Getting Your First Freelance Writing Job: 5 Things That Can Help You Land It Quicker

In a recent post, 10 freelance writers discussed how they landed their first gig. In that post, I promised to divulge how I got mine, which I’ll do here, as well as outline five things that stood out to me about the freelancers in the previous post.

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How I Got My First Freelance Writing Job

If you’re a regular reader of this blog, you know that I worked at a legal publisher in New York City for 10 years (1987-1997).

Six years into working for the company, I started freelancing on the side for them, but it wasn’t as a writer. It was doing coding (WANG and SGML) and proofreading work. Long story short, after a couple of years of doing this, me and my sister – who worked at the company as well and actually got me the job there while we were both in college – started earning more from this side work than we were as full-time employees.

Around this time, the company decided that we could no longer work as freelancers and as full-time employees. So my sister took the brave step to quit her full-time position and start Inkwell Editorial. When it was first started, Inkwell Editorial was an editorial outsource company. We took on proofreading, copying editing, editing and word processing jobs.

We eventually landed clients like Random House, McGraw-Hill, Pearson Publishing and McKinsey & Company. Yeah, it was a lot of fun.

One day, a client contacted us as asked if we did writing projects. I don’t remember exactly how the conversation developed, but I do remember that I wound up taking on the job.

They were a dental company and wanted some kind of brochure done as best as I can remember.

What I Learned from My First Few Freelance Writing Jobs

The project didn’t go well, and I don’t think I wound up charging the guy (I’m really scratching brain cells trying to remember here). What I do remember clearly is that writing scared the bejeezus out of me. I had zero confidence in my abilities in this area, as I’d never “written” for a living.

I’d been a legal copy editor and proofreader, but of course, writing is a whole different ball of wax.

The next writing project to come my way was via an acquaintance. This project was different because it didn’t start out as a freelance writing job. It started out as an editing job. But, the author’s writing and grammar were so terrible that I wound up, in essence, writing the article. It was for a small, start-up magazine in Brooklyn.

This gave me the confidence I need to see that, “Hey, you’re kinda good at this, and you like it.” That was the official beginning of my freelance writing career. I haven’t looked back since.

The most important thing I learned from those first couple of jobs is that confidence is everything. Some forms of writing have frightened me over the years, eg, case studies. But I always think back to how afraid I was of that first job. I, in essence, gave into my fears. I could have done the job – if I had more confidence in myself at the time.

So if I have a fear now, instead of giving into it, I go in the opposite direction. I push myself to tackle the project. And even if a form of writing is not exactly my forte, there’s little that I’m afraid to try as a freelance writer, eg, press releases, SEO content, writing and publishing my own ebooks, developing e-courses, etc.

Looking back, I realize that if I’d never confronted the fears that gripped me on that first job, I wouldn’t be where I am now. So I’ll always be grateful for that experience.

Now, back to the post from a couple of days ago.

5 Things That Can Help You Land Your First Freelance Writing Gig

Following are some things that stood out to me about the stories shared by the freelance writers in the post a couple of days ago that can help you land your first job.

1. Content Mills: A Love/Hate Relationship

Many new freelance writers turn to places like Upwork to try to land their first few freelance writing clients. What usually happens is that they either fall in love with them, or hate them altogether. It all depends on the type of clients they encounter there, of course.

I’ve written for a few content mills in my day, eg, Media Shower, eHow and the now defunct AssociatedContent. Mostly I did it because it was easy-to-get work and/or because I could promote my own products and services via the content I wrote.

For what it’s worth, I think that content mills are better for finding jobs nowadays than they used to be. Why? Because the quality of client is better – thanks to the popularity of content marketing. Companies are investing heavily in it – and if companies are spending money on it, it means they expect to get a return from it (a ROI).

A $5 per article writer is not what they’re looking for. They’re looking for writers who understand how to produce content that gets results.

2. Writing for Free Can Pay Off in the Long Run

Freelancer Bamidele Onibalusi spent a year writing for free on his blog and guest posting before landing his first client – via a content mill no less. And what a client it was; the client paid him $85 to $100 per article – and this was a few years ago.

So get that blog up. Even if you’re not actively “starting” your freelance writing career right now, you’ll have content that can serve as your writing sample when you do if you start blogging.

Tip: Blog within a niche you think you might want to enter. This way, when/if you do start to freelance, you’ll have niche-specific writing samples to show potential clients when you start marketing.

3. Independent Streak

What many of the freelancers featured had in common is that they wanted to make a living doing their own thing. And they did what they had to do to make it work – everything from writing for very little, to placing expensive ads in a local newspaper.

Sometimes, you have to try something “99 ways to none” to make it work. With this kind of determination, it’s not “if” it’ll happen, it’s “when” – if you keep trying.

This reminds me of the Thomas Edison quote, “I have not failed. I’ve just found 10,000 ways that won’t work.” That’s the attitude that’ll get you wherever you want to go in life by the way.

4. Get Visible on the Web (Blog)

Several freelancers found gigs just by having their writing visible. See freelancer in #8 in that post, for example, who blogged on LinkedIn and her posts got noticed. This led to her first writing gig.

As noted in #2, blogging – whether it’s on your own, personally hosted blog, or on a popular social media outlet like LinkedIn, it can get you noticed and land you your first gig.

5. Go For It

Apply, even if you don’t think you qualify. The freelance writer mentioned in #10 proves this point beautifully. He flat out states that he didn’t have all the technical knowledge he thought the client wanted, but he threw caution to the wind and applied anyway.

I can’t tell you how many times this has worked for me. Even if I’m only tangentially qualified for a gig, I’ll still send in my credentials if I’m interested. Thanks to my experience as a SEO writer, I can write on almost anything. FYI, this is why it’s important to have keen research skills as a freelance writer.


Funny how things come full circle. It takes balls (confidence) to succeed in this career; the very thing I didn’t have in the beginning of my freelance writing career. So if you don’t absorb anything else from this post, remember – confidence in your abilities goes a long way.

It is as vital as knowing how to write well-crafted copy. Internalize this – and go for it!

What Did You Learn from Your First Freelance Writing Gig?

Please share in the comments section below.

P.S.: If You’re Serious about Starting a Freelance Writing Career, You Need a Web Presence. Learn why and how to start one.

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