Life Lessons from Dave Perry

I’ve been learning lessons about racing sailboats from Dave Perry for thirty years, since first reading his legendary book Winning in One Designs. So I was pretty excited last fall when the editor of Seahorse Magazine asked me to write a profile of Dave, which appears in the February 2020 issue. We sat down at Yale Corinthian Yacht Club and talked for two hours, digging deep into how Dave came to be such a respected sailor, sportsman, teacher, and rules guru. Here are three of the many surprising lessons I learned that didn’t make it into the profile.

1. Nice guys don’t always finish last

Dave has at least three different perpetual sportsmanship trophies named after him, but he’s also won plenty of important championships. Playing by the rules works.

2. People remember a personal voice

Dave compiled Winning in One Designs from a series of columns he wrote for what is now Sailing World Magazine, based on questions that came up at racing seminars he taught around the country. “People say, Dave, your articles are almost like you’re sitting there talking to me—and that’s because I was.” The personal voice (combined with excellent, easily digested information) is why the book has remained in print since 1984. All most readers really want is to feel like they’re in a conversation with the author.

3. Planning is overrated

Though Dave admitted to a few significant sailing regrets, he says he’s “always sort of lived in the moment. I’ve never been one to say, well if I do this and this in five years, I’m going to be here. My attitude is I have no idea, but right now here’s what I want to do.” As long as you’re doing something “good and useful and productive,” he adds, it always seems to work out.

Seahorse has given me permission to reprint “Winning in Life” for you, but to read Ken Read’s piece “Don’t let the perfect be the enemy of the good” or to learn what Grant “Fuzz” Spanake is up to, you’ll need to subscribe. Before you go, leave a comment below or send me an email with your favorite Dave Perry story!

Read other stories I’ve written for Seahorse

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7 Replies to “Life Lessons from Dave Perry”

  1. Dave might be a better teacher than a sailor…if that’s possible! What I know is
    he has figured out a way to combine the two and remain passionate about both. Sprinkle in his humor and genuine love of people and you’ve got a recipe for success and fun!
    Dick Loomis

    1. Dick, that’s a great observation about why Dave P remains “relevant” (his words, not mine). Combining two skill sets with humor and generosity is a sure win!

  2. Winning in One Design was a huge help when I read it 20 years ago. I think it is time to dive back in.

    And if you love sailing, subscribing to Seahorse is a must. I read it cover to cover and learn something new every time.

    Thanks Carol

  3. Great article. I guess one of my mistakes in life was not applying to Yale as an undergrad so as to have been part of that YCYC scene at that time. I’d might not have needed to buy a copy of Dave Perry’s book!

  4. Carol, nicely done.

    Among many blessings in my life was to be coached by Dave in the late 1970s at YCYC. Who knew the inspiration would continue another 50 year’s.

    1. Thanks Todd. I remember you and Peter Shope talking about YCYC, but I never went there until last November to interview Dave. And it’s not that far from CoCo.

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