What's the Worst E-Mail Mistake You Ever Made?

The other day, I received an e-mail that I shouldn’t have. While my name was indeed in the list of addressees, and while I knew some of the other addressees (as well as the sender), my name was plainly included by mistake. It took me about three seconds to figure this out, since the topic under discussion had nothing to do with me.

But not only did it have nothing to do with me: it was a confidential e-mail about an upcoming strategic move by a large American corporation, the news of which had the potential to move the market substantially.

The main purpose of this e-mail was to coordinate the announcement of this move without having any information leak to the public before the company could announce the move on its own.


In this case, the sender got lucky: I don’t plan to use the information against the company, or to profit from the confidential message (unless you consider this blog post a profitable maneuver). But it could have easily worked out differently. And perhaps the erroneous inclusion of my name on this e-mail was a good indicator that, alas, this company’s news will indeed leak to the public before it is ready.

I have long prided myself on not making any such disastrous e-mail mistakes. Sure, I’ve sent things to the wrong person now and again, but the stakes were always low. A few months ago, however, I messed up, royally.

Oddly enough, my mess-up was directly related to someone else’s mess-up. Let me explain.

There was a team of academics who had done some interesting research that Levitt and I hoped to write about. However, the member of this team with whom I communicated — let’s call him William — was rather brusque in response to my inquiries.

As time would reveal, William had a fairly complicated political agenda that he feared would be ill-served if his research appeared in a Freakonomics article — so, while the other members of his team wanted us to write about their research, William was evasive and a bit rude in his replies to me.

Then I received another e-mail — this one from another member of the research team (we’ll call him Zachary), which was intended for William and the others, but not for me. It said, in part:

INSERT DESCRIPTIONE-mail dramatization.

I thought the best thing to do in this situation was to write Zachary directly and let him know he’d inadvertently sent the e-mail to me. So here’s what I wrote:

INSERT DESCRIPTIONE-mail dramatization.

His reply:

INSERT DESCRIPTIONE-mail dramatization.

That seemed to break the ice, and communication got better. We were prepared to write about the team’s research, either on this blog or in our Times column. But then they got evasive again, and stopped communicating.

Then we got a surprise when a prominent article about their research suddenly turned up in a major publication. William had sandbagged us, and then Zachary had done the same.

It wasn’t a big deal — academics and journalists and politicians (and everyone else) are constantly competing over material — but if they had said from the outset that they were talking to another journalist, we would have happily left them alone.

Once I figured out what had happened, I dashed off an e-mail to Levitt:

INSERT DESCRIPTIONE-mail dramatization.

The only problem is, I sent the e-mail not only to Levitt but also to Zachary!

In the end, I believe Zachary thought I couldn’t have been so foolish as to mistakenly send him a critical e-mail after he’d inadvertently sent me one. Zachary seemed to think I sent him this last e-mail in order to directly insult him.

To date, that is my worst e-mail mistake that I am aware of. Perhaps I have made worse mistakes that people had the good heart to not tell me about. I recently heard about a family whose child is having some trouble in school, and in an e-mail to his parents that discussed psychological counseling, etc., the school inadvertently cc’d the entire class list. Ugh.

What are your worst e-mail mistakes?

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  1. Mike says:

    Stephen, are you sure the email was an “accident”. You didn’t put many details in your post, but if this is from some person you’re not acquainted with it could have been a spoof email from anyone (eg. not actually that person) in hopes of bumping the stock price. What better way than to get their rumor into the NY Times?

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  2. Kyle says:

    In college I served on a board that handled the cases of students turned in for cheating. I recall a case involving an introductory programming class. One member of a group of students would complete the assignments, email the code off to his friends, and they would simply change comments and edit for style. This student got caught when he accidently put the email subject text in the cc space. He had used the title of the course as a subject, but put in the cc space, this happened to be an email group name that was automatically router to the course instructors. Imagine the confusion on the professor’s face when he opened an email containing the final code to a class assignment which had been sent to himself and several other members of the class.

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  3. Aaron says:

    I’m gay and my partner’s name is Mike. At my company, one of my vice presidents who is two levels of management above me is also named Mike. When I first started at my company I was constantly sending personal emails to my vice president that were inappropriate and embarrassing give the situation. Email address auto-fill is NOT your friend! I never sent anything salacious but more like, “Hey Pumpkin! What’s for dinner? Do you want to go to the movies on Friday?” Luckily, the VP Mike had a really good sense of humor and teased me about it a bit. But when I first realized that it happened, I was mortified.

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  4. Josh says:

    What would Freud say about your little “mistake?”

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  5. Matt says:

    I had an email address at BU that was exactly the same as a new hire in the physiology department, whose previous email address was @havard.edu. Most people knew he switched jobs and just changed it to @bu.edu. Therefore for about a year I got all kinds of emails from his colleagues and one desperate potential patient, about psychology conferences, studies ect. I eventually found his email address and started forwarding his emails on him. While also telling the sender the emails were not getting to the correct person.

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  6. Will says:

    Once, when I was an undergrad (back in the mid-1990’s), I reconfigured my email software to make it appear as though I was a professor, and sent an email to two fellow students (good friends of mine), chiding them on their in-class behavior.

    To show that this was a harmless prank, I signed it with a derogatory nickname for this professor that we had used amongst ourselves. I thought that this would suffice to signal “Hey, this is a joke from one of your friends!”

    It did not suffice. One of the recipients did believe that it was a genuine email from the professor, and replied with an apology (as hitting “reply” sufficed to send the email to the professor).

    Fortunately, it went no further than the professor, who curtly replied that she had not sent the original email, that the student’s behavior had never troubled her in the slightest, and that she always signs her own name.

    Nobody got into any formal trouble, although the incident did leave its mark on the friendship.

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  7. Anonymous says:

    I sent this over work IM. I meant to send it to a friend but instead it went to one of our VPs. C’est la vie.

    “I drank waaay too much last night and I’ve been having $h!t attacks all morning.”

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  8. PDB says:

    I was involved with the College Democrats in college. Our group had two mailing lists: one for the entire club (~200 members) and one for the people running the club (4-5 members, myself included). At some point, my friend, one of the 4-5 members in charge, sent an e-mail to both mailing lists mentioning the political group Feminist Majority. I sent a reply to what I thought were the 4-5 in charge saying “The last thing we need right now is a feminist majority.” (This doesn’t exactly describe my political beliefs, so bear with me.) As you can imagine, this message was also sent to the list of 200 members. Boy did I get a lot of irate e-mails back (some of them rather humorous but annoying).

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