Say Goodbye to Boring Cover Letters

Sometimes my friends ask me to read their cover letters and give them some feedback. Those who know me well have learned I will take my giant red pen of doom and scribble scrabble all over their paper because I hate what they wrote.

They bore the hell out of me and I imagine they bore the crap out of recruiters and hiring managers who read 1,982,328 of these each day.

This is not a brothel...

It might not be the right place but it is memorable.

Heck, if I worked in recruiting the makers of Ambien and other sleep aids would probably sue me for starting a side business where I’d cure insomnia by passing out copies of these cover letters.

I gather that some of the proponents of writing stale reading, insomnia curing, so boring they make Buffalo look exciting cover letters are concerned that you can get yourself in trouble by not writing something serious.

When Can You Loosen Up?

It depends on the position you are applying for or so I would argue/think. Certain positions lend themselves to attracting cover letters of a certain type and others provide some more flexibility.

If you want to be a police officer you might take a different approach than if you are trying to get a gig writing for reality television.

Today I decided to share some more colorful cover letters that may or may not have been used by people looking for work.


Dear Hiring Manager,

I fooled around and fell in love and now I need a job to support my baby mama.

Just kidding. I didn’t exactly fall, I was tripped and it was intentional. She pushed me and I ended up swimming through a burning river of flames and spent 12 years trapped on a deserted island with some crazy people.

One of them was this amazing scientist who knew how to create almost anything out of cocoanuts and palm fronds but for some reason could never figure out how to build a boat to get us off the damn island.

The good news is that we were rescued and now I am ready to use what I learned on the island to help your company grow.

My skills include building slingshots (I am deadly with fruit from 20 yards), bonfires, skinning wild animals and maintaining order in a society without police, courts or judges.

That translates into project management, supervisory skills and problem solving all of which are applicable at your place of employment.

Email me at





My buddy Joe McGinty says I should send you to see the guest post I wrote about buying a cellphone over at the Wonder of Tech as a sample of my writing and I always listen to Iron Joe.

Mostly it is because I owe him a couple of bucks and if I let him run off at the mouth he forgets about the cash I don’t have to pay him back with.

What you don’t know is that very few people are clever enough to get away with not paying Iron Joe the dough they owe him.

Of course that doesn’t mean much to people who don’t know him and are unaware of what he is capable of.

So let’s cut to the chase here, I know how to write and I know how to tell a story.

I can do that for you and I can make your clients happy by helping them come up with copy that is memorable and interesting.

Let’s schedule some time to talk about it. You can reach me at 867-5309 or

Hope to speak soon.




Dear Human Resources,

I am submitting my informal application for a position as the Buckeye Master on Hampshire Road.  I’d give you the formal one but the eighties are long gone and black tie isn’t in fashion any more.

Your job description reminded me of a chemistry exam I took during my sophomore year of college. I didn’t understand a damn thing on the test but I managed to earn an ‘A’ on the exam because I wrote about what I did know in a compelling way.

I can do that for you too because I know things.

Water is wet, the sky is blue and you never put mayo on a corned beef sandwich or buy a bagel made with berries.

Peanut Butter is better when it is not refrigerated. Beaches need salt and sea water and The Sound of Music is awful.

Nirvana was overrated and if Kurt Cobain was still alive he’d be a cranky old man playing country fairs with Eddie Vedder.

You might wonder what this letter has to do with your position the same way I wonder if that job description was written by an inhuman android or a pack of wild monkeys.

We can answer that in a couple of ways.  We can say there goes two minutes you’ll never get back or we can say someone just used an unconventional method to engage with you and that if he can do that with a letter that took less than 1 minute to write imagine what could happen if he really had time.

Hopefully you are not really looking for scientists and are interested in working with people who are good with people because if that is the case you should contact me at



In Conclusion

Are those a little over the top and kind of silly?

Yeah, they really are but sometimes we take some of this too seriously. Sometimes we forget that we are people dealing with people and instead of acting like interesting human beings we produce content that really would cure insomnia.

Would it really be so bad to write a cover letter that shows some personality as well?

What do you think. Is it time to say goodbye to boring cover letters?

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  1. Larry November 22, 2014 at 7:26 pm

    I try to get creative with my cover letter. Well, at least I do with my intros. I hope I can grab their attention and get them reading.

  2. Damien Riley November 22, 2014 at 12:41 pm

    With linkedin and technology that makes all the robotic changes to cover letters FOR people, they are bound to have to come up with clever hooks to stand out from the crowd.

    • Josh November 23, 2014 at 12:03 am

      @rileycentral:disqus Exactly, if we don’t take the extra step we risk sounding like we are just part of the collective. Automation isn’t always useful.

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