As a senior healthcare executive and fellow in the American College of Healthcare Executives (ACHE), I am often asked by junior colleagues how I became a leader. Since many women administrators still encounter difficulty in breaking through the glass ceiling to the executive suite, gender equity and personal values are frequently central to my narrative. Although more recently characterized as a labyrinth, which is neither simple nor easy to navigate, the glass ceiling, a visible, but clear and impenetrable barrier continues to prevent women from executive advancement (1). Thus, for many female leaders, negotiating a path to an executive position requires persistence and self-awareness. In describing my own career trajectory, which culminated in a position as a Chief Operating Officer, I emphasize the useful lessons which shaped my leadership behavior and the learnings that can serve as helpful hints for early careerists. Since my career path spanned work in a local health department, clinics, hospitals, medical groups, and health plans, I frequently address the mix of agencies by highlighting my dual interests in macro policy development and micro level operations. As a female senior executive, faced with countless gender expectations, I stress the critical importance of promoting women into leadership roles. Within the hospital industry where women comprise more than 75% of the workforce, yet men are 74% of the chief executives; the opportunities for women’s advancement to the c-suite remain limited (2). Early in my work-life, though there was an occasional nun or former nurse who stood at the helm of a large healthcare organization, most women leaders were clustered in department head or senior leadership roles. The executive suite was not entirely restricted; rather, women were underrepresented in general management and tended to fill nursing, planning, and marketing roles, not traditional pathways to executive advancement (3). This double standard played out on a daily basis, when male colleagues were praised for bold, visionary thinking, while women were chided for aggressive outspokenness. As a result, when it came time for CEO recruitment, boards of directors and other governing bodies tended to hire people who looked and spoke like them, typically meaning senior white males. Promotional opportunities that did exist were relatively few, and often demanded frequent moves, long-distance commuting, or family re-location, which were difficult for two career couples. Twenty five years later, despite the progress made in educating and promoting women, this longstanding imbalance endures. Recent research indicates that men advance to hospital CEO positions at twice the rate of their female counterparts (2). In addition, since women constitute only 17% of top US corporate boards of directors, interviewing with male dominated executive boards continues to challenge women today (4). This stark reality contrasts with the perception held by many that because discrimination based on gender is illegal, the issue of gender bias or gender equity no longer exists. In fact, some men even claim that “although things might have been bad in the past, everything is fine now” (5). Three decades ago, in nearly every healthcare setting, executive women mentors were either unseen or unknown. Consequently, my female colleagues relied upon our male bosses or female peers for career advice. While this informal support was helpful, mutual aims of professional advancement and work-life balance remained complex and unresolved. By choice, necessity, and a commitment to lifelong learning, I pursued self-reflection as a means to better understand the challenges, situations, and opportunities I encountered as a woman healthcare professional. To assist leaders at all levels of responsibility, and to examine their philosophy, values, and behavior, The Leadership Engine, a book by Noel Tichy, Professor at the University of Michigan School of Business and former head of General Electric leadership training, provides a useful tool called, “the Teachable Point of View” (6). Deceptively simple, this four step tool charts key nodal or life events on a timeline with positive, affirming experiences shown above the line, and challenges, failures, and unhappy incidents recorded below. The second step involves reflecting on these events relative to both favorable and disappointing outcomes and searches for recurring themes and repeated circumstances. Step three considers the principles and lessons learned and how these events influence leadership. The final step demands careful reflection and candor, sharing the self-assessment with others. In applying this approach, six themes emerged in my timeline including: Projection, Preparation, Perseverance, Parity, Proof, and Play. Together, these six Ps constitute the fundamentals that fuel my leadership engine and serve as lessons learned that ultimately guided my leadership behavior. As such, they may provide a helpful roadmap that can be emulated by others.