Joan Gilmore: I started out chartering with friends in the early ‘90s on Lake Superior. For me, this was late in life! I remember looking up at all the halyards, and wondering how I’d ever figure it all out. I think that the feeling of being an adult rank beginner has really helped me as an instructor. My memory of being overwhelmed by everything new has helped me, as I know exactly which skill to present first, so that the skills are scaffolded logically, and learning is faster for students. I think that learning to sail later in life gives me a real advantage in working with my adult students. I have hired instructors who have sailed since they were little. They often have a hard time communicating how to do something that comes as naturally to them as walking.

Joan Gilmore: Once while sailing through the Apostle Islands off the coast of Wisconsin on Lake Superior in a 103/104 class with 5 students on a glorious summer day, a middle-aged burly male student, who happened to be on the helm, suddenly broke into a baritone operatic aria. His exuberance so completely typified that wonderful feeling you get when the sun is warm, the wind is crisp and the boat is clipping along like a dream.

Joan Gilmore: I never get tired of the British Virgin Islands. I have taught a total of over 70 weeks in the BVIs. There’s always a new spot to explore. The people are wonderful. There’s virtually no crime, so we can leave the yachts at anchor without worry.

Joan Gilmore: I majored in philosophy as an undergrad, and studied existentialism and utopianism. Existentialism is about self-actualization and self-determination. Sailing is something that helps people realize their unique individualism. Besides as a mode of transportation, sailing is the perfect melding of self with the laws of physics and the laws of nature. It is very grounding, which is ironic since it can only happen in a fluid environment. All puns aside, sailing can be a solo sport and it can be a social sport. Big boat cruising is by nature a cooperative sport. A live-aboard boat becomes a wet lab of social interaction. Every person on the boat has to cooperate for the boat to proceed. And any problems must be solved on the spot, as perpetual motion is a given. And it is a self-contained environment so that the only forces at work are the boat, the whims of nature, and the skills and resourcefulness of the crew. I find this very profound, as a crew is literally a small, self-contained utopia for the duration of the cruise. It can be wonderful or it can be hell; it all depends on the combination of the people onboard and what they make of what they have.

Joan Gilmore: More than any other sport, sailing is so adaptable to any age group or personality type. The lawyers can enjoy contesting the race results; the athletes can sail fast, tippy scows; retirees can cruise along on keelboats; and princesses can enjoy basking in the sun on a level-sailing cruising catamaran. Of course, these are just caricatured stereotypes, but the fact is that there’s no other sport that has such a diversity of expression.

Joan Gilmore: Lots of students come to me when they are going through life transitions. Often it is empty nesters who want to develop parts of themselves that they haven’t had time for yet in their lives. Developmental psychology has shown that as people age they are attracted to endeavors that will develop untested aspects of themselves. For people who have spent a lifetime working in an office, being in nature and dealing with the physical world is a refreshing change.