The Challenges of Being a Freelance Writer


Considering a career in freelance writing? Here are some hurdles that you might face, along with suggestions on how to get over them.

Type “freelance writer” into a search engine, and you’ll find many articles with tips on how to launch a freelance writing career. If you’re an office-bound worker, you may think that being a freelance writer sounds wonderful because your time is your own, and you also get to see your name on a newspaper, a magazine or website. Freedom along with a tiny bit of fame, and money in the bank to boot. What an awesome proposition right? Not exactly.

There seems to be a lack of information about the difficulties of starting and sustaining a career in freelance writing. Those that do address the downside, talk about financial instability, living without employee benefits and not getting paid on time. These are all very valid points, but there are other reasons why freelance writing can be an exhausting career option, and not what an aspirant might expect.

Thankfully it’s not all bad news. If you’ve decided to become a freelancer writer, there’s a good chance that you love writing and are somewhat good at it. That’s a great start, because your passion is your best weapon for the long battle ahead.

As I share some of the challenges of working as a freelance writer, I’ve also included some tips on how to overcome these obstacles.

Administrative Work. When I left my job as editor for a lifestyle magazine, I thought I would finally be able to devote myself to simply writing good stories rather than attending unnecessarily lengthy editorial team meetings, lunching with potential clients, subediting content, selecting photos, checking and replying to emails (this usually takes about three to four hours a day when you work for a large publishing house), guiding junior writers with stories and designers with layout.

This was not the case at all. As a freelance writer, I still have deal with most of the responsibilities of a staff writer. In addition, I also need to read contracts, research publications to approach, brainstorm for story ideas and pitch them, create and send proposals, quotations and invoices, keep track of my income and expenditures, file receipts for tax deductions, and constantly think about how I can grow my business. Phew! Here’s what I do to ensure administrative work does not bog me down.

Get Over It

  • Never forget what it is you’re selling.

It’s easy to lose precious writing time to the dozens of little tasks that pile up during the day. When I am tempted to “tie up all the loose ends” before starting on a new piece of writing, I ask myself two questions. “How important is it?” and “Can it wait?” I usually start my day by checking my email. I reply to those that need my immediate attention, like a query from an editor who is getting ready to layout a story I had submitted earlier in the week. I make a list of all the other things that need to be done before the day is over, then I put that list aside and get started on the writing.

Writers are splendid procrastinators, so it’s important that you don’t use administrative duties as an excuse to avoid tackling the most important task of the day. Your priority should be your product ­– content. Your main job is to write an interesting and informative story, so make sure that is always where you focus your mental energies first. The more mindless tasks always seem more appealing than sitting in front of a blank page and filling it. There is always the temptation to check my inbox, send another reminder to a source for information, or check my bank account to see if an overdue payment has been remitted. But I’ll leave them till after I’ve completed the first draft of my article. Then I “take a break” and tend to them before returning to rework my article till it’s ready for submission.

  • Move from most scary to least scary

I do the things I least want to do first. If there’s a particular phone call that I dread having to make, or one article that I think will take much more time and effort than the others, that will be the first thing I do. If you do the most difficult thing on your list first, then everything else you have to do during the day just feels a little easier.

Loss of Industry Cred. When I was a staff writer, I could hand out my business cards and people immediately viewed me a credible journalist because they were familiar with the magazine I worked for. I could show up at a black tie event and say, “I’m with [name of a popular magazine, newspaper or agency here]”, and there’s a good chance that my name would be on the guest list, and I’d be warmly welcomed. As a representative of a publication and an organization, doors open easily for you. Working for a company gave me access to stories, sources, new restaurants and hotels, invites to parties and press events and even occasional travel junkets.

Those in the industry view you as a business associate because you come with the backing of a brand. But all this disappears when you leave the safety of the publication, agency or firm. There will be no entourage of PR executives spoon-feeding you the latest news, your presence at press conferences and events will no longer be requested. When someone asks you, “So who do you write for?” or “So which agency are you with?”, you won’t be able to confidently say [name of a popular magazine, newspaper or prestigious agency here]”, but will feel a little mousy as you recite a long list of publications that your interrogator may or may not be familiar with.

On your own, you’ll have to hustle to get a slice of the pie. You will become an industry persona non grata, and you’ll need to work at developing your own professional reputation. When you strike out on your own, you must become your own brand. This takes time and effort. The key to being taken seriously as a professional freelance writer is to ensure that you become and stay visible. Here are some ways to do so.

Get Over It

  • Have a website

Your website should clearly show clients what you can do. I organized mine according to subject categories, so if a client from a particular sector wants to see samples of published work, I can direct them to the relevant page on my website.

  • Collect and showcase your published work

Always make sure you get soft copies of your published articles from your editors and clients. If you can, get reference letters too. Make sure you get at least two articles published a month. Use social media. Upload your recently published articles on Facebook, Linked-In, Twitter, Instagram, on your website, and on any appropriate platform.

  • Register your company, get a logo and company stationary

For tax purposes, some employers will require that you provide them with your company registration number. Not only does registering your company boost your professional image, it also helps you to take yourself more seriously as a business. Create a logo for yourself, get business cards and stationary with company letterheads made. It is important that you present a professional image to your clients.

  • Business development and networking

At least once every month, sit down and make a list of industry professionals and organizations (agencies, magazine editors, PR firms, marketing department heads etc.), then make contact with and introduce yourself to them. As a self-employed writer, you need to make sure the industry knows you exist and are available for hire, so send out emails to let the right people know that you like what they do, and will be happy to work with them if they need help in the future.

  • What’s next?

As a freelancer, you are in charge of your own marketing and promotion, so should constantly be thinking of new ways to sell yourself. This involves learning new skills, such as basic web design, SEO optimization, technical writing, and writing in formats other than those you are familiar with, so you can expand your portfolio of services.

Finding and Keeping Employers. As a freelancer, you won’t have to answer to a boss; you’ll have to answer to many bosses – your editors. Editors are elusive creatures. They don’t much like being bothered with phone calls, and it is not uncommon for them to ignore your pitches and queries, or reply three months later. Editors are very busy people; everyone wants their attention and they are often stretched thin. To protect their sanity, most editors take a “Don’t get in touch with me. I’m swamped, so leave me in peace. I’ll get in touch with you if I need you” approach to new freelancers. Patience and courtesy is essential when working with editors. Here are some ways to expedite the communication process.

Get over it

  • Keep your introductory emails short and sweet

When reaching out to a new editor, keep it simple. Make sure you get their names. Emails that begin with “Dear Sir/Mdm.” are not a good idea. Let them know who you are, how long you’ve been writing for, magazines that you’ve been published in, or clients whom you’ve worked with, and your areas of specialty (e.g.: architecture, dining, finance etc.). Let them know that you read their magazine and understand the type of topics and formats they are looking for. Let them know that you will be happy to send over your resume and writing samples if they would like to know more about your work. Let them know that you are available for commissions, and make sure to give them your contact details so they can get in touch.

The point of the introductory email is simply to put yourself out there, to let editors know that if they need someone, you are ready to work. They may not reply right away, but when it’s crunch time, and one of their unreliable freelancers (there are more of them around than dependable ones) bails on an assignment, they’ll have your number, and that will be your in. 

  • Craft a good pitch

The best way to get a new editor’s attention is send them a really good pitch. Read the magazine that you plan to pitch to, so you know the type of content that suits the magazine and won’t be pitching blind. Some publications have writer’s guidelines, which outline the format that you should use when pitching. These guidelines are there for reason, so stick with them or risk having your pitch deleted. Include the main details in your pitch as well as links so the editor can see sample images and get an idea of how the story will look on page.

There are three important points to consider when pitching. Timeliness – does the story fit with the season, the theme of the issue or upcoming events? Novelty – is your idea fresh, or has it been overdone? If you are pitching a restaurant, trend or project, how current is it? Sources – can you secure the interviews and images that you need to make the story work?

  • Be meticulous and thorough

Establishing a relationship with a client or an editor takes time, but such relationships are easy to destroy. Sometimes, things don’t work out for reasons outside of my control, but I am ashamed to admit, in my early years as a freelancer, there have been times when due to carelessness on my part, I have jeopardized an otherwise good editorial relationship because I trusted my computer’s spellcheck function with my proofing, or worse still misspelled the name of a source.

Always proof, spell check and fact check. I cannot stress the importance of accuracy. Make sure that all facts, figures, names and addresses in your copy are correct. If your editor spots something that could get his or her publication in trouble, you’re probably not going to get more work from them. Make sure your photos are of professional quality and high resolution. Editors do not want to use photos taken by amateurs in a glossy magazine, so make sure that the visuals you provide are of a high standard and compliment the content in the text, otherwise there’s a chance your editor won’t come back to you.

  • Staying in touch

Even if an editor likes your work, it is still easy for you to fall off their radar. If you haven’t heard from an editor in a while, feel free to drop them a line to let them know you are still alive, brimming with ideas, and interested in taking on new work.

You Become Dispensable. As a full-time editor and writer, my company’s sales and marketing department needed me to create copy to help them serve their clients; my managing editor needed me to get things done. My team of writers and designers needed me to edit and proof their work, and I was given a regular paycheck to avail myself to them all. As a freelancer, no one really needs me anymore, and I am easily forgotten.

I am no longer the first person that a company approaches when they need work done. In fact, in most cases, I am the last. As a freelancer, you’ll be the afterthought, once all the best stories have been assigned to in-house staff. You’ll be called on at the last minute, and asked to meet tight deadlines. You’ll become the “in a pinch” person. The good news is people are always in a pinch in the world of publishing. There’s no getting around the fact that you will be crossing your fingers a lot and doing a lot of waiting around. Here are some ways that you can help make yourself the first freelancer on an editor’s or client’s roster.

Get Over It

  • Error-free copy

Editors are always busy and there’s nothing that bugs them more than receiving copy with typos, spelling, punctuation or grammar mistakes, articles that requires extensive rewrites, or that haven’t been fact-checked. If you deliver copy that is clean, smooth and flawless, there’s a good chance that an editor will return with more assignments.

  • Meet or beat deadlines

Always submit copy and photos on time or earlier than the assigned deadline. One of the most painful tasks for an editor is chasing writers for material, so make your editor’s life easier by delivering work on time, and you’ll increase your chances or being asked to work on another assignment.

  • Get good, high-resolution photos

Today, almost all journalists working with commercial presses need to think about images that will accompany the articles they submit. When you have been commissioned to work on a piece, you’ll also need to secure all the photos according to the specifications of the publication you work for. Certain editors might require you to take the photos yourself, others will expect you to liaise with a photographer to arrange a time for both interview and photo shoot, while others will require you to email your sources for images. Your work is not complete until you have provided both text and images, so make sure you have a system in place for efficient image sourcing.

  • Don’t expect handholding

While it’s important to make sure your assignment brief is clear before you begin (word count, deadline, fee, how many photos are required, do transcripts and reference sources need to be submitted for fact-checking etc.), do not contact your editor with questions at every stage of the job. Editors like writers who won’t take up too much of their time. As a freelancer, you are expected to know more than a rookie writer, so take charge of your work (and your sources) and don’t bother your editor until you have all your materials ready for submission.

  • Be available and ready for prompt rewrites and clarifications

Though your editor may be elusive, you should never be. Because you work from home and not two cubicles down the hall from your editor, he or she should feel that they can still call on you anytime, and count on you to meet their needs pronto. When an editor emails you with a request for clarifications, revisions or rewrites, let them know you will take care of things as soon as possible, then do it. Nothing fosters trust between remote workers and their employers better than a sense of immediacy. If your editor knows you are reachable and available, and that they can count on you from start to finish, they will most likely come back to you again.

Trust is Not Just a Contract. One of the best things about being a freelancer is that you have the option of walking away from bad bosses. You aren’t bound to any one company or employer for any longer than the duration of your project or assignment.

There are as many editors, publishers and clients as there are freelancers, and some of your superiors may be completed idiots. If you are working on a long-term project, make sure your employer delivers a signed contract or contributor’s agreement. Be clear on what you need to deliver, and be wary of employers who are always haggling for freebies or subsidized fees.

You will certainly encounter some clients that are more demanding than others, which isn’t always a bad thing. A little flexibility goes a long way, and it is good to know how to improvise and adapt when required.

I have found that there are three red flags, what I call the three Ds that I watch out for when starting work with a prospective employer. I have learnt that it is best for me to walk away from employers who are consistently Dishonest, Disorganized or Disrespectful. These three traits are not a matter of professional inaptitude, they are personality problems. I have worked with clients who have lied or simply not paid me for work delivered. I have worked with clients who have had no idea what they want, ridiculous expectations, and who were unable to communicate at all or stick with agreed-upon schedules or deadlines. I have worked with clients who were downright condescending and rude. If you find yourself working with someone who strongly exhibits any of the three Ds, complete your job to the best of your ability, then say goodbye.

Get Over It

  • Live and learn

Difficult clients are not always bad. They challenge us to grow professionally, and teach us how to handle unexpected obstacles gracefully and confidently. Encounters with the three Ds can help you develop better business acumen. When you’re starting out, it might be even be useful for you to deal with a few “bad” employers. This will help you to develop the shrewdness necessary to make wise business decisions. In the beginning, you might have to take a few punches and tweak your processes a little as your progress in your career, but if you learn from your bad experiences, your exasperation and indignation won’t go to waste!

  • Black and white

Make sure you get either a contract, or if you are working on a single magazine article, an email confirming the assignment and fees. Before you begin on a project, find out what you need to deliver (how many words, how many photos, or how many hours of work are expected, deadline, angle, how many revisions are expected at no extra charge etc.), and the payment terms (what you will be paid and by what date at the latest).

  • Learn to say no

As you get busier, you won’t be able to take on every project that comes your way, so be selective about the ones that you do commit to. Saying no to a potential client who is not paying you a fair fee, or whose values are not in line with yours means you have more time, creativity and mental energy to do excellent work for your existing clients whom you do care deeply about and respect.

Competition From Other Writers. Since I began freelancing in 2009, the market for freelance writers has exploded. There are so many of us now, that sometimes I get a little fearful that there won’t be enough assignments and projects available. This is when I have to remind myself that my voice is unique, my ideas are valuable, my work ethic is sound, and that there is enough work for all who are willing and committed to laboring well and with love. To keep pitching and writing when no one is cracking the whip is not something everyone can do with ease. You’ll be surprised at how many people give up after a few hacks. In the second year of my journalism degree, almost one-third of the class quit. Success as a professional writer is all about staying power; the longer you keep at it, the more exposure you will get and the better your craft will become. This will certainly make you stand out from the pack.

Get Over It

  • Know the market

In any business, it is important to always stay current with what’s happening in the industry. Publishing has a high turnover rate, because they work is mentally grueling and many editors jump ship and migrate to marketing, public relations or fitness (strange but true). Sign up for industry newsletters and online publishing groups that keep you updated on movements in the market, new hires, new publications and available assignments.

  • Write captivating content

Reporting and writing are very different. A reporter conveys researched information in a straightforward, no nonsense way. A writer entertains. Good writing, in particular feature writing is about getting your reader to like and trust you, and to feel relaxed by your manner of “speech”. To write captivating copy, you need to find your very own voice and use it with confidence. You need to be able to draw your reader close and make them feel as if they are about to embark on a grand adventure with you.

  • Make the unoriginal exciting

Most ideas are not new, and as the saying goes “today’s news is tomorrow’s history”. So what can you do to hold your reader’s attention? Find a new angle. When writing about a subject most people are familiar with, try doing it in a new and delightful way, perhaps by adding a personal anecdote or simply by using a different tone of voice.

  • Read more

There are two things that one always has to do if one wishes to become a better professional writer. Keep writing, and read widely and consistently. While many full time writers write everyday, sometimes with a nine-to-five job and family obligations, it becomes difficult to read as much as one would like to. If you’re not reading, you won’t be able to see into the minds of other writers, and learn what works and what doesn’t. Access to the styles, voices and ideas of your peers is crucial in helping you develop a rich and full-bodied “writer persona”, so make sure you’re always reading something.

Living with Uncertainty. When you freelance, there is no one handing you a monthly agenda. You don’t know how much money you will make, or whether or not you’ll even make any money from month to month. You don’t always have regular work and there will be periods when no matter how many introductory emails and pitches you send, your inbox remains empty. So how do you keep your chin up during dry spells?

Get Over It

  • Keep your momentum

I believe that as long as I’m moving my legs, the ground will soon touch my feet. Entrepreneurship is a way of life where business development and marketing become modes of thinking. When I am not working on assignments, I keep myself busy researching companies that I hope to contribute to. I send introduction emails to new contacts and “hello, I’m still here and available” emails to existing contacts. I attend media events and always keep an eye out for new publications or openings in the market, as well as potential stories. I stay active on social media with blogs and post articles on Linked-In or Facebook. I throw my net far and wide and just keep reaching out to as many people as I can. I do what I can and what I know I ought to be doing, and trust that eventually opportunities will present themselves.

  • Never stop learning

Read the news, read a novel, expand your vocabulary, learn a new language, learn how to build a webpage or use a new app, write essays, write short stories, write poems, start a blog, paint, develop an obsession with extinct birds of Central America, talk to people, listen to people, travel, watch Ted talks, sign up for a meditation group, join a gardening club and learn how to grow orchids. We live in a big big world, and the more you know about it, the more valuable you will be to any organization. Be a sponge for knowledge, and in the process, you will increase your skill sets and thus your employability and the range of services that you can offer as a freelancer. If nothing else, you will simple become a more interesting person and a better conversationalist.

  • Be an inventor and a self-starter

To keep up a career as a freelancer, you need to have high levels of motivation. If you work from home, it is easy to be distracted – by the cookies in the pantry, the reality TV show that comes on at 2pm, or your bed. If you’re not genuinely excited by what you do (writing, networking, growing your business, communicating with the public), then you’ll probably waste half of your day doing non-work related things. I usually have a few “personal” projects, such as writing professional development articles like this that are indirectly related to income generation. So when things are quiet, I do not feel as if I am unemployed or unproductive. Instead, I use the downtime to get active on Social Media, trawl through Linked-In profiles, update my website, recharge, get new perspectives, come up with new ideas, develop new platforms or services, and find renewed purpose in what I do. With technology at our fingertips, anything is possible for us writers, and everything you publish will have an impact on your professional value, so don’t stop at just paid work.

Copyright® Michele Koh Morollo 2016


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