Sailing with Bob

Jake DiMare went looking for sailing and found so much more.

As a boy I spent a lot of time sailing small boats on ponds and lakes around New England at one summer camp or another. I was fortunate enough to have a close friend whose dad was a retired Captain in the Merchant Marine. As teenagers he took us out for countless day sails in and around Boston Harbor on his 28′ Southern Cross, the “Truant”. During summers off from high school we also went on a number of extended trips, including a tour of coastal Maine, the Cape and Martha’s Vineyard.

The times I spent aboard the Truant are genuinely among my fondest childhood memories. Out there on the water I learned how to sail, but I also learned how to work with whatever situation I was dealt, and how to rely on my meager but growing ability. I developed a sense of pride from being capable of harnessing the elements. Sadly, like all of my childhood interests, this pursuit soon took a twenty-year back seat after I discovered booze and women.

I remember the moment when sailing became part of my life again very, very clearly. I was riding my incredibly loud motorcycle down the road one night when I looked down at my heavily tattooed arms and suddenly realized there was simply another way I wanted to spend my free time. Much to the confusion of my friends I sold my motorcycle within weeks and declared an intention to sail around the world someday.

I began attending boat shows obsessively and spent hours pouring over listings online and talking to dealers. One thing became evident to me very quickly: There are economic reasons why sailing isn’t a more popular sport.

Fortunately, as I soon learned, there are many alternatives to buying your own boat and that’s how I discovered Courageous Sailing. In addition to giving paying, adult members a way to get out onto Boston Harbor whenever they like, this community organization provides free sailing to local youth. I joined immediately and attended every class I could fit into my schedule.

This past spring, beginning my second year with Courageous, I decided to take up racing. At the time my goal was only to get more time on the water, hopefully improving my seamanship in the process. My plan was as simple as it was self-absorbed: 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 discover most of the other sailors had done this before. However, almost everyone else was already broken up into teams. As I glanced around the field of competitors, while reliving the 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 genuinely 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…”

As Bob and I set sail I promptly discovered every assumption I made about his sailing ability was wrong. He was an intelligence officer in the Navy and had only started learning to sail a couple of years ago, when he turned 72. This was a disappointing setback in my master plan. As we trailed the pack in our first race I remember thinking I was in for a summer of losses and long, dreadful conversations with a septuagenarian about his favorite shows on Fox News channel.

However, Bob didn’t live up to any of my assumptions on or off the water. Quite contrary to the image of the cantankerous old conservative I anticipated, Bob is an energetic, positive-thinking progressive, who spent much of his career at the Environmental Protection Agency after leaving the Navy. And, as incredible as it may seem for a man at his age, Bob’s activities are hardly limited to racing sailboats. Although retired he’s very active with political organizing, non-profit work and, of all things, yoga. 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, and I was once again reminded of that old adage: 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 a talented young sailor named Chris who raced in college. With him on our team we became extremely competitive. Wins started to stack up, and with them came a sense of growing pride and ability.

As it turns out, I ended up learning much more than I had anticipated about sailing this year. However, I also picked up a few, much 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.

But incredibly, and as great as it was to learn all these things, something even more important happened for me this past summer at Courageous. I went looking for sailing, and I found it, but I also found community. A group of people with a genuine sense of fulfillment from being surrounded by other people with common interests.

Believe it or not, this is a new trick for this old dog. Up until that night on the motorcycle, when I decided to get back into sailing, almost every decision I had ever made was based on some external pressure or unhealthy desire. Some influence other than simply realizing this…This is how I want to spend my time. What a gift it is to have people to share it with.

For anyone who is interested in seeing what racing sailboats with Courageous Sailing looks like, I put together this video montage for my teammates. The footage is a little shaky but there are some epic sunsets…

About Jake DiMare

Jake DiMare lives in Boston, Massachusetts with his fiancee Jackie. In addition to writing for the Good Men Project, Jake is a digital strategist managing large scale web projects for government, health and higher education clients. When Jake’s not at work he enjoys sailing, Brazilian Jiu-Jitsu, movies and hanging out with friends. Jake blogs at and can be found on Twitter @jakedimare

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