Systems take on life from the existing conditions in the surroundings. Living systems are complex and what emerges comes from the interaction of various forces in the system rather than from a purposive cause-and-effect linear sequence. Human beings have the capacity for self-organization and making meaning to what is happening. As people come together to share their narratives, they come to sense what might the future be and what they may do today to somehow make the future possible. Using the Two-Loops model of Meg Wheatley and Deborah Frieze as well as borrowing from the practice of Dave Snowden on complex adaptive systems, Chris Corrigan shares a down-to-earth narrative of the evolution of communities of practice in Bowen Island, BC . He demonstrates through a walk of some significant community projects how the people of the island evolved from disconnected pioneer-settlers to a united community with a common purpose, continuously co-creating a future, and building bridges for the rest of the community to move forward from higher grounds.