I Wish I Had. I’m Glad I Did.

At a pivotal time in my life I was given a gift I’ve come to treasure: a bookmark.

It’s not even one of those cool glossy bookmarks with a tassel on top you used to be able to find near the register at bookstores. No, this was a homemade jobby. Printed on regular card stock paper and laminated with that old school see through contact paper.

But it wasn’t the piece of paper that I’ve grown to treasure, it was the words imprinted on that very ordinary card stock: “I Wish I Had. I’m Glad I Did”.

The giver of the gift presented it as I was embarking on a new chapter of my life. The message delivered was simple- at the conclusion of this particular phase of my life I should strive to look back and find myself saying “I’m Glad I Did” far more frequently than “I Wish I Had”.

It’s become an interesting score that I’ve kept in my head over the months and years since receiving that gift.

I was reminded of my little bookmark as I read David Brooks piece on Life Reports from those older than 70. They reveal many ways people have chosen to navigate their lives and the lessons they’ve drawn through the years. One in particular jumped out at me:

Lean toward risk. It’s trite, but apparently true. Many more seniors regret the risks they didn’t take than regret the ones they did.

Like so many others, these folks looked back only to have more “I Wish I Hads” than “I’m Glad I Dids”.

Whether it’s starting something, saying something or doing something I’ve found this little scorecard a powerful one for me.

PS- there’s another riff on this idea from Allspaw in his post related to building fault tolerant systems in which he advises to:

Follow the path of least regret.

That works too.