Should You Become a Freelance Writer? An Assessment Test (Answer These 10 Questions to Find Out)

Fall is right around the corner. (I know, I know – how dare I bring this to your attention while you’re in the middle of deciding whether to have margaritas or Sangria on your beach outing this weekend!).

But, it’s almost here. And the reason I point it out is, this is the time when many turn their attention back to business, career and educational issues.

And one of those issues is, “Should I start a freelance writing business?”

I’ve discussed these issues a few times over the years on this blog. So, I decided to put together an assessment test of sorts. It consists of 10 questions that will give you some insight into if freelance writing is a viable career option for you.

Following are the questions and how to assess your answers. Note: These are from my personal point of view as a publishing professional (since 1987); a freelance writer (since 1993); and an editorial recruiter (since 1996). Here goes . . .

Is Freelance Writing a Career You Should Pursue? Find Out by Answering The Following

1. Are you a good writer? You don’t have to be a great writer a la Toni Morrison or John Steinbeck to make a living as a freelance writer. But, you do have to be a good writer.

Should You Start a Freelancing Writing Business? Take this assessment test to find out.FYI, this is the hardest thing for me to tell some freelancers who write to me wondering why they’re having such a hard time finding jobs. And I’m not talking about the obvious horrible writing you see all over the web. That type of writing is easy to dismiss.

But some freelancers have writing skills that are not “bad, bad,” but it’s “just bad enough” that it keeps them from landing well-paying writing jobs.

How do you know if your writing skills are up to par? Ask a qualified writing professional; tell them to be brutally honest with you. And, then find a class that will help you. This is something that can be fixed, so don’t despair.

2. Are you self-motivated? Freelance writing is a business and must be treated as such – plain and simple. If you’re not motivated enough to get up and put in the behind-the-scenes work that it takes (ie, marketing), you’ll forever struggle.

3. Do you like working alone? I go for days sometimes without leaving my house. It’s just me, my computer and the view out my home office window.

I happen to like this way of working, but if you’re the type who needs interaction, just know that as a  freelance writer, you’re going to have to create that. I’ve read where some freelancers like to work in coffee/internet shops for this very reason.

4. Are you patient? Whether it’s waiting for a job to roll in, a prospect to get back to you about a query you sent in, or waiting on payment from a client, patience is a necessary personality trait for this career.

FYI, things like waiting on payment have gotten better with the popularity of companies like PayPal. I remember when I ran my editorial staffing agency in New York back in the late 90s/early 2000s, it wasn’t uncommon to wait 30 to 60 days for a check to come in.

When I started writing mostly online/SEO content, it was unusual to wait more than a week to get paid. So this has been a good change!
Ebook Release: Freelance Writers: How to Stop Taking on Low-Paying Writing Jobs Once & For All. Follow the 5 steps outlined here, and you’ll never have to worry about even considering low-paying gigs again.


5. Are you good at figuring stuff out on your own? When you freelance, there is no tech department to call when your computer gets a bug, or you want to upgrade to wordpress, or you want to know why your text keeps disappearing.

You have to get really good at figuring out a whole bunch of stuff out on your own, from website design to how much to charge for certain services.

This is the thing I dislike the most about being a freelance writer. While I have people in place I can call on for certain things (eg, web design/technical issues), it seems that something always pops up where YOU are the decision maker – even when it’s beyond your expertise. So, what’ya do? You figure it out – and keep moving.

6. Are you an effective planner? Any type of business requires planning to grow – freelance writing is no different. So whether it’s landing higher-paying clients, or increasing traffic to your blog, or starting to create and promote your own line of products, all of this has to be planned for because you’re still probably going to be writing for clients.

So, you must plan how and when you’re going to fit your projects in around all of this.

7. Are you thrifty? Freelance writing can be a feast-or-famine existence. Sure, there are things you can do to mitigate the dry spells (ie, market consistently), but there is no paycheck on a consistent basis. So one habit you must cultivate is to learn how to live below your means.

Notice I didn’t say within, I said below. As I explained in the post, How to Freelance and Not Go Broke: 5 Pieces of Financial Advice from a Freelancer with 20 Years of Experience:

I earn a pretty decent living and I still live pretty frugally compared to how I could be living. And the reason is, I remember all too well what it’s like to be flat broke and wonder how I was going to pay next month’s electric bill. . . .

So this is why I advise all aspiring freelancers to learn how to live frugally; embrace it as a LIFESTYLE (not just something you do when you first start out or when things are slow). If you do this, you’ll be able to set aside enough to always cover your bills as a freelancer.

8. Are you good at handling money? Piggybacking on the point just above, if handling money is like Chinese math to you, then it’s something you’re going to have to get a handle on.




Because . . . you’re going to be responsible for everything from your own healthcare to your retirement if you decide to start a freelance writing business. So, get used to adding, subtracting, dividing … and deciding what happens to and with your money.

9. Do you know how to say no? Saying “no” is one of the best skills you can develop, not only as a freelance writer, but as a human being.

If you don’t learn how to do things like . . .

Tune out friends and family who make demands on you because you’re “available;”

Turn down clients who want to lowball you because they feel like they’re doing YOU a favor even though they want to pay pennies; and

Ignore wannabe freelancers who will sap your time with question after question after question . . .

You’ll find yourself always exhausted, not earning enough and stressed.

Saying no is not rude. It’s actually one of the nicest things you can do for yourself – and those you love. Why? Because a productive, stress-free you is a happier you. And, don’t you want to them to have the best you possible?

10. Are you a procrastinator? You can’t be a procrastinator; you must be a motivator – of yourself. If you constantly put stuff off as a freelance writer, one of two things will happen.

(i) You’ll forever live a feast-or-famine existence because you won’t gain the traction you need to build your career, instead of just sustain it; or

(ii) You’ll find yourself looking for a job proclaiming that “there were no jobs out there; there’s too much competition.” This is hogwash.

In this age of content marketing, NOT being able to earn a living as a freelance writer is like starving with an ocean full of fish at your front door. Proof? Did you know that a recent survey found that 62% of companies outsource their content marketing?

This is proof that there’s plenty of work (fish) out there for freelance writers; but if you don’t keep a baited fishing pole in the water (ie, market for it), how will you ever catch anything?

Should You Become a Freelance Writer: What Your Score Reveals

FYI, answers to all questions should have been yes, except number 10. Following is some insight into how you “scored.”


Missed 0-2: You have a really good shot of making a go of it (especially if you answered numbers 2 and 10 correctly).

Missed 3-4: You might want to reassess. Carefully assess the questions that revealed some weak spots. If you’re willing to work on these areas; there’s no reason you can’t make a go of freelancing.

Missed 5 more: In my opinion, freelancing writing is probably not a career you should pursue. It will be difficult and you’ll likely give up in frustration.

Now this doesn’t mean you can’t find freelance success doing something else – but remember this test was to assess whether you would be successful as a freelance writer.

What Do You Think about This Freelance Writer’s Assessment Test?

What questions would you add to this assessment test? Which areas are your strong points? Your weak points? Do you think this test is an accurate predictor of who will fail/succeed as a freelance writer? Please share your thoughts in the comments section below.

Have a good one!

P.S.: Gain More Insight in the Freelance Writer’s Assessment Test Ebook

I’ve been a freelancer since 1993 and there are just certain traits that spell success; they’re evergreen to the mix of being a successful freelancer –- of any kind.

So if you’ve ever wondered how to become a freelance writer, or wondered if you have what it takes to succeed in this discipline, this detailed assessment test will give you some great insight.

I’m a serial entrepreneur, and let me tell ya, there are some businesses I never would have started had I gotten some detailed insight — like this test provides — beforehand.

P.P.S.: Learn everything you need to know to start a successful freelance writing business from the comfort of your home — and take up to 6 months to pay.


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    1. Trying to break in to tis business.I answered yes to all questions..Need help getting started..Whar is the best way for a newbie???


    1. […] I still do). None of it has paid off. ********************************* Editor Note: Take the Freelance Writer’s Assessment Test to Determine If This is a Viable Career Option for You. […]