The Misunderstood Role of a Trustee - Torri Hawley

What to do when you don't have to work - Episode 23

What does it really cost to not have to work? This week we discuss the paradox of comfort, the counterintuitive challenges that arise when financial wealth removes the necessity of working. It sounds like a dream. But for trust beneficiaries, next-gen family members, and anyone whose financial security has outpaced their sense of purpose, the absence of need can quietly erode confidence, identity, and readiness for life's inevitable responsibilities. This is a conversation about redefining work — not as the way you pay the bills, but as the way you create meaning, build resilience, and show up for the world. And it comes with a practical framework: five coaching questions to help you (or your clients) get unstuck and design a life with intention. Topics covered: -The mental health costs of living without purpose-driven work -Why identity and self-worth are so tightly tied to what we do -Real responsibility: what happens when life demands it and you haven't built the muscle -The pendulum problem in multigenerational families -How to redefine success on your own terms If you work with wealthy families, are part of one, or are simply thinking about what your relationship with work should look like, this one's for you. Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/ Follow Vincent: https://www.linkedin.com/in/vincentvaleri/ Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge

How to Turn Strategy to Action | Keita Demming | Episode 22

Why do we put off the conversations that matter most? Whether it's a tough call with a business partner, a long-overdue chat with a family member, or feedback you've been sitting on for weeks, avoidance has a cost — small misunderstandings turn into resentment, and resentment turns into broken relationships and lost opportunities. In this episode, we sit down with Dr. Keita Demming — award-winning educator, coach, and Director of Development & Innovation at The Covenant Group — to talk about how to stop dodging hard conversations and start having them sooner, with more clarity and less damage. In this conversation, Keita shares: * Why leadership is fundamentally about noticing what others ignore — and saying it out loud * The ISI Model (Indisputable, Sense-making, Interpretation) and how it keeps difficult conversations grounded in facts instead of feelings * How to separate what actually happened from the story you're telling yourself about it * Practical techniques for family enterprises, where personal ties and professional roles collide * Why collaboration — not winning — is the real goal of any hard conversation * How to set up a conversation so the other person can actually hear you Learn More about Keita  * 🌐 Keita's website: keitademming.com [https://www.keitademming.com/] * 🏢 The Covenant Group: covenantgroup.com [https://www.covenantgroup.com/] * 📘 Buy Strategy to Action: Run Your Business Without It Running You:  * Amazon (US) [https://www.amazon.com/Strategy-Action-Business-Without-Running/dp/1774582708] * Barnes & Noble [https://www.barnesandnoble.com/w/strategy-to-action-keita-demming/1144040520] * Page Two (publisher) [https://pagetwo.com/book/strategy-to-action/] Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/ Follow Vincent: https://www.linkedin.com/in/vincentvaleri/ Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge

The Paradox of Wealth & Happiness - Episode 21

We keep seeing the "paradox of choice" show up in our coaching work with Rising Gen clients from affluent families. The theme has re-emerged with a vengeance: young adults in their 20s who have every door open to them, and yet can't seem to walk through any of them. Thats why this week we're unpacking  why access and abundance can actually stunt decision-making, and why high-achieving kids who thrived with a clear rubric in school can become completely disoriented when the rubric disappears. This Week We Are Discussing -Why Rising Gen clients from affluent families keep getting stuck -The paradox of choice — and how the jam study explains it -Why shame and fear make it harder to ask for help -A practical framework for building your own rubric and getting unstuck -Why the first decision at 25 doesn't have to be the right decision — just a decision Shout Out To The Following Books The Defining Decade by Meg Jay [https://www.linkedin.com/preload/#] Designing Your Life by Bill Burnett [https://www.linkedin.com/preload/#] & Dave Evans Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/ Follow Vincent: https://www.linkedin.com/in/vincentvaleri/ Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge

The KPIs of Family Succession - Dr.Dan McDonald | Episode 20

In this episode, Dr.Dan McDonald (human factors psychologist with military and government experience) breaks down how trust, leadership, and culture actually determine whether family wealth lasts or falls apart. We get into: -Why “soft skills” are actually hard ROI drivers -How to use simple frameworks (like logic models) to measure what matters -What families can learn from the military about leadership and succession -How AI, tech, and generational shifts are changing everything Follow Dr.Dan:https://www.linkedin.com/in/dr-daniel-p-mcdonald/  Performance Absolute: https://performanceabsolute.com/ Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/ Follow Vincent: https://www.linkedin.com/in/vincentvaleri/ Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge

Planning For End Of Life and The Silver Tsunami - Robin Norcross | Episode 19

This week we're talking about one of the toughest conversations of all - how to ensure a meaningful peaceful death of a loved one.  We're joined by Robin Norcross (Purposeful Passages) who guides us through proven strategies to normalize death talk, helping you can prepare for the inevitable with dignity and love. We Discuss -The surprising truth about why most people fear talking about death and how to overcome it -A simple framework to start meaningful conversations with family about end-of-life wishes -Why planning ahead leads to less pain, suffering, and conflict when the time comes -The impact of the coming “great transfer of wealth” on caregiving and legal systems -How embracing death as a natural part of life transforms our relationships and legacy Follow Robin: https://www.linkedin.com/in/torri-hawley Purposeful Passages: https://www.ourpurposefulpassages.com/meet-robin Follow Kristen: https://www.linkedin.com/company/legacy-coaching-llc/ Follow Vincent: https://www.linkedin.com/in/vincentvaleri/ Watch Us On YouTube: https://www.youtube.com/@TheFamilyWealthEdge