While much has been written about theories and practices of management and leadership in education in recent years, what school Principals actually do on a daily basis is relatively unresearched in Ireland. Moreover, how Principals experience the job personally goes largely unnoticed. To investigate such questions, the researcher adopts a case study approach to gathering data from a group of 31 Irish primary school Principals. Researcher-driven diaries offer opportunities for self-observation by recording Principals’ personal reflections on management and leadership activities as they arise during the day. On completion, all of the diaries are collated into a single bound volume and a copy of the booklet is returned to each participant. Principals report that it is both interesting and worthwhile to read the entries of others and to gain insights into the daily work practices and lived experiences of colleagues. 21 of the 31 Principals are available in the following weeks for a second round of data gathering in recorded interviews. They comment about their own experiences of keeping the diaries and about their impressions of the experiences of other school leaders also. The diary and interview data are then coded and queried using QSR’s NVivo computer application and an organised framework of thematic flowcharts. The results are presented in a case study report with supporting empirical evidence and 12 different aspects of journeying in the Principal’s shoes through a myriad of daily work practices are explored. A narrative account explores Principals’ engagement with the internal and external school environments. It demonstrates evidence of positive work ethic and time management issues. It details Principals’ involvement with Boards of Management. Principals are vocal about their emotional investment in their roles and about the many positives and negatives that they encounter. Conclusions are drawn about career progression and about the sustainability of certain practices within the current system. The collated Principals’ diaries are available in the Appendices. They offer the opportunity to readers in different contexts to draw relevant and meaningful conclusions of their own.