Self-employment or best known as freelance is a career path that many would prefer over a regular nine-to-five. It’s easy to know why—you get more time for traveling, you get to choose what work you’d like to do, and you may even have some time for yourself. While this may be true, freelancing is daunting.

There are several unknowns even for the most experienced employee: How much should I charge for my freelance work? What should I include in my contract? How should I do my taxes? How does billing work?

Work-From-Home Freelancer
Having a headache is part of the ‘job’.

And those are not even the worst. It’s (almost) a fact that freelancers are not being taken seriously and independent workers tend to struggle to be treated fairly in the professional world.

There’s no one-size-fits-all methodology to become a good freelancer; it relies heavily on your industry, level of experience, and numerous other personal traits.

Anyway, here we shed some light on the adversities a freelancer may face, lessons you may learn, and, most of all, what you wish you’d known before you dive into freelance work.

You’d be facing more anxiety than you’ve ever had

Examples: Financial instability due to lack of jobs, negative psychological impact such as pressure and low self-esteem, etc.

Work-From-Home Freelancer
This is not what I signed up for.

We’re pressurized by society to hold on to a regular job. It’s not a bad thing actually; you don’t have to worry about paying your monthly mortgage bills, you’re financially liberated to buy nice things, and you can even splurge a little on your loved one.

Because of these perks, many would agree that it takes loads of courage to leave stable work behind.

Taking the plunge to transit from stability to uncertainty will undeniably be packed with anxiety, and it’s something that a freelancer would have to go through. To ease the stress a little, make sure you do the following:

  1. Have a sufficient amount of money, several month’s worth to be exact, to live off of
  2. A back-up career plan (networking will come into great use in this aspect)
  3. Discover and establish a few relaxing routines or activities that can help take the stress off

Prepare to do work that you’re not interested in

Examples: Writing on dry topics, etc.

Work-From-Home Freelancer

To survive in the world of freelance, you’d have to be strategic with balancing passion and survival. Sometimes your passion doesn’t necessarily pay the bills.

You’d have to learn to pitch for work that you’ve not pictured yourself doing, such as designing commercial flyers when you’re more eager for creative social media content.

However, these are the jobs that are going to support your income throughout the year, while you can still engage in lower paying jobs that you’re truly passionate about.

You’re most likely to do work out of your expertise

Examples: Doing up invoice and quotations, dipping in sales/pitch talk when you’re a creative, etc.

Work-From-Home Freelancer
I’m pitching because if I don’t, I’d be broke.

Imagine completing your job for a client. Time to celebrate! But before that happens, you’d have to prepare an invoice. Well, you never had to do that while you’re with a company.

And that’s one of the hardest parts of working independently: You’d need to deal with matters that you’re absolutely unfamiliar with. Thankfully for the internet, you can obtain useful learning resources (such as how to invoice for freelance work) that’ll help you breeze you through these matters.

The next most possible thing you’d have to do is perhaps networking to build your freelance business. So when you were dealing with your daily grind, you needn’t think about how to differentiate yourself and sell your skills to people as much.

But for self-employment, selling your skillset is a constant duty. To get new jobs, you’d have to expand your social and professional circle. If you’re not a salesperson, you may not find pleasure in the process.

Your money will be in a mess

Examples: Tax filing, delayed payment from clients, etc.

Work-From-Home Freelancer
Question: Is this all I have left for the month?

It’s almost the cold hard truth that your finances will be a huge mishmash (or not if you’re a money-savvy person). It’s predictable that you’d be experiencing more financial inputs and outputs once you start freelancing.

And as you start the process of self-employment, you’d not just need to take control of your finances now, you’d also have to plan for the future. If you’ve no experience in money issues, like tax filing, it’s best to engage someone for help. Or for the time being, save up 30-40% to pay taxes on every income you make.

As a freelancer; most of us don’t get paid what we’re worth. What you really want is to keep the money coming in but oftentimes you’d be doing a lot more work for less.

Other than insultingly low bids, the unpaid invoices by clients, paying medical bills, transport reimbursement, etc. also contribute to the jumbled finances.

You won’t have as much time for yourself

Examples: Working through the weekend, not having meals at regular hours, etc.

Work-From-Home Freelancer
This is just my dream.

Few people aren’t aware of how much work a freelancer undertakes each and every day. Like those mentioned above, you’d have to wear a lot of hats: Be your own worker, take on accounting responsibilities, do administrative works, etc.

All of these attribute to a lack of time for yourself. Freelance work gets you quick buck, but it takes a whole load of effort and time to get money in bulk at a sustainable level.

Drudgery is inevitable for a freelancer; you’d need to go through lots of work to acquire jobs and make sure payment gets into your bank account. But we wouldn’t say it’s impossible: it’s still possible to take some time off for a well-deserved vacation despite the piling workload.

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Your bank account may be empty at some point

Examples: Depleting bank account

Work-From-Home Freelancer
Don’t let this wallet deceive you: I’m really broke.

The one thing that worries freelancers the most: Late payments and the lack of savings. It’s a worldly worry that all of us are inclined to, even for those who have a nine-to-five. To avoid that, here’s what you can do:

Determine the amount of money you need each month, that includes the monthly credit card bills, household bills, insurance, and other miscellaneous payments.

Add on 30 to 40% more and use that amount of money as a minimum threshold. From there, find out how many projects you need to complete in order to reach that number.

But sometimes, things don’t go smoothly.

A heart-sinking study shows that 58% of freelancers have experienced not getting paid for their work. The other reason for the lack of money is not clinching enough freelance deals. As much as you may feel like giving up at times due to late or non-payments, you’d still have to keep going.

Although you can’t control the way your clients deal with payments, what you can do is train yourself with negotiating in order to secure jobs. As you negotiate, make sure your energy is positive, strong and amiable.

Toss away that defensive shield that’d seem overbearing to potential clients. The negotiation process should always consist of convincing your potential clients you’re doing quality work for a fair price and making your client feel that it’s worth it. If it goes well, you might just have gotten yourself a solid deal, and possibly for long-term!


As horrifying as being a freelancer may sound, especially hearing a lot talking about the disadvantages of freelancing, the life of a freelancer sounds like a dream for many, particularly for those who have a specific set of skills such as writing, designing or coding.

No established hours, no dress code and no micro-managing boss—now who wouldn’t want that? Good news is, Singapore has an increasing number of freelance jobs because of the changing demands of firms, a shift in workers’ mindsets, and advancement in technology.

It’s hard; but not impossible to build a freelance career that would work for you. Toptal, a talent network that provides freelancers to organizations based on requirements, suggested 4 important tips – loving what you do, communicating assertively, the desire and action to keep learning, and being productive – to establish a lucrative freelance career.

To have a smooth-sailing freelance career, think about and work on those that we’ve mentioned above. Once you get these points covered, you’ll find your freelance life become significantly easier.