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Wealth of Wisdom

The Top 50 Questions Wealthy Families Ask

TOM McCULLOUGH | KEITH WHITAKER

Section 1 - Thinking Through What Matters Most

Introduction

While he was Dean of Religious Studies at Stanford University, one of our contributors (Scotty McLennan) would invite guests to lecture to the university community on the topic, “Whatmatters most to you and why?” His invitees, who were all well-spoken and accomplished leaders in their fields, regularly reported that this lecture was one of the most difficult – and most rewarding – that they had ever been asked to give.

It is in a similar spirit that we begin this collection: with a focus not on the experts or the answers but on you, the reader, and your questions. Business, wealth, family, and life itself all have a way of drawing our attention away from what matters most to what matters now, from the important to the urgent. The essays in this first section are meant to help correct that natural tendency.

Patricia Angus begins that process with the question, “Are you wealthy?” This question may seem at first blush easy to answer, just a quantitative matter. But of course it all depends on what you mean by “wealth.” She invites readers to think through that question in ways far beyond money, including the impact that each of us has on the world around us.

Scotty McLennan then offers a different way to think through these large matters: engagement with serious literature. He shares several examples that touch upon the relationships between parents and children, meaningful work, and death. He closes with several lessons that he has drawn from decades of such reading as concerns that enormous question, “What are the most important factors in living well?”

The next two essays then focus more closely on thinking through what matters most within the context of significant wealth. Thayer Willis takes on the large topic of legacy: What is it? She offers a path to answering that question for yourself that begins with identifying and clarifying your values and moves to specific ways to speak about your values with your heirs. Building upon this approach, Ellen Miley Perry then offers five lessons for passing on values to children and grandchildren, lessons that concern modeling desired behaviors, telling stories, and attending to the growth of human capital.

In the fifth essay in this section, Paul Schervish introduces readers to the Ignatian practice of “spiritual discernment,” which provides a framework for thinking through – and “feeling through” – the questions facing someone who has resources that exceed his or her personal needs, such as questions about how much to give to charity and how much to leave to children or other heirs.

Finally, for most people, the answer to the question “What matters most?” depends not only on where we are going but also where we have come from. This is particularly true when the context is family. Heidi Druckemiller explores how important stories are – even or especially stories of adversity and loss – when it comes to building a legacy and connecting families across generations. Indeed, such stories might be one of the largest “asset classes” of our true wealth.

Preview Section 2

Chapter 1 – Are You Wealthy?
Patricia Angus

Chapter 2 – What Are the Most Important Factors in Living Well?
Scotty McLennan

Chapter 3 – What Are the Key Considerations in Crafting Your Legacy?
Thayer Willis

Chapter 4 – What Does Passing on Values to the Next Generation Really Look Like?
Ellen Miley Perry

Chapter 5 – How to Think Through Using Resources That Exceed My Personal Needs?
Paul Schervish

Chapter 6 – Does Family History Matter?
Heidi Druckemiller

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