Family, Leadership, and Career Transitions (Ep. 29)

What does it take to navigate success, setbacks, and career transitions at the highest level? Jamie Hopkins and Kate Duffy sit down with former Phillies General Manager Rubén Amaro Jr. for a conversation about family, leadership, resilience, and the lessons that shape a lasting legacy.

Amaro reflects on his family’s remarkable baseball journey, from his father’s path from Cuba to the Major Leagues to the values of perseverance, education, and hard work that have guided multiple generations. He discusses the realities of leadership, learning to manage former teammates, developing new skills, and the mentors who helped shape his approach to leading people and organizations.

Along the way, Amaro offers insights on handling adversity, building confidence through setbacks, and  creating opportunities for the next generation. Whether you’re leading a team, navigating a career change, or thinking about the legacy you want to leave behind, this episode delivers timeless lessons on growth, leadership, and purpose.

Rubén discusses:

• Why negotiation was the skill he most needed to develop, and how a boss who gave him autonomy helped him build it
• How he learned to stop measuring his worth by daily results and handle setbacks differently later in his career
• Why separating himself from teammates who were close friends was the hardest part of moving into the front office