The 10 most embarrassing tech flubs that could happen to you

Call it the “oh-no second.” You know–the interval between clicking the Send button on a private e-mail and realizing you just cc’d the entire universe.

But it’s not just e-mail. Thanks to the ease, speed, and reach of technology, we now have the potential to be bigger doofuses in front of more people than at any other time in history.

For example, nothing says “I am a professional” more than intimate messages from loved ones popping up on screen during a presentation to the board. Then there are the pricey pocket-size gadgets that always seem to wind up in the swimming pool, the washing machine, or worse.

Don’t forget about social networks that allow you to get up close and personal with the mucous membranes of complete strangers. And if you’re wearing a wireless microphone while you read this, turn it off now. You’ll thank us later.

Here’s a comforting thought: Whatever mortifying things you’ve done, somebody else has probably done worse. In fact, following are ten examples of real people who have been shamed by technology, along with some ways you can avoid a similar fate–lest you end up in articles like this one.

Tech Embarrassment 1: Bad Husband, No Nookie

Making snide sexual comments about someone in an e-mail and then accidentally sending it to them is embarrassing. Making snide sexual comments about your wife’s colleagues–and accidentally copying her boss on the message–is a recipe for unemployment…if not celibacy.

Mike, a book author in New York, learned that the hard way.

“I was writing about a Christmas party thrown by my wife’s employer,” he says. “She’s a professor of nursing, and they had an annual ‘Nurses Ball’ for faculty and student nurses. I sent one of my frequent ‘what we’re doing now’ e-mails to several friends, and I accidentally included the dean of the nursing school where my wife taught. I jokingly referred to the party as the annual ‘balling of the nurses.'”

In his defense, Mike says he was taking medication at the time. As for the dean: “I don’t believe she was at all happy with me,” he writes, “which may be why my wife no longer teaches there.'”

How to avoid having this happen to you: Before you send your pharmaceutically enhanced e-mail, try on a pair of Google Mail Goggles, which make you solve simple math problems before sending late-night Gmail missives.

Tech Embarrassment 2: Is That a Laser Pointer, or Are You Just Happy to See Me?

You can probably think of many things that you don’t want to see displayed on a wall of a classroom, but there’s one thing in particular that you don’t want to see ten times larger than life.

Karen, a technology instructor in Texas, was showing a roomful of teachers how easy it was to get onto the Apple Learning Interchange. She writes:

“My computer desktop was being projected up on a 5-by-5-foot screen. I started typing the Apple Web address in my browser. Unfortunately, I mistyped one little letter–and suddenly there appeared lots and lots of mad, male porn on the screen. The faster I closed the boxes, the faster new ones appeared. My copresenter was laughing too hard to help me.”

After a few seconds (which she says seemed like a few years), Karen managed to turn off the projector. Fortunately, the audience was amused. Maybe they learned a few things.
How to avoid having this happen to you: Bookmark the URLs you need before you get up in front of the crowd. And bone up on your Ron Jeremy jokes, just in case.

Tech Embarrassment 3: The Audience Is Listening

Christopher Buttner, founder of PRThatRocks in Northern California, had just finished a 2-hour speaking engagement in front of a large university crowd when he dashed off to the loo for a long-awaited respite. With his wireless microphone still on.

“I had to go so badly that when I made it to the urinal, I let out an incredibly loud moan of pleasure, augmented by the sound of streaming water-on-water,” he writes. “The wireless lavalier mic I was wearing was still broadcasting live through the PA system in the lecture hall. My lecture, and subsequent moment of relief, was also being recorded.”

When he returned to the hall, Buttner received a standing ovation. And, apparently, immortality. “I think my moaning sound sample, and various water-on-water audio clips, are used in a sound library somewhere at a major digital recording institute in Northern California,” he says.

How to avoid having this happen to you: If you can’t remember to unclip the mic, be sure to strap on a Motorman’s Friend.

Tech Embarrassment 4: Your Cell Phone Is Not a Flotation Device

We don’t know what it is about smart phones, but they seem magnetically attracted to bodies of water–particularly in the bathroom.

Patti Wood, a motivational speaker in Georgia brave enough to use her full name, writes:

“I was in a hotel room, talking to my sister on the cell phone while I put on makeup to give a speech. I got mascara in my eye, so I reached over the toilet to get some tissue. Sure enough, I blinked, and the cell phone dropped into the toilet. I reached in and grabbed it soaking wet, and managed to dry it off. It is still my cell phone. My sister still teases me about talking on the phone near the toilet.”

Not to be outdone, Jill, a chef (and CrackBerry addict) in Chicago, says she was on a flight home and really had to use the facilities. So, she…

“…went to the lav and sat down, and heard a disheartening ‘thunk.’ It was my BlackBerry hitting the airplane toilet–never to return to my hands. In my confusion and rushing to make the flight, I had slipped it into my back pocket before getting on the plane, and I forgot to take it out.”

Fortunately, she had both insurance and current backups of all her data. Less than a day later, she was up and cracking again.

How to avoid having this happen to you: When you really gotta go, leave the phone behind. And be sure to back up your mobile data daily, just in case.

Tech Embarrassment 5: When You Animate E-Mail, the Terrorists Win

Generally it’s a bad idea to send e-mail with cute little animations embedded. But if you must send e-mail with cute little animations, don’t do it the day after a national tragedy.

Neal, an executive with an Internet consulting firm in Georgia, shares a story about working for a small midwestern Web agency in 2001 that had just opened an office in New York:

“We were planning to have an open house in early October. The e-mail invitation was scheduled to go out on September 12 (yes, one day after 9/11). That morning I told the owner’s secretary not to send the invitation because nobody was in the mood for a party in New York. I was overruled, and the secretary pressed the Send button. The invitation embedded a small animation: An airplane leaving Milwaukee and flying to New York City–directly toward the Twin Towers.”

Within a minute the phones started ringing. Angry e-mail poured in. Neal says the company disabled the animation, but it was too late. The party never happened, and the New York office closed shortly thereafter.

How to avoid having this happen to you: Did we mention that it’s a bad idea to send e-mail with animations inside?

Tech Embarrassment 6: Change Your Wiki Ways

Getting caught “sprucing up” your own Wikipedia entry is embarrassing. Getting caught doing it for your girlfriend–and then breaking up with her via Wikipedia–can only mean one thing: You’re Jimmy “Jimbo” Wales, founder of the online encyclopedia.

In February 2008, Wales publicly dumped former Fox News commentator Rachel Marsden after a brief fling, following accusations that he had changed Marsden’s Wikipedia entry to be friendlier to her. She apparently found out by reading a statement he’d posted to his personal Wikipedia page (now since moved to his own blog).

Marsden responded via an e-mail that magically found its way to Valleywag:

“You are the sleazebag I always suspected you were, and [I] should have listened more carefully to my gut instincts–and to my friends. No, in fact, you are much, much worse than I ever expected. You are an absolute creep, and it was a colossal mistake on my part to have gotten involved with you….There is nothing good left to say whatsoever. Goodbye Jimmy, and good riddance.”

After sending the e-mail, Marsden sold clothes that Wales had left at her apartment on eBay.

For the record, Wales denies giving Marsden special treatment. We suspect she doesn’t think it was all that special either.

How to avoid having this happen to you: 1. Don’t date Jimmy Wales. 2. Don’t date Rachel Marsden. 3. And if you must date either of these people, don’t leave dirty laundry behind.

Tech Embarrassment 7: Good Morning…Now Please Clean Out Your Desk

Firing people via e-mail is truly tacky. Writing a sample fired-by-e-mail message for the bosses to review–and then sending it to the entire company instead–is something worthy of The Office.

But on September 3, employees at a struggling New York ad agency came to work and found the following message in their inboxes:

“I have some difficult news which that affects you and your position with the company. Based on the continued reduction in our client’s’ spend …we no longer have a role for you. …Your last day with the company will be _____________. If you would like to go home today and come back tomorrow to clean out your desk or office, you are free to do so.”

According to Roger Matus, author of the Death By Email blog and CEO of InBoxer, that message was to be sent to 10 percent of the employees at New York’s Carat agency after approval by senior management. Instead, everybody got it–along with detailed charts, PowerPoint slides, and strategy memos for the as-yet-unannounced companywide reorg.

Did we mention that the person who sent it was the company’s “Chief People Officer”? We’re guessing there’s at least one person at Carat who was asked to clean out her desk.

How to avoid having this happen to you: Get an enterprisewide e-mail management system from a company like InBoxer or Permessa. And, really, drop the cute job titles–it isn’t 1998 anymore.

Tech Embarrassment 8: Don’t Show, Don’t Tell

When your computer is hooked up to the big projector in the room, you want to give off a professional impression. That doesn’t include intimate chat with your lover boy.

Laura, a tattoo artist in Pennsylvania, was in a computer training class when she decided to check her e-mail.

“Halfway through [my] reading a scandalous e-mail from a then-boyfriend, someone said, ‘Um…you probably want to get off of that,'” she writes. “I forgot that the computer I was using was the ‘sample’ screen broadcast in front of the whole audience.”

Jennifer, a PR associate in California, says she was giving a presentation during a meeting when her Outlook e-mail kept appearing on screen.

“At the time, I was dating this guy that kept calling me Babydoll,” she says. “He sent me an e-mail saying, ‘Hi Babydoll, last night was great ;-)'”

How to avoid having this happen to you: Unless you absolutely need to go online during your dog and pony show, disconnect from the Net first, Babydoll.

Tech Embarrassment 9: Photo No-No’s

The embarrassing online photo is such a staple of the Internet age that we dedicated an entire story to it earlier this fall. Even then we missed a few good ones from people who really should know better. If these guys aren’t embarrassed, they should be.

Like Sergey Brin in drag, for example. As a Stanford undergrad, the Google cofounder apparently liked to explore his feminine side.

Not to be outdone, blogger Chris Pirillo is just ten fingers away from an obscenity charge in this candid outdoor shot taken somewhere in Alaska. We understand he has unusually large hands. Really.

Meanwhile, tech blogger Robert Scoble makes Pirillo look like Brad Pitt with this PR photo for his Naked Conversations book, substituting a laptop for a big pair of mitts. We think Bob needs a bigger computer–much, much bigger.

(Thanks to former Valleywagger Nick Douglas for digging these up in the first place.)

How to avoid having this happen to you: 1. For pics that escaped in your carefree college days before you sobered up and got a real job, services such as Reputation Defender will search for and destroy them for a fee. 2. When your publicist tells you “don’t worry, these photos are fine,” it’s time to get a new publicist.

Tech Embarrassment 10: Twitterrhea

Twitter and other microblogs have inspired folks to share everything. And we mean everything. If you can say it in 140 characters or less, it’s guaranteed somebody has said it on Twitter.

Here are tweets from five different Twitterati found via These people should be embarrassed, but probably aren’t.

  1. One of us is puking, one has diarrhea, one has tension headaches and one has a sore throat and congestion. Playdate, anyone?
  2. Parasites, Parasites, Parasites. Where else can you find such words as “diarrhea,” and “megacolon,” together?
  3. Awesome…the lady behind me just coughed phlegm all over my jacket. Gross.
  4. Forgot I ate lots of fresh beets the last 2 days, almost thought I had hemorrhoids. Happy Thanksgiving!
  5. Check out these beautiful bowels

(Note: That last tweet actually linked to an eBay auction for bowls.)

People, people, people. Please. Does the phrase “too much information” mean anything to you?
How to avoid having this happen to you: Besides deleting all your gross friends, using tools such as Twits Like Me or Twubble can help you find Twitter users who share your interests in (we hope) less earthy matters.

(Note: If you can contribute more embarrassing tech-related anecdotes, feel free to comment on this story.)

Contributing Editor Dan Tynan likes to embarrass his wife and children on a regular basis. The rest of the time he tends his blogs, Culture Crash and Tynan on Tech.

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