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In this chapter, I share my experiences as a doctoral student to answer the questions: How do you know if a doctorate is for you? How do you find a supervisor with whom you can connect on both a professional and personal level? And how do you know what to research and how to research it? I also share the bang-ups and hang-ups of my doctoral journey and the strategies that helped me cope with the inevitable mental wellness challenges of dissertation-writing, including, in my case, navigating the COVID-19 pandemic. I stress the importance of finding a supervisor who appreciates the learning process and understands that learning is often convoluted and messy. I highlight the need for taking the time to fully explore the theoretical and methodological approaches of your field and subjecting your thoughts and ideas to regular scrutiny.