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How to Work as a Successful Freelance Writer

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Within the context of the contemporary economy, it is becoming more and more common for people to work for themselves and make a living in nontraditional ways. Nicholas Lemann of the New Yorker has characterized this as a shift from the organization man paradigm to the network man paradigm:

"Work is already becoming more temporary, sporadic, and informal, and this change should be embraced. Many more people will become entrepreneurial, if not entrepreneurs. The keeper of your career will be not your employer but your personal network."

Freelance writing is in great way for entrepreneurs to be their own bosses and participate in this new model of making a living within the evolving economy. This article will discuss several aspects of how to make a living as a freelance writer. Topics covered in this article will include the following:

  • Background context
  • The meaning of being freelance
  • Identifying personal strengths and weaknesses
  • The importance of deadlines
  • Places to find jobs online
  • What to look for in a company that's hiring
  • Proper etiquette for working with clients
  • How to tell reasonable from unreasonable demands
  • Other insights

By the end of this article, you should have a good idea of what it means to be a freelance writer, and whether this is a career opportunity that you may like to pursue.

Work is changing. Enter freelancing.

Current developments within the economy have provided a plethora of opportunities in a range of different kinds of work for people to find work in an independent way. The Internet has surely facilitated this trend by making it much easier for potential workers to meet up with potential customers who want their service; in other words, the Internet has greatly helped supply meet up with demand. Here is a list of a few examples of available kinds of freelance work in these times.

Freelance work opportunities
There are many ways to freelance in the current economy. The companies below list available opportunities for freelancers to offer their services.
Company Type of work Website
TaskRabbit Home repair and maintenance https://www.taskrabbit.com
Uber Ridesharing https://www.uber.com
Upwork Writing and editing https://upwork.com
Toptal Software development https://www.toptal.com
99designs Design https://99designs.com
Project4Hire Various https://www.project4hire.com
Ultius Writing, editing www.Ultius.com

This article will be specifically about freelance writing. It is worth bearing in mind, though, that there are various other kinds of freelance work out there as well, and that a lot of what is said for freelance writing in particular may also be somewhat applicable to all kinds of freelance work in general.

Millennials: The job-hopping generation

There is a good deal of evidence that more flexible and/or innovative work arrangement, coupled with a lack of traditional loyalty to a given company or employer, is a strong characteristic of the Millennial generation. According to a study conducted by Gallup in 2016, 1 in 5 Millennials have changed jobs over the past year; 3 in 5 Millennials indicated that they are open to new work opportunities; over a third reported that they will actively seek new opportunities over the next year.

Job hopping (Millennials versus older generations) Source: GLLP
Millennials are less inclined than previous generations to stay with the same employer year after year. A study by Gallup shows that 21% of Millennials changed jobs in 2016.

This data may be the result both of the inherent preferences of Millennials and a generational adaptation to a changing economy. In any event, all this job-hopping may make freelance work seem especially alluring, both as a sustainable career in itself and as filler employment for times when a given person is in between jobs.

What it means to be "freelance"

The original freelancerSource: PDP
Freelancing has been around since the Middle Ages. In fact, the word "freelancer" comes from "free lance" - a term that refers to a lance-owning mercenary available for hire.

Linguistically, the modern term "free lance" has most likely emerged from the original medieval usage, where it referred to a mercenary who literally had a free lance available for hire. And this meaning is not really dated: a freelance worker is in fact still a kind of mercenary, who works with clients in exchange for money but ultimately only works for himself. In short, there is good reason why the concept of freelancing tends to evoke romantic notions for many people.

At the legal level, a freelancer always owns his own business. Technically, it would be a form of sole proprietorship, where the freelancer is a one-man business, and that business enters into contracts with customers and clients. This is true even if the freelancer, as is the case with most freelancers, works under his own personal name and does not formally incorporate a business.

Given that the freelancer has no employees, the paperwork involved in running the business remains at an absolute minimum. The process is especially simple for the freelance writer, who typically needs to expend nothing on resources in order to get his contracts done. (See U.S. Small Business Administration for more guidelines on this subject.)

According to an important study published by the Freelancers Union, there were 53 million Americans, 34 percent of the American workforce, who were self-employed as freelancers as of the year 2014. Moreover, this number was projected to rise to a full 50 percent by the year 2020.

Freelancing in America Source: FU
Freelancing is undoubtedly becoming more common. The Freelancers Union projects that one in two Americans will be freelancers by the year 2020.

Freelance and tax

From the tax perspective, the freelancer is classified as an independent contractor. There are a few main things that this means

  1. You need to pay an additional 6.5 percent or so in taxes; this is called the self-employment tax. This is normally a 13-percent tax that is split with the employer. But in this case, you would be both the employee and the employer.
  2. You need to make estimated quarterly tax payments. No taxes are taken out of your paycheck as they are for a normal employee. So, you need to save up your own tax fund, and make payments every three months. The penalty for just waiting till the end of the year, though, tends to be very minimal.
  3. You need to give each of your clients a W-9 form: this is a form in which the client fills out the nature of the work that you did, and the amount of money you received for the work. Which means you might get less back to spend your return on during refund season.
  4. You need to fill out a 1040-MISC form: this is the tax form that is used for all independent contractors.
W-9 and 1099-MISC forms
Traditional workers and freelancers both pay taxes, but the process is different for freelancers. As an independent contractor, a freelancer will need to fill out a W-9 form and a 1099-MISC form as pictured below.

It would be beyond the scope of this article to get into further details about the specifics of figuring out your taxes as a freelancer. There is a great deal of information available on this subject online; and of course, you could always consult a tax professional as well, if you are concerned about anything.

Identifying personal strengths and weaknesses

Before deciding to be a freelancer of any kind (including a freelance writer), you will need to accept the fact that the enormous freedom of being a freelancer comes with a corresponding uptick in responsibility. Among other things, being a freelancer means that you are wholly responsible for managing your own time. A normal 9-to-5 job tends to structure your time for you. It is very different when you work as a freelancer.

Daily schedule - Freelancer vs. traditional employee
One of the biggest differences between traditional employment and freelancing is flexibility. The table below outlines a typical daily schedule for each type of worker.
Time of day Traditional employee Freelancer
12 AM - 4 AM Sleep Come home; sleep
4 AM - 8 AM Sleep; wake up; get ready for work Sleep
8 AM - 12 PM Commute to work; work Sleep; wake up; work
12 PM - 4 PM Lunch break; work Run errands; happy hour
4 PM - 8 PM Work; commute home; dinner Relaxation
8 PM - 12 AM Relaxation; sleep Work; go out

This flexibility, can sometimes be both a blessing and a curse. On one hand, no one will tell you when you need to work—but on the other, no one will tell you when you need to work. With most jobs, if you don't work, you'll get fired. While you won’t fire yourself as a freelancer, the problem becomes that if you don’t work, you simply won't have any money.

Freelancing versus publishing

If you want to pursue the path of a freelance writer, you should probably take an inventory of your own strengths and weaknesses as a writer. In general, you are probably not going to find many freelance opportunities writing poetry or fiction. You could, of course, submit your original content to magazines and publications that may pay money upon acceptance of the content. But this is rather different from engaging in contract writing per se that is meant to meet the writing needs of a specific client.

This is a little confusing, because if you are able to make a living from (say) submitting your poetry to magazines, then you would still be a freelance writer in a sense. For the sake of clarity, though, let's make a conceptual distinction between freelancing proper on the one hand and publishing content on the other.

Freelancing vs. publishing
There is a vast difference between working directly with clients and submitting content for publishing. The table below compares aspects of each mode of working.
Aspect of work Freelancing Publishing
Content Must fit the specific needs and instructions of the client at hand Must express the author's own original vision
Attribution Generally anonymous, with copyright for work transferred to the client Author is given byline credit, with copyright usually reverting to author after publication
Pay schedule Can expect a regular cycle of work that pays out upon completion, either immediately or on weekly or biweekly intervals Magazines can take several months to respond to a single submission, and the payout can take even longer than that
Genres Journalism, blogging, essays, unique orders from clients Poetry, fiction, essays, unique requests from magazines
Earning potential High: there is usually a lot of demand for written content, and the freelancer can line up work for a full livelihood Low: unless you have developed a strong name for yourself, it is unlikely that you will get published consistently enough to make a living

For present purposes, freelance writing will refer to producing content through contract work that meets someone else's demands and specifications, and not original creative content produced by the writer for the sake of his own literary ambitions. While this distinction is admittedly somewhat arbitrary, it is needed in order to clarify the focus of the present article.

Strengths and weaknesses as a writer

Within the realm of freelance writing per se, you can figure out what you think your relative strengths and weaknesses may be. For example:

  • Were you always good at writing term papers when you were in college? Then you could look for work that involves academic writing, either as tutoring and help for people who are now in college or for other agencies or groups that want in-depth research conducted for them.
  • Maybe you are extremely savvy with social media and are always on top of pop cultural trends. In that case, you could perhaps look for work in blogging: many websites that are publishing content these days have a need for this kind of writing, done on a regular basis and meeting certain provided parameters.
  • Are you a good writer but often don't know what to write about? The you could think about looking for ghostwriting opportunities. On many job boards, there are at least some clients who have ideas for a memoir, novel, or whatever else and would like to find a writer who can help the realize their concept.

Why meeting deadlines is important for freelancers

It has been noted above that one of the main challenges of being a freelance writer consists of learning how to manage your own time in an effective way, since no one else is going to do it for you. This is especially important when it comes to meeting your deadlines for the writing orders that you have accepted.

The main reason for this is that as an independent professional with his own business, your name and reputation are very important forms of value. If potential clients don't feel that they can trust you to produce quality work on time, then this could cause your business opportunities to close down fast.

A case study: Uber

Let's take a look at the ride-sharing company Uber as an example of how important reliability can be for a company. Before Uber, the only way to catch a personalized ride was to hail a taxi cab, either on the street or over the phone. As most people know, however, taxicabs had notoriously poor reliability. It could be difficult to find one available on the street; and if called during a busy time (such as closing time at the bars on a weekend), then there was a good chance that the cab might just not show up at all.

Then Uber showed up on the market—and as Tim Stenovec of Business Insider has indicated, Uber has caused severe disruption in the taxicab industry around the nation. It turned out that the taxicabs had been benefitting from a de facto monopoly, and when a new option emerged, people went over to it en masse. And it is not hard to understand why. An Uber ride is hailed through an app on one's phone; there is a clear map provided of where one's ride is, with the car icon moving in real time, along with a fairly accurate ETA.

The Uber appSource: Pexels
As a company of one, a freelancer must establish herself to clients as reliable. The ridesharing company Uber stands as an example of the importance of reliability. Uber drastically disrupted the taxicab industry by proving itself more reliable than taxi companies.

Being trusted to meet deadlines

As a freelance writer who accepts an order or contract, you are making a commitment to your client that you will have the work done according to their specifications, and by the time that they have asked to have it. Think of your client as your professor and if this was college, not turning your paper in on time is a failing grade.

In some cases, it is possible to negotiate with the client for an extension, in the event that this proves to be necessary. This is especially feasible if you have done work with the client in the past, and the client knows that you can be trusted. But in many cases, the deadline may be absolute, due to the fact that the client's need for the content may be time-sensitive in one way or another.

If you regularly miss your deadlines, then clients will eventually learn that you cannot be trusted, and that if they have important work that needs to be done, then they would do well to find someone else who is able to manage the work in a professional manner. In short, if you miss deadlines, then you run the risk of becoming the taxicab of the freelance writing world. And we’ve seen what happens to taxicabs: they get their businesses devastated by rivals like Uber, because they never developed an adequate sense of accountability toward their clients and customers.

Where to find freelance jobs online

There are several companies that specifically focus on providing a venue or marketplace where freelance writers can encounter potential clients and pick up jobs. Other than Ultius of course, another relevant company in this regard is Upwork, which consists of the fusion of two previous companies known as Odesk and Elance. This is how Upwork has has described itself on its website:

"Through Upwork businesses get more done, connecting with freelancers to work on projects from web and mobile app development to SEO, social media marketing, content writing, graphic design, admin help and thousands of other projects."

Essentially, the freelance writer creates a profile on the website, including special skills and the average rate for which the writer is willing to work. Then the writer can browse a board filled with jobs posted by potential clients, and the writers can place bids on the jobs. If the client accepts the writer's bid, then the writer has a contract on his hands: It's as simple as that.

There are several other websites that offer a similar service, albeit often with somewhat lesser professionalism, and less resources than you would find with a company like Ultius.

Freelance writing job websites (IAPWE) Source: IAPWE
Freelance writers can search for work on the following list of websites provided by the International Association of Professional Writers & Editors (IAPWE).
  • CareerBuilder
  • LinkedIn
  • Upwork
  • Indeed.com
  • Monster.com
  • SimplyHired
  • Freelancer.com
  • JournalismJobs
  • Guru Writing
  • Linkup
  • PeoplePerHour
  • Dice.com
  • ZipRecruiter

In short, there are a large number of websites that offer a platform for freelance writers to potentially find clients. Most of these websites require you to develop a profile with them. You could, of course, post personal ads in the appropriate sections of Craigslist pages. You could even post ads in big cities where you do not live, given that for freelance writing work, your physical presence is often not necessary.

Platform work versus true freelance work

As a freelance writer, you will never be "employed" by a platform you work with. Rather, the situation is that either the platform itself will become your client, or the platform will mediate between you and your clients. Upwork, for example, takes a fee from every transaction that is done between a writer and a client; and the company also provides securities, such as escrow service (i.e. the company holds onto the client's money while you do the work), in order to enhance trust and credibility within the transaction as a whole.

You could always try to find your own clients, and resources without the assistance of any platform or middlemen. But there are two main drawbacks to pursuing this route.

  1. Workflow. Unless you are unusually well-connected, you probably do not personally know enough people who need writing services in order to make a consistent living. Platforms such as Upwork, on the other hand, have a huge amount of work available for the taking. This is kind of like the difference between insisting that people come over to your house, and going out to the mall where people already know to congregate.
  2. Credibility. In general, a client—especially a remote client who is not going to meet you face to face—would greatly prefer to go through a trusted middleman, as opposed to gambling on your personal trustworthiness. Likewise, platforms generally have policies that protect the writer as well and minimize the amount of hassle the writer must experience in terms of peripheral tasks such as customer service.

What to look for in a company that hires freelance writers

Now, if you are a freelance writer who is looking to contract with a company who can deliver individual clients (as opposed to trying to find those clients in a personal and direct way), there are certain key things that you should look for in order to make sure that the company is legitimate, and that you are not falling for a scam. Avoid online writing scams with our helpful guide.

  1. Does the company seem to be marketing primarily to the potential customers, are primarily to potential writers?
  2. Is the company based in the United States or at least an English-speaking country?
  3. Does the text on the website, as well as the communications you engage in with the people with the company, suggest that they know what they are doing?
  4. Is the pay grade (or likewise, the pricing for the customer) reasonably high?

Key criteria of freelance writing companies

Characteristics of quality writing companies
Not all writing companies are made equal. A writing company's characteristics can provide clues to its overall quality. The table below describes how key characteristics of writing companies reflect company quality.
Characteristic What it says about the company
Marketing angle Legitimate companies primarily market to potential clients, not potential writers
Location Good companies are based in the United States
Professionalism The name, web design, and communication of a company says a lot about them
Pay grade Pay grades that are too low and/or too erratic are signs of an untrustworthy company

Point 1

There are many companies that advertise essay writing services but actually seem more intent on persuading the potential writer than potential customers. (The present writer has seen several of them, but cannot recall specific names at this time.) This is a good tip-off that you are probably dealing with a scam. As Michael Porter and Mark R. Kramer have indicated in Harvard Business Review, any legitimate business directs its value proposition to its potential customers. So, if a writing company's formal website is paying more attention to the writer than the customer, then this is a good sign that the company is primarily just trying to play you, and has no actual product or service it cares to deliver to real customers.

Point 2

Another criterion to consider consists of whether the company is in fact based in the United States, or perhaps Great Britain. Manty writing companies advertise themselves as being located in the United States, since this would greatly enhance the credibility of a company that purports to provide services involving the English language; but even some basic investigation can usually reveal whether or not they are lying about this.

Point 3

You should look at the company's website in order to evaluate its apparent level of professionalism. For example, there is one company called WriteZillas that actually has four differently named websites for its services: Custom Paper Help, Write My Essayz, My Custom Essay, and Paper Camp. The generic names of these web pages undermine credibility and confidence in the trustworthiness and stability of the company itself. It’s essential for freelancers, or any writer to make sure a site is credible.

Likewise, if you begin to communicate with persons with the company and you receive responses in broken English, then you could take this as a sign that the company is not in fact based in the United States, or at the very least that the company clearly lacks the professional competence to effectively provide English writing services to customers.

Point 4

Large deviation in writer payouts (WriterBay.com)Source: WB
A large deviation in writer payouts should raise red flags. The following payout information from WriterBay.com may give the attentive freelance writer cause for suspicion.

Finally, you should look at the average pay grade offered for jobs taken with a given company. If the pay grade is lower than what you an American could be expected to work for, or if the pay grade seems wildly erratic, then this is a sign that the company is not based in the United States and/or that the company is reporting false data for nonexistent jobs.

The numbers posted by the company Writersbay in the screenshot above indicate that orders go for anywhere from $6/page to $45/page; it is difficult to imagine any sort of legitimate market-based approach that could produce this kind of real deviation in payouts. Moreover, the chart in the corner (if valid) clearly indicates that only about a third of the writers for the company are based in North America. This is not a strength for an English writing company.

An exception to this rule, however, may consist of platforms that inherently open up the marketplace to an international horizon. For example, there may be bidders on Upwork who live in India, and thus are willing to work for much less in U.S. dollars than would the average American writer. The platform may still be professional, and that bidder may well be highly qualified. This would likely be a quirk of global economics more than anything else.

Client etiquette for freelance writers

As a freelance writer, you need to develop strong professional communication skills. You must also bear in mind that your potential clients may not possess such skills: after all, if they were good communicators, especially through writing, then they would not be in need of your services in the first place. It is thus necessary for the freelance writer to bring not only communication skills to the table, but also patience that is founded on an understanding of the nature of the situation.

A freelance writer may sometimes encounter a client who communicates in a very informal way. In general, the writer shouldn't mimic him on this, because it is important for the writer to get the client to feel confident about his own writing skills. Bad grammar or punctuation or spelling, even within the context of communication, is sure to not make a good impression in this regard.

The case of the unreasonable client

The unreasonable clientSource: Pixabay
Successful freelancers know how to manage unreasonable clients. Understanding how to respond to unreasonable requests and expectations is key to succeeding as a freelance writer.

Sometimes, the freelance writer will encounter a client who is making clearly unreasonable demands for work. If you want to be a freelance writer, then you will need to develop a sense for telling what is and is not reasonable, as well as how to respond when you are confronted with the unreasonable.

It is worth considering the following piece of wisdom written by John Butman for Harvard Business Review regarding the unreasonable client:

"Impossible clients can, in fact, be managed; but only if you resist the temptation to fight fire with fire. Instead, deliver—and let your talent speak for itself. If you fulfill your end of the bargain, it's much easier to find positive outcomes when clients behave badly."

The main idea here is that however a client acts, it is your responsibility to act like a professional, and get the contract done to the best of your ability. This could also be understood as a form of setting a good example. Even if the client becomes rude in their communications, you should respond with courtesy, and thereby demonstrate how the interaction is actually supposed to proceed.

Kinds of unreasonableness

In general, there are a few key ways that a client for a freelance writer can be unreasonable.

  1. The client wants their order sooner than what was agreed upon.
  2. The client wants content included in the order that goes above and beyond what was originally requested for the order.
  3. The client fails to provide adequate materials for the order in a timely manner.
  4. The client has generally unreasonable expectations about the nature of the work they are requesting.
Unreasonable clients of freelancers Source: HBR
Clients are occasionally unreasonable. Some clients make unreasonable requests while others have unreasonable expectations. The following table explains how freelancers can manage unreasonable clients.
How the client is unreasonable Potential reason Solution
Early deadline The client isn't aware of the normal workload of a freelance writer, or that their order is one of many in a queue Cooperate with the client if possible (perhaps for an additional fee), or clearly state that it won't be possible
Content beyond the original instructions The client doesn't understand the assignment itself well enough to clearly describe what needs to be done Early on: cooperate, if possible. Later on: affirm that you are only responsible for the original instructions, unless new content is ordered and paid for
Failure to provide materials The client does not want to uphold his own end of the work that needs to be done Request the materials, and proceed as well as you can if no response is forthcoming in a timely way
Generally unreasonable expectations The client wants the work to be as deeply felt, personalized, and thorough as if he himself had done it Clearly let the client know the limits of what you can and can't do: a contract to be fulfilled in a few days just cannot be the same as content produced with a year of loving work

Ultimately, in order to deal with an unreasonable client in an effective way, honesty is always the best policy—not honesty about the client's poor communications, but rather honesty about what you can and cannot actually do for them. More likely than not, the client will respect this. And if they do not, then perhaps the contract just wasn't meant to be: if nothing could make them happy, then it would probably be better for everyone if you both just moved on.

Insights from experience

On the basis of personal experience as a freelance writer, the author of this present article believes that the gist of being a freelance writer can be summarized with three main principles.

  1. Personal time management
  2. Maintaining professional relationships
  3. Balancing work and play
  4. Always work in improving your writing skills

A lot has already been discussed above regarding the issue of time management. The main point here is that as a freelance writer, you will not have a boss, and you will be fully responsible for managing and structuring your own schedule. Most people know that they need to get to work on time, or they will get fired. As a freelance writer, though, there is no such thing as "on time" (except when it comes to deadlines). You will have to make sure that you are able to motivate yourself to put in regular hours every day in order to make your own living.

Regarding professional relationships, the main idea is that as a freelance writer, your reputation is everything. Your clients need to know that they can trust you; and if they know that, then they will likely keep coming back to you for future contracts. In fact, over time, you can expect that a large part of your jobs will consist of work done for return clients, or new clients that are the friends of previous clients. If you're just getting started, then it may take some time to get this ball rolling. But in general, the work becomes much easier and more consistent over the years.

The life of a writer

Finally, you should bear in mind that being a writer of any kind, especially a freelance writer, is essentially lonely by nature. When you do your work, you are by yourself, and you cannot interact with other people. Just compare this, for example, to the nature of being a bartender.

A lonely job?
Life as freelance writer can get lonely. While jobs such as bartending involve a lot of socializing, writing can require hours of concentration in solitude.

Image Source(s)

Especially as a freelance writer, you probably won't be meeting people at work (seeing as you work for yourself, often from home). It’s important to take breaks from writing in order to not drive yourself mad, and breaks also help if you’re experiencing writer’s block.

If your social life is important to you, then you will need to work toward developing the right kind of balance between making your living on the one hand and enjoying the company of friends on the other. Of course, an advantage of being a freelancer is that you can structure your own time in order to see people whenever and as often as you want.

Works Cited

Adkins, Amy. "Millennials: The Job-Hopping Generation." Gallup. 12 May 2016. Web. 8 Apr. 2017.

Butman, John. "How to Manage Impossible Clients." Harvard Business Review. 5 Dec. 2013. Web. 11 Apr. 2017.

Freelancers Union. Freelancing in America. 2014. Web. 8 Apr. 2017.

Hamill, Kate. "So You Want to Be a Freelance Writer." Freelancers Union Blog. 10 Sep. 2014. Web. 12 Apr. 2017.

Lemann, Nicholas. "The Network Man." New Yorker. 12 Oct. 2015. Web. 8 Apr. 2017.

Porter, Michael E., and Mark R. Kramer. "Strategy and Society: The Link between Competitive Advantage and Corporate Social Responsibility." Harvard Business Review. 2008. Accessed 4 Nov. 2014.

Stenovec, Tim. "More Proof that Uber is Killing the Taxi Industry." Business Insider. 7 Jan. 2016. Qeb. 8 Apr. 2017.

Upwork. "About Us." Author, 2017. Web. 9 Apr. 2017.

U.S. Small Business Administration. "Starting a Freelance Business." Author, 23 Sep. 2016. Web. 8 Apr. 2017.

WriteZillas.net. "Write Better Essays with WriteZillas.net." Author, 2017. Web. 9 Apr. 2017.



Ultius, Inc. "How to Work as a Successful Freelance Writer." Ultius | Custom Writing and Editing Services. Ultius Blog, 26 Apr. 2017. https://www.ultius.com/ultius-blog/entry/how-to-work-as-a-successful-freelance-writer.html

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