To Whom It May Concern

This week’s episode falls into the category of straight up writing advice. I mostly enjoy embedding my advice about narrative construction through personal stories, but sometimes on this show I feel compelled to address the writing process more directly. I did that earlier this season in episode three “Give the people the free writing advice they need (but didn’t ask for)” and in the opening episodes of season one including “The Author as an Arborist” and “Blankness and the Blessed Backspace.”

Recently I’ve worked with a number of folx on applications, including cover letters. And then this week I surprised myself by writing a cover letter of my own. So I decided to break down that process, using my cover letter as a case study. It gets real embarrassing. But hopefully useful also.

Here goes.

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I just did something unexpected. 

I applied for a job.

OK now don’t worry: WRENCO and WRENCast and not going anywhere.

This is what happened. I’m in a couple of facebook groups for alums of my college, including one for job postings and seekers. A couple of times I’ve plugged my own services on there, but mostly I enjoy the thrill of, from time to time, connecting someone with an opportunity or a resource. 

So a few days ago someone on there posted about looking for writing jobs. I jumped into the thread when she made a stray comment about wishing she could just write the story of her life, and I of course offered to have her on WRENCast anytime she wants to share. But then I started looking around for writing jobs for her–what’s 20 minutes on LinkedIn between fellow alums and new Facebook friends?

To my absolute shock, I came across a job that I was actually interested in: writing posts about family and relationships for a really wonderful website. I checked out the application and found myself writing a cover letter before I knew what I was doing. 

So what I want to share this week with you on WRENCast is about the cover letter writing process using that cover letter as a case study, because I think it’s representative of many folx’ attempts to tell the story of themselves, their experiences, and their interest in a job–and the way that the first impulse of that narrative may need to shift in order to craft a compelling cover letter. 

Ok step one: get clear about what you bring to the table

Something that you’ve doubtless heard me say if we’ve worked together is that conveying who you are to someone is the hardest narrative to construct. It’s simply the burden of carrying too much information and nuance about yourself to know what major elements to extract and details to highlight. 

Think on the other hand if you were introducing someone else. You’d likely have no trouble knowing what experiences, skills, and qualities your best friend has to offer the world. If I wanted to, I’m certain I could submit a successful nomination for my friend Megan to win the Nobel Peace Prize, that’s just how great I think she is.

But when it comes to ourselves we often face decision paralysis about what to share, before even typing a single word. 

So for this reason, I recommend starting any cover letter or personal statement for an application by writing a list of relevant skills, in an attempt to externalize yourself.

For example, in the case of this job writing family articles the list of what I bring to the table was:

-writer (including weekly long-form narrative podcasts touching on family and relationships)

-previous roles were communication-heavy (many modalities, many stakeholders, marketing, policy, process, wrote for the web)

-my own appreciation as a parent for thoughtful and reliable online sources

-my experience as a parent and host parent, and child to aging parent

-intercultural experience means I can think flexibly for the audience

-wrenco means I have a full wfh office set up with reliable internet 

-remember to link to the portfolio of my writing as examples

Some folx will have a longer list, and others will have a shorter list.

If you have a long list, go through it and order it according to relevance to the position at hand. Some items may not fit in your cover letter but you can ensure they are in your resume.

If you have a short list, go through the posted job description and write out 6-8 of the top skills they are looking for, and/or points about the organization. Next to the skills they ask for, fill in your relevant experience. If you are still struggling, consider speaking to someone in your life who is your cheerleader–it may be a friend, partner, parent, or online forum–and explain to them you think you would be a good fit for the job but you’re having trouble thinking it through, and likely someone will step up with the clarity and confidence you need to get going.

Step two: start writing

Next, I put that list in its own document and moved it to the side of the screen, next to which I opened a new blank document where I would do my main writing. As my writing incorporates elements from the list, I would strikethrough the used items. I also occasionally added items as they occurred to me.

As I wrote, I chose not to worry whether anything was in the right order, or concise, or “professional.” I just gave myself permission to express my excitement at the opportunity. 

My first draft sounded nothing like a cover letter. It began: 

“The internet changed for me when I became a parent. Before parenthood, I used the internet for entertainment, news, and distraction. When, ten years ago, I first became a parent, I still used it for that during long hours of nursing and late night shushing. But as I encountered any number of firsts–first hand, foot, and mouth, first time hosting the holidays with a newborn, first time learning about parenting a child with ADHD–the internet became less of a place for entertainment and more of a source for information and community. It became an irreplaceable compass to navigate these firsts.”

And so on. 

Reading this back now, I cringe as a writer. Not totally because of the contents, but because how ill-fitting this paragraph is to the purpose of a cover letter.  But as a writing coach, this is an example of what I call a “runway”--the writing necessary to achieve lift-off. Some folx may have longer or shorter runway processes, but the point is not that it’s good it’s that it gets you moving, and it gets you processing your thinking. 

If the runway metaphor doesn’t work for you, think of it as stretching before exercise. 

Or if you want more literary credibility behind this concept know that Annie Lamont writes about this process in an essay called “Shitty first drafts.”

Actually let’s hang out with Annie for a moment as she describes her process of writing restaurant reviews back in the day. 

For me and most of the other writers I know, writing is not rapturous. In fact, the only way I can get anything written at all is to write really, really shitty first drafts. … So I'd start writing without reining myself in. It was almost just typing, just making my fingers move. And the writing would be terrible. I'd write a lead paragraph that was a whole page, even though the entire review could only be three pages long... But because by then I had been writing for so long, I would eventually let myself trust the process -- sort of, more or less. I'd write a first draft that was maybe twice as long as it should be, with a self-indulgent and boring beginning, stupefying descriptions of the meal, lots of quotes from my black-humored friends… and no ending to speak of. 

What Annie and I are saying is, the first draft is going to run long, and shitty. Just get it out there. 

And so I continued to write, pivoting from pontification on the value of reliable and positive sources on the internet to my experience as a parent, and then as a writer. That’s right friends: for the job as a writer, I, an actual writer, only mentioned that in paragraph four. 

Ok onwards.

Step three: invert the narrative

So the shitty first draft, with its lengthy runway and pontification, is actually a slowed-down, externalized version of one’s own thinking process. 

When we decide to apply for something, or if we’re writing a restaurant review, we construct a narrative for ourselves of why something would be great to do or how something we did happened. I like this because. I can do that because first I did this and then I did that. And if you’re lucky you’ll remember in that shitty first draft to add something along the lines of And you’ll want me because I can do this for you.

Extend yourself grace. What has ended up on the page–over long, poorly organized, and likely too focused on you rather than your reader–is just a reflection of most people’s first attempt at thinking something through, kind of like in Bridget Jones’ Diary when Bridget runs through in her headhow she’d introduce her odious work colleague: “Perpetua is a fat-ass old bag who spends her time bossing me around.” Obviously she can’t actually say that so she takes a beat before saying “Perpetua is one of my work colleagues.” 

So, like Bridget Jones, take a beat to revise.

And by “take a beat,” I recommend a couple of hours or an overnight. 

In my case, I returned to what I’d drafted that morning later that afternoon and I realized immediately: I can’t start a cover letter with a story about what the internet means to me! Duh. 

So I copied and pasted the whole thing into a fresh doc (FWIW I never delete drafts). I moved the three thick paragraphs about the internet and gushing about their website to the bottom of the page, and brought to the top the paragraph that began “I have a degree in English language and literature from Smith College and spent over a decade… etc.” Double duh. 

The most important thing to remember when writing any piece of persuasive writing–whether a cover letter, application, or argument for debate club–is to prioritize the needs of your audience in understanding your argument. It is so tempting to start with a story, and then narrate your resume in chronological order, and then slip in something about the company before slamming the thing shut with a sincerely, bye.

So I put at the top the information they needed to know about me: I have a degree in English, I’ve had a career centered around communication, and I founded a business as a writing coach, for which I publish a weekly podcast of personal narratives. Better. I no longer need to pray that they’ll stick around til paragraph four to know that I’m a writer, and they won’t think I’m singing their praises because I’ve got nothing else to sing about. 

That being said the paragraph was still dense. 

Here it is in full as of draft two:

I have a degree in English Language and Literature from Smith College and I have centered my career around writing, though in somewhat indirect ways. I spent over a decade working with students at a prestigious liberal arts institution, Bowdoin College, in communication-heavy roles for which I frequently penned wide-reaching messaging regarding opportunities, policy, and processes, as well as contributing substantially to my office’s public-facing website. Among my roles at Bowdoin was that of fellowship coach, supporting students in writing personal, persuasive, and competitive applications to the Fulbright student program. With my leadership, student awareness of and applications to this program increased dramatically, resulting in the college becoming #1 nationwide and boasting a win yield seven times higher in my last years (2021) compared to the year before I joined that role (2012). 

Step four: tighten that thing 

I love that I have imposed no minimum or maximum word count for this weekly podcast, because it has allowed me to play with increasingly complex narratives. 

But for any other kind of writing: I love a good page limit. 

A page limit, to me, is like the frame around a photograph. It ensures that you have captured and composed an image that is intentional. There is no setting I like less on my iPhone than the panorama. It’s so big that it’s too damn small. It shows me so much I can’t see anything. And there’s no focal point. Bleck. 

So for a cover letter, and most resumes, I commit sincerely to a strict one-page limit. 

The page limit functions to ensure that I trim the excess details that don’t serve my argument and tire my reader. In the process of making the letter more concise, I often find myself doing a second round of rearranging. 

For example, when I sat down the next morning to take a third pass at this letter, I immediately recognized that I should move my direct writing experience above my experience supporting the writing process of others. Duh. And even though I’d already made the decision to narrow my narrative about my time as a student advisor to the most relevant aspect of the job, did I really need to enumerate so many aspects of that experience that are indirectly related to the job at hand when perhaps I should make the connection more directly?

I also spent time identifying phrases and sentences that were longer than necessary. Why did I need to say I had a degree in “English language and literature” when I could totally get away with just saying “English”? And when I wrote about the kinds of articles they had published did I need to describe one kind as “no-nonsense, action-oriented, and solution-driven” when I could just say “action-oriented”?

Here’s how my first full paragraph (after the obligatory opener about applying for X role at Y company) goes in my final draft:

I have a degree in English from Smith College and I have centered my career around writing and communication. In 2022 I founded a writing support business, Written English Collaboration (or Wren Co), which assists individuals in crafting personal, professional, and creative writing projects, along with applications and admissions materials. In addition to the support I give others in their writing, I am writing actively for the weekly podcast of long-form personal writing I release in lieu of a blog or newsletter. Each episode interweaves topics related to parenting, family, relationships, grief, travel, and narrative building. Due to the remote nature of this work, I have an excellent home office setup with all-new Apple hardware and fast internet connectivity, as well as an understanding of web publishing, SEO, and independent work/time management. 

After this paragraph came one about supporting fellowships, but that information was framed by some of my rationale for wanting to join the company. I wrote:

“My work as a writing coach and podcaster is enormously fulfilling, however, I miss the companionship of working with a team of colleagues. Before founding Wren Co, I worked for more than a decade advising students in an interdisciplinary office at a prestigious college. There I supported the crafting of personal, persuasive, and competitive applications to the Fulbright fellowship. With my leadership, the college increased its wins seven times compared to the year before I joined the team, becoming the #1 college nationwide. The success of those applications I supported gave me considerable practice deploying many of the qualities necessary in successful freelance writing, including awareness of reader perspective and attention span; attention to detail; narrative balance between facts and opinions; and a strict adherence to deadlines and word counts. 

And in case you’re wondering, this was followed by a paragraph in which I expressed my admiration for the work of the company and my thoughts on how I would like to contribute, but I’ll keep that section off-air. 

Then I signed off, stating truthfully that “I am not looking to work just anywhere doing just anything. In fact, I am not actively job-searching… But I have done so now because I am so sincerely interested in the opportunity [for role x at company y]. If therefore my skills, experience, writing style, and perspective on x would be a good fit for y, I would welcome the opportunity for a conversation to get to know more about y and this x role.”

And I even had a couple of lines to spare at the bottom of the page. 

Look I’m happy to be sitting here, writing this comfortably cross-legged in yoga pants and an oversized sweater. I look at Kim Kardashian at the 2022 Met Gala, and at Elizabeth Swan in Pirates of the Caribbean, or any European queen from 1500-1900 and I just get out of breath thinking about how restrictive those corsets were. But when it comes to this phase of the cover letter, I say strap on the corset, suck it in, and pull them laces as tight as you can. 

Step five: little stuff

Here’s my quick and dirty of the little stuff after you’ve finished the shitty first draft, inverted narrative, and trimming that thing down to size. 

Download Grammarly if you haven’t already and accept no more than 90% of their recommendations (if you take 100% of them you’re not paying attention.)

Download and save your file as a PDF, and give that thing a sensible name. I recommend “Firstname LASTNAME documenttype monthyear company,” for example “Elizabeth SWAN cover letter December2022 FendixRihanna.” This makes things easier on the end of the hiring manager, and you want to be considerate of their process (can you imagine how many documents they receive named simply “resume.pdf”?!) 

Use this same naming format across all of your documents, as well as the same font, size, and general formatting. This reinforces the impression of attention to detail, professionalism, and I believe makes for a more pleasant experience for the folx reviewing your materials. 

Finally, ensure your resume makes sense for the job you’re applying for. Many people have different versions of their careers–the version that’s more communications based, or sales-driven, or related to data and organization, or what have you. Don’t be afraid to tweak that resume every darn time you apply to something. I downright re-did it completely for this opportunity because sometimes I find starting fresh to be easier than modifying something else. 

Step six: hit submit and move on

I believe in revisiting materials while they’re in development. But when you’re done let yourself be done. Hit submit, turn off your monitor, and treat yoself. Personally, I got a triple chocolate gelato in a fresh waffle cone from Dolomitti, the Italian gelatieri a few minutes from my house. And then I came back to my computer and wrote this episode for you. 

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I don’t know what will happen with that opportunity. As I said, I hadn’t been looking for a job, but they say the things you regret in life are the things you don’t do. So I threw my hat in the ring. Maybe it’ll work out and it will be a fun new way to express myself as a writer. Maybe it won’t be a good fit. 

But if anything, it had been a long time since I wrote a cover letter. As a writing coach helping so many other folx with their applications, it was a terrific opportunity to go through the process and put into practice my own advice.

And as I’ve said before, if you want or need help with an application, cover letter, personal statement, or admissions document, don’t hesitate to reach out. Though it’s possible to do that kind of writing solo, it’s so much better to do it with someone else there to help you along, to ask you questions, remind you of your strengths, suggest where to embellish and where to cut, and help hold you accountable to the process, deadline, and word limit. So reach out!