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Philanthropy Helps Families Preserve Wealth, Values and Legacy

Best practices for avoiding shirtsleeves to shirtsleeves

When meeting with affluent family clients, advisors frequently invoke the warning: “shirtsleeves-to-shirtsleeves in three generations.”

This popular quote strongly suggests that, without careful planning, a family’s wealth will be dissipated by the time it reaches the grandchildren of the wealth-creating generation. It’s thought to derive from the old English proverb, “There’s nobbut three generations atween a clog and clog.”

Over the next 35 years, the largest transfer of wealth in history will take place.

In the United States alone, it’s estimated that more than $40 trillion will transfer from baby boomers to the rising generations. In addition, the ownership of thousands of family businesses will transfer to younger family members.

Most families aspire to preserve wealth, values and legacy over the generations. Research demonstrates that a number of factors influence a family’s ability to reach that goal.

Almost always near the top of the list is a family’s shared commitment to community, service and philanthropy.

Preparing Heirs

A major study focused on 2,500 affluent families who owned and sold businesses or who had inherited money.

The authors discovered that, over 20 years, 70 percent of those families lost control of their assets (and family harmony) in the first, second or third generations following wealth transfer. Sixty percent of the time, those failures were due to a lack of trust and poor communication.1

“Where heirs were encouraged and intelligently guided to participate in family philanthropy,” said the authors, “it had a profound impact in three major areas of their development and preparation for later life. The three major areas were values, mission and accountability.”2

Best Practices

Another study of nearly 200 families that successfully navigated the “shirtsleeves-to-shirtsleeves” challenge found that shared family philanthropy and community service was a leading best practice among those families.3

Dennis Jaffe, a professor of organizational systems and psychology at Saybrook University and a family business consultant, one of the authors of the study, observed in a later paper, that:

  • “The shirtsleeves situation arises from the behavior of the older generations, and their unclear invitation to the next generation, not necessarily from the motivation of the next generation.”4
  • “Far from being lazy or unmotivated, faced with the reality of their family’s abundance, inheritors want to expand the family’s mission to include socially responsible business, investment and community service. Too often they perceive that it is hard to offer their contribution, since it sometimes is not offered in a traditional package.”5
  • “Instead of worrying so much about their children, founders might better look to themselves to consider how they invite their children to be their partners, and how they begin to change their role from controlling owners to generative mentors.”6
  • “The elders have to create ways to reach out, listen and learn from their children who may have different values and a different approach to the family wealth.”7  


In the work I do with wealthy families, thoughtful, facilitated communication around values, worldviews, passions, interests and visions is an essential part of planning and implementing a meaningful family philanthropic journey—effectively and strategically.

Across the generations, the deepening of good relationships (and the repair of those that are challenged) is an important result of working together as a family to identify shared values and collectively design philanthropic initiatives.

The bottom line is clear: In the transition of wealth and values from generation to generation and the avoidance of  “shirtsleeves to shirtsleeves in three generations,” successful families look to rising generations as irreplaceable resources.

Philanthropy is a remarkably effective table at which all family members can sit, where they can share, teach, learn, value, grow, change and consistently improve.


1. Roy Williams and Vic Preisser, Preparing Heirs and Philanthropy, Heirs and Values (2005).

2. Ibid., at p. 5.

3. Dennis Jaffe and Jane Flanagan, “Three Pathways to Evolutionary Survival: Best Practices of Successful, Global, Multi-Generational Family Enterprises.”

4. Dennis Jaffe, “Riding the Shirtsleeves: Deconstructing a foundational family business myth,” FFI Practitioner, 2015.

5. Ibid.

6. Ibid.

7. Ibid.


Bruce DeBoskey is a Colorado-based philanthropic strategist working with The DeBoskey Group to help businesses, families and foundations design and implement thoughtful philanthropic strategies and actionable plans.


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