an alarming lack of alarm

In stark contrast to last season's feverish preparations and mental rehearsals for the possibility of running aground, I'm having a rather inappropriate and casual attitude about it this season.

Examples:

1.) While out for a sail with a friend from the office and his family members visiting from Romania, attempting to steer clear of the beer-can race, and inadvertently bumping the rudder a few times in the shallows: "Oops. That's not good."

2.) While out for a sail with my boss and two fellow managers for some team-building fun, again attempting to steer clear of the beer-can race, and this time bumping both the rudder and the keel: "Hmmm... I think we just hit bottom. That's not supposed to happen."

3.) While out for a moonlight sail with my friend Scott and his sister and a nice bottle of wine, feeling a little too serene (lazy) to interrupt the quiet with the noise of the outboard, and deciding that it might be fun to make my first attempt to return to my dock under sail in pitch darkness with a light breeze on the nose: "We're getting a little close over here. Oh well... we tried."

What I'm wondering is...

Which attitude is the most normal/healthy?

I get the impression that most people don't obsess about things (all things) as much as I do, but in the case of keeping my boat in deep enough water (> 28 inches) to float, I think that maybe I've gone too far in the direction of 'oh, whatever!' So now, I'm faced with the completely unfamiliar need to obsess a little more. Wonders never cease.