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6 Epic Online Fails and How to Avoid Them Everyone makes mistakes, but the online world makes them a lot more visible. What not to do, if you want to keep your job.

By Steve Tobak Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.

The other day Twitter executive Anthony Noto tweeted what was supposed to be a private direct message about a possible acquisition. Techies call that a DM fail. Not a bright move for the CFO of a public company, not to mention the irony of that company being Twitter.

For years I've been telling people about the evils of shooting themselves in the foot on social media, email, messaging apps, whatever. Does anyone listen? Apparently not.

While this particular snafu isn't likely to cause any real problems, plenty have. People have made enemies, harmed their reputations, and even gotten fired over the same sort of thing.

Here are six stories of epic online fails of various sorts and how to avoid them:

1. Putting your stupidity in writing.

It's OK to make dumb mistakes; we all do. But the one way to ensure your mistakes come back to haunt you is to put them in writing. Former PayPal president David Marcus wrote a scathing email slamming the company's San Jose employees. He was obviously angry and it never should have gone out.

It was leaked to the media and he resigned a few months later, although parent eBay denied he was forced out.

Lesson: If you don't want the entire world to see it, don't put it in writing.

2. Hitting "Reply All."

Yes, this is probably the oldest mistake in the history of the digital world, but it's potentially the most devastating, as well. I once knew a pretty abusive and mercurial (bad combination in itself) editor-in-chief who thought he was sending an email to his editor ripping apart two reporters that he thought should be fired.

It went out to everyone, including the reporters. He was gone a few weeks later but, in an ironic twist, the reporters remained.

Lesson: I've made the "reply all" mistake myself, but that was years and years ago. Now I reread everything, including the "to" list, before I send it. Everything. It's a good rule to follow.

Related: 7 Things Successful Entrepreneurs Do

3. Writing self-serving blog posts.

After pleading guilty to two misdemeanor counts of battery and domestic violence, instead of admitting he screwed up, apologizing and letting things settle down, RadiumOne CEO Gurbaksh Chahal took to his blog where he painted himself as the victim and lashed out at everyone, including his girlfriend, police, prosecutors, the media and his board of directors.

For that, he was fired.

Lesson: If it's not going to help your company, don't post it.

4. Bad-mouthing the boss via messaging.

On a long instant message rant to his VP of human resources, Oracle EVP Keith Block vented about everything from the company's products to his boss, then Oracle co-president Mark Hurd. That wasn't very bright. The messages came to light via discovery in an unrelated court case.

Sure enough, Block reportedly resigned soon thereafter.

Lesson: Don't bad-mouth the boss, either in writing or verbally, and don't assume anything you do on a company computer will remain private.

Related: The One Trait Successful Entrepreneurs Have In Common

5. Posting confidential information.

Former H-P vice president of engineering Scott McClellan foolishly shared previously unreleased details of the company's cloud-computing strategy on his public LinkedIn profile, tipping off competitors to confidential information that should have remained under wraps.

I don't know if that cost him his job but after spending his entire 26-year career at HP, McClellan later took a demotion to work for Red Hat, a much smaller company.

Lesson: Remember, your competitors know how to use the Internet too.

6. Drunk dialing, texting or tweeting.

Not to pick on PayPal, but two months after joining the company as director of strategy Rakesh Agrawal unleashed a bizarre and mostly incoherent tirade on Twitter that began at 1 a.m. and went on into the wee hours of the morning in which he called a company VP a "useless middle manager" and a "piece of s--t." Hours later, the company tweeted that Rakesh "is no longer with the company."

Agrawal later blamed the epic rant on a DM fail, but considering the time of night and inarticulate nature of the tweets, I wouldn't be surprised if alcohol was involved.

Lesson: If you're having too much fun, don't dial, text or tweet.

The sad thing is that I can probably write an entire book with stories just like these. It's hard enough to get ahead in spite of all the obstacles you'll face throughout your life and your career. Try not to make yourself one of them. Don't be your own worst enemy.

Related: Don't Try to Be What You're Not

Steve Tobak

Author and Managing Partner, Invisor Consulting

Steve Tobak is a management consultant, columnist, former senior executive, and author of Real Leaders Don’t Follow: Being Extraordinary in the Age of the Entrepreneur (Entrepreneur Press, October 2015). Tobak runs Silicon Valley-based Invisor Consulting and blogs at, where you can contact him and learn more.

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