Most charitable giving research focuses on individual donors at a specific point in time and uses quantitative surveys with limited data about donors' experiences. This study uses reflective interviews to examine the life trajectories of a cohort of women donors who have made gifts of $1 million or more to causes that benefit women and girls. By drawing from developmental psychology, we illustrate the iterative process of learning about giving—shaped by life experiences—that comprise the journey to becoming a million‐dollar donor. We find that, in their journeys toward making their million‐dollar commitment, women donors followed a shared trajectory with distinct stages and prompts for progression. Our findings provide guidance for fundraising professionals to recognize the stages of a potential donor's readiness to give and to facilitate progression in the journey, thus increasing the potential for more large‐scale gift commitments in the future and deepening the donor–fundraiser relationship.