Check out this experiment, which shocked even me. Here is the description of it from

A Seattle web developer named Jason Fortuny started his own Craigslist experiment. The goal: “Posing as a submissive woman looking for an aggressive dom, how many responses can we get?”

He took the text and photo from a sexually explicit ad (warning: not safe for work) in another area, reposted it to Craigslist Seattle. In 24 hours he received 178 responses, with 145 photos of men in various states of undress.

In a staggering move, he published every single response, including full names, phone numbers, and email addresses. Read the responses (warning: sexually explicit material).

So why is this on Brazen Careerist? Because among the many responders was a guy who used his Microsoft company email address. And included a naked photo of himself. Or at least a part of himself.

Casual sex on Craigslist is a lifestyle. Whatever. But the work email address. That’s another story. My first reaction was, what an idiot. But then I decided that it’s not that idiotic.

At this point in the history of the Internet, adults understand not to use their work email to send naked photos of themselves. Adults know this will come back to haunt them. So I am convinced that people who flagrantly ignore common workplace precautions are actually looking to get caught.

Guy Kawasaki addresses this issue on a smaller scale. He didn’t back up his computer, and it crashed, and a friend recommended he read Why Smart People Do Dumb Things. The four reasons people do stupid things apply to Mr. Kawasaki and Mr. Microsoft as well: Hubris, arrogance, narcissism, unconscious need to fail.

The question is, degree. If you are very [arrogant, narcissistic or in need of failure] you will do something very big and stupid. Most of us just do small stupid acts. I immediately recognized my problem as unconcsious need to fail. I wish I could say it was arrogance, because I think that might sound better.

But, as usual, understanding what motivates someone to do something stupid at work automatically makes me have more empathy and less judgment. Understanding peoples’ motivations is a good exercise to keep you evenhanded and compassionate at work — two skills that are essential to leadership success. And if it can work with Mr. Microsoft, it can work with anyone.