In the season 1 finale, I sit down with Shannon Alfonso, recently retired insurance executive who led Marsh McLennan Agency’s Florida Region to remarkable success during her nearly 30-year career. From an unplanned start in underwriting to becoming the region’s first female CEO, Shannon’s story is one of curiosity, courage, and staying true to her core beliefs. She shares how a willingness to learn, embrace new challenges, and build strong teams shaped her journey. Shannon reflects on overcoming imposter syndrome, trusting her instincts, and the pivotal moments that defined her career. Her advice for aspiring leaders? “You very well can be the right fit. You just have to embrace it. Be confident. Go for it.”

Now retired at 54, Shannon reveals why she chose to step away from the corporate world while at the peak of her career, challenging the traditional norms of retirement. She speaks candidly about the sacrifices she made for her career and how those shaped her decision to prioritize time with her family. Shannon shares how she's embracing the next chapter with rest, reflection, and the freedom to pursue meaningful work on her own terms.