For 36 years, the author grappled with the insidious trap of people-pleasing. A revelation during a yoga retreat sparked a journey of self-discovery, exposing the unspoken transaction that fuels resentment and self-harm. Through the lens of celebrities and experts, the author explores the telltale signs of problematic people-pleasing, its generational roots, and the transformative power of setting boundaries. The article highlights various therapeutic approaches, emphasizing that unlearning people-pleasing is a process, with mindfulness and self-validation as crucial starting points.