The algorithm is gonna get you…but probably not.

Cover letters are boring.

I take it upon myself to make them less so.

Writing cover letters for jobs sucks. I can think of only one thing worse when looking for a job. Actually reading cover letters. But then, when it comes to eye torture like that, I think the Human Resources (ahem) professionals can handle it. It is one of their job functions, right? Or do they outsource that now too?

No matter the job you have, if you are not looking, you’re lying. I’m looking. As such, I have to send these introductory missives, along with my resume, in the hopes that the two documents will find their way through the algorithmic labyrinth that is the modern day job search.

Because my father was an HR executive, you would think I would know better and be all formal and proper in my cover letter approach. You would think that…and you’d be wrong. Of course, the truth is I do know better, but cover letters suck. And the hard fact is that they rarely make it into the spindly fingers of a Human Resource person.

Now you may be thinking I am shooting myself in the foot with writing a cover letter where I inject a little personality. Maybe I am. BUT, if someone actually reads it and looks at my resume and then calls me in for an interview? Well, they certainly know they are getting someone with, at a bare minimum, a personality. How many times do these HR (ahem) professionals bring someone in because they went to the right schools and have the right credentials only to discover that the person ends up being a horrendous fit into the culture? My cover letters serve as a way of introducing my personality and if they are interested, they’ll proceed to my resume to gauge my skills.

What follows below are a couple of cover letters I sent out recently, And if you read them and find yourself asking “Did he really send this as a cover letter?”

Yes. Yes, I did.
Seriously, how often do you get to quote Gloria Estefan in a cover letter?


As I look over this one above and the one below again, there are a couple of mistakes and a couple changes I would have made to tighten them up. And maybe I could have done that here in order to make myself look better, but alas, I think it’s best to see these letters as they went out.

Some of you may be wondering what my success rate is with turning these cover letters into actual interviews. It’s low. Very low. Not zero low, but low.
But these days, in New York City, in my industry, to do what I want to do, without a connection or Ivy League education, I am not convinced my success rate would be much higher.

Given that most cover letters and resumes usually end up in some sort of digital employment purgatory (note to companies, you all need to seriously re-think your digital hiring process…BrassRing, still? come on!). I decided to have a little fun with my cover letters and exercise some creativity. Think about it, if they’re interested after reading these, then I know it’s the type of company I would want to work for.

So yea, I sent this one too.

(I obviously redacted any libel information)