A full academic career encompasses both successes and failures. The purpose of this study was to delve into academic successes and failures, going beyond the conventional focus on objective measures, such as performance, rankings, and funding. Through semi-structured interviews with twelve senior academics from seven countries, we explored personal definitions of success and failure and lessons learned from these experiences. Key findings reveal shifts in senior academics' perceptions of success and failure over time and provide a window into what matters to academics throughout their careers. Drawing on concepts from research on 'regret' and 'polarities', we identify 'core realms' of success and failure. We also propose a reconceptualisation of success and failure that goes beyond positioning these as binary opposites and present a more integrated, nuanced, and holistic view of what it means to lead a 'good academic life'. We provide pragmatic reflective prompts for institutions to consider in reimagining policies and practices to better support this vision.