From the Blog

Dec
02

Sailing with Bob

Posted by Jake DiMare on December 2nd, 2012 at 4:12 pm

Last spring I decided to take up racing sailboats at Courageous Sailing in Boston, MA. At the time my goal was to get more time on the water, hopefully improving my ability as a sailor in the process. My plan was simple: Find the most experienced sailor I could and get in his or her back pocket for the season. When I arrived that first Thursday afternoon I was relieved to find most of the other sailors had done this before. But, almost everyone else was already broken up into teams. As I glanced around the field of competitors while reliving anxiety of being picked last in gym class I noticed someone who seemed to be alone.

When I first met Bob Burke he was joking with the girls at the front desk. He was an older guy and had an easy-going, confident demeanor. His hat, the kind only a Navy veteran would wear, read “USS Franklin D. Roosevelt”. I remember the absurd idea he had stepped out of a Hemingway novel just to teach me to sail crossed my amazingly self-centered mind. I walked straight up and extended my hand to introduce myself thinking “This is so perfect…”

Bob on watch

Bob on watch

As Bob and I set sail that first evening I promptly discovered every assumption I made about his sailing ability was wrong. Bob was an Intelligence Officer in the Navy and had nothing to do with the ship’s operations. In fact, he had only started learning to sail a couple of years ago. This was a disappointing setback in my master plan to latch onto a more experienced sailor. As we trailed the pack in that first race I remember thinking I was in for a summer of losing and conversations with a septuagenarian about his favorite shows on the Fox news network.

However, Bob didn’t live up to any of my assumptions on or off the water. For instance, he wasn’t slow, or pessimistic, and he doesn’t watch Fox news. Instead, Bob is an energetic, positive thinking guy, making the most of life in retirement. We quickly became good friends.

Regardless of our friendship, on the boat, it seemed evident we were not going to be doing much winning. Against a backdrop of breathtaking sunsets at the back of the pack we dubbed ourselves ‘Team Gratitude’, after deciding winning was secondary to being on the water with friends week after week.

However, as the season unfolded a surprising thing happened: when you do the work, you get the results. We slowly improved our timing and tactical ability while inching our way up the field of competition. By mid-season we were sailing consistently above average and eventually, we even placed in a couple of races.

In September we were joined by Chris, an extremely talented young sailor. Chris, who also became a good friend, had taught Bob to sail a couple years back when he raced in college. With Chris on the team we were suddenly an extremely competitive program with growing skills. Wins started to stack up, and with them came a sense of pride.

As it turned out I ended up learning more than I hoped for about sailing this year. However, I also picked up a few more important lessons:

  • It’s never, ever too late to pursue your dreams.
  • Age is meaningless when it comes to making good friends.
  • Even when the wind doesn’t cooperate, sailing is better than most other ways to spend time.
  • Time spent with friends is more important than winning.
  • Gratitude is more rewarding than winning.
  • But winning…After a season of painfully slow, incremental improvement…Is very, very fulfilling.

Check out the video below for a montage of all the action this year. I can’t wait for 2013.

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5 Responses to Sailing with Bob

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  2. Pingback: Bob Burke off-line | Village 14 City of Newton, Massachusetts

  3. Bruce Henderson |

    Many thanks, Jake, for this wonderful view of sailing at Courageous. The video is terrific. It’s great that you got to sail with my good friend, Bob, and that you wrote about him, too. He’s written about others the same way, and it’s fitting that it comes right back to him. It’s an honor to know Bob.

  4. Jake,

    This is WONDERFUL!!

    Thank you for sharing these lessons…I agree…it’s what Sailing is ALL about!

    It’s never, ever too late to pursue your dreams.
    Age is meaningless when it comes to making good friends.
    Even when the wind doesn’t cooperate, sailing is better than most other ways to spend time.
    Time spent with friends is more important than winning.
    Gratitude is more rewarding than winning.
    But winning…After a season of painfully slow, incremental improvement…Is very, very fulfilling.

    Thank you!

    Maureen
    Director of Development and Community Outreach
    Courageous Sailing