Inflection Points, Portfolio Careers, and Bravery with Kristen Fitzpatrick of Harvard Business School

If you have ever wondered what HBS alumni learn about reinvention after graduation, Kristen Fitzpatrick has the inside view.

In this conversation, I sit down with Kristen, Senior Managing Director of Alumni Relations and Career & Professional Development at Harvard Business School, who has spent over two decades guiding students and alumni through pivotal career moments. Kristen brings brilliant wisdom on reinvention, resilience, and building lives that truly reflect our values.

In our conversation, we explore the reality of inflection points, those moments when we’re called to pause, reassess, and sometimes radically shift course. Kristen shares her own personal journey, the lessons she’s drawn from working with thousands of HBS alumni, and her perspective on how to embrace bravery, banish perfectionism, and see yourself through the eyes of someone who believes in you unconditionally.

If you are navigating uncertainty, questioning your next step, or simply craving inspiration from one of the sharpest minds in career development, this episode is for you.

In this episode, you’ll learn:

• Kristen’s winding journey from chemical engineer to career development leader at HBS
• Why so many career pivots happen through “happy accidents” rather than careful planning
• The surprising truth about Harvard alumni: even “the best of the best” wrestle with uncertainty, layoffs, and reinvention
• Why portfolio careers may be the future for mid-to-senior professionals in their 50s and 60s
• The four elements of career decision-making developed by HBS psychologist Dr. Tim Butler
• Kristen’s biggest advice: see yourself through the eyes of someone who already believes you can do anything

Resources Mentioned

• The Portfolio Life by Christina Wallace

• Dr. Tim Butler’s Four Elements of Career & Life Decision-Making

• Jeremy Schifeling’s “The LinkedIn Guys” Masterclass

• Lovable AI for presentations