Sailing is fun. Teaching sailing can be fun, too. Once you get past the worrying part. And once you get past the culture shock.
For the last 9 years, I've been helping my friend David teach sailing at Skye Farm Camp. They've got about 10 Sunfish of various vintages.
This year, we had 10 campers, and three outstanding days of sailing during the week. There's nothing better than steady winds, 7-15 knots, from a consistent direction. Strangely, each day that had wind, had this kind of remarkably perfect wind.
Some years we have storm fronts and shifty winds. Some years we have those swirls and eddies that happen in lakes surrounded by mountains --- kids get frustrated because they sail from wind into calm into opposing wind.
Sailing as Teamwork
Sailing is a wonderful team-building exercise. Since David is a Captain in a Fire Department, he has that mysterious property folks call "Command Presence". He can, without yelling, impress the kids as to the importance of working together, doing things safely, wearing their PFD's, helping to carry the heavy Sunfish hulls, helping each other with righting a boat and with all the various details of safe sailing.
We've been fortunate in always having a mixture of kids who've done this "sail camp" with us in the past, kids who know their way around a Sunfish and complete n00bz. Pairing experienced with n00bs helps both sailors.
The experienced have to refine their own skills as part of teaching the n00bz. And the n00bz learn from the skilled.
And -- bonus -- since David is an charming, affable, sing-around-the-campfire guy, we have great evening sing-alongs, also. That's often a bonding experience for all of us, kids and counselors alike.
Worrying
Outside the fun, there's a lot to worry about. Some of the boats are old, so things break. We've got a toolbox full of spares, but... we've never had a failure on the water. So far, everything that has broken was spotted when rigging or stowing a boat. (Knock wood for luck.)
Some kids are wild. We've had a few injuries, but they've all been minor. We have a chase boat in the water, PFD's on all campers at all times. Everyone passes the "deep water" swim test back at camp. Except on the last day, they sail with buddies.
Plus, there's that social thing: kids clique up quickly. Imposing buddies on them tends to suppress the cliquishness by forcing interactions. Also, a kid that might get isolated -- if they can sail -- can earn a position in the group. Kids that are striving for "alpha" status may not be able to sail well, leveling the playing field for pack dominance.
Rules for Living
We had a little bit of culture shock this year. In prior years, I was just a fat guy from Schenectady there to teach sailing. Nothing special.
This year, I was a fat guy from Norfolk, VA -- a guy who doesn't own a house -- who drove 10 hours to teach sailing. Some kids sort of ignore this, but a few had questions. Mostly of the "wait, you don't own a house?" variety.
My explanation of my life-style included "The Commodore's Two Rules for Living":
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Go Big or Stay Home
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Don't Come Back Until You Have a Story
We want to see the world cheaply, so we're combining cheap transportation with living accommodations. We aren't hedging our bets with a "home base" or a "fall-back plan".
It almost seems inappropriate, but Sun Tzu's Art of War, Chapter XI, has some advice in paragraphs 23-25. You have to paraphrase it to remove the violence. Here's one translation "If there is no place of refuge, [you] will stand firm." I think this is an important piece of advice.
On Red Ranger, we think that commitment is essential. And, we've found that once we committed, it was much easier to get past the worrying.

