Is Freelance Writing a Good Career? 5 Questions to Ask Yourself

The idea of a freelance content writing career is intoxicating. Successful full time freelancers set their own hours, are their own boss, and can work from anywhere. In short, a pretty sweet gig. No wonder there are 57.3 million freelancers in the US already.

But there’s also a downside. Although freelancing is very popular as side income, its reputation as a long-term career choice is murky. Freelancing is entrepreneurship, and that comes with risks. Leaving a stable job for the joys of finding reliable clients, keeping on top of accounting, and paying your own pension (just some of the challenges freelancers must face down every month) is very rarely the obvious choice.

Is Freelance Writing a Good Career

Moreover, understanding the nature of the tradeoffs is not easy. Uncertainty breeds indecision; indecision breeds paralysis; paralysis breeds frustration. Anxiety can run high as you go back and forth between feeling like you are missing out, and feeling like you are about to something completely and utterly idiotic.

Whether you are just starting out as a freelancer and wondering whether or not to ramp it up, or are on the precipice of making a big decision, here are 5 questions to ask yourself to help with the decision:

Do you have a freelance writing niche?

Freelance writers receive the advice that you need to learn how to write what you know very often. This isn’t wrong, but it is incomplete. Publications and companies pay writers to deliver information or insight on a specific topic of interest for their readership/target market. Choosing one of these niche areas is a requirement for long-term success.

You gravitate towards your interests. For many people, focusing on what you “know” is code for focusing on what you “like”. But liking something is not the same as having a deep knowledge or understanding in a way that will engage others to view your writing authoritatively.

Take a deep dive not just into existing content but also the business model of the subject matter and content you want to write about. Read not just for content but for narrative, angle, and messaging. Only after you understand who is gaining what from the conversation can you expect to get paid to join in.

Do you have a freelance writing network?

Freelancers do get to be their own boss, but that doesn’t mean they don’t have to interact with anyone ever again. The opposite is actually true; successful long-term freelancers need to constantly maintain and expand their network of contacts.

Social proof is powerful. Freelancers can use traditional word of mouth recommendations, as well as a strong profile presence on popular freelancing sites to accomplish this. Without this built-in resource, it’s unlikely you will be able to remain financially viable as a business.

Building this network up is difficult but not impossible. Click here to learn more about how to get your freelancing career started.

Do you have an iterative writing process?

Despite the freedom, freelance content writing is still about trading time for money. The faster you write quality copy, the more money you can make. Writing for pleasure is often done without too much consideration about time. When you are sitting down to write, you are looking for the perfect words to say exactly what you want to say.

B2B content writing, and content marketing in general, does not work this way. Professionals use a writing system they know will get them the results they need as quickly as possible. Systematic writing is not to be confused with lazy writing. In fact, the opposite is actually true. It’s a process you know works for you to consistently create structured content.

By taking the guesswork out of the process, systematic writing ensures you create value heavy content.  And because it is iterative, you can also get the quality faster. Before you strike out on your own for a full-time career, spend as much as time as you need figuring out what process works for you.

Can you deal with criticism?

Back to that no boss thing. Just because you won’t have someone breathing down your neck all the time doesn’t mean you won’t have to answer to anybody. Your freelance clients will often have comments and edits that you will need to make.

Even if you are ok with criticism, there is an additional layer when you freelance – not all of your clients will want the same thing. It can be difficult to keep all of the different styles straight; you might feel like you wrote something excellent, but if it doesn’t fit the style the specific client you are writing for wants, you will find yourself redoing work.

Unlike at a salaried position where after an adjustment period you learn and can faithfully reproduce the style, freelancing is about hitting a constant moving target. With the pressure you’ll feel to get as much done as quickly as possible, make sure you are prepared for this type of situation to avoid burning out or quitting entirely.

Do you have a plan for when you lose business motivation?

Which is a good segway into the final question you need to ask yourself. What will you do on the days you don’t feel like writing?

Salaried jobs will pay you the same now matter what your output is. All you need to do is show up enough to not get fired. The opposite is the case with freelancing – you only get paid for what you produce. If you are having a bad day, week, or even month you can find that your productivity will decrease. That means lost cash for you. Stay like that too long and you’ll quickly find yourself in financial trouble.

These moments are inevitable in your career, and having a plan for how to attack them is a prerequisite to success. Even if you are disciplined enough to treat your freelancing like a job day in and day out, productivity remains a challenge. We all react to stress differently, so the best way for you to answer this question is to pay attention to your own track record.

Before you take the plunge into full-time freelance writing as a career, understand your limits. Don’t benchmark what you are capable of against your best day. Take an average and be realistic about what it means for your earning power.

Knowing that you are able to produce enough writing over the long-term to make ends meat will give you the willpower to push through the difficult times.



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