I was having one of our many hours-long phone conversations with Tino recently, and we got talking about something I think is very important to any tech company: failure.

"I don't want your learning to be me, flying around whacking at you with a sword, saying 'She was leaving you, Pan!', and then smacking you down like the hand of God until you smash your head against the deck of a ship twenty feet below."

Any of you who have a soul will recognise this as the climactic battle in the 2003 version of Peter Pan, but that’s really irrelevant. I just get a small payout every time I write about that movie, so I mention it wherever possible. (Not really—I just love the movie.) Really, the point is that Peter couldn’t better himself (or turn pink, for that matter) until he got smacked around a bit.

No Rest For The Wicked

There’s something that I’ve been harping about for months now which is pretty obvious. I’m not sure if people haven’t thought of it or if I’m just running around stating the obvious, but it’s an important enough point that I don’t really care either way. Here it is: you learn nothing by being expected to perform at the level of skill you currently have. Basically, if you’re not being asked to do things you don’t know how to do, you’re not learning.

Obvious, right? You’re not learning unless you don’t already know what you’re doing. And yet, and yet… Failure is still frowned upon. Why? Why is it so bad for us to try and learn something? In tech, you need to be constantly learning new things or you’ll fall behind pretty quickly. I’m not just talking about new technologies, either; Tino and I were having this conversation because Tino has an uncanny knack for prophesy and I have a bull-headed insistence on trying new things in terms of our relationship with users.

The only way you’re going to get better is if you work at it. The only way you’re going to improve is if you eschew the comfort of familiar tasks and pursue the alien, the confusing, and the complicated problems before you.

This Must Be What Pain Feels Like

So if we accept the [widely] (http://thenextweb.com/entrepreneur/2010/07/12/the-importance-of-failure/ “The Importance Of Failure on The Next Web”) held belief that failure is not only okay, it is actually good, it’s irresponsible of us to not also issue a warning: it really sucks to be failing.

I was pretty beaten up over having one of my core beliefs fail in a pretty spectacular fashion. And when Tino pointed out that he warned me it would, I told him I thought he was right even when I was arguing that we needed to try it. I needed to know. I knew there was a risk of failure, but I had to try anyways. That doesn’t make the failure any less painful. It’s not just embarrassing, it doesn’t always just make you feel worse about yourself; in this case, it was exactly as he phrased it. It was like I was flying in the clouds of Neverland and the real world came and smacked me back down to earth. And sometimes that happens. Sometimes our failures will end with us in considerable personal discomfort.

But without that discomfort, Wendy can’t make us more than we were.