The Planning Perspectives Podcast

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 d

Planning for a loved one with special needs can raise difficult questions about benefits, inheritance, caregiving, and what happens when family members are no longer able to provide support. In this episode, Kate Duffy speaks with Sheila Gibson, Senior Wealth Advisor at Bryn Mawr Trust, about special needs trusts and guardianships. They explain how a properly structured trust can preserve assets while supporting access to means-tested government benefits. Sheila also covers trustee responsibilit

Building a successful business is one thing. Building one that endures for decades is another. In this episode of the Planning Perspectives Podcast, Jamie Hopkins and Kate Duffy sit down with Chris Bailey, Founder and CEO of Bailey Brand Consulting, to discuss the principles that have helped his firm thrive since 1985. From leadership and mentorship to brand strategy, client trust, and navigating technological change, Chris shares lessons learned from nearly four decades of helping organizations

Your past experiences, emotions, beliefs, and mindset can have a powerful influence on how you spend, save, invest, and make financial decisions, even when the numbers seem straightforward. In this episode, Jamie Hopkins and Kate Duffy explore the growing field of financial psychology, examining how emotions, behavioral patterns, and money beliefs shape financial decision-making. They discuss the lasting impact of childhood experiences, scarcity mindset, spending habits, and unconscious money sc

What happens when a successful career no longer aligns with your values, strengths, and sense of purpose? Many professionals reach a point where they rethink how they want to make an impact and what meaningful work looks like. In this episode, Jamie Hopkins and Kate Duffy sit down with Kenny Holdsman, co-founder, president, and CEO of Philadelphia Youth Basketball (PYB), to discuss career transitions, purpose-driven leadership, and youth development. Kenny shares his journey from practicing law

How much is enough for retirement, and what does a successful retirement really look like? While many people focus on reaching a specific savings number, the bigger challenge is building a plan that supports the life they want to live and gives them confidence to actually enjoy it. In this episode, Jamie Hopkins and Kate Duffy explore why retirement is about more than money. They discuss how values, purpose, flexibility, and a written income plan can help transform retirement from a financial mi