The distinguished Harvard Business School Professor Emeritus, Richard Tedlow, and the Chair of Psychiatry at Massachusetts General Hospital, Maurizio Fava, are holding in Boston on October 14, 2023 a highly interactive workshop on “Psychological Challenges and Leadership.” Psychological challenges often play a critical role in leadership. Sometimes these challenges can be harnessed to the advantage of the leader and the organization. At other times, such challenges can be severely detrimental to both the leader and the organization. The purpose of the workshop is to host a discussion about how psychological issues can be identified by executives who are not mental health professionals. How do subordinates “manage up” in the face of a visionary leader whose visions are not altogether rational? How do leaders deal with talented employees whose talents are entwined with irrational issues? How can the leaders themselves achieve a perspective on their own behavior and manage it to the advantage of all constituencies? These are some of the issues which will be discussed at the workshop. We will analyze these questions through the lens provided by three remarkable individuals: General George S. Patton (1885-1945), fashion designer and entrepreneur Kate Spade (1962-2018), and industrialist and entrepreneur Henry Ford (1863-1947). The stories of these leaders contain lessons from which people ambitious to “make a dent in the universe” can profit. These lessons will be the focus of the workshop.