Freelance writing is a great side gig: it doesn’t require a ton of equipment or specialized skills (like Photoshop or InDesign) to get started. And it’s flexible enough that you can fit it in no matter how busy your schedule.

But getting those first few freelance gigs can be tough: you send out applications, hope for the best, and often never hear back. Websites like

and offer lots of opportunities (for a price), but there’s tons of competition for any job and the pay is often laughable.

I recently oversaw the hiring of several new freelancers here at Money Under 30, and, as a sometimes freelancer myself, the experience was eye-opening. Here’s what I’ve learned:

Nothing you can do can guarantee you’ll get the job

I know that can be hard to hear, as we hate to learn that something is totally out of our control, but it’s true. There’s so much you simply can’t know about that could be the deciding factor.

Before coming to Money Under 30, I worked at a literary magazine during graduate school. While there, I learned that you can’t take a story rejection personally. There are too many factors in play, and most of them have nothing to do with you or the quality of your story. Screeners for lit mags are overworked, burnt out, and often have to make quick decisions to keep up with the constant flow of new submissions. If your piece doesn’t grab them immediately, it gets the “reject” label without a second thought. You also might get assigned to a reader with an aesthetic completely different from yours, who, in the best of circumstances, probably wouldn’t like it. This doesn’t mean your story isn’t good.

The same is true for most freelance writing jobs. We received dozens of applications (probably more than 100), and I had to sift through them all myself. I didn’t have a ton of time to decide who went into the “maybe consider” folder and who went into the “don’t bother” one. All of this was influenced by my schedule and workload that day, my mood, and when a particular email arrived. Did it arrive in a flurry of six others? It probably didn’t get as much of a look, unless there was something in the application that really struck me. Did it arrive during a relative lull, when it didn’t have eight other applications and my to-do list vying for the same attention? Then it probably got a closer look, by virtue of nothing but the complete accident of its arrival time.

Several of our finalists’ applications came in later in the cycle, and I’m sure many other worthy applicants were overlooked because they arrived in the midst of the deluge.

Here’s a bit of counterintuitive advice: While most guides say you should get your application in ASAP, it actually might be better to wait a few days. By then, the initial avalanche of applications will have ceased, and the exhausted hiring editor will feel less overwhelmed and more likely to give your application a serious, unhurried look.

Regardless, if you don’t get the gig, don’t give up. And don’t presume you did something wrong.

Get to know the audience, and tailor your pitches

I’d get some applications that included pitches on really basic topics, the kind of stuff that our almost decade-old site had covered long before. This suggested two things: they hadn’t read our site, or certainly not all that closely, and they weren’t trying that hard.

One applicant included a pitch that was specific and interesting, but that’s basic point was pretty much completely counter to our site’s position on the topic of robo-advising. If this writer had taken merely a few moments to peruse our site, he probably would have seen that we’ve written positively about a number of automatically managed investment accounts, and might have reconsidered his pitch. (Or simply seen that he wasn’t a great fit for our site, and might have found one more suited to his more do-it-yourself, down-in-the-nitty-gritty approach.)

Again, this isn’t a reflection on the writer, who seemed smart and savvy. It’s just about finding the right fit between writer and venue.

In a content area as well-trodden as personal finance, finding a new angle is key. Search the site for common topics, and try to think about one approach they haven’t tried yet. What’s missing from the site? What do you have extensive knowledge or experience of that could give a stale topic a fresh perspective?

Don’t send seven!

The editor is not going to read all seven, and you don’t want to risk them clicking on your comparatively weaker stuff. Pick the two or three that are your best, that are most relevant to the publication in question, and that obviously display your fitness for the job. Quantity won’t make you look better; quality will. 

Don’t give them a reason to reject you

If you’re responding to an ad (on craigslist or a freelance site), you can be certain that the editor doing the hiring will receive more applications than he or she can handle. They’ve got to find ways to whittle down the pile to a manageable number. Don’t give them an excuse to throw your app in the “don’t bother” pile.

Your cover letter or email application should be flawless, in terms of grammar, style, and punctuation. You’re auditioning to be a paid writer – if you can’t handle a basic introductory note, why should they trust you can handle a much larger writing project? Writing a brief cover letter that is engaging and well-written is difficult, but that’s why it’s so essential. It shows them what you can do.

Make sure you don’t come across as overly demanding, unreliable, or straight-up unhinged. No matter how good your samples are, no one wants to work with someone who, in the course of their brief application, makes it clear they will regularly blow deadlines, make unreasonable requests, or just be generally unpleasant. Give them every reason to have confidence in you.

Avoid boilerplate. I threw so many applications in the “nope” file because they used tired, cliché-ridden prose in their introductory letter. (Often while claiming to love language!) If your pitch paragraph sounds like a parody of content marketing evangelism drivel, re-write. If you can’t make it through your own cover letter without falling asleep, re-write.

Don’t be overly casual in your email. I know it’s a casual medium, but the same rules apply here as to a standard cover letter. It’s your introduction in a professional capacity – include a proper greeting, a few complete sentences that explain why you are writing, and a sign-off. Use those manners your mama taught you.

Another note: Unless the ad is specifically for “content marketers” don’t call yourself a content marketer. I realize it’s the new buzzword, but it’s off-putting, especially when our ad was specifically for “writers.” It may be unfair, but advertising still has slightly slimy connotations, a slickness that isn’t well-suited to every situation.


Jump-starting a freelance writing career (either as your full-time job or a side gig) can be tough. To increase your chance of success, get to know the publication you’re applying to write for, put your best work forward, and avoid minor mistakes that can get you thrown out of the running.

Read More:

  • Why You Should Be Freelancing Now And The Secret To Getting Started
  • Time Management For Freelancers: How To Find Extra Hours For Earning More