On & Off Campus Blog

The importance of mentorship
The importance of mentorship
By Tess Holland '23


Sailing has been my summer escape for years. Ever since the whimsical decision to take a chance and sign up for “baysail” at my camp for a week in summer 2016, I now jump at every opportunity I get to go sailing. I love being out on the ocean for hours, seeing little fish slither below the boat or the seals that pop their heads above the surface to say hello when passing by. The best days, however, are when excitement is at a fever pitch because the wind gusts fill the sails with such force that you feel as though the boat is going to take off flying, or better yet, capsize into the chilly water that is home to scary sharks.

Previously before trying baysail, I had only sailed a tiny Sunfish on relaxing and comforting Cape ponds. However, sailing on Cape Cod bay (hence the activity name, baysail) was a whole different kettle of fish. It was intimidating, frightening, and where only the “big kids” at camp went, so as a shy eleven-year old, I was feeling unsettled about my bold decision. The entire time leading up to getting on the sailboat, I was second guessing my decision and regretted my chosen activity, longing to be on the pond with my friends who were sailing with no fear, only fun. And to my dismay, it only got worse once I got on the boat. With the wind, the waves, the clanging of the boom, and continuous ducking to avoid being thwacked off my tiny noggin, I was practically on the verge of tears the entire time on the bay, but I resisted crying for my own dignity. I was with a counselor I didn’t know, and campers who were older and much scarier, so I held back the tears to avoid making my already bad situation, even worse.

However, after getting past the first day scaries, I quickly came to the realization just how liberating and blissful the experience was. One could even say I became obsessed; each day I would arrive early to camp just to ensure I could sign up before the slots filled. I practiced my knot-tying all day when not sailing until my fingers were sore, and snuck rope and papers that listed all awards and their requirements in my bag to study when I got home. Thus, I quickly earned my “camp swag” through racking up Sailor of the Week (four times, to be exact) and blowing through the skill levels until I reached intermediate, one of the hardest to accomplish. But more importantly, I learned independence, reliability and responsibility, and confidence in myself that I had previously lacked.

The summers of sailing continued on until two years ago when I became a junior counselor and my sailing abilities were put to the test. I not only had to handle myself on the water, but also had to handle a sailboat full of energetic and spastic little campers who had never sailed before. Many were nervous and filled with hesitancy, just like me on my first day of baysail years before.

However, one boy in particular reminded me of myself more than any other campers there. When he was the only one assigned to my boat, I was relieved he was the only camper I would be responsible for. He was a bit shy, yet eager to be out on the water, but after rigging the boat and waiting to receive the castoff signal, I noticed he started to get anxious. Slight anxiety quickly turned to full on fear when we ultimately launched. The boy started panicking, tears streaming down his face, and a look of pure horror. It was an hour of sailing, filled with screams, tears, and white knuckles gripping the side of the boat.

Back on shore, the little boy was still shaking from his traumatic experience, just like I had been when I was his age. He told me he would never sail again and that it was the worst hour of his life. I could understand and empathize with him, but I knew he had to give it one more chance just like I did. I hugged him and made him promise that he would come back tomorrow and sail with me again. I saw a little smile peeking through when our pinkies locked.

Although I had my doubts when he left for the evening, the next day he came back, followed by the day after that, and the day after that. The little boy ended up embracing and loving baysail, which gave him confidence in the water, always asking to steer the boat and catch the mooring. He eventually achieved Sailor of the Week and asked me to help him start on his requirements for his beginning awards.

This experience taught me the importance of mentorship and how influential someone can be in helping another improve and become a better version of themselves. If I didn’t encourage him to try sailing one more time, his love of sailing may have never emerged, and he wouldn’t have experienced the confidence-building of conquering a fear and learning to trust yourself.