Does thinking about web projects for digital libraries make you feel as though you're trapped between a rock and a hard place? You will need to engage digital library partners and stakeholders; collect and analyze diverse data streams to understand use of your current digital library; define the roles of project team members; develop a comprehensive communication plan that serves a diverse audience; produce and disseminate project plans; and that’s all before web development of the project even begins! Talk about a Sisyphean task! Instead of pushing that rock up the mountain only to have it tumble back down again, join us for a presentation that highlights effective strategies for planning digital library web projects. This presentation will describe the planning process for the University of Houston Digital Library Redesign Project. We’ll tell you how we rocked it and we’ll point out where things got rocky. No matter what web project you are hoping to initiate for your digital library, you can be the project planning rock star.