There’s something highly rewarding about telling someone how you really feel in a long, heart-felt, brutal email. We’ve all sent them. We’re all received them. It’s almost too easy.

When you yell you get interrupted. You have to listen to the opposite perspective. You have to have some level of decency. A face-to-face almost requires it. But when you email, all protocol for being a decent human is abandonable.

The Compose box becomes a canvas of hate, and your masterpiece of degradation would make Van Gogh proud. After only a couple of sentences the recipient has been sucked into the black hole of your anger and any of their attempts to stop reading are futile. You’ve got them. They’re in your world now and they’ll have to read every word.

You press send, and you’ve won! At least until they respond back because that’s where the ’email hangover’ begins.

Like waking up in a strange place after a seemingly awesome night; the headache, nausea, and internal bleeding pain ramps up quickly. Usually the email sent back is more inflammatory than the one you sent out. Now you’re the one getting picked apart. You’re the one that can’t look away. You’re the one that feels like a midget at a dunk contest.

Then the lawsuit threats start and things go from Howard Dean scary to Jihad scary. This email you crafted to help you feel better starts eating up hours in time and worry. More importantly your reputation and the possibility of your email ever resurfacing are things you can never get control of again.

Some people just don’t get that any email they send is no longer theirs. Might as well post it on the internet yourself. There are some famous examples of this.

Sean Parker’s Napster email to the record companies was later used as major ammunition to take them down. In a recent interview with Jason Calacanis, he told me that during his public fight with Michael Arrington he had received lots and lots of emails that would embarrass its authors. How many  Steve Jobs emails have been reposted?

If it’s bugging you enough to seriously consider sending, you’ll probably need to let it out before it goes away. I suggest writing the email. The only difference; before you hit send, hit delete instead.  I can tell you from personal experience that there’s a relief that comes from writing things out, and there’s another relief that comes from hitting delete.

Each time I’ve lobed an email grenade it’s had a negative effect. Every single time. The response I received made me feel worse than before. Each time I’ve received one it’s turned out worse for the author. Some people have come back months later and apologized saying they have felt guilty for months. What a waste.

This happened to me as recently as this week after a particularly obnoxious relationship hit a boiling point. I typed an email, put all my feelings on paper, and then hit delete.

You can do it. It only takes one keystroke.