WANTED: Your Jerkiest, Most Unprofessional, Inappropriate Business Emails. (You Can Keep The Sender.)

IN: Hard Stuff

You ever get an email that just pisses you off?

All you’re trying to do is go about your day, maybe fire off a few invoices, maybe do a little creative work, maybe try to avoid having a mid-day myocardial infarction.

And then it arrives.

You can’t tell if it’s an email or maybe somebody laid their elbow on the wing ding button. You scan it and see a wall of exclamation points, capital letters, and percent signs and asterisks flying all over the screen. It’s Symbols Gone Wild, Gmail edition.

At first your internal alarm goes off: Heart starts racing, adrenaline starts flowing, eyes start widening. You instantly take all the blame, telling yourself you must be as horrible a human being as they say you are; obviously strangers who email other strangers and say mean things are surely in the right. THEY MUST KNOW SOMETHING YOU DON’T. And because: *%!!$#@!

But then, after the fourth line or so, your balls drop and all the sudden you’re all, “Wait a minute, what the hell is this? Whhhhhhat? What is wrong with them? I did nothing of the sort!” (Yelled in your best 16th century accent.)

…and then you go get some ice cream. Because ice cream works for this kind of thing.

Shortly thereafter, you settle in and queue up to write your reply.

Dear Rumpelstiltskin,


Too aggressive.

Maybe if you hadn’t insisted on a CAN’T! MISS! RUSH! DEADLINE.

Don’t stoop to their level.


Too personal. Also: Vin Diesel.

Dear Rumpelstiltskin,

Rot in hell.

And then, and only then, after you’ve written and subsequently deleted at least four versions of imaginary emails you’d love to send, do you queue up to write the real one you do send:

Dear John,

I’m so sorry to hear you weren’t satisfied. What can I do to make it up to you?

Because that, folks, is the life of a small business owner.

No matter who spits in your face, you can’t spit back, because you apparently have an adult-child relationship with every client in the history of clients, and what kind of adult spits on children?

I know. That’s some imagery right there.

Then again, so is having a child spit in your face…

…and letting them get away with it.

What’s the jerkiest, most unprofessional, inappropriate email YOU’VE ever received?

Visit (and vote on!) the jerkiest email business owners around the world have gotten, and even upload a screenshot of your own to automatically be entered to win an exclusive license for access to the newest (and biggest, most important) product we’ve ever developed, LOVE, BUSINESS OWNER, a place for business owners who suck at saying the hard stuff (including new peer-to-peer “what do you do in THIS situation?!” support forums), launching Tuesday, November 11th. Let the cat get your competitor’s tongue.


Spill it!