This article examines how with proactive preparation, districts can manage the downside risk, and seize the upside opportunity that the current uncertain economic environment creates. The key to transforming the current crisis into a strategic opportunity is to accept the uncertainty of the current fiscal situation, recognize the uncertain dimensions of each individual decision, and structure the strategic planning process accordingly. This article details the more rigorous set of tools required to successfully navigate the future amisdt the global fiscal crisis and unpredictable federal stimulus funds.