This article is a reflection on eight, then seven, now five womens collaborative efforts to explore the development of our own leader identities. While each of us conducts research on women and leadership, we are a diverse group of women: we were born in three different countries (United States, Paraguay, and New Zealand) and currently live in three different countries (United States, Canada, and New Zealand). We are of diverse races, sexual orientations, and generations; we have leadership experiences in a variety of disciplines and industries; and we vary in the priority we place on this study. In this paper, we review our experiences conducting research during the first three plus years of our collaborative autoethnographic study and share what we learned from those experiences. We address previously published considerations for developing collaborative autoethnographies including: the number of participants involved; the extent of involvement of the participants and the level of collaboration during the study; the collaborative approaches used in the study; and the approaches to writing. We add a reflection on our leadership practices throughout the study and on the confidentiality challenges that emerged. We also discuss how our division of the study into multiple life stages and multiple projects within the life stages has influenced our experiences and how the challenges resulting from the long duration of our study have influenced our productivity and are expected to influence our future plans. Our lessons learned should prove useful as other autoethnographic research groups begin their own research processes.