While working as director of counselors in training at Camp Mishawaka in northern Minnesota, the author observed that while sailing, children were beginning to understand their surroundings and becoming aware of where they stood in nature. By spending time connecting to their physical location, children develop a relationship with the subconscious space around them. Once a child has grasped this connection, his or her mind opens to the potential of peace, freedom, and learning. A child sailing by himself or with a crew of peers in a large lake is just one example of children learning to connect with their environment through risk taking. Activities that have inherent dangers or that force students to take risks--like sailing--encourage their understanding and development of their own caution meter. Risk taking in the outdoor environment supports and encourages risk taking in one's academic life. It is the job of teachers and mentors, to prepare the environment so that the child can learn through multiple experiences--failures as well as successes. Offering this path to self-discovery to children allows them to develop a true and natural understanding of themselves and their unique place and space within the world.