I don’t like to disappoint. It is a big part of who I am.

The first time I remember really screwing it up was when I was five years old.

My family was visiting my uncle in Florida. He didn’t have kids of his own and talked to all of us like we were adults. It was cool and made you feel important. He was also a rough tease.

On our first night there, he brought out a coloring book and a big plastic crayon holder, filled with perfectly pointed colors. They looked like they’d never been used. He said they were his special stash – but I was free to use them all.

“Just. Don’t. Break. Any.” He said it with a startling directness and a straight face. I didn’t break a lot of crayons. I figured this one condition would be easy to uphold. I agreed to the terms and absconded to the upstairs room to try my hand at filling in the finer parts of a Snoopy scene.

I might have lasted five minutes.

These weren’t thick Crayolas. These were those thin, special shades and they clearly couldn’t withstand the enthusiasm of this young kid set on creating the perfect Peanuts coloring sheet.

As the wax cracked in my hand, I remember how I suddenly felt sick to my stomach. Tears started to burn.

“YOU HAD ONE JOB” I could imagine my strange, very adult uncle bellowing.

I didn’t know what to do.


Flash-forward most of three decades and the scene is reset. But now I am in the adult role and my son is the enthusiastic borrower.

Instead of crayons, we are trading in CDs. His long-held music obsession has been aided and abetted recently with access to my extensive collection of tunes in the basement. But he has been told in no uncertain terms to take extra special care of these shiny round things and the cases they call home.

One night before bed he suddenly can’t find one of our favorites and when I start to press him on it, I suddenly see a look on his face – that crumple that starts to happen before a broken-hearted cry – that I recognize.

He has let me down.

He doesn’t know what to do.

I am unmistakably transported back to my uncle’s spare bedroom and can almost feel the wax cracking again.


As we get older, the things we are breaking and taking and abusing and returning get bigger and more meaningful and the damage is harder to absorb.

We find ourselves holding broken expectations and relationships and lost jobs and empty bank accounts instead of cracked art supplies or scratched CDs.

We don’t know what to do.

Turns out that we have to do the adult version of what I did all those years ago. We have to do what my son did. We have to go to the people we hurt and the organizations we let down. We have to feel them out for mercy. We have to examine our options. We have to take the consequences and somehow we have to figure out how to live with them.

And then we have to make sure that all the damage has taught us something.

I used to keep a certain Seth Godin quote about disappointment above my desk. The guru says that we will all be disappointed by others and we will all disappoint the people we love.

That’s part of the deal of being in the world, He writes.

The alternative, I’m afraid, isn’t to choose a path where we make everyone happy and always exceed their expectations. Nope. The alternative is to hide, to fail to engage and to produce nothing.

As Seth says, A pretty easy choice.

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