Why a writer hired me, a freelance writer, to write her cover letter


The job was like plenty of freelance writer tasks I’ve bid on at Upwork. The client, I will call her “Lois”, needed a cover letter for a job application. She needed it quickly.

There was no other information.

I wrote a version of my usual bid (everything is individualized — though there is a common structure and some descriptions I re-use in nearly every bid, there is very little cutting and pasting for me.) I started by restating her needs as I understood them, then I briefly explained my extensive history hiring people and helping others apply for college and for work.

I hit send. And, as usual, I didn’t hear back.

That’s the most common outcome of bids on Upwork and, we understand, in job applications everywhere. Two days passed.

She needed the work done by Wednesday, so on Wednesday I checked back.

“So it looks like your deadline has passed. : / Still need my help?”

Another day passed. I assumed the work was given to another freelancer. Then, this:

After I thought the contract was expired, I received this lifeline.

We exchanged some details. I sent her a questionnaire I use for clients who need cover letters to make sure I have all the relevant information before getting started. When she sent me the contract information and the completed questionnaire, I was surprised to see her profession.

What? A writer was hiring a freelance writer.

She was applying for a social media position. However, the details in the application and her resume made it clear that she was a social media writer. A WRITER. Experienced at selling and branding. And she was hiring me to write her cover letter.

Writers hiring freelance writers. What next?

Why did a writer hire a freelance writer?

This raised a question that is important for writers and freelancers to consider.

Why did a writer hire a writer? Her education, training, and experience all prepared her to write a solid cover letter.

I never asked her directly. Based on my conversation with her during the process, I discerned that there were several reasons why she hired a freelance writer to write her cover letter. These are actually the reasons why EVERY writer should hire a freelance writer at one point or another.

· She wanted a cover letter specialist

· She wanted a second perspective

· She needed a creative jolt

These are all valid reasons that one writer would hire another. The misguided thinking that we writers are all experts on every type of writing actually devalues what we do. It devalues what makes us unique.

Sure, words are words. But the correct word choice and placement matters a great deal. We all have access to the best words, as President Trump famously reminded us, but the words we choose are very important. This is true in every situation.

I want to explain more in detail each of the three reasons Lois hired another writer. (Not me in particular.)

She wanted a cover letter specialist

Lois is a writer. She has worked as a writer in social media and other communications for a small non-profit organization. Her college education was in writing and branding. She had the skills to easily write an adequate cover letter.

But she did not want an adequate cover letter.

The misguided thinking that we writers are all experts on every type of writing actually devalues what we do. It devalues what makes us unique.

– Jack Jose

This writing is different than what she had been trained to do. Her training and experience taught her that what she really needed to do was not to try and write her own cover letter. She had been trained to hire the right person for the work.

A cover letter is NOT a Facebook post is NOT a Twitter post is NOT a press release.

See my point? Each of those specific types of writing differs from the others in subtle but important ways. How words are used, and which details are chosen and emphasized, are slightly different in each of them. The cover letter is the longest of those forms of writing. More space means more chances to include information.

More space also means more chance to make a mistake.

And no, Lois was not suffering a crisis of self-doubt. She just understood the importance of finding a specialist instead of becoming a generalist.

Lois wanted someone who specialized in cover letters. Someone who was comfortable with the flow of the full-page letter, who could help her decide which information would catch an employer’s eye.

She knew that experience and training at this form of writing, just like her experience and training in social media, better prepared the specialist to get the final version exactly right.

She wanted a second perspective

Lois sent me links to three articles she had read about creating a cover letter. She had done her homework. As it happened, I had read two of the articles. Of course, I promptly read the third one too.

Then I sent her a draft that fully incorporated the ideas. I wrote the complete letter. I even got creative with the introduction, following the very specific advice of one of those articles. The letter emphasized interesting personal qualities and experiences which I thought were fascinating to help her stand out from the crowd.

I added this note:

That’s a proud “Mission Accomplished!” statement.

I was proud of my work.

She didn’t love it, as her reply showed.

Mission not accomplished.

Okay. That’s feedback. We were involved in an iterative process.

My goal was to make her delighted with the final product. (I promise “delight” right on my home page. Maybe it’s too much? But words are powerful. I think that delight is implied as an intended writing outcome.)

So I listened to her feedback. I had provided a perspective, and so had she. In fact, at this point I explained my reasoning and pushed back a little against her direction. A little.

She replied,

Look for it … the hidden praise.

So, progress. She felt the opening was “clever.”

Note that she now had a second draft in her possession. But she was not yet delighted. That goal is a lot loftier than “done.”

It was clear that she was shifting, though. And so was I. This is the power of a second perspective. Our opinions and input were working us toward a better understanding of what the final product should look like.

Remember, as a freelance author, part of our work is to help our client be confident in our work. Not budging off a stated position is a strong-arm tactic better suited to editors-in-chief than freelance authors. These discussions were helping her feel confident in the final version.

She wanted a creative jolt

Writers spend a lot of their time creating alone. It can be tiring, even for introverts or others who don’t generally mind spending time alone.

Creativity is taxing.

One way to keep up your energy in an imaginative endeavor is to work and to create with others. Of course, this is most obvious in music, where bands and orchestras are the norm rather than the exception. In fact, jazz can look a lot like a business that is expertly prepared to handle mistakes. But that’s a different article.

Writing seems so very different. You do it alone. Day in, day out. You’re in your mind, alone. You aren’t using your ears. You aren’t using your voice. Well, metaphorically you are, but not physiologically. You’re not even using much of your body.

However, one key similarity between writing and making music is the potential for a second writer to spark new thoughts. Two people can create something better, more quickly. A second set of ideas can be accepted or rejected, and, there can be someone there to let you know you have come up with a bad idea.

In the movie “Bohemian Rhapsody” Freddie Mercury attributes the poor quality of his solo records to his bandmates’ absence. He says it was because there was no one to tell him “no.” He was still the same creative genius, but when they recorded together, his ideas were made stronger through the selective rejection of his friends.

As we neared the end of the project, Lois’ questions became more specific:

See the shift? The client and the freelancer are now problem-solving together.

Spoiler alert: it was NOT her last question! But that was okay.

So now, instead of a client talking to a freelancer, a boss to an employee, our relationship had changed. Sure, the agreement was the same, but now we were co-authoring.

This conversation didn’t sound so different from any of dozens I’d had with my co-author at my educational blog. We were wordsmithing, problem-solving. Working together.

Same objective, but a very different workflow. We exchanged dozens of messages over the course of this day, narrowing in on specific details, until, finally:

So, now … freelancer mission accomplished?

All in all, we exchanged 42 messages including the contract, corrections, and several of what I thought were final drafts. This was because we were creating together, and that requires communication.

In the end, she gave me a tip that was almost 25% of the contract price. Maybe she WAS delighted?

Why hire a freelance writer if you are a writer?

Too often, writers toil in silence and solitude. We ignore chores and the phone, or get distracted by social media, only to return to the same deadlines staring us in the face.

We worry that our voice and our vision might be compromised if we work with another writer.

We worry that it might not be “pure” or it might not be “our” voice in the end. And, to be sure, for certain types of writing that is entirely the case.

I can’t imagine a poem written by a committee. (I found some poems ABOUT committees, but none BY committees. If I’m wrong, please let me know via email at jack@thebestwordsllc.com.)

However, in an era where content is king, and so many of us toil away to create “content” (I’m hearing your voices in my head, Jon Favreau @johnfavs and Jon Lovett @jonlovett) it is okay to reach out to another writer.

Whether you need a specialist, a second perspective, a jolt of creativity, or simply to get a job done, consider hiring a freelancer … specifically consider hiring me.

Jack Jose is a freelance writer at thebestwordsllc.com and on Upwork (https://www.upwork.com/fl/jackjose).

First published by Jack Jose on Medium on .

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Exported from Medium on March 25, 2021.