There is learning in repetition: what cover letter writing has taught me about myself

I’ve been busy looking for a new job these last few weeks, and that has meant writing a lot of cover letters. In general, writing is something I enjoy immensely. Writing cover letters is not the type of writing I tend to enjoy. But why is that? Let’s examine the cover letter as an artifact.

What does a cover letter do?

The job of the cover letter (in tandem with a resume) is to provide enough useful information to a decision maker as to whether they ever want to meet you, let alone work with you. I’ve done this work before, sorting through piles of resumes and cover letters, and I’ve talked to a lot of people who have done it, and so I know that for the most part, these decision makers are overworked and will spend generally less than a minute going over what took you sometimes an hour to write. That’s pretty disheartening, I know. But what options are there? If it’s unrealistic to examine each letter in detail, to really read every word and think very deeply about what the person is communicating, then the options are to use the cover letter as a screening proxy or to throw it away. Of course, a proxy is a useful tool in this case, so scanning quickly for requirements and typos/misused words can reveal at least some information about the candidate in question. Moreover, once you learn to scan professionally, you can sense whether the letter was written fresh (and thus means the person either generally cares about this job or is just beginning their job search) or is a rehashed mishmash of past cover letters (and thus the person is demonstrating a lower level of commitment or desire).

Cover letter = symbolism gone mad

camus would have hated cover letter writing

camus would have hated cover letter writing

And this is really the whole crux of what is so disheartening about cover letter writing – that what you are creating is, in many ways, not a real letter, but instead a symbol, or a signal if you will. It says something about you on a meta-level without it even having to be read. And because it has to pass this smell test first – that is, it has to appear to be something that someone gave a damn about – the symbolism of the cover letter actually has primacy over what you are literally communicating. That is the thing that I find nauseating. That the whole task of baring your passion for a position, matching the position requirements to skills you own, tweaking your resume to match the job, and then communicating in way that is fresh without being creepy – that that whole song and dance can be undone by something as simple as incorrect typesetting, or a missing period. Or addressing the letter to ‘Hiring Manager’ because despite googling for 30 minutes you could not find out the appropriate person’s name, or whether a certain ‘Pat’ or ‘Robin’ or ‘Manu’ was a man or woman.

Everything would be fine if you heard all the time about how Sally down in HR found a real gem and interviewed this guy whose been with the company five years now, all this despite the fact that his cover letter had a sentence that ended nonsensically. But she took a chance and interviewed him and kaboom! Look where we are now. Guy practically saved the company. Thank God we don’t use cover letters as a simple proxy for screening candidates.

And for me, even after all that, what makes cover letter writing unbearable is that it is so rote. Do these things in this order, say this, don’t say that, jump through this hoop over here and now wiggle your ears. It’s so damned repetitive. I prefer trying new things, learning about and mastering them, then applying them and moving on. Sadly, until I get the job I want, I will not be moving on from this task. So clearly I still have some learning to do.

Which brings me to the point of this post: I believe the cover letter is dead.

Eric Romer's campaign to get hired website

Eric Romer's campaign to get hired website

Or maybe it’s not dead, but it has got to be dying, because it turns out there are a lot of creative people out there who felt something similar to me, and instead of analyzing and complaining about the situation (or maybe they did as well, who knows), they tried something else. And in general, it worked.

There’s this guy, Eric Romer, who went out and bought a domain name ( and started a social media campaign to get hired by HeadBlade, the very company looking for a great Marketing Manager.

Or this girl, featured over on Steve Pratt’s blog (of CBC Radio 3 fame) – Sabrina didn’t get hired at the time but as Steve points out he would never forget the resume and would recommend her in a heartbeat.

Sabrina's amazing facebook-style resume

Sabrina's amazing facebook-style resume

And then of course you can simply search for ‘creative resumes’ and get lists like this one. A lot of brilliance on that list, and of course, Sabrina’s brilliant facebook resume is there at number two.

Obviously, we will always need to set ourselves apart so long as the cost of interviewing and hiring is high. So, you know, maybe it’s not that the cover letter is dead, it’s just that it’s changing, and I’m excited to see that creativity is becoming more affordable in the sense that it is both rewarded more frequently and the cost to using the technological tools is rapidly approaching zero.

What I learned about myself

When you hate cover letter writing as much as I do, don’t apply for jobs that are going to be repetitive or force you to operate within a narrow band. That should have been obvious I guess, but thinking back to some of the first cover letters I sent out quite a while ago, clearly it was not.

When you have as little experience in areas you care about as I do (if you can follow that), don’t go for a standard cover letter/resume combo. You’re already behind the eight ball in the hunt for those positions, so you better step it up a notch if you want to make it through the initial screening.

Apply to places that require curiosity and creativity and for roles that require a love of ambiguity.

When in doubt, refer back to this list.