June 29

Sailing mentors – Who’s yours?

6  comments

One of my favorite bloggers and twitterers is Mark Hendy. He lives in the UK and shares a common passion for sailing. One of his recent posts was  about how he got into sailing thanks to his sailing mentor, Tony. One outing on a boat with Tony and he was hooked:

Once we got the main sail up and switched off the engine I could feel
the boat moving through the water under natures own power;  the sound
of the water along the side of the hull was magical and I was in a
place I liked being.  It became obvious within the next few hours that
I loved sailing and I knew I needed to own my own boat.  Not a shared
boat, my own.

This got me thinking about my own sailing mentors. I have been sailing for over 20 years and there have been four. The first two were both called Tom and could have not been more different.

Our first sailing instructor was a retired engineer called Captain Tom, who was retraining to be a Lutheran minister. At weekends he taught sailing on his Morgan 42. What a lovely guy! A great teacher who took us under his wing, taught us how to sail and then helped us find our first boat a Cape Dory Typhoon. Coincidentally we bought it from one his former mentees. Without his help and advice we would not have become addicted to this great way of life.

The second Captain Tom was a skipper for the Offshore Sailing School who taught us to live aboard in the BVI's. He was a gruff, rum-drinking, Floridian who taught us more in a week than I have ever learned. We saw him a  year later and he hardly remembered us – so not much of a mentor/mentee thing. You can read more about him and our exploits in this post.

Since then I was mentor-less until fairly recently. I am lucky to have two great and fairly recent friends who are both highly experienced sailors. Like any good mentor, they are generous with their insights if requested but don't feel the urge to ram it down my throat. Always helpful without being patronizing.

One of my mentors is my mate Phil, an Aussie who is the proud owner of a beautiful Swan 42 that he has double-handed in the Newport to Bermuda several times. Most of the time he cruises her out of Sag Harbor. I have been out on the boat with Phil and his wife Joy a few times and out for beers even more often. He has been a great source of ideas about the pros and cons of owning your own big boat and where to sail in the region. I feel much clearer about what I am looking for long-term thanks to Phil.

My other mentor is Howard, the skipper of Knot Again. Howard owns a C&C 34 that he races in Raritan Bay with yours truly frequently on the starboard winch. Howard is mostly self-taught and has clearly studied sailing well. He has been a frequent winner at RYC and drives his wife crazy with all the silverware. Every time I am on the boat with Howard I learn something new. He is a great tactician and a great person to answer technical questions about sail trim etc.

Howard is a "skipper factory". There are several other boats at RYC owned and skippered by Howard's former crew who have learned from him and then gone on to campaign their own boats.

I would love to hear about your mentor stories. I will of course share them back on this blog.


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  1. You overlooked another kind of mentor which is much less obvious, and that’s the mentee who consistently ask just the right question to force me to face and overcome my own deficiencies.
    I try to operate under the Feynman Rule (basically, “You don’t truly understand something until you can explain it to someone else.”), not just in sailing but in life. I find that the best mentees are those who ask the questions I am least prepared to answer at that time.
    Sometimes I can work out the solution and the explanation with a little thinking, sometimes we just experiment. I’ve re-learned opportunities for improved sail trim because I’ve gotten into a habit until prompted why I’m doing or not doing something. Other times, I can refer to a reference book, and some times I just flat admit I don’t know–yet.
    But invariably, I find that I’ve become a better and better-informed sailor simply for having been subjected to a fresh point of view.
    And I’ve also found that for many people, realizing that in sailing there is never omniscience, but rather only varying degrees of ignorance is quite comforting as they grapple with learning even the basics of everything that goes into sailing: sail handling, helmsmanship, crewing, captaining, cruising, racing, owning and just generally loving to sail.

  2. Online, I’d have to say my mentor is Tillerman. It was reading the insanity on his blog that got me to say “yes” one fateful day when I was asked if I might be interested in learning racing sailing.
    Offline, in the real world, anybody who has looked at my blog knows about Zorro. He’s selfish, egotistical, and the best racing skipper in New Mexico or West Texas. I never pass up an opportunity to sail with him, as I always learn something. Lately, chaos in my and Pat’s life, as well as some crazy things with women in Zorro’s life, have meant that we haven’t sailed together in a while. I’m hoping the drought ends soon.

  3. Great topic. Stan Lander – a retired USCG officer and working captain/instructor in SF was a huge mentor for me as I became a professional instructor/captain. As a recreational sailor, I learned from the best: Joe of Horse’s Mouth fame…

  4. A friend who’s been sailing all his life has taught me a lot over the years. He’s a genius at sail trim, reading the wind, working the tricky currents of the Bay, and coaxing the last tenth of a knot out of a boat. But his most valuable lesson, for which I’m forever grateful, is one he never realized he was teaching me.
    He started on 505’s – boats with a million strings to pull, every one of which will buy you some speed if you know what you’re doing. When he took friends out on his Catalina, in his head he was still racing that 505. He fidgeted constantly with headsail changes, whisker pole, vang, cunningham, outhaul, backstay, and anything else he could find to adjust while we were all supposed to be enjoying a day on the bay. I soaked it all in, but he was driving his wife nuts. Eventually, she stopped sailing with him altogether.
    When we finally got a boat of our own, I had to learn sailing all over again – how to see it from my wife’s perspective. I had to forget about pushing the boat to its max.
    I learned how to power the boat down so guests were comfortable when the wind came up. I learned to relax and enjoy the day, even if sail shape wasn’t perfect. I learned I can put my wife on the helm even when it’s screaming if the boat’s buttoned down tight enough. She may be happier back at the slip with a Merlot in her hand, but at least when we get there, she feels like she’s earned it.
    For all that my old mentor showed me about trim and boatspeed, the lesson that he never learned himself was the most valuable one he taught me.

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