Part 3: Accepting The Cons of Freelance Writing

As with most things in life, freelance writing comes with its own unique setbacks and cons that many people prefer to overlook or ignore. Its easy to get caught up in the glitz and the glamor of the job to try and silence all the nagging negatives, but at some point a writer has to face the facts: almost no line of work is perfect, and there are always going to be aspects of a job that not everyone is going to like.

Hopefully if you’re considering becoming a freelance writer you’ll have done your due diligence and researched the pros and cons that come with the job. For those who also want to make a career out of the job, or maybe just some extra income, I wish you all the best!

For the final part of my Freelance Writing posts, let’s take a look at all the things most people try to either avoid or not think about when they prepare to start their journey as a freelance writer.

The Cons

Freelance writing can be a soul-crushing, self-esteem killing job if a writer allows it to become one. There are certain things to keep in mind when going into freelance writing, but writers that are mindful of finding a balance between the good and the bad (or figure out how to overcome the negative aspects of the job entirely) will have a much more enriching experience. For those that simply don’t want to deal with some of these cons while working for others, freelance writing might not be the right fit, and some careful though and considerations should be taken.

Your Motivation = Your Income

Unlike a regular 9-5 job, you don’t just get to show up and get paid with freelance writing. Many find that the initial act of getting their foots in the doors with clients is the most difficult part of freelance writing – and that’s all done before you’ve even typed up a single word for profit! If you lack the motivation to put yourself out there, dig through the vast internet to find viable clients, take rejections with grace and humility, and engage in the back and forth of negotiation to finalize a client-writer contract, then it’s very unlikely you’ll find a client or land a job in the first place.

Many writers who want to move up the ranks to becoming a freelance writer will often be tempted to start working in a content mill ( because it’s guaranteed work that almost anyone can do. Unfortunately, the jobs provided by such companies pay far less than what most decent writers are worth, and as such don’t go very far to provide stable income or a sizable side wage. Even if you’re highly motivated to write garbage for pennies, you would be doing yourself a disservice if you didn’t redirect that motivation towards finding better paying clients who know the real worth of a writer.

Large Barrier For Beginners

As seen above, beginners have a hard time getting their foot in the door in regards to becoming freelance writers. Some turn to content mills, others just start cold-calling (emailing in this day and age) companies hoping to get lucky, and some even make entire websites dedicated to showcasing their available services. While many writers start hungry for their first client, it might come as a shock that landing a continued contract or even a well paid assignment doesn’t come easy, nor does it come quickly. Those that aren’t patient enough to put in the time and effort it takes to become a respectable, reputable freelance writer are doomed to fail.

As most freelance writers know, having a portfolio of your work is one of the greatest assets you can showcase to potential clients. The more work you do and the more samples of your amazing writing you have on hand is what leads to easier engagement with clients who are looking for reputable freelance writers to handle the creation of their content. This means that for a writer starting from scratch, you will have nothing to show potential clients to prove that you are a good fit for their company and the direction they want to take in regards to their content. This leads us into our next con, which can come from scraping the bottom of the barrel to find your first few assignments and projects.

Topics That Tank

Whether you’re a reputable writer who’s had more clients than you can count or someone just starting out in the crazy world of freelance writing, there will likely come a time that you’ll have to write about a topic that you just really couldn’t care less about. What’s a writer to do when a long-term client asks if they can write up a 5000 word article about the mating habits of sea sponges? What happens when a new freelance writer gets a contract dangled in front of their faces on the stipulation that they write about the average time it takes for concrete to dry depending on various weather conditions? Most writers just suck it up, do the work, and complain about it after they get paid.

((If you liked either of the above sample topics, please imagine that they’re something you don’t enjoy so this example works for you. Also, if you do genuinely find either of those topics to be interesting, I suggest you write your own article about it! Though I’m sure some people would dread going through the research for either topic, the resulting articles would actually be quite interesting to read and learn about. Your welcome for the great idea!))

Regardless, there will always be a topic or assignment that you don’t want to write about, or a topic that you’ve written about so many times before that you can’t possibly imagine being able to come up with original ideas for the same subject yet again. If you run your own blog or website, you have the luxury of getting to choose the content you create and show to the world. As a freelance writer, you’ll likely find your topics and articles are at the discretion of your client.

In case you couldn’t tell, I chose to write about freelance writing on my own website because it was a topic that interested me. Little did I know that all three parts would amount to over 5,000 words of advice, thoughts, and experiences in the world of freelance writing!

Worldwide Work Means Worldwide Currency

This is honestly one of the biggest issues I’ve encountered with freelance writing. If you’re living and working in your home country and don’t plan on branching out to other areas around the world (even though the internet makes that easier now more than ever before), then you likely won’t have to deal with this negative aspect. For those who live wherever they please and work for clients in multiple countries, this can definitely be an issue.

Not only is it a hassle to understand what amount you’re actually getting paid when going from pounds, euros, yen, dollars, etc. to your country’s currency, but it can sometimes be a real hassle exchanging money and processing invoices when everything is done online. Many freelance writers choose to use PayPal for invoicing, which has the option of exchanging payments from one currency to another. Sadly, not all invoicing programs and websites have such options, and not ever client is open to paying their freelance writers through PayPal. Even worse, when you do exchange currency, you still have to find a way to get that currency into your bank account, whether you currently live in your home country or abroad. The exchanges can become tiresome to track, and make life a whole lot more difficult for the next con on this list as well.

Make Sure You Save For Taxes (And Know What You’re Doing)

Did I mention that even if you’re not getting paid in your home country’s currency you might still be taxed by your home country for your income? Either that or you’ll have to pay taxes for each of the countries that your currency came from. Thankfully I’ve only ever dealt with two different currencies and countries for my freelance writing work, and have done my due diligence in figuring out what to write on the tax forms required for each country.

-Side note for Americans: Yes, you still have to declare any income you make in another country even if you’re not currently living in America. Unless you’re making over a large threshold of income (last I checked it was something to the tune of $100,000), you won’t owe any taxes in America. However, you still need to file all income and report it to the IRS each year. I’ve been told other countries have a much simpler process, but America has a confusing and questionable taxation method that many people forgo learning about until it’s too late. If you’re an American living abroad and are wondering if you should file your American taxes, this article is a sign that you should definitely do your research and start filing if you need to. A site I started with was Tax for Expats, which had some helpful articles that explained in simpler terms what I should be doing while living abroad and earning foreign income as a U.S. citizen.-

Even if you’re only working as a freelance writer within your home country, taxes are still going to be an interesting project come the end of the year. Freelance writers are required to report their gross income, but can make deductions for business expenses. I’ve always used TurboTax to file my taxes while abroad, and they have some pretty clear guidelines on what you can deduct and what you have to file, which can be found on their website.


In the grand scheme of things, these cons are pretty easy to get over. Sure, you might not always be writing about your favorite subject, it might take a while to find your first client, and taxes can get confusing and scary. Add to that the fact that your motivation is the driving force behind whether or not you’ll get paid and the workload seems insane. Yet, if you can work past these cons and learn to take the good with the bad, you’ll go far in this business. I wish you all the luck, and hope that there’s a great deal of success in your future!

Have you ever thought about becoming a freelance writer? Are you currently working as one now? Have you encountered any of these cons or are scared of the day when you finally do encounter one? Let us know in the comments below! Let’s get a discussion going, yeah?

Happy reading, writing, working, and living!

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