Thinking critically about the future is a mainstay of best practice in any organization, and an important aptitude for school leaders, yet many feel as if the world is changing too rapidly for traditional methods and timelines to be effective. As a result, many organizations are transitioning away from discrete moments of strategic planning and, instead, nurturing a culture of continuous reflection and ongoing innovation. In this article, Matt Glendinning describes what one school in Providence, Rhode Island. did with new strategic planning tools, and the processes that resulted from seeking not just a plan for growth over the next five years, but a culture adapted for growth over the long term.