3 Big Challenges Every Freelancer or Self-Employed Person Faces and How to Deal

3 Big Challenges Every Freelancer or Self-Employed Person Faces and How to Deal

If you’ve ever wished your boss would just cease to exist, you’re not alone—in a 2014 report, difficult bosses were cited as a big reason Singaporean employees wanted to quit their jobs.

Being your “own boss” might sound like a dream come true, but when you think about the fact that taxi drivers, hawkers and freelance cleaners are all also technically their own boss, it starts to dawn on you that there just might be a ton of drawbacks to working on a freelance or self-employed basis.

Whether you work from home on the computer, are a private tutor, own a small business, ply the streets in a taxi in search of customers or are doing a 9 to 6 office job on a freelance basis, there are some challenges every freelancer faces and you will too. Your success as a freelancer depends on how well you manage the following challenges.


Unstable income

When I first started freelancing, there were months when I was earning little enough to qualify for the Workfare Income Supplement if I had been a couple of decades older. But I didn’t have to borrow from loan sharks to pay my credit card bills because, well, you don’t use your credit card to buy kaya toast at the kopitiam, which was what I treated myself with to celebrate not starving at the end of the month.

While some months might be like goldmines, others are going to be dry as a desert, and you have to be prepared to weather the storms in the months when your income is down.

The amount of volatility you experience will vary depending on what work you do, but every self-employed person experiences some degree of instability. Even if you are working from 9 to 6 in an office, once that assignment ends you could find yourself jobless for a couple of months until the next gig comes along.

And even the most solid stable of clients is not going to pay you for existing if you get sick and need to take some time off.

What this means is that you’re not going to be able spend as much of your average monthly income as your peers in stable jobs. An employee earning $5,000 a month can spend $4,999 without fear of repercussions, but a freelancer with the same average monthly earnings should be giving himself a much wider buffer.

If you’re a freelancer and your income is anywhere from $2,000 to $8,000 a month, if you’re spending $7,000 a month you’re going to be very nervous in the dry months, and will start eating into your savings in certain months. Conversely, if you spend no more than $2,000, you’ll never have to worry about whether you’re earning enough to keep your bills covered in any given month.


Having to work efficiently all the time

Many Singaporean employers like to think they are squeezing as much work out of their employees as they can for as little pay as possible by demanding that they spend long days and nights at work, but in fact some are unknowingly paying workers to spend long hours at the office surfing Facebook or gossiping with the other office aunties.

When you’re a freelancer, work in the same way and you’re better off looking for a “real” job. Every minute you waste watching cat videos or replying to WhatApp messages is a minute for which you are not being paid. The slower you work, the less you are being paid per hour.

That means people who have trouble concentrating on their work or who are just plain slow are at a distinct disadvantage when trying to launch a freelance career. Imagine a taxi driver who is only able to drive at 50km/h and you get the idea.

As a freelancer, unless you’re being paid on an hourly basis (like tutors) you absolutely need to hack your work processes to get as much done in as little time as possible, unless you like the idea of working 20 hours a day.

That doesn’t just mean you tell yourself “I’m going to be efficient and not browse Facebook all day!” and leave it at that. Efficiency is something you get better at not only with time, but after trying out many new methods. This is easier said than done, because sometimes your energy levels just aren’t high enough to sustain uninterrupted focus.

A friend of mine who works from home swears by the Pomodoro Technique, while others might find they get more done while listening to music, working in cafes or disconnecting their laptops from the internet. Replying to all emails the minute they are sent disrupts work flow and you might be better off responding to all queries at one shot at the end of the day.

Taxi drivers these days are all about apps like GrabTaxi, while even hourly-paid private tutors have to get creative with scheduling students so as to teach as many as they can in as short a timespan as possible.

The point is, efficiency as an ongoing challenge, and as the years go by you should continue to work on optimising your work processes further. When you manage to increase your income to a certain point, it might then make sense to outsource administrative tasks or to hire employees.


Prospecting for customers

As an employee, unless you’re in sales, all you have to do is sit at your desk and you can be sure your boss will find some work for you to do. If he doesn’t, the one who’ll be losing money will be him, not you.

As a freelancer, however, you’re responsible for finding your own work, and failure to do so will be met with starvation. If you’re going to be successful, you’ll need to come up with a system for soliciting for work—even if you don’t really have to use it now, or often.

How often or how intensively you have to prospect depends on your line of work and how many existing contacts or clients you already have. But as a general rule of thumb, freelancers tend to have to hustle a lot more at the beginning of their careers, and when they have a regular stable of clients or a decent income flow they do it only occasionally or not at all.

For instance, rookie insurance agents often take to the streets, trying to set up appointments with anyone who doesn’t instantly turn tail and run away, but after a couple of years on the job few of the successful ones have to do that anymore.

Beginning tuition teachers need to know how to find clients—one of my friend offers his students money in exchange for referring their friends, while others get their assignments from tuition agents.

And freelance designers need to have great online portfolios, as the internet is often a source of leads.

Heck, even taxi drivers need to know how to find surcharge-paying clients as quickly as possible, whether by taking bookings through apps or hanging around party areas after midnight (and, annoyingly enough, strategically refusing to pick passengers up between 11:40 and 11:50 pm).

Learning not to fear hustling is important for new freelancers not just because they need it to find work, but also because it gives them the peace of mind that they won’t be at a total loss should their current sources of work dry up.

What other challenges have you faced as a freelancer? Tell us in the comments!