide to be their own bosses.

That all sounds nice and rosy—imagine never having to grapple with your boss’s curious obsession with face-time, and being able to work in your FBT shorts.

But ask any freelancer and he’ll tell you that his life isn’t as easy as you think. You might be your own boss, but it also means you often end up being your own teacher, accountant, lawyer and cheerleader too. Here are three big challenges freelancers face. Don’t resign from your day job until you’re willing to shoulder these responsibilities.


Upgrading your skills

One of the biggest advantages of working in an organisation is that the company usually takes on a certain amount of responsibility in training you and making sure you’re competent enough to do your job. Over time, a decent employer will groom you to take on new responsibilities by making sure you pick up the necessary skills. If you feel like you’re in a dead end job where chances of career progression are low, you simply start looking for a new job.

When you’re a freelancer, the possibility of spending the next 10 years doing the exact same job is totally possible. If you’re not proactive about not only upgrading your skills, but also marketing your new areas of expertise, the possibility of stagnation is high.

Let’s take the very basic example of the private tutor. Just about anyone can teach primary school math, which is why so many start out doing that. But if you really hope to boost your earning potential, you want to refresh your knowledge of O level or, even better, JC subjects, simply because you earn a lot more per hour teaching them. Some tutors then go on to conduct group classes and crash courses close to exam period, all of which take time and planning.

Nobody’s going to push you to upgrade your skills or point you in the right direction. It’s up to you to find out how, and to connect with others in your industry so you’re more informed about your options for growth. If you just want to relax in a cubicle and be spoonfed, don’t quit your day job.


Protecting yourself from unscrupulous clients

For the majority of Singaporeans, payday is something that happens like clockwork. Every month, your salary gets banked into your account and your CPF contributions paid.

As a freelancer, getting paid is a lot more complicated. You need to be the one to monitor who is supposed to pay up and when. If you have several clients, this can be very troublesome—I recommend maintaining an Excel spreadsheet on which you record the date of every invoice you’ve sent out, so you can chase people for money regularly. I have one or two horror stories of clients who only paid up one year after the job was done.

Payment aside, there are other ways you might get screwed over by your clients, including accepting an assignment only to have the client try to sneak in all sorts of extra work, to the point where you’re working for peanuts.

As you get more experienced, you’ll have to put in place systems to protect yourself in such circumstances. One rule of thumb is to always have clients sign a contract before commencing work, setting out rules such as when payment should be made, details concerning any deposits that must be paid ahead of time, and the scope of the work to be completed.


Hacking your work processes to be more efficient

Efficiency is a lot more important to a freelancer than it is to an employee who’s paid to sit in the office from 9 to 6 no matter how much work actually gets done.

Two freelancers charging the same amount for a project can have vastly different earnings at the end of the month if one works twice as fast as the other.

Heck, two ComfortDelGro taxi drivers have meters that charge the same amount per ride, but how much each one takes home and how hard each one has to work depends on how smart they are at picking up passengers and strategising where to go at what time.

Part of the challenge of getting better at your job is learning how to work more quickly and more efficiently. At the start, it could simply be a matter of honing your skills—for instance, as a web designer you’ll want to make sure your HTML, CSS and design software skills are sharp.

But don’t forget there’s a lot more you can do to boost efficiency. If you have trouble being focused and find you’re wasting lots of time surfing the internet or getting distracted by your surroundings, you need to find ways to force yourself to concentrate.

Some people listen to music as they work to block out what’s going on around them and some use time management techniques like the Pomodoro Technique. It might take months of experimentation to find a system that works for you, especially if you have the attention span of a fly.

But never give up—being able to finish your work faster is tantamount to giving yourself a raise as you’ll be able to take on more jobs, and if you finish your work for the day early you won’t have to waste your time waiting for 6pm to arrive.

What other challenges do freelancers face? Tell us in the comments!

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Joanne Poh

In my previous life, I was a property lawyer who spent most of my time struggling to get out of bed or stuck in peak hour traffic. These days, as a freelance commercial writer, I work in bed, on the beach, in parks and at cafes, all while being really frugal. I like helping other people save money so they can stop living lives they don't like.