Introducing: Big Oops

We all make mistakes. They come in different shapes, sizes, and colors. And they have varying consequences.

I think we should talk about those mistakes. For three reasons:

First, talking about mistakes yields vulnerability. And vulnerability is an effective way to connect with other people. A team will be more successful if its members feel connected to one another, and vulnerability can really help with that.

Second, when mistakes are shared by those with more experience, it can help those with less experience learn what not to do, or at least what to look out for. By coming from someone accomplished, these stories can also show that we should roll over our mistakes — remember them, but accept them and move on.

Third, and more important than the other two, they're usually pretty funny!

Allow me to elaborate for a moment ...

I have a podcast, or at least I did. I haven't produced anything in years. It's called Squirrel Stories, and the premise was that people would share their weirdest and most embarrassing stories for the entertainment of the listeners.

Why would someone do that? Why would they join me on stage and tell me about that time a room full of people at a restaurant saw them naked on the toilet?

Because it's really, really funny.

Now.

After some time has passed, it can be healthy (and fun) to laugh at the stupid things we've done, as it enables us to realize that those things that seemed so important in the moment really don't matter in the long run.

It may sound crazy, but I've had legitimately funny stories on the show about funerals, about loved ones dying, about sexual harassment, and about racist Wal-Mart customers. If we can laugh about those things, I'm sure we can laugh about deleting a month's worth a data that wasn't backed up.

And so I'm going to spin off a series called Big Oops. My aim is to poke people around the web development industry to share their biggest mistakes for our entertainment and education.

I think it's going to be fun.

Stay tuned.