Lessons Learned

October has been an amazing month. For me, it has been a really busy finale to the sailing season. Usually, I’m sailing on Chesapeake Bay because of the traditionally strong wind in the fall. However, this year I had two out of town regattas – the J/105 North American Championship in Rye, NY, and the Helly Hansen Sailng World Regatta Series Championship in the British Virgin Islands, as well as delivering the J/105 to Rye before the NAs.

This is a lot more travel than I normally do and it is intense people time. We are very focused racing on the boat during the day, and then at night we have regatta events or team dinners since we are all staying together. We are meeting new people, seeing old friends, and competing and connecting at the same time.

All of this has happened so fast that I have not had time to analyze it all, and this newsletter is later this month than usual. So, here are some of the lessons I have learned this month, and I’ll share more in the months to come!

Humility Has Its Place

For the J/105 North Americans, we were short two of our regular crew, and we had two “guest crew” that we do not normally sail with. In fact, I had never sailed with either of them before. They are amazing sailors, and I was excited to learn from them.

?My usual position on the boat is to trim one of the sails, the jib. We were using a new sail for the regatta, and one of our guest sailors is a very good sail trimmer (several people had told me that in advance). I deferred to him quite a bit and listened to his thoughts on what we should do to trim the sail.

However, I have been sailing on this boat for 23 years and I have had several sailmakers coach me on how to trim the sails. We have also won major regattas with me making the calls on how to trim the jib. I did not use any of this experience and I abdicated all the decision-making to this guest. I was being respectful, I thought, but it did not help the team. I should have been more collaborative and put forth my theories and experience. I was, in some respects, a “negative leader.”

I have figured out why I held back, and I have apologized to the team. I have also been working to improve the knowledge areas where I know I am weak. One of the people I talked to was the winning skipper, who also won the NAs last year.

At the awards ceremony, the winner offered to have anyone call him to find out what they were doing. He appreciates having an amateur-only fleet, and wants to support it the best he can. I got his email, and he quickly scheduled a call.

The generous man and former Olympian spent an hour talking to me on the phone, and covered everything from sail trim and sail selection to boat heel. At the end of the conversation, he offered to do a zoom call this winter for our local fleet. I asked him how many of the other boats from the NAs had taken him up on his offer and called him. He said none. Not a one.

Why in the world would you NOT call the winning skipper if he is offering to teach you his secrets to success?

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• What would you have done in these situations?
• How would you have collaborated with the expert?
• When are you a negative leader?
• How would you approach the winning skipper?
• When has humility served you well?
• When has humility hurt you?