A traditional learning methodology known as self-directed learning (SDL) is used in this study as a foundation to design a learning management system that can help students improve their abilities to self-manage and monitor their overall learning activities and performances. Such capabilities have been shown in past research as being critical to success in on-line learning environments. While research has demonstrated that SDL skills exist to a degree in all learners and their competency levels can change, this study investigates whether students’ SDL abilities can improve as a result of using a designed personal learning system, Self-Directed Learning Management System (SDLMS). SDLMS is aimed at enabling students to be more proactive in planning, organizing, and monitoring their course activities. The features of SDLMS are designed based activities that are deemed critical according to literature on SDL and its related fundamental concepts. Initial results of an exploratory study indicate that while learners feel it is very important to manage their online learning activities, they do not have a comprehensive systematic process. Study participants strongly agree that they would benefit from a tool that empowers them to actively interact and collaborate with others, tracks various course-related tasks, and measures milestones as a means to provide a self-monitoring mechanism to achieve learning goals.