In this autoethnography, I explore the process and emotional experience of trying a new drug to improve my quality of life. In so doing, I synthesise personal history with extant research on chronic illness by analysing ways in which my experiences reflect and reject social norms. I also incorporate perspectives from research on aspirations and attainment, and the mental health consequences of cyclical disappointment. By weaving together lessons from each of these literatures, I articulate an integrative psychosocial understanding of the micro‐level processes and experiences involved in illness management as well as the ways that experiences of illness management may require integration of varied sociological insights concerning health. In closing, I draw out theoretical implications for understanding the integration and variation of insights from many areas of health research in the lived experiences of people with chronic conditions. A Virtual Abstract of this article can be seen at: https://youtu.be/5aoaWGItDgM