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Case Studies

Courageous Sailing (4th through 12th grade)

August 20, 2025

Participants in Courageous Sailing’s summer programs learn teamwork and cooperation through sailing. Students participate year after year and can eventually become Instructors-in-Training.

Key Takeaways

  1. Good peer relationships take time to cultivate, but can be facilitated through group activities.
  2. Cooperation and teamwork can be learned as necessary strategies for reaching a goal (such as sailing a boat).
  3. Positive peer interactions are evidenced by genuine concern for and desire to be with one another.
  4. Daily reflection can be used as a strategy to troubleshoot conflict or other difficulties.

Q: Describe a typical relationship between peers at your program (e.g. are they best friends?). What does your staff do to promote these types of relationships?

A: For our Swim Sail Science program, the kids come from four different schools and two different grades. We intentionally separate the children into four different groups that are a mix of grade level and schools. The first day is spent playing name games and doing team building activities. We incorporate team building into our daily schedule to continue to build relationships throughout the summer. The kids do not typically know each other well at the start but by the end of the five weeks, most have cultivated friendships with their peers, and often when they come the following year, they are excited to see their “best friends.”

Our Steps To Lead program is a little different. Students hail from all corners of the Greater Boston area and our younger students do not usually know anyone in their Step. Our program is super sticky and often kids start with us at age 8 and go all the way through age 15. By the time they’re 10 or 11, they’ve been coming to Courageous for several years and have built strong friendships with the peers moving through the Steps with them. Again, we make sure we do a lot of very intentional team building at the very beginning, and sailing is a natural team building activity.

Then there’s our Instructors-in-Training (IIT) program for 15 and 16 year olds. The majority of IITs have been with us since they were 8 years old. Most enter into the IIT program as best friends, and we have some that will refuse to leave each other’s side; the camaraderie in that particular group is very high as they have spent many summers together sailing. Even so, IITs that are new to Courageous are welcomed quickly into the fold.

Q: Do you mind giving an example of one of the team building activities?

A: We incorporate names games into the beginning of the program and usually do some kind of scavenger hunt at the beginning. Some staff team building favorites include “chocolate river,” and “human knot”.

Q: What are some examples of positive interactions you’ve seen between youth at your program?

A: My favorite: we had a student that had developed a close friendship with one of the other students. While sailing, we have three in a boat and an instructor. It was a windy day and one of the girls had her favorite hat on and the wind blew her hat off, into the water. If you’re familiar with sailing, you know that it’s not particularly easy to maneuver a boat back to where her hat came off. The student was notably upset but the rest of the group did a great job of working together to tack back around to where her hat had fallen off. They were genuinely concerned for her and wanted, almost as much as she did, to find the hat. It was really cool to watch the kids work as a team and be so invested in someone’s well being.  At first, they weren’t able to find it and concluded that it had sunk but refused to leave it at that and insisted on all pitching in to buy her a new hat. Luckily, when they arrived back to the dock, they found it on the rudder. That’s one of my favorite stories, that’s what it all about.

Overall, in our Instructors-in-Training (IIT) program, they insist on doing everything together. Some have graduated to staff this year, and emailed us saying, “I really enjoyed spending time with one of our other Instructors-in-Training, I would love to be able to work with them as staff, I think we would do so well together.” Emails like that aren’t uncommon and are more evidence that are students are building strong peer-relationships.

Q: What do you do to ensure that youth respect and listen to each other?

A: We put a big emphasis into our training on listening to students’ concerns. We train our staff to make sure that when something happens, that they’re addressing both their own and their student’s concerns; it serves as a good way to model for our students. We also build in time for reflection into our program, to make sure that we’re addressing challenges, and that usually helps us troubleshoot conflict before it escalates, and helps our staff better facilitate respectful conversations. We rely a lot on our staff both to model and to facilitate those respectful interactions.

Q: What do you do for the reflection activities?

A: It’s short and simple, all we’re asking is, “What’s challenging today? What could we have done better? What do you think went really well?” And our students do a really good job of articulating that, and then our instructors try to troubleshoot based on what they say.

Q: What do you do to ensure that youth cooperate with each other?

A: Sailing naturally lends itself to learning cooperation, and that’s our core activity. In sailing, you can’t get anywhere without the help of someone else; we use it as a platform to teach teamwork and communications skills. Our instructors are also given a wide variety of drills and practice suggestions to do each day that are geared towards promoting work as a team. They’ll do scavenger hunts on the water, they’ll do races which, again, promote teamwork between two people, or they’ll do drills that promote teamwork. We play tack a tag a lot, which is basically tag on the water: there’s two people on a boat that have to get somewhere so they can throw a tennis ball at another boat.

At Courageous Sailing, youth experience sailing as a platform to develop leadership skills, gain confidence, explore Boston Harbor, and delve into hands-on science. The Swim Sail Science program is a 5-week summer program for Boston children that blends academic support with sailing lessons, swimming instruction, and hands-on marine and physical science. The Steps to Lead program involves youth experience sailing as a platform to develop leadership skills, gain confidence, explore Boston Harbor, and delve into hands-on science. The Instructors-in-Training program is a 7-week summer job-training program where students make the transition from student to instructor, developing their abilities to teach, lead, and inspire the next generation of Courageous kids.

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/wp-content/uploads/2023/10/logo-sized.png 0 0 competenow /wp-content/uploads/2023/10/logo-sized.png competenow2025-08-20 11:15:232025-08-20 11:15:25Courageous Sailing (4th through 12th grade)

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Achieve

How do you achieve tasks or goals?

The Achieve skills are Critical Thinking, Creativity, and Perseverance.

These skills help young people process information, assess situations and potential outcomes, and connect actions to future goals. When young people Achieve, they engage in disciplined thinking that is rational, open-minded, and informed by evidence; consider consequences and alternatives; and evaluate information to reach a conclusion. They demonstrate imagination and originality, and stay focused on their goals despite obstacles or distractions.

The Achieve skills are most closely associated with academic outcomes, including college and career readiness. Critical thinking is one of the most crucial competencies for job preparedness (American Management Association, 2012; Kress et al., 2005). Creativity is important for classroom engagement, which in turn can impact academic achievement (Boxx et al., 2013), and is also a crucial skill for the workforce (Hadani & Jaeger, 2015). Perseverance is associated with academic success, including higher educational attainment and higher course grades (Farrington et al., 2012; Duckworth et al., 2007; Vandell et al., 2007).

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Critical Thinking

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Critical thinking is conceptualizing, applying, analyzing, synthesizing, and evaluating information to reach an answer or conclusion. Critical thinking involves disciplined thinking that is clear, rational, open-minded, and informed by evidence.

Research shows that critical thinking is linked to college and career readiness. Young people with strong critical thinking skills analyze relationships between ideas, consider perspectives other than their own, explore multiple solutions to problems, and use evidence to support their conclusions.

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Creativity is exhibiting originality, imagination, inventiveness, or ingenuity.

Research shows that creativity is important for classroom engagement, academic achievement, and workforce preparedness. Young people with strong creativity skills will generate multiple solutions to a problem, show originality, ask questions, and demonstrate curiosity.

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Perseverance

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Perseverance is focusing on a long-term goal despite challenges, consistently performing required or important tasks and demonstrating initiative in spite of obstacles or distractions.

Research shows that perseverance is important for academic success, including educational attainment and school grades. Young people with strong perseverance skills will set goals, persist in completing a task even when challenges arise, connect a current task to future goals, and try again when they fail at doing something.

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How do you connect to others?

The Connect skills are Social Awareness & Relationships, Communication, and Teamwork.

These skills help young people make contributions to their community, and develop healthy, supportive relationships with peers and adults, including those from diverse backgrounds and cultures. When young people Connect, they work constructively and cooperatively with others, empathizing with and taking the perspective of peers, advocating for their views respectfully, understanding social and ethical norms for behavior, and sharing ideas clearly and compellingly.

Not only are Connect skills useful for a young person’s ability to interact with others, but these skills have also been shown to influence academic success and engagement in the classroom (Pierce et al., 2010; Caprara et al., 2000; Furrer & Skinner 2003). Teamwork and communication are considered two of the most important skills by employers (American Management Association, 2012). Relationship-building is an important aspect of achievement in school for all ages (Birch & Ladd, 1997; Arbreton et al., 2009).

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Social Awareness & Relationships

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Social awareness and relationships involves empathizing with and taking the perspective of others; understanding social and ethical norms for behavior; and cultivating positive, supportive connections with friends, classmates, and adults.

Research shows that social awareness and relationships are important for academic achievement and engagement in the classroom at all age levels. Young people with strong social awareness and relationship skills will show respect and consideration for their peers, form friendships with peers, share interests and ideas with adults, and demonstrate disagreement or ask questions in a respectful manner.

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Communication

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Communication is making clear and compelling oral presentations, sharing ideas, clarifying information as needed, and adapting communication styles to meet audience needs.

Communication is important for interacting with others and conveying one’s thoughts and feelings, but communication skills are also important for career preparedness. Young people with strong communication skills will share ideas or information with others effectively, ask and answer questions, listen actively, and be able to summarize key points.

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Teamwork

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Teamwork is the ability to work constructively and cooperatively with others.

Research shows that teamwork is linked to improved academic achievement and improved self-efficacy. Young people with strong teamwork skills compromise during disagreements, listen to different points of view, and know how to give and receive feedback.

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How do you help yourself thrive?

The Thrive skills are Growth Mindset, Efficacy, and Self-Regulation.

These skills help young people recognize and manage their emotions, anticipate the impact of their behaviors on others, and take ownership over their actions. When young people Thrive, they believe that their abilities can grow with effort; have confidence in their ability to accomplish an outcome or goal; and are able to manage their emotions, thoughts and behaviors as appropriate to different situations. This first requires an awareness of self – the recognition of their emotions, thoughts, motivations, strengths and weaknesses.

Research demonstrates that the Thrive skills can impact a variety of behavioral outcomes, including health, safety, and good habits (Roeser et al,. 2002; de Riddler et al., 2012; Moffitt et al., 2011; Galla & Duckworth, 2015). Growth mindset has been shown to improve achievement test scores in mathematics (Dweck, 2006; OECD, 2015). Self-efficacy influences school grades and classroom engagement (Bandura et al., 1996). Self-regulation influences academic achievement, including test scores and grades (Duckworth & Seligman, 2005).

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Growth Mindset

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Having a growth mindset is believing that talent and intelligence can be developed and improved through continued learning, practice, and effort.

Research shows that a growth mindset is associated with academic success. Young people with a growth mindset will understand that mastery comes through effort, embrace feedback and constructive criticism, and seek to learn from their experiences.

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Self Efficacy

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Self-efficacy involves believing in one’s ability to succeed in specific situations or accomplish a task; is often task or situation dependent.

Research shows that self-efficacy influences school grades and classroom engagement. Young people with high self-efficacy will show confidence in their own abilities, know they are in control of their own behavior, and be open to risks and challenges.

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Self Regulation

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Self-regulation is managing one’s emotions, thoughts, and behaviors effectively in different situations.

Research shows that self-regulation influences academic achievement, including test scores and grades. Young people with strong self-regulation skills will reflect, plan, and think ahead; consider the impact and consequences of their behaviors; gain control or adjust their behavior as necessary; manage stress and delay gratification; and work well independently, focusing on tasks.

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Critical Thinking

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Critical thinking is conceptualizing, applying, analyzing, synthesizing, and evaluating information to reach an answer or conclusion. Critical thinking involves disciplined thinking that is clear, rational, open-minded, and informed by evidence.

Research shows that critical thinking is linked to college and career readiness. Young people with strong critical thinking skills analyze relationships between ideas, consider perspectives other than their own, explore multiple solutions to problems, and use evidence to support their conclusions.

Case Studies

  • Case Study: Inquilinos Boricuas en Accion (2nd through 3rd grade)
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