Although she retired in 2003, Felicity has remained active in academic and scholarly life. Among her recent publications is an edited book, Philosophy in Schools (2016, Routledge).As Immediate Past President of PESA and as a scholar with a keen interest in equity, gender, and identity issues (e.g., Jackson, 2019;Jackson & Peters, 2020), I reached out to Felicity as I was curious to learn from her experience over time. Thinking about the hurdles I have faced in my career, I was interested in knowing if she had similar challenges or experiences, and what advice she might have for others to succeed in the context of higher education and the field of philosophy of education.In this interview, which was conducted through a series of emails in early 2021, I enjoyed learning from her broad view. Felicity shares in her interview a variety of challenges faced, as a woman and as a philosophical thinker, over time. She also provides an entirely unique perspective, informed by her own philosophical and life journey, and shares a great deal of practical wisdom related to how to be a leader, face challenges, and move forward as an ethical and caring actor.The following interview has been lightly edited and reorganised with confirmation from Felicity, but it is basically published here in its entirety. I wish to thank Felicity for her generosity with her time and for her warmth and friendliness during this unique spell in our history, where we cannot meet face to face given COVID-19 restrictions and related complications, which makes an email conversation with richness and depth a special treat.