Job searching is tedious, frustrating, and a wellspring of intermittent disappointment. Yet, there is one part that I savor: writing a cover letter.
I think of it as a teaser trailer - an introduction to a larger narrative that can take many forms. At turns heartfelt and exacting, a good cover letter is an exercise in storytelling, providing just enough detail to pique the interest of the reader.
Recently, all the cover letter writing sparked a question: if I was completely transparent (to a fault), what would that cover letter look like? What if all niceties were removed and pith and sarcasm seeped in? Can I compose something that’s funny and searing, heartfelt and brutally straightforward?
Sounds like a fun challenge.
Dear Hiring Manager/HR/latest trendy moniker for HR -
I’m putting a significant amount of creative energy into this letter, so I’m hoping it makes it past the layers of automation and AI between you and me. Right now I’m not working, but when my leave runs out, I need to have something lined up that won’t exacerbate the existential dread and disillusionment I feel. The way I imagine it, after you finish reading this, you’ll be reasonably impressed with my ability to write and, hopefully, all of the buzzwords on my resume match the ones you’re looking for.
We’ve never met, but I already feel a sense of camaraderie with you. You know what the culture of your company and work unit are really like, behind the veneer of catchy slogans and feel-good aphorisms. I can only guess. I suspect there are also unspoken attributes you’re looking for, so if we ever have the opportunity to speak I’ll do my best to mirror them back to you based on whatever clues I glean from your written and verbal communications.
Okay, yes, my work history. Like a lot of folks who were aimless in their early 20s (at the height of the Great Recession1), my resume is a mishmash of low-level roles that finally culminate into a career. Let’s be honest, a fair amount of where I ended up boils down to luck: the middle class family I was born into, the education that enabled, some unconscious choices and/or mistakes, and plenty of happenstance with timing. If you changed any of those variables I might have ended up as an electrician2. My point is none of this was inevitable and I won’t be peacocking about it.
Careers are all well and good and there are patterns and signifiers you’re going to scan my resume for. I’ve been at the same organization for 10 years, is that a red flag or a green one? How about my shortage of processional certifications - should I have been spending more time at work instead of pursuing other interests? What about my personal brand? (I can barely utter that phrase without feeling the urge to vomit, by the way) What about the other candidates - am I less impressive or on par in your view? Did you take that bias training which makes you completely impartial?
I’d like to suggest that my ability to learn and communicate with people is a much better predictor of success than anything you see on my resume. If you decide I’m worthy of an interview, you’re going to ask me a bunch of questions that I’m probably ill-prepared to answer on the spot. Some people are very skilled at this sort of performance, but I’m not. My talents are more difficult to quantify and I’ve always been a generalist - so you’ll have to trust me when I say that I can learn whatever systems, methodologies, or approaches your organization uses. The truth is that specialization is not a marker for overall competence, even though that’s the prevailing notion in our culture3.
You’d probably like to know something about the value that I’d bring to your company. Here are a few that characteristics and skills that come to mind:
In the context of technology projects4, I know how to get from idea to reality
People enjoy working with me (often underrated but oh-so-important)
I’m deeply curious, and constantly searching for new and interesting ways to solve problems
I love to learn and share knowledge with others, and I’m damn good at it
Communicating with people and building approachable narratives is something I excel at
I know these aren’t as specific as your job description, but they highlight what I look for before composing a cover letter. Hopefully they are resonant for you too. Oh, I forgot one: I know how to make work less of a soul-sucking enterprise and inject lightness, humor, and fun into it.
In my time away from the grind of the 40 hour workweek, I’ve learned a lot about my capacity to experience the world, create things, and be present. Despite my reticence, I am ready to give your company the full spectrum of my intelligence, insight, and creativity in exchange for $XXX,XXX a year, which is a good deal. Again, you’re going to have to trust me. If we make it far enough in this process, my references will confirm what I’m saying.
Thank you for your consideration. I plan on taking a nap now because writing these things well takes a lot of energy.
Cheers,
Jonathan
And the subprime mortgage crisis. For a time, I even worked for one of those banks. For shame.
Absolutely not throwing shade on trade work - more young people should become electricians. I probably would’ve made a pretty decent one.
I’ve likely referenced this book before, but it’s worth sharing again: Range by David Epstein. Very eye opening, highly recommended.
Or any project really, but I’ve only really put this to the test with software, events, building/home improvement, electronics, and digital design thus far.
That was very entertaining and hope this gives you edge over others. Because if this doesn’t, nothing will. Also, Cassie and I really like this piece. We should meet up soon!
Why not give it a try? Send it, it’s delightful and real and will definitely get your resume to the top of the pile. Authenticity and the courage to take risks set you apart. 💕