By Claire McKinnon

I have been working at Courageous since I was 15 years old. Instantly I fell in love with working in Step 2. I could write an entire encyclopedia on why I love Step 2 but in the end it all boils down to the students I have the privilege of working with everyday. The kids are all unique as individuals but form a clear Step 2 community for everyone else to see. Each student is kind and wants each other to succeed as much as they want to succeed them selves. This breads a unique kindness and strive for fun and knowledge that creates the Step 2 community.

Having worked in Step 2 for many years now I have seen many kids come, learn, and graduate on to bigger steps. As I walked around this year I came to the exciting and slightly unsettling realization that I have taught a majority of the children in older steps. It fills me with such pride that all of my Step 2 children have moved on and become better sailors. It unsettles me because it draws further attention to my age and that one day I will need to graduate and leave Courageous, like they have left Step 2.

What makes me even happier that they have also kept the same kindness and community, despite being from all over the city with different backgrounds and personalities.As more of my Step 2 kids graduate this year I could only hope they achieve the same experience as all the students who have graduated in the past.

 By Ali Maas

Nestled between three highways and an ocean of urban sprawl lays Jamaica

Pond. My entire life I have driven past Jamaica Pond and for years, I sat in my car,

saw a flash of white sails, and wished to be on the water. All I knew of the pond

was tiny moments speckling my life. This year many young Bostonians just

entering Swim Sail Science, Summer Learning Project, and Summer Youth

Program, and I discovered the vastness of Jamaica Pond. Led by veteran pond

travelers of summers past, we discovered the draw of Turtle Island and its

incredible ability to act as the perfect mark in any wind condition. We discovered

where the wind dies, and where the wind strengthens. Our ability as sailors

intensified as winds shifted ninety degrees and when winds died, we mastered

pointed drifting. The pond is never still. It is constantly in flux and forever

testing ones skill as a sailor to adapt. On any given day, one can see a little

turtlehead peeping from the surface.


The pond alone could make any summer job great but what makes this the

greatest summer job is truly the students. The only sad day I have had this

summer was this past Friday when I had to say goodbye to the students I have

spent the last four weeks teaching. Seeing two Swim Sail Science students who

came as best friends leave with fifteen new friends. Remembering when one such

student led his own chalk talk and each of his classmates jumped to lead their

own. Watching three Summer Youth Program students who had never sailed

alone tack on the whistle in perfect synchronization while skippering their own

periwinkle( a small wooden sailboat). Wiping glitter off the counters from

Thursday Race medals (coined the Jamaica Pond Cup) the Summer Learning

Project students begged to race in each week. What made me smile most that

Friday was hearing one student proclaim that he wanted to sail in college one day

just like me. I told him I would tune in to ESPN to watch him in nationals.


Sometimes it can be hard to remember why we sail. When its thirty

degrees outside and I’m sitting in the eighth hour of racing, gusts of thirty

nipping at my cheeks, I can forget why it is I sail. Now, all I have to do is

remember that little kid, soaked from capsize drills, so in love with sailing that he

gave up a week of baseball camp to come back, telling me he wanted to sail just

like me. I am so lucky to have been able to teach him, to see so many students fall

in love with sailing just as I once did. Most of all, I will always have the reminder

of my younger self, looking out the car window at Jamaica Pond, wanting only to


By Emily Hart

I’ve been working with the Instructors in Training (IITs) on service learning projects of their own design throughout this summer. As future sailing instructors, the IITs need to know more than just environmental facts; it’s also essential for them to practice their skills in facilitation, organization and leadership. We decided at the beginning of the summer that a multi-week project, rooted in environmental education, would encourage the development of these important skills.

Yesterday, I had the opportunity to check in with the IITs about the progress of their CANdy project, where they were encouraging students to bring in redeemable cans and bottles for a candy prize (get it??). About 30 minutes into our work on the project, the group energy plummeted. It turns out that none of the IITs really supported the project, even though they developed it as a group and decided collectively to move forward. Project CANdy was subsequently canned.

During our debrief of this project, the students talked about how everyone harbored thoughts at the back of their mind about project feasibility, yet everyone voted in favor of the project. I posed the question: In another situation, perhaps with a child’s safety in your hands, will you speak up even if no one else does? What do you say when your peers are silent? Even in our rather low-stakes environment, we found ourselves addressing real world questions around leadership and limits. I am so proud of the IITs for their insight into their process and our ensuring conversations around leadership, knowing our limitations and the power of our voices.

Because I won’t let them off the hook that easily, we decided to move forward with a new project based in our learning from CANdy. I proposed a project that has been stewing in my brain all summer: a Courageous Sailing coloring book based on local Boston Harbor species. The IITs took the idea and ran (sailed?) with it. We did a storyboard, made a few prototypes and broke the work into manageable chunks for our class next week. I’m also proud of myself for releasing the idea to their creativity and letting go of what I had originally envisioned. What they have planned is so much better than what I had thought of and I can’t wait for you to see it! 

in Green

By Morgan O'brien

For the past two summers, I have taught in the Swim Sail Science and Summer Learning Project programs at Courageous. These programs, as said before in an earlier blog post, are taken from difficult and challenging areas of the city. It is fascinating to watch these nine to eleven year-olds learn how to sail. For many of them, this is their first time on a sailboat; and for a few others, a first time on any boat at all. But they are all fascinated to be sailing on the water.

The kids, whether they know it or not, are all learning new things while on a sailboat. Such as how to drive a sailboat, how to tell where the wind is coming from, and how to trim the sails. Besides learning sailing skills, they also ask questions about sailing, the things they see on Boston Harbor, or whatever crosses their minds. Questions can range from whether or not it will rain to asking permission if we can flip the boat over. Occasionally, the kids I teach will try to teach me something new or something about the harbor that I didn’t know about or the rules in the popular Pokemon card game. One student, JJ, has tried to teach me many things. JJ has been a student in the Swim Sail Science program the past two years, and has a very vivid imagination. He has told me many new fascinating things about the harbor, one of these facts about the harbor is that “the water is green because Irish people have been in it.” JJ has also told me and other instructors countless other pieces of information about sharks, dogs, and dog sharks. Taiquan, another Swim Sail Science student, has also taught me several interesting facts about myself and the harbor as well. One of the things he has said is that “humans don’t have hair, they have feathers”. 

Several other students in the SSS and SLP programs have tried to each me new things as well. Without the students in these programs, I would be completely oblivious to dog sharks and the feathers that are growing out of my head. It is great to see that kids at such a young age have a vivid imagination that help keep the program and the day sailing interesting. It would be a very different program if the kids did not feel that they could question how the sail boat works, what was in the water, or anything else that came across them. Really, the kids make these programs enjoyable for themselves and their fellow campers, all I do is teach them sailing.

By Emily Hart

On Thursday, our Summer Learning Project students learned about fossil fuels and went coal mining to explore the effects of mining on our environment.

We simulated coal mining by mining chocolate chip cookies (the “land”) for chocolate chips (the “coal”) with only toothpicks (“very high tech mining equipment”). It was great to see so many heads down in concentration! After carefully counting the total number of chocolate chips in two different kinds of cookies, I caved to the ongoing pleads to actually eat the cookies. But before they could eat them, I told the students they needed to put their cookies back together.

Stunned silence. “I can’t put my cookie back together!!”. This activity illustrated the effects of coal mining and other extractive industries---it’s difficult and sometimes impossible to restore the land to its original condition. What followed were conversations around energy use and other options, like solar and wind, which we had learned about the previous week.

I was reflecting on this activity during a meeting the follow day with Dave, (Courageous Executive Director), Chris (a board member), Kate (Director of Youth Programs) and Rebecca (Youth Program Outreach Coordinator). It was great to talk about the environmental education program this summer and to look towards the future together. There are so many opportunities to expand the Courageously Green Initiative, from seascape murals on the boathouse walls to air dryers in the bathrooms and the elimination of paper towel waste. There is a lot of potential with the Instructors in Training (IIT) program and with staff education, in addition to continuing to refine the student curriculum. I’m keeping track of our ideas and would love to know—how do you think we can continue to be Courageously Green?

in Green