Why Your Cover Letter Sucks - Freelance Writing Tips

This week, a good friend of mine sent me her cover letter, asking for feedback. Now, keep in mind: this friend is talented, experienced, and confident! Still, she wasn’t getting any bites when she applied to jobs.

Once I took a look, I knew why.

I also knew that many of the writers in our freelance writing community have had similar struggles in the past. Cover letters tend to be an aggravating, confusing part of the job-securing process.

After sending my feedback, I asked my friend if I could post her cover letter and my reply on the DJO blog. I had a feeling it might help some of you guys, too.

If you feel like you’re flailing in the dark when applying to gigs and not getting any replies, this post is for you.

Below, find out why your cover letter sucks (and what to do about it).

The cover letter in question:

Dear (so-and-so),

I am very interested in the junior graphic design position at (company).

I’m a (college) alum and have since worked in visual design and digital media roles – I have a diverse skill set of web and print design, marketing strategy, social media content creation, digital ad animation and video editing that I would bring to the table.

Some recent accomplishments include redesigning the email marketing visuals and strategy of the (company), increasing the click rate by an average of 20%, and proposing/designing the first annual report microsite for the (company name) studio.

I am a self-starter, an extremely fast learner, and am actively looking to move from the non-profit sector to an agency design role in which I can grow and build my multimedia skills.

Working at (company) in this role seems like a perfect fit, especially given my passion for healthy lifestyles (being a lifelong dancer and athlete!).


That might look familiar. It might even look like a cover letter you’ve written at some point.

So, what’s wrong here? She’s included important information about herself, offered data proving her skills, and wrapped it up with a hint at her interests/passions. What else is there?

Unfortunately, this all-around amazing friend of mine has made a common mistake.

Let’s break it down.

The biggest thing almost everyone misses when writing a cover letter is this: When you start off by talking about yourself, the employer zones out.

They actually make this face: 😐

Can you understand why? I mean, put yourself in their shoes for a second.

99% of people applying for jobs say “I’m very interested in this opportunity. I went to this school, have X years of experience, these skills, and these accomplishments.”

Here’s how it looks to the person reading 100+ cover letters: Blah-blah-blah.

It’s the logical way to reply, but in reality, the employer has no reason to care about the information you’re giving them.

This is why you can be totally qualified for a job… and never hear back.

Frustrating, right?


There is a way to stand out!

The trick is to give them a reason to genuinely care about you first. Once you’re more than a name on a page, you can reinforce your candidacy with credentials.

You might be surprised at how emotional and personal the hiring process can really be. Having someone care about you or like you can go a long way toward landing a role.

And no, I’m not talking about being BFF’s in the first line of your cover letter.

People take just a few seconds to decide whether they “like” someone or not after meeting them, both online and offline.

If you imagine the last time someone “rubbed you the wrong way” before you even got to know them, you already understand this concept. The same goes for the last time someone just gave you a “good vibe”, and you weren’t sure why.

You’d be more likely to interact further with the good vibe person, right?

It’s something like that!

To inspire the recipient of your cover letter to like or care about you, all you really need to do is make a personal connection.

It isn’t effective, though, unless it’s the opening of your cover letter itself: the first sentence.

Use that sentence to talk about them first.

Talk about their business, their project, why they are so great—before you talk about why you’re so great.

People love reading about themselves. They love being addressed, recognized, and complimented. It’s simply human nature.

Here are a few examples:

“I read about the research you published last month on X topic, and it basically changed the way I think about X.”

“First, I want to say I admire the way you handled X material on the company blog. We’re on the same page about X.”

“Your brand ethos is really inspiring — I’m a huge fan of heart-centered brands who are making the world a better place, and through X initiative you guys are definitely doing that.”

“I saw your latest update and I totally agree. My Mondays would be so much worse without Trello!”

See what I mean?

Do some research. Check out the company’s website, Twitter account, or anything written about the company in the news. This is a timely, effective way to find a talking point to open your cover letter with.

It’ll prove that you’re not simply changing a few words and firing off a template (like the vast majority of those looking for work).

Go even further and find the hiring manager on Linkedin. See what they are working on or care about, or see if you can make a connection through their professional background.

Here’s an example of this technique in action:

Last year, I saw a cool remote copy job at a big fashion company posted on a large job board.

Knowing that I was blasting my resume into the abyss, perhaps never to be looked at, I submitted it anyway.

The thing is, I really wanted the gig!

I knew that the only chance I had at standing out was finding a way to make an actual connection.

I clicked over to Linkedin and searched for the company. Bingo! On the company’s page, an employee was highlighted who went to F.I.T., which is my alma mater.

In my case, it was a school connection, but it could have been a common interest or cause, an article she posted, or anything else that I could genuinely connect to.

Sidebar: Don’t fake it. They’ll be able to tell. Find a real way to relate to the person you’re writing to, even if it’s seemingly small (see Trello reference above).

Anyway, I sent this employee an email and introduced myself in a way that was non-pushy.

I also didn’t try to hide my agenda.

“Hi, (name) I see we both went to FIT! I know you’re busy, so I’ll make this quick: I applied for the copy role at (her company) and I was wondering if you could connect me with (name) in marketing to introduce myself. If so, I can be reached here or via email/phone: (info). Thanks so much!”

Since the Linkedin message feature limits your characters, you’ll have to keep it short—but be colloquial and friendly.

In this case, the employee connected me to the appropriate department for an introduction within an hour.

The next day, they interviewed me and I got the position.

So yeah, this works.

The bottom line…

While freelance writing jobs may not always require a cover letter, you can apply the above approach to any kind of outreach, including emails and Upwork proposals.

There are a huge amount of hopeful candidates scrambling for jobs online. You have to stand out.

Be human. Make a connection. Allow them to care about you.

It might sound counter-intuitive, but the answer to that puzzle…?

Talk about them first.


If you’ve tried this cover letter tip, we want to hear from you! Drop a comment below!

Want to hang with other writers like you? Join us in our Facebook group, Wi-Fi Writers Club

Freelance Writing Tips - Day Job Optional Newsletter

Michelle Christina Larsen is the Co-founder of Day Job Optional. Strong coffee, strong wi-fi, and absurd inside jokes are some of her favorite things. While a self-proclaimed side project addict, writing remains the ultimate focus of her life. After a decade of freelance writing in the fashion industry, she's teaching fellow freelancers how to dominate their niches and make full-time incomes online.

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