The Challenges Of Freelancing

Still contemplating on quitting your job and starting your own business where the only investment required are your brains, your time, and your own brand of hard work?

Freelancing might seem too easy, most especially when you get all tangled up in destructive online literature that try to sell you the “Top 10 Secrets To Become A Successful Freelancer” ebook or, the “The Best Strategies To Earn Six-Digits As A Freelancer” course. Ha! So, be careful.

It’s A Whole Lot Of Sweat, Blood And Tears

I started freelancing in 2013. I was not contemplating on quitting my day job but just to pass the time and distract my mind from the very serious literature that came with my work in the world of social development. When I’m working online, I realized that I didn’t have to waste two precious hours debating the problems of the world with people who could hardly understand what  people on the ground really need. Working online meant completing a task, usually just one very specific task — in my case, that could be writing an article, a web copy, a blog or, an ebook, and delivering these on agreed timelines and to the specs provided by my clients. Simple, ain’t it?

Not. If you’re seriously courting the idea of working as a freelancer, whether as a writer, graphics designer, applications developer, accountant, virtual assistant, and what not, there are certain downsides of freelancing that you must become aware of and take into consideration before jumping ship.  Listed below are just the top five challenges of freelancing (well, from my perspective, of course):

Challenge No. 5: Dealing with difficult clients. Aha! Now, even if you don’t have to deal with annoying officemates when you’re freelancing, you still do have to deal with difficult clients. I am blessed, I guess, that in my less than five years of freelancing, I’ve so far been duped, unpaid (wawa!) by just one client. I had to really study the material. It was for a graduate school course work about tuberculosis. I got paid for the first milestone then, the client disappeared!

Unfortunately, freelancers do have to bite the bullet. You have to accept that, in most situations, you’re on the losing end of the table. Eventually, you will be able to find honest clients who hate to make their workers feel short changed. Even then, what I’ve found useful is to negotiate the terms of work and payment with your client beforehand. For example, request to be paid 50 per cent of the total amount when you’ve drafted half of the book, and the remaining amount upon completion.

Protect yourself from unfair requests for revisions too by defining how many times your client can send back the work with his or her comments for you to revise BEFORE you exert any effort on the assignment. Where there is anything vague, make sure to ask, clarify, and reach an agreement with your client — and document it by email or by chatting.

There are also online platforms for freelancers that help you stay protected and make sure that you get paid for your hard work. These platforms facilitate the work contracts and payments, some even making sure that the client has funded the work and holds it in escrow. The funds are released as soon as you and your client agree that a milestone has been achieved. The downside of these platforms is that they take a percentage of your pay which serves as management or facilitation fee.

Challenge No. 4: Meeting your deadlines. There’s all sorts of work opportunities online, and if you’re keen enough and have the drive to keep learning new things, you’ll never run out of services to offer other people. Thing is, your energy is a constant — you can only do so much in a day because you need to sleep, no matter how organized you are or, how diligently you fill out and try to stick with your notes on your Starbucks planner. That’s how our bodies work and there’s nothing that you can do about it.


I’ve found myself several times in challenging situations where I have committed to overlapping deadlines with multiple clients. The most number of clients I’ve had to serve at the same time was four. I find myself in these situations when my primary clients aren’t sending over work so, the remedy is to look for other work opportunities.

I would say I’ve been lucky enough to have been able to meet my deadlines in spite of the crazy requirements and timelines. It’s being familiar with my work pacing that I’ve been able to negotiate reasonable deadlines. Of course, I also made sure that each of my clients felt that my output was the product of blood, sweat, and tears — and sleepless days and nights. (Seriously, sometimes I don’t even know what day it is!)

Key takeaway: Negotiate. May I also add that you should keep your clients updated of how far and long you are to completing the job.

Challenge No. 3: Making yourself available 24/7. So, how do you make yourself available 24/7? It’s not possible. All it really means is that you are consistently online at specific times of the day and make sure that your client knows about it.


I have to confess I’ve been guilty with this point lately, mostly due to unreliable Internet connection — the biggest “no, no” when you’re doing online work. Unfortunately, my current residential arrangements neither permits a Fiber nor a DSL connection. I see this issue dragging on for the next couple of months or so. For now, the only track I can take is to let my clients know that I am on unreliable broadband and LTE connections. Nevertheless, I made sure I had redundant means to stay online, even though that still does not permit me to spend 24 hours on real-time apps, such as on Skype, because LTE and broadband are more expensive and do not give me unlimited Internet time.

There are some types of freelance work, like serving as a virtual assistant, where less than a DSL connection cannot apply. Often, clients will define their IT requirements, most especially when they need you online at specific times of the day or, if they have to consistently reach out to you.

Challenge No. 2: Keeping up with the “K’s” and “Q’s”(“Kings” and “Queens”) of freelancing. There’s no dull moment if you’re a freelancer. Heck! That’s why I couldn’t even post a single article on this personal blog for months now. I have to keep myself valuable to my clients by delivering valuable work. Unlike in a traditional 8 to 5 job where employees are protected by labor rights, including tenure, freelancers are highly dispensable. That’s partly because there’s so much talent all over the world.

So, when you do get all serious about becoming a freelancer or, if you are already freelancing, think about what added value (a value proposition) you are bringing to your clients. In my case, a lot of people can write but, not too many can connect with their readers, plus I also keep proving that I am worthy of my client’s trust not to plagiarize, to research my topics well, and to consistently deliver top grade work (Ahem!). They’re very smart and they will be able to tell if you are worth their money or not.

Challenge No. 1: It can’t be all about the Benjamins, Baby! If you’re really hardworking and have the  stamina to be the best of the best in your chosen field of freelancing then, you can literally see those Benjamins credited regularly to your account. Once you get the hang of it, you’re going to keep wanting more!


Here are just some of the situations where your interest for those Benjamins have to take the backseat:

  • When quality has to come first. Don’t turn in work just because you need to hit your financial targets for that specific period. Keep in mind that freelancing has a lot to do with earning a good reputation for delivering quality outputs which is not very common in the world of online work.

When you recognize how difficult it is to find a client who is as hardworking and honest as you are, you will learn to always put quality first, even above your Benjamins. That’s because you respect your client, and you know he or she is smart and will be able to tell good from bad quality of work. If you turn in less than stellar output, it’s likely your client will find a replacement. In the end, you lose big time.

  • You simply need to get offline. As a freelancer, you will be spending most of your time online, even when you’re the first person in your home to get up in the morning and still be the last to hit the sheets after midnight. You need to raise your monthly financial targets and that’s your reality. However, you do have to set aside time to do other things than just working on your tasks, negotiating with your clients, and looking for your next client.

You’re wanted by your clients any time, all the time but, your loved ones need to spend time with you too. After all, that’s one major benefit of freelancing that you do have to learn to take advantage of. Besides, when you get downtime, your productivity bounces back more fiercely so, find time to close that laptop and do something more personal.

Just last month, I had to re-learn the wisdom of taking a break. Normally, I would run my basic errands throughout the day — do the household chores, and fetch the kids from school, even pick up stuff from the market or the mall — but, always with my laptop in tow. I’m writing my articles while waiting for school dismissal. I type away during guitar class. I’m up before I prep breakfast, and I’m still online long after my family is in deep slumber. My body had to force me to stop for a full week with a terrible headache and flu that came with sore eyes, as if making sure I wouldn’t peek into my Skype or email while I’m on my flu meds! I’ve forgotten to set aside “me” time. We all need that constantly.

  • Your client is facing business difficulties. You must not offer your services for free or, at a bargain. However, when your relationship with a client has grown to become more personal, you also cannot help but care — it’s human nature. It also comes so much more naturally when you realize that your long-time, repeat client has been financing your freelancer lifestyle and paying for the bills.

You have to realize that when your client succeeds, you succeed with him or her too. That means you have to be ready to negotiate for a win-win situation, not just you winning on one end, even when that might mean getting lower rates. One of my clients re-negotiated my rate once. I agreed for a lower rate that was still acceptable to me which came with a promise that I will get higher volume of work which, in turn, translated to higher total earnings — win-win.

  • Humanity calls. Other than my recent bout with flu, there was one other time I remember when I had to tell my client I had to be offline for two full weeks. That was when I got involved in humanitarian work for Tacloban City which Super Typhoon Yolanda devastated in 2013. I was surprised how my client even thank me for putting in work for the people who badly needed help and relief. Sometimes, there are just some things that need to be on top of your freelancing business, and among those moments is when you have been given the power and the opportunity to help others.

What’s It Going To Be?

Still think you will succeed as a freelancer? You probably will. You’ve heard what entrepreneurs have shared about putting up your own business and making sure it succeeds? They say you need patience, a lot of hard work, and the heart to take the leap and risk it. The same is true with freelancing. It may or, may not be for you but, you’ll never know unless you try.

See also: What pros aren’t telling you about becoming an online freelancer


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