This paper proposes a metaphoric perspective based on chaos theory for strategic planning by institutions of higher education. It offers 10 propositions for planning: (1) the ideal outcome of planning is planning, not a plan; (2) planning begins with a distillation of the institution's key values and purposes; (3) the widest possible universe of information should be made available to all members of the institution and should include ongoing feedback; (4) dissent and conflict are creative, healthy, and real; (5) linearity doesn't work in strategic planning, dictation, or collation; (6) the institution should budget fiscally and psychically for failure; (7) the considerable expense of time on the front end is an investment which is recouped, with interest, in the future; (8) the executive is not demoted or minimized but ultimately is empowered by the planning process; (9) that which can be quantified is not to be overvalued, and that which cannot be quantified is not to be discounted; and (10) the future is a creation, not a prediction; this power of agency is the distinguishing context of human chaotic systems. These propositions are applied to case studies of four diverse institutions: Blue Ridge Community College (Virginia), Carson-Newman College (Tennessee), the University of Calgary (Alberta), and Red Deer College (Alberta). (DB)