The purpose of this exploratory study was to develop categories of work meaningful to elementary school principals that are significant at the beginning of one's career and after ten or more years on the job. A total of 15 public elementary school principals were interviewed. Using grounded theory, the interview data were analyzed and coded for topics that represented work concerns in beginning and later career. The results were interpreted within the Dreyfus model of learning to identify the principals' levels of performance and through the Greenfield model to identify the areas of principal work that presented continuing challenges for both novice and veteran principals. The analysis of the data revealed that principals confronted by time management issues such as the pace and multiplicity of demands in the first year of work have difficulty gaining control over their jobs, primarily in the Managerial and Social Interpersonal Dimensions. Veterans continue to incorporate changes in the Instructional Dimension that is the focus of educational reform initiatives. Data also suggested that the performance and behaviors of principals in their first two years indicated that they are functioning as learners at the Novice and Advanced Beginner levels of the Dreyfus model. Based on the results of this study, it is concluded that the work of principals is learned primarily through job experience, with little or no formal help. Feedback in the form of clear expectations and guidelines for calendaring and district procedures will enhance principal learning and make them more efficient managers of their time; opportunities for guided reflection will provide ongoing support for continuous learning on the job.