This study is an autoethnographic piece which conducts research through personal reflection to identify the mindsets of male primary educators. These mindsets are broken down into three distinct stages which show the progression based on experience and challenges. The first stage focuses on training and the disposition of male students who are in the process of becoming a teacher. Stage two highlights the challenges and difficulty of being a male provisionally registered teacher and the isolation of working in a feminised career. Finally, stage three investigates the role of male educators as mentors and learning from their experiences. Data has been found by using my own experiences and deeply personal reflection into historical events in my life which build a picture of these different stages and how I progressed through them. This research notes that some of the findings which influence these mindsets include personal belief systems, effect of upbringing, as well as the challenges and pressures from society. All of these are shown to either help or hinder the progress through these stages. Additionally, there is discussion into the potential differences between the genders when teaching and how society has an impact on the male educators based on media perspectives. This research concludes with insights and recommendations to help create a diverse workforce that supports the minority of men who choose to teach young children.