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Geek Ethicist: Murphy’s Law of Email

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“Dear Ethicist–
I recently received a long, personal email from a complete stranger. The email was not addressed to me, so I can only guess that they misspelled the email address and ended up sending this email to me instead of it’s intended recipient. This must happen pretty often. My question is: what should I do? Delete it and pretend I never got it? Reply to the person informing them they sent it to the wrong address? What would be the proper ethical thing to do?

Sign me-

Dear Wondering:
Stop wondering. The instant you discovered you were not supposed to receive that email you should have done THREE things: 1. Stop Reading. 2. Delete it. 3. Forget about it.

There is a legal concept called “larceny by finding.” It means if you find a wallet and take the cash you are a crook. Same idea applies to a found personal email. It ain’t yours; don’t read it. And since you cannot return it without risk to yourself, delete it immediately. After all, if you return it that means you probably read what wasn’t yours to read.

Some might urge you to be a good Samaritan. After all, the sender does not know the email went adrift and may be harmed by his ignorance. The cavalry will never come to his rescue if they never receive the message and now you alone hold that urgent plea for help…

No! Stop. Not here. Stranger danger!

To be a real, good Samaritan you have two obligations. First, you should not put yourself at undue risk. Second, and maybe even more important, you have to be absolutely sure you really can help. That’s called prudence. You are not really being a good Samaritan if you attempt amatuer open-heart surgery in a parking lot because you think it might help the guy clutching his chest. It’s not quite murder, but foolish enough to be pretty darn close.

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You have absolutely no idea of the context in which this email was sent or why. Every email is part of a larger story, and this email may well have been an attempt to pull you into that story. That could be a real danger to you. So again, if you receive an email not meant for you? Stop. Delete. Forget. Be prudent.

Now, what if you are the sender who discovers YOU have made that mistake?

Murphy’s Law of Email (MLE) says:

“Any time you send an email to the wrong email address it will be highly personal, very embarrassing, and may well lose you at least one friendship and/or possibly your job.”

 Five Things Never to Forget Before You Hit Send:

1. Never Reply to All

Holy Cow! At first I thought you must have been reading MY email too. I recently sent a near career-ending Reply to All email. I only discovered it when I received this response from an intended recipient: “Reply All: the work of the Devil.” This is the Joe Biden effect: When you have something you want to say, particularly when you think it is true, the tendency not to use caution regarding Reply to All is very high. But Truth is no excuse for stupidity. And thinking that through experience you know better is no protection from being stupid about telling the truth. Make it a habit never to hit Reply to All. As Aristotle tells us, Ethics requires Good Habits. Use email groups and send to those groups and add in people as needed. Sometimes your boss’ peculiar managerial style is best discussed privately in person, never behind her back in front of her face and dozens of others because of Reply to All.

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2. Double and triple check email addresses

I know Outlook and Gmail are just trying to be helpful, but don’t trust them. A helpful fool is still just a fool. Your email auto address is a fool. Always check that your email is actually going to the right John Smith, maybe not the human resources John Smith.

3. Always proofread your email

Even the Oatmeal  hates bad grammar. Because sometimes a comma does mean more than you expect: “Oh well, let’s just eat grandma.” Spell check and Autocorrect allow for some crazy Freudian slips as well! I refer you to “Damn You Auto Correct” if you require proof. Sure, that “trip to Virginia may have advanced your career here,” but be sure that is actually what emailed. Your helpful fool may have said something else.

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4. Use a separate account for personal email

Anything you send or receive on your business account is legally a part of the business record. Virtually every institution has guidelines for saving and deleting company emails since they can become a part of any legal investigation from IRS to whistleblowing. In this age of free email accounts, there is no reason to put yourself at risk by sending personal emails through your work email account.

5. Emoticons are lame (email is not the same as actual speech)

Irony easily becomes literalized in email. So, when in doubt, just be literal because odds are your email will be received as if it were. This problem arises because the speed of email makes it easy to confuse email with speech, but the written word never winks, and emoticons don’t work. Repeat: emoticons are always pretentious and slightly insulting. The human species evolved over hundreds of thousands of years to read facial and body expressions, even micro expressions, and we use these expressions when we speak to each other to add meaning to our speech. You may think that because someone knows you well they will get the irony or sarcasm of your statement, but think again! It’s only email.


Send your ethical dilemmas to  I’ll give you my ethical analysis and you may find it helpful…or not.


Emily Cantin researched, co-authored and created original artwork for this article.


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