Is Freelance Writing For You?

How would you know if freelance writing is for you?

Before I proceed, let me tell you a story:

While teaching in a small college, my student told me that he couldn’t see himself being self-employed or running his own business. He said he just felt that way and admitted that having a boss or a supervisor above him suits him well.

At first, I thought that was weird.

For many years, people are made to believe that owning a business is the only way to be financially independent by becoming one’s own boss. How many times have we seen advertisements, programs, and self-help books advocating being your own boss?

I’ve been advocating working from home and being a freelance writer for years. The freedom and the comfort are just a few things I experienced that made me believe in freelancing.

But upon reflection, that student made me realize that not everyone is cut out to be self-employed or a full-time freelancer.

Below are ten questions with two choices of answers. There are no right or wrong answers in this pop quiz. Your answers will just help you gauge if you have what it takes to become a freelance writer.

Reflect on each question and be honest with yourself when answering. Let’s go through each item and see why the questions matter when pursuing a freelance writing career.

How do you view the role of a boss?

1. A boss provides the crucial structure to the job.
2. A boss is a micromanager who sometimes gets in the way of doing things.

For most employees, a boss can be an immediate supervisor, manager, or director. Most organizations have a hierarchy and each level of leadership has its own job description. Thus, having a boss entails responsibility and accountability.

One time, I was given a big responsibility to organize and manage a big 1-week event. During the preparation stage, my boss advised me not to micromanage things and let the respective committee heads do their job.

As a freelance writer, you consider yourself self-employed or an independent contractor. Thus, you should think and act like a boss when conducting your freelance writing career. You decide which projects to take on and how much you should be paid. This may sound like micromanaging but in a different way. You treat those who “employ” you as clients, and not as employers.

However, 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 to go out and look for work?

1. You want to know in advance what you have to do for today, the next day, week, or month.
2. You are comfortable with projects coming in on an ad hoc basis.

There are people who thrive in routine jobs. Others, especially most creatives, don’t. Creative people prefer variety and something new every once in a while.

However, freelance writing jobs don’t just come in easy. Most of the time, freelancers seek work in all places.

My first writing gig in 2001 came from my connections. When I started working from home in 2012, I started looking for writing jobs on various online platforms. Gradually, I got confidence in seeking assignments on my own until I started getting referrals and inquiries from my website.

During lean months, work comes in one at a time (sometimes, none). During peak seasons, work assignments come simultaneously.

Pitching or looking for writing gigs is like starting all over for me. I find it interesting and exciting as I always imagine myself seeking an adventure, expecting to learn something new.

So the next time you’re looking for a writing gig, ask yourself:

• If you don’t have anything to write right now, will you be seeking writing jobs?
• Will you wait for the job to approach you?
• Will you be applying for two or more jobs at a time?
• Will you wait and see the result of the first application before you apply for the next one?
• Will you be ready if your client or your current writing assignment will be the last for this month?

Honestly, the last question happened to me recently. I had a good time writing for this client for more than a year. Suddenly, she told me that she would discontinue the project due to budgetary constraints. I was surprised and felt down. To make things worse, I got scammed and lost my money and cell phone after. I felt devastated. I wasn’t ready for that double whammy.

Can you switch focus easily and without compromising quality?

1. No. You’re like a horse that has your peripheral vision covered for focus.
2. Yes, multitasking is your middle name.

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

I do Bullet Journal daily. There are times I use the Pomodoro Technique. How about you? Do you have your own time management system?

To be productive doesn’t mean you have to be busy all the time. There are task or project management tools that are available for freelancers like us.

Can you advertise yourself?

1. No. You are not comfortable talking about yourself because you feel embarrassed or people may view you as a show-off.
2. Yes, because you know what your strengths are and you can talk about them confidently without boasting.

This question refers to your own confidence level in promoting yourself as a freelance writer. In reality, we always “sell” ourselves to others.

There are many writers out there — some have already earned their reputations while others are still creating a name of their own. Some use social media; others use the traditional way of advertisement (flyers, brochures, call cards, etc.) That’s why it pays to have a website that serves as a portfolio so you can establish yourself as a freelance writer. In this freelance writing world, it’s okay to toot your own horn.

Do you live paycheck to paycheck?

1. Your bank account gets filled every month and emptied every month.
2. You have enough savings that would last you more than a month if ever you don’t have a paycheck coming this month.

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. Financial experts advise that you should have cash on hand at least equivalent to three months’ salary before entering freelancing.

Financial experts also advise that you should have multiple sources of income, just in case your freelance writing career is in its lean season. That way, you have a continuous cash flow every month in case of an emergency.

Since I’m working at home, I also have a small convenience store in front of our house. Also, I maintain a time deposit account in the bank.

Are you prepared for all the admin work?

1. No, the mere thought of it gives you a headache.
2. Yes, you can handle the administrative work.

Since freelance writers are self-employed, then you should handle all of the administrative 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.

If you can afford it, you may outsource the administrative task to an assistant, or to an accountant.

Do you do what you say without excuses?

1. You might be late sometimes but you always get it done in the end.
2. Yes, because a deadline is a deadline.

This question refers to your attitude towards work. Do you do what you really promise?

A former advertising executive once told me, “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 rather than vice-versa.

Also, because freelance writing is competing with other freelance writers for a writing job, there are instances that you have to utter big words that would convince your client to get you. Thus, not only do you have to say what you mean but also mean what you say.

Do criticisms affect you?

1. Sometimes, you take criticisms of any kind as a rejection of you as a person, not just as a critique of your work.
2. For you, everyone is entitled to his opinion. If the criticism is constructive, you’ll be happy to make changes to the work.

In freelancing, feedback is almost instantaneous and it comes from all sides. Thus, freelance writers should be thick-skinned not to be affected by harsh criticisms or at least know how to filter them.

Somehow, humility comes in handy, too.

Can you deal with the small details?

1. You like thinking on a grand scale and having other people handle the nitty-gritty.
2. You’ll come up with the plan and then follow through with the legwork.

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

Do you have a good network in your industry?

1. No, because you’re an introvert and you avoid socializing at work.
2. You’ve built up a decent network of people you can call on for professional help.

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.

The only really committed artist is he who, without refusing to take part in the combat, at least refuses to join the regular armies and remains a freelance.

– Albert Camus

How Well Did You Do?

Now count the number of (1)’s and (2)’s you’ve answered. If you answer (2) 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 (1). It means you have more opportunities for improvement. Think of them as challenges that you could address and overcome gradually. Answering more (1)’s than (2)’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.

After answering this quiz, you already have an idea of your own readiness to embark on a freelance writing career.

Let me know how well did you do on this quiz. If I have missed anything, I’d appreciate your feedback. And if you like to read more about freelance writing, productivity, or creative writing, please subscribe and join the tribe.