Time management planning (TMP) is a practice where people plan what they intend to accomplish and when in a given day. The literature indicates behaviors associated with TMP, but not how people specifically engage in them or how technology is involved. We examined TMP practices of 19 graduate students, noting their methods and how they engage with tools. Students utilized different combinations of TMP behaviors, both in comparison to each other and within their own experiences. We then asked them to plan following specific guidelines over five days. Participants implemented these guidelines in unique ways using unstructured tools (paper, notes applications). Together, these findings suggest that to be useful, TMP software must not impose a specific structure. We demonstrate opportunities to incorporate these findings through the design of a flexible mobile application based on notes applications to facilitate planning while encouraging, but not requiring, the use of TMP behaviors.