Part 1: Considering the Factors of Freelance Writing

Many writers, myself included, were likely attracted to the prospects of becoming a freelance writer because of the numerous opportunities that the position presents. At first glance, the job seems like a great fit for anyone who has a way with words. For someone like me who can barely go a day without writing (whether it’s for my own personal projects or someone else’s), it seemed like a great idea to monetize my hobby and talent. Yet, there were quite a few things I didn’t consider before diving headfirst into the world of freelance writing.

Hopefully if you’re considering becoming a freelance writer you’ll have done your due diligence and researched the hard work and responsibilities that come with the job. All things considered, I do believe with my whole heart that freelance writing is a career I can pursue, given time. 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!

While I’m not going to get into how to get clients, or how to prepare your independent contractor taxes (sorry if you came here for that!), I will go into the things to keep in mind when you’re just starting out as a freelance writer. The initial appeal of the job (doing what you love, being your own boss, etc.) sometimes gets in the way of the actual work that’s done mainly on the end of the freelancer.

For the first part of my Freelance Writing posts, let’s go over some of the factors that you’ll have to consider when you start writing for profit.

The Factors

Why list out the factors of freelance writing? Mainly because not all pros and cons will apply to every person’s unique situation. Freelance writing can be done at home, in an office, on the road, while abroad, or any combination of places. Some freelance writers are on contracts while others report their hours to their clients. Some people are finding clients to work with to pay for rent, utilities, debts, and everything other expense they have in life. Others are just pocketing the cash for a rainy day or using it to supplement their income.

All of the factors should be taken into consideration before a person decides whether or not to become a freelance writer. It’s important to know exactly what you expect to get out of this time-consuming job before you start searching for clients.

Remote vs. Telecommute vs. In-Person

Freelance writers often have the freedom to work for companies and clients around the world without ever having to set foot outside their door. Some clients prefer to hold phone conversations or meet in person prior to a project to ensure that they’re making the right choice. It’s hard to fault these companies for being careful – if you want your freelance employee to write in a certain language, you definitely want to make sure that they are fluent by verbal confirmation.

In the past, I’ve had the pleasure of meeting two of my freelance writing clients in person before any work every commenced between us. Since I don’t live very close to the nearest big city (Tokyo), meeting with my clients was a full day event for me. I had to make a six hour round trip journey, arrive early to make sure I was in the right place, and go over everything beforehand so I was well prepared and didn’t waste anyone’s time. In the end, the meetings I had were productive and allowed me to better understand my client’s needs than just reading through an email ever could. It’s also nice to put a face to a name, and have clients remember that you’re a real person.

Other clients I’ve had in the past didn’t require a face-to-face meeting. Many simply ascertained through email that I was indeed a native English speaker and started throwing work at me. More than once I’ve been asked to at least have a phone conversation to ensure my client and I were on the right page with what they wanted moving forward. Phone conversations and meeting in person are especially difficult when your clients aren’t even in the same country, so be prepared for such occasions. Skype or FaceTime are often used in substitution, as it’s the closest thing to a face-to-face meeting people in different countries are likely to get.

Before you get excited about a potential contract with a client, be sure you know exactly what they expect of their freelance writers. Some clients and companies want their writers to work onsite and clock in and out like a regular 9-5 job. Others expect regular calls or visits to the office, but expect the majority of the work to be done remotely. Those that allow their freelance writers to be fully remote and work from anywhere in the world can be hard to find, and even harder to renew contracts with. From my own expereince, I’ve noticed that the less personal you are with your client, the higher the chance you have of being easily dismissed or replaced.

Full Time vs. Part Time vs. Contract

Every client is different, just like every situation is different. I’ve talked with clients who pay per project, clients who pay for the hours spent working on a project, and some clients who have offered a salary payment per week or month. My personal preference is to accept payment per project, as it’s rare that clients and freelance writers will have the same idea of how long something will take to accomplish. I’ve looked at some ideas and outlines that clients have presented me with in the past and said, “Wow, this should only take about an hour to write up. Easy!” Six hours later, I realized that I didn’t consider the fact that there would be extensive research involved, or that I would want to educate myself further on the topic to write a better piece.

In regards to which is best, many freelance writers who are trying to make a living off their work prefer the full time or part time positions as they bring in a steady, manageable income. Knowing that you’ll be working for your client for a set number of hours per week allows you to more accurately estimate your relative income. Working on a contractual basis means that you’ll have highs and lows of working period, and likely won’t be able to accurately forecast your weekly or monthly earnings.

Although many people believe that submitting the number of hours you’ve worked to your client is the better option, many clients don’t share the same belief for their remote workers. Unless they have an online check system where you digitally “clock-in and out”, smarter clients won’t risk freelance writers submitting time sheets on an honor system. As with all things, if you want to have a lasting relationship with your client, you should probably look into making sure your terms are in writing, clearly agreed upon, and signed (physically or digitally) by both parties.

Extra Cash vs. Income

Do you want to start freelance writing to make extra cash or to make a living? The answer is important in regards to how you conduct yourself in your pitches, where you find clients, and how you keep track of your payments and expenses. The ultimate dream of many freelance writers is to live off of their writing work alone, but often times it just isn’t possible. In order to live off of your writing, you’ll likely need either several clients who offer relatively steady work, or a full-time writing position that might take away some of the freedoms that freelance writers normally enjoy.

You’ve likely heard stories of people who quit their day jobs in pursuit of writing as a career, but it’s mainly only the success stories that get posted online or written about in books. Countless writers have had to give up on their dreams of becoming a professional freelance writer throughout their careers, which isn’t a bad thing. If it was a simple process to become a successful freelance writer, many people would give up their jobs to do so, and the market would become saturated.

Freelance writing is fraught with disappointment, setbacks, and dry spells. Even those who do everything in their power to fill up every possible moment of their day with writing work still experiences days, weeks, or even months of no income from freelance writing. Unlike a regular 9-5 job, you can’t just show up and do the work to get paid. You have to put yourself out there and work for every single project. For those looking for extra cash, that’s not a big issue; for those looking for a steady income, it can definitely become a huge problem. Make sure your expectations for how much income you’ll be making through your freelance writing are not set so high that you quit your day job before being secure in your freelance work.

Hobby vs. Career

Much like the distinction between doing freelance writing for extra cash versus doing it for your entire income, considering your writing work to be a hobby versus a career is also an important factor in how your freelance writing experience will play out. Many people consider those that do freelance writing full time to be in a writing career, while those that have a full time job and do writing on the side to be hobbyists.

In many regards, freelance writing can start as a hobby with the potential to become a career later on. Consider this situation: a person has saved up enough funds from a full time or part time position to live comfortably without working, quits their job, and focuses the majority of their time and effort into gathering clients and becoming a full time freelance writer. Is it considered a hobby until they have a client or two that give them steady work? Or a career because they’ve given up everything to peruse it?

In the end, your personal goals and drive are what determine if you’re treating your freelance work as a hobby or career choice. Not every freelance writer will start with a job that pays enough to become their only income, and not every freelance writer is willing to give up everything to dive into the world of writing for profit. It’s up to the individual to decide how they want to approach the job, as well as how quickly they want to advance (if at all) from hobby to career.

Beginner vs. Expert

Similar to the section above, you mileage may very on becoming a productive freelance writer depending on the amount of experience you have in regards to making and maintaining client relationships, being responsible for filing taxes on your income, and keeping a set schedule that’s both productive and flexible.

If you’re just beginning your freelance writing journey, you’re going to need a lot of things in preparation for the hurdles you’ll eventually have to face (and hopefully overcome). The number one thing all new freelance writers need above everything else is quite simply: knowledge. Study the job; the requirements, the responsibilities, the avoidable pitfalls, the pros, and the cons. Hopefully if you are new to the freelance writing world you’re reading this to help give you an idea for what you’re in for.

If you’re not new to ghostwriting, article writing, creative content writing, copywriting, researching, accounting, communicating, and bargaining that go into being a freelance writer, then you’re likely to have a much easier time selling your work to clients. Knowing your way around negotiating a contract, contacting a hard-to-reach client, and keeping all of your paperwork in order are some of the more intricate parts of the job that take time and experience to master. That being said, even if you’re proficient in these skills you may have other places that need work. Never stop trying to better yourself and perfect your craft.

All things considered, whether you’re new to the game or jumping back in after leaving the freelance world for a period of time, educating yourself with the inner workings of freelance work is imperative. Even if you’ve been writing commercially for the past few decades, there’s always something new to learn in this ever growing and expanding profession.


If you know your limitations, preferences, and writing ability, you should be able to sell your writing skills to clients in need. Knowing what you’re willing to put up with for a side job or career is important for almost any work, though many people overlook that fact and try to just jump straight into a new line of work and hope for the best. If you really want to be prepared to give freelance writing your all, take some time to understand your own working needs before you try and fulfill the writing needs of others.

Have you thought about freelance writing? If you’re a freelance writer, what’d you think of these factors, and which did you have the hardest time with? Let us know in the comments below! Let’s get a discussion going, yeah?

Happy reading, writing, working, and living!

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