
I’m presently writing this weekly dose on a train down to NYC.
Earlier today, I addressed 1,100 or so folks at The Hartford in CT.
In some ways, Courageous and The Hartford are in the same business.
They are in the insurance business. So am I.
As I shared with them (about them)…
They are in the calm before the storm business.
They are in the calm during the storm business.
They are in the calm after the storm business.
When people worry themselves with potential chaos they need calm.
That’s the role The Hartford plays.
It takes a lot of upfront work, trust, and preparation to successfully deliver in that business.
Funny enough…
While The Hartford is in the insurance business…
I am in the Regret Insurance business.

When people are too calm I often try to nudge them (admittedly) into what feels like organized chaos.
Not for the sake of chaos itself but for the sake of good, healthy and relevant uncomfortable change.
It’s rarely calm.
Growth rarely feels calm in the moment.
But neither does becoming something bigger.
Perhaps being closer to the Maine and Massachusetts border has reminded me of the lesson of the lobster.
A lobster only grows by outgrowing its own shell.
When it does, it becomes exposed, uncomfortable and vulnerable before a new shell can form.
Maybe that’s true for us too.
Maybe the tension you feel right now isn’t a pickle or a punishment.
Maybe it’s proof you’ve outgrown an old version of yourself.
As just stated…
Growth rarely feels calm in the moment.
But neither does becoming something bigger.
Courage might just be the best regret insurance policy money can’t buy.