Failing Fast

August 6, 2014

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“Forget your perfect offering. There is a crack, a crack in everything. That’s how the light gets in.”
-Leonard Cohen

How’s that for a weird quote? I heard it the other day on the radio and it stuck in my head. It has a resonance for me that I just can’t seem to shake. You see, like most folks, I’m intimately familiar with imperfection. I’m faced with it in many of the projects I’m most passionate about: My writing, my career, my boat…

Yeah, I’m building a boat. Technically, it’s my second boat. I think just admitting that qualifies one as insane. The first boat was a mere 9 foot skiff I made for my daughters. It took me almost 3 years to complete it. I should probably mention that I have absolutely no woodworking skills. So after I finished the first one, I decided to build another. This second boat is just for me. Well, me and my brother actually. We’re building it together in his garage. We’re about a year into it so far and it’s coming along pretty well.

OK, honestly it’s a little early to tell. We make a lot of mistakes.

I don’t know what it is about working with wood, but any mistakes you make tend to jump right out at you. Of course, the bigger the project the more room there seems to be for error. I’m discovering that a 17 foot boat leaves lots of room for error. Cutting parts to shape is hard. Getting screws to bite and not strip. Glue everywhere. One false move with a power tool and there are splinters galore. The whole project really is just a glorious catastrophe waiting to happen.

If ever there were a case study in failure, this boat is it for me. Now that might sound terribly defeatist, but it’s not meant to. You see, I’ll finish this boat too, one way or another. It’s just that I’ve got a whole lot of failing to do in between now and the day I finally launch her.

Of course, given all this failing, it’s still pretty astonishing how slowly I manage to learn. For instance, I’m noticing that I don’t seem to give up my standard ways of learning, even in the face of overwhelming evidence that they are not paying dividends. I’m fairly sure I’m not alone in this behavior.

First there is my innate impatience to see quick results. This whole measure twice, cut once thing just doesn’t seem to come naturally. For some reason I’m always in a rush. I find it extraordinarily difficult to slow down and just take my time. Maybe it’s some american thing where we are just impatient with anything that impedes progress…No, I don’t buy that either. I think slowing down is really hard work. It takes discipline to slow down and treat things in a very thoughtful and conscientious manner.

Savoring the moment and appreciating how things feel in the moment is not something that just happens to you. You have to make time for it. I can show you all of the places on the boat where I rushed the job. The places where I tried to drive the screws in with a power drill (I drove them right through the panels – genius!). The areas where the wood split because I didn’t take the time to test the bend first. The evidence of my own impatience is writ large in the construction of this boat.

Do you want to know the really amazing part? I still keep rushing!

Scary. Did I mention that slowing down is hard?

Another area where I struggle to learn: working as a team. Working as a team is hard too. First you have to keep those you are working with in mind all the time.  That doesn’t come naturally at all for me. I’ve never really been a good team player. I grew up participating in individual sports like running, wrestling and weightlifting. I operate very well solo. Working as a team has been an alien experience. For example, when my brother and I are working on the boat, I often struggle to figure out what he can do to help. I’ve seen this on software development teams too. Ask a developer what needs to be done, and you will get a detailed list of all of the work that remains. No problem. Ask that same developer how someone else can help them get that work done, and often you will get a blank look. When you are not accustomed to working on a team, it’s hard to picture what teamwork looks like.

To make matters worse, my brother and I have different skill levels when it comes to woodworking. This means that sometimes I need to take the time to show my brother how to do things (or vice versa). I find that hard to do when I’m rushing to get things done (see above). But without taking that time to show him how to do things, I lose the benefit of his help. I lose the teamwork. I’m finding that teamwork takes some serious patience. Ultimately I know I will go faster if both my brother and I can work at the same level, but that means initially I will have to slow down to achieve that goal. Slowing down to go faster.

I’m very lucky to have someone to like my brother to put up with all my mistakes. In a peculiar way, building a boat with him is teaching me a lot about software development. That’s probably good, because God knows if we’re ever going to finish that boat.

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I’m Helping!

August 22, 2013

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I used to race with a really experienced crew on a J120 (a flippin’ nice sailboat). We were all very hardcore about our racing. Many on the crew had been racing sailboats since their childhood. These guys were good – really good. We pushed each other hard and we expected a lot of ourselves and each other when we were out on the race course. So there was plenty of pressure.

I came to sailing relatively late in life compared to some, so I was very self-conscious. I didn’t want to make mistakes. In sailboat racing, there are a million little mistakes you can make that will slow the boat down. However, since it’s a team sport, you can cover for each other too. Not only are you trying to perform well yourself, ideally you are trying to help your teammates perform well too (at least on the successful teams). In sailboat racing you are always trying to anticipate what needs to happen next: clear the deck of loose sheets, make sure the spinnaker is prepped for the next rounding, re-run fouled lines, and Lord knows what other details. I always feel a bit like a bobble head doll when I’m racing – always trying to look in every direction at once.

I remember there was one guy on the boat who was really talented. He’d been sailing since he was in diapers. Things just seemed to come naturally for him. He was always where the help was needed most. He was easygoing and relaxed, learning was easy around him. But even he made mistakes from time to time – just like the rest of us. He’d pull the wrong string, blow the wrong halyard, grab the wrong winch. Whenever he screwed up he would yell,

“I’m helping!”

He would do it in an uncanny imitation of the Sesame Street muppet Grover. Super Grover to the rescue! We’d round a mark on the course and he would miss grabbing a sheet (in all the chaos and madness that we call making a left hand turn in sailing…).

“I’m helping!”

Usually everyone on the boat would bust up at this point. It broke up the tension we all felt when we failed a maneuver. It got us past the “Oh shit!” moment and allowed us to shrug it off and keep focused on our goal. I’ve been on other boats where someone made a mistake that cost the team on the race course without the help of ‘Grover’. Generally, on those boats we experienced something that felt like blame and recrimination. Perhaps we were less experienced, less able to forgive each other our mistakes, less able to cover for each other. Less able to allow for normal human nature to express itself. The problem was, we would struggle to recover our equilibrium for far too long after the event occurred.

A couple years later I was on another boat in a long distance race. It was early evening and the sun was setting over the Olympics on Puget Sound. As is often the case at that time of the evening, the wind died and we were left trying to race in the barest breath of wind. The water was flat and the sunlight was turning a deep shade of orange as it hit the mountains and reflected off the flat water around us. In fickle conditions like this, even the smallest mistake can cost you the race. As we all tacked into the shore to get relief from the current, I watched a nearby boat fail to release a sheet and blow the tack. They came to a stop and as we drifted past I heard,

“I’m helping!”

In the unmistakeable voice of Super Grover.

I remember feeling two things at the time:

  1. Damn, that’s funny
  2. We’re going to get our asses handed to us

Frankly I wish I saw more of Super Grover in the Agile software development community. All too often I see teams that are under tremendous pressure to deliver (is there any other kind?). When someone makes a mistake, it can all too easily turn into a situation where blame and recrimination slow the team down. There is no one there to help them shrug the mistake off. Someone with experience and the respect of the team. Someone who can look at his/her own mistakes and laugh,

“I’m helping!”

Sometimes I think that a team needs someone who can see that even though their efforts were well intended, even skilled – they were mistaken.  It is easier when someone you respect and admire can completely blow it and laugh about it. Suddenly the job doesn’t seem quite so serious. The task doesn’t seem quite so critical and we allow ourselves to get back to doing what we really enjoy.

Or perhaps I’ve got it wrong. Maybe this kind of thing doesn’t really apply to software teams. Maybe there is a better explanation for this kind of behavior. If so, that’s OK,

“I’m helping!”