Complex information management implementation projects develop cyclical downturn patterns that, if not managed effectively, can throw them off course. These cycles are intrinsically related to contradictions that are normally embedded in the project's goals and expectation. the position presented in this article is that managing these cycles is more effective than attempting to eradicate them. Human services information systems are examples of systems that embed enormous contradictions. This paper uses the context provided by homeless management information systems to present a model of project management evolution. It explains how the cyclical pattern presented here can be used as a learning model that recognizes the limitations of deterministic project management thinking and the value of deferral planning, experimentation and balancing. The paper proposes a strategy to deal with this.