A friend of mine sent me her cover letter this week, asking for feedback. She’s a talented, experienced, and confident person… but she wasn’t getting any bites. Once I took a look, however, I knew why.

The cover letter debacle is one of the most common themes amidst freelancers and job-seekers.

These pesky intros tend to be an aggravating, confusing part of the client/job-securing process. The templated stuff we were fed in school doesn’t work in the real world. When you Google ’round the web, the advice is a mixed bag. No one tells you what an effective cover letter actually looks like.

So! Let’s end that deficit of info right here, right now.

If you feel like your cover letter is preventing you from getting gigs—or you just need to refresh this part of your client-seeking strategy, scroll on. I’ll tell you why your current cover letter is a snooze-fest. Then we’ll get into the nitty-gritty of creating one that gets writing jobs.

Fact: Most cover letters look like this…


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!).

Jane Doe


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

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 amazing friend of mine has made a common mistake. When you start off by talking about yourself, the client zones out.

They actually make this face: 😐

To understand why, you’ll need to put yourself in their shoes for a second.

99% of people applying for jobs say the same variation of: “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 this looks to the person reading 100+ cover letters: Blah-blah-blah, me-me-me.

It’s the logical way to reply, but in reality, the client 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? Luckily…


You can stand out by making a connection.


Give the client a reason to genuinely care about you by making a personal connection and coming off as likable.

Yes, once you’re more than a name on a page, you can reinforce your candidacy with credentials… but we’ve gotta do some charming, first.

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.

Try to notice how quickly you develop strong opinions of people as you’re scrolling through social media! We judge people based on comments, typos, profile pictures, and anything else available to us.

Our brains have evolved to seek out specific digital evidence of overall likeability so we can file that user name away under “like” or “dislike” and move on.

It’s the same deal when a client is reading your email. They want to hire someone they like for the job.

Qualifications end up being secondary—whether they want to admit to that or not.

If you sling them a mediocre introduction or come off as self-absorbed (despite the fact that you’re just trying to give them the information they need), you might be ruining your chances despite being qualified.

So how is this “connection” or likability achieved?


“Connection” really means focusing on them.


To inspire the recipient of your cover letter to like or care about you, a bit of reverse psychology is involved.

Remember how your old cover letter was basically a self-absorbed sales pitch of how awesome you are?

Well, this client would probably default to the same self-congratulatory speak in their own cover letter, were they to write one. We’re programmed to tout our credentials and accomplishments in the professional world because we think it will reaffirm our worth to others. It’s a default.

It turns out that reaffirming our worth, feeling validated, and above all, feeling liked is paramount to our ability to function confidently… even if that seems silly.

Most of us prioritize people, opportunities, and experiences that make us feel good and reaffirm our confidence.

We do this more often than we seek out challenges that will remind us how much growing we have to do.

This all ties into the human condition. We seek comfort because there’s a part of the brain left over from our caveman days that’s dead set on preventing any dangerous or uncertain scenarios. Since it doesn’t have any saber-toothed creatures to save us from at the moment, it picks any notion of discord to fend off.

It’s our built-in helicopter parent, if you will.

This part of the brain is why a hiring manager or a client will choose someone they feel is likable over someone they feel may cause discord or problems—even if those assumptions are unfounded.

You can use mental bias to our advantage when seeking out new client relationships by shifting the spotlight off of ourselves and onto the client.

We do this by using the very first sentence of an email or cover letter.


The note-passing theory.


Imagine this: you’re back in high school.

You’re sitting in class when suddenly, a note plops onto your desk—or via text message if you’re Gen Z and haven’t known the whimsy of folded paper notes.

The note is from the new kid in school. When you open it, the note says…


“To whom this may concern: I’m an aspiring captain for the football/cheerleading team. I have a driver’s permit and a solid GPA. I’ve had 6 girlfriends/boyfriends since Freshmen year and I never get caught without a hall pass. I’ve attached several yearbook photos from my previous school for you to review. Will you go to prom with me?”


Teenage you would be like, “What the eff?” (For so many reasons.)

Now, imagine if you opened the note and it said…


“Wow, you’re brilliant and gorgeous! I saw your science fair presentation last week and it was the most amazing thing I’ve ever seen. I’ve been thinking about you ever since. I’d love to get to know you more.”


You’d probably think “Still pretty long and excessive for a note, but I’m flattered! Maybe I’ll get to know this kid more and actually, it’s nice to get a note like this with prom right around the corner.”

Okay, I know this isn’t how kids in high school talk, but you get the idea.


(Honest) flattery will get you far.

If you take nothing else from this post, please take this piece of advice:

Use the first sentence to talk about them. First. Before yourself.

Talk about their business, their project, their recent tweet or blog post, their successful acquisition. Whatever matters in their world that is relevant for you to bring up.

Tell them 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. But apart from that, you really should have some kind of stake in their business or interest in their recent events if you’re reaching out to collaborate.

Check out the company’s website, Twitter account, or anything written about the company in the news. Be interested. Be involved.

Read their freaking Tweets, already! 

I digress. 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?

This is what it means to make a connection in a relevant way, to start a conversation based on something they care about.

As lovely and talented as you are, they have a business to run. They don’t have time to soak in your self-congratulatory sentences and register them as valid. If you start emails by rambling about yourself, you’ve already lost.

For the love of all living things, drop the templated approach. Find an effective 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).


Putting the technique into 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 (as is often the case with these kinds of sites), 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. Bingo again!

I reached out to them, starting the very first sentence with this trait we shared. The message went something like this:


“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 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, my message was direct and non-pushy. I didn’t try to hide my agenda. I wanted the gig, I was honest about that, and I was determined to find a “friend” in the company who would forward me to the right person, hopefully with enthusiasm!

In this case, the employee had me connected with the head of marketing within an hour.

The next day, I was sitting in their midtown office, laughing and having a lovely, informal chat. I was hired immediately as a remote copywriter.

I was told during the interview that LinkedIn is a stressful way for companies to find talent because hundreds of resumes pour in constantly. The fact that I made that personal connection is the reason they were so eager to learn more about me.

Out of everyone who had already fired off their resume. Out of everyone who applied after me.

I bothered to make the connection.

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.


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