Is Freelancing For You?

Note: This post was originally published in a previous website and has been completely revamped and updated for accuracy and comprehensiveness.

A decade ago, I worked as an instructor in a small college. In class, a student told me that he couldn’t see himself being self-employed and running his own business. I asked why. He said he just felt that way and admitted that having a boss suits him well.

At first, I thought that was strange. For many years, people are made to believe that owning a business is the only way to get financially rich because of being one’s own boss. But stepping back to think, that student made me realize that not everyone is cut out to be an self-employed entrepreneur or a freelancer.

So how would you know if freelancing is for you? Below are ten questions with two choices of answer: (a) and (b). There are no right or wrong answers in this quiz. Your answers will just help you gauge if you have what it takes to become a freelancer. Reflect on each question and be honest with yourself when answering.

1. How do you view the role of the boss?
   a. A boss provides the crucial structure to my daily job.
   b. I see a boss as a micromanager who sometimes gets in my way of doing things.
2. Are you prepared for all the administrative and managerial tasks that go into running a business?
   a. No, the thought of it gives me a headache.
   b. Yes, I could handle them well enough.
3. Can you deal with the small details?
   a. I like thinking on a grand scale and having other people handle the nitty-gritties.
   b. I’ll come up with the plan then follow through with the legwork, too.
4. Do you just want to get on with the work, or are you prepared to go out and look for work?
   a. I want to know what I have to do for today, the next day, week, or month in advance.
   b. I’m comfortable with projects coming in on an ad hoc basis.
5. Do you have a good network in your industry?
   a. No, I’m an introvert so I avoid socializing at work.
   b. I’ve built up a decent network of people I can call on for professional help.
6. Can you advertise yourself?
   a. No, I’m not comfortable talking about myself. It’s too embarrassing and people may view me as a show-off.
   b. Yes, I know what my strengths are and I can talk about them confidently without boasting.
7. Can you switch focus easily without compromising quality?
   a. No, I’m like a horse that has my peripheral vision covered for focus.
   b. Yes, multi-tasking is my middle name.
8. Do you do what you say without excuses?
   a. I might be late sometimes, but I always get it done in the end.
   b. For me, a deadline is a deadline.
9. Do criticisms affect you?
   a. I sometimes take criticism of any kind as a rejection of me as a person, not just a critique of the work
   b. Everyone is entitled to his opinion. If the criticism is constructive, I’m happy to make changes to the work.
10. Do you live paycheck to paycheck, or do you have savings for the rainy days?
    a. Normally, my bank account gets filled every month and emptied every month.
    b. I have enough savings that would last me more than a month if ever I don’t have a paycheck coming this month.

Now count the number of (a)’s and (b)’s you’ve answered. Let’s go through each item and see why this quiz matters when pursuing a freelance writing career:

How do you view the role of a boss?

Freelance writers are considered self-employed individuals. You can choose your client, your schedule, your pay, and your project. Thus, you have to think and act like a boss when conducting your freelance writing business.

In my freelance writing career, I treat those who “employ” me as clients because I view myself as my own boss.

If you feel that you need someone telling you what to do most of the time, you may be like the student I mentioned earlier who prefers to be employed rather than striking it out as an independent contractor.

Are you prepared for all the administrative and managerial tasks that go into running a business?

Since freelance writers are self-employed, you should handle all the admin work that goes into running your own business. That includes business registrations and processing of necessary licenses and permits. Not only that, you have to learn a little bit of bookkeeping to record financial matters.

Can you deal with the small details?

Freelance writers are creatives that are more into the ‘big picture’ way of thinking but can also be into the nitty-gritty details if they want to. This is about follow-through. Balance these two and you’re sure to get the projects done.

Are you prepared to go out and look for work?

Freelance writing jobs don’t just come in easy. Most of the time, freelancers look for work in all places.

I started out looking for writing gigs from my connections and gradually increased my confidence in seeking assignments on my own from online job platforms. It took years until I got referrals and inquiries through my website.

Do you have a good network in your industry?

To be successful in freelance writing, one should nurture relationships despite the “politics” of it. In fact, to start your freelance writing business, you have to start with what you have right now — family members, relatives, and a few friends or acquaintances. Soon, you’ll be able to grow your network, if you maintain to be professionally sociable.

Take advantage of the power of social media. Having connections on Facebook, X (formerly Twitter), Linkedin, etc. may help you build a good network within your niche.

Can you advertise yourself?

This question is about your own confidence to promote yourself as a freelance writer. There are many writers out there — some have already earned their reputation while others are still creating a name of their own. That’s a tough competition. You really have to stand out from the crowd. That’s why it pays to have a website that serves as your portfolio so you can establish yourself as a freelance writer.

Can you switch focus easily and without compromising quality?

This question is about how you deal with multiple assignments. Since freelance writing jobs can come to you all at the same time, you should have that ability to switch focus easily without compromising your quality of work. This requires time management and self-discipline.

During the COVID-19 pandemic, I had two clients at the same time — a doctor based in Arizona and a lawyer in London. My writing tasks with the doctor included web pages, blog, and e-books. My writing tasks with the lawyer included essays about laws in Great Britain. You could just imagine how I switched tasks, style of writing, and different English (US and UK). Yet, I was able to satisfy both clients until the projects ended.

Do you do what you say without excuses?

The question is about your attitude towards work. Do you do what you really promise? A former advertising executive once told me about “under-promise, over-deliver”. It means that it would be better for you to set low expectations but deliver much more than what is expected than vice-versa.

Do criticisms affect you?

In freelancing, feedback is almost instantaneous and it comes from all sides. Thus, you should learn how to be thick-skinned not to be affected by harsh criticisms or at least know how to filter them. Don’t take criticisms personally.

Do you live paycheck to paycheck?

While it’s common among struggling artists to live paycheck to paycheck, it is better for a freelance writer to have enough funds for the rainy days. Most financial experts advise that you should have cash at least equivalent to three months’ salary on hand before entering freelancing.

If you answer (b) on all or most of the questions, well done! You’re ready to be a freelancer and freelancing suits you well.

However, don’t worry if your answers are mostly (a). It means you have more opportunities for improvement. Think of them as challenges that you could address and overcome gradually. Answering more (a)’s than (b)’s doesn’t mean that you shouldn’t consider striking out on your own. It just means that you have more prep work to do.

If I have missed anything, I’d appreciate your feedback. And if you like to read more about freelance writing, please do subscribe and join the tribe.