How to Start Your Own Freelance Writing Business

Contel Bradford
10 min readJun 15, 2022

Never in a million moons would I have imagined myself in this scenario. I honestly don’t think most people believe me when I tell ’em what I do. They give me a look that reads like, “I’m surprised you can even read. Good for you!” I find those exchanges very amusing, to say the least.

Yet here I am, 15 years later, having enjoyed what I could call a fairly successful freelance writing career.

It has been a long road, dotted with peaks and valleys amid a steady flow of work. While my journey is no doubt unique to my experience, I like to think it has followed a rather elementary path.

So how do you blaze your own trail to a prosperous freelance writing career? Settle in, and I’ll share my perspective on the game.

Build a Writing Portfolio

No matter the profession, you instantly improve your chances of securing gigs when you can illustrate a competent body of work. Freelance writing is no exception. Clearly, it’s a case of easier than done when you’re just starting out with little to nothing to show for your ambition. This is where a little creativity pays huge dividends.

I went in touting my experience as a self-published author, which was a tad risky considering that the books I write are controversial, at best. Luckily, it added just enough credibility to pique the interest of potential clients. And in this game, all you need is one foot in to bust the door wide open.

If you’re an author with a few titles under your belt, great. If not, don’t sweat it, because there are other avenues that may be even better suited for building out a nice portfolio. Take Medium, for example.

Medium lets you write and publish stories on the topics of your choosing til your heart is content. It’s a self-service platform, so it may not wield the same weight as a portfolio amassed from clips published by your clients, but it can give you an opportunity to showcase your writing skills. And if the content is good, then all the better.

Learn to Sell Yourself

Some of my highest engaging social media posts are silly little one-liners with me ranting about manwhoring. I’m sure most of my friends/followers have no idea what the hell it means … some might actually take the shit quite literally. Whatever the case, these posts almost always garner a few laugh emoji thingies.

In most cases, the manwhoring references are code for my adventures in freelance writing. While I am most certainly grateful for all I’ve accomplished, whatever money I’ve made, the clients that have taken a gamble on me, the luxury to work from home, etc., I wouldn’t exactly call this my dream job. Honestly, I’d rather write and sell fiction, but for whatever reason, that’s a mountain I just can’t seem to scale, so freelancing is the alternative I’ve settled on, and appear to be somewhat good at. I’m being a tad dramatic here, but it’s akin to selling my soul. You know … manwhoring.

Shenanigans aside, mastering the art of selling yourself is vital to carving out freelance writing success. When a potential client narrows that list of prospective candidates down to a handful of names, a potent pitch can make all the difference in the final decision. It’s a delicate balance of putting yourself over ( to steal some pro wrestling jargon), and illustrating how hiring you will help the client meet their objectives.

I’m not sure if I’ve mastered the aforementioned art form. However, I’ve been fortunate to secure steady work and stand confident that when the chips in my other endeavors are down, freelance writing is always something I can fall back on.

Know Where to Look for Freelance Writing Gigs

The freelance industry has been a major beneficiary of the internet age. In fact, most freelancers run their entire business online, complete with an exclusive list of web-based clients. For beginners, finding said clients is the challenge. Luckily, there are a wealth of options at your disposal.

I started my search for freelance writing gigs with crowd-sourcing. I’m referring to sites like Guru, Upwork, and Freelancer, which is actually where I landed by very first gig. These sites are sort of like eBay for digital services. Companies post jobs they’re looking to fill, then writers, designers, and other freelancers apply by placing their bids.

There’s a lot to like about freelance-friendly crowd-sourcing platforms. For starters, there are hundreds to thousands of job opportunities to vie for. The best of these sites let you target your efforts, drilling down into writing categories such as articles, blogging, and copywriting.

Establishing a presence in this domain is noteworthy as the underlying platform will highlight the number of projects you’ve been awarded and completed. And if clients like your work, they’ll typically shout it in the form of a compelling review. This activity builds credibility that comes in handy as you bid for future gigs.

Now here it comes … the downside … well, there are actually two major issues I see with using crowd-sourced sites to score freelance writing gigs. You’ll notice the first right out of the gate, and that’s the fierce competition.

These sites literally cater to freelancers from all walks of life, meaning you could be bidding against dozens upon dozens of other professionals for a given gig. The competitive aspect works to the disadvantage of beginners with little to no presence on the gig site. Even if you have experience under your belt, potential clients are naturally inclined to favor service providers who are highly rated on the platform in question.

How do you win an eBay auction? Simple. You bid lower than the next guy. Companies recognize this, so you’ll see a lot of gigs paying ridiculously low rates that border on offensive. How low, you ask? Well, my very first gig paid $2 per 500-word article. IKR? I had to crank out 20 to 30 articles a week to make it remotely worthwhile. Considering how grueling writing a single article is nowadays, albeit at a much higher scale, I don’t know how the hell I did it.

Now that’s not to say every prospective client is out to low ball the masses. There’s also a mix of decent paying gigs, alongside a handful that actually pay exceptionally well. The best paying freelance writing jobs on this scene are generally reserved for seasoned professionals who are comfortable handling high-level projects. Content that requires extensive research, and the utmost quality and style standards.

I had outgrown the Freelancers of the world almost instantly. However, after taking a little hiatus, I returned many years later to find that nothing much had changed in the way of competition and lackluster pay scale. There’s a place for these sites in the freelance writing game. Just make sure you understand the scope before heading out into the shark-infested waters.

Pick a Lane

Coming in as an author, I chased any freelance writing gig that looked remotely interesting. My specialty was limited to erotica and urban fiction, so everything else was foreign territory. The results of this approach were weird, at best.

I started with IT, and while I did well enough to warrant repeat work, I literally had no idea of the topics at hand. I guess that says something for my penchant to conduct good research and translate the material into something that jived with the client’s vision. Still, I was probably six months in before I had a firm grasp of these topics. Madness!

I dabbled in a litany of categories: gaming, sports betting, parenting, porn, medical marijuana … I even had a Russian client hire me to write fake user reviews for a phony product. I think dude was a hacker. Hey, I was young in the game and needed the money. Don’t judge me!

Over time, it became clear that information technology was my calling. Transforming highly technical subjects into language that everyday humans can understand hasn’t always been easy, but it’s something I’ve managed to pull off with relative proficiency. Some how, some way.

Obviously, it’s great when you can tout yourself as a jack of all trades. At the same time, it makes sense to carve out a niche that speaks to specialized skills. The writing community is made up of many disciplines, so don’t hesitate to target a handful of areas and become a master of those domains.

Establish a Web Presence

When novice writers and authors pose the question of whether a website is important, my answer is a definite YES. In this internet-driven world, a website acts as your virtual headquarters. The place where you list your menu of services, share contact information, and even showcase samples of your work. A website creates instant credibility.

Having a website for your freelance writing business also provides access to other features that can add an extra coat of shine to your presence. Take the basic email address, for example. JoeBlow@JoeBlow.com looks a lot more professional than JoeBlow@gmail.com. In this case, your email address is pointed to the same domain reserved for your website. It’s a simple detail that can make a huge difference in terms of how you’re perceived by potential clients.

Of course, establishing a presence stems far beyond a website. Many freelance writers choose to lay down roots across the social web. From LinkedIn and Facebook to Twitter and YouTube, social media puts a plethora of outlets at your immediate disposal. These sites offer potentially impactful networking opportunities, in addition to the ability to build a community around your freelance writing brand.

Put Word of Mouth to Work

Business gurus say that word of mouth is still the most powerful marketing tool of the bunch. You can reap the rewards of that power in your freelance writing efforts.

Over time, I reached a point where I stopped actively seeking freelance writing gigs. Opportunities were packaged and delivered to my doorstep, giving me the freedom to pick and choose what I wanted to take under consideration. These gigs were were primarily presented on the strength of recommendations from past clients. I’ve scaled back on freelancing to pursue other business endeavors, but I still have a few of these offers and inquires every now and then.

This goes without saying, but the word of mouth is contingent on your ability to produce quality writing content. If you really knock it out of the park, satisfied clients may take the initiative to recommend your services to colleagues in the market for a good freelance writer. That’s cool, but don’t hesitate to give them that extra nudge.

I’ve made it a habit to request a review of my freelance writing services after completing a project for a client. This feedback goes right to my Testimonials page. The more positive feedback you can accumulate from credible references, the more your profile as a professional writer stands out.

Know Your Worth

This last part is tricky. It’s also vitally important. Your pricing strategy can literally make or break your ability to secure work. Now if they’re really digging your presentation, a hopeful client may be willing to negotiate a rate that’s agreeable to both sides. On the other hand, aiming too high off the bat could send them clicking to the next candidate.

So how much are you worth as a freelance writer? I can’t answer that, but any competent writer, regardless of experience, is worth more than two damn dollars an article. Shit, even $5 is borderline criminal. SMMFH.

Freelance writers are severely underpaid, man, I swear. Factor in all the research in the prep stage. Client specific style and formatting requirements during writing. Rewriting and revising, if you’re lucky enough to work with an editor. Break all the time and effort into a conventional hourly rate, and that sweet paying gig suddenly doesn’t look so lucrative.

The good thing about all this is that you call the shots. You set your rates, and can choose to be as fluid or firm as you wish. Taking the time to understand the going rates for certain writing categories, and how freelance writing experience factors into the equation may prove instrumental in determining your own flexibility.

Final Thoughts

SHEESH! This ran a lot longer than I initially planned. And I’m almost certain I overlooked a fundamental point here and there. That said, I hope you were able to walk away with something of value.

I jumped into freelance writing upon the sober realization that my once surefire ambitions of making it as a successful author may not come to fruition. I suck at everything else, so what did I really have to lose? The gamble paid off, and if a numbnut like me can make it happen, I’m confident that any capable writer can.

Contel Bradford is a mystical and multi-layered individual. You can attempt to unravel some of the mystery by visiting his freelance writing site at contelbradford.com.

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Contel Bradford

A seasoned freelance journalist and author, Contel Bradford is into reading, botanicals, horror, video games, and pro wrestling. Moreover, he LOVES adulting.