Philanthropy Helps Families Avoid Shirtsleeves-to-Shirtsleeves Challenge

Bruce DeBoskey of the DeBoskey Group
Bruce DeBoskey of the DeBoskey Group

When meeting with affluent family clients, advisers 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 is 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 U.S. alone, it is 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.

Best practices

A 2012 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. The study is “Three Pathways to Evolutionary Survival: Best Practices of Successful, Global, Multi-Generational Family Enterprises,” by Dennis Jaffe and Jane Flanagan.

Words of wisdom from Jaffe include:

  • “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.”
  • “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.”
  • “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.”
  • “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.”

Preparing heirs

Another important 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.

This research was conducted by Roy Williams and Vic Preisser, and published in 2010 in two books: “Preparing Heirs and Philanthropy,” “Heirs and Values.”

“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.”


In the work I do with wealthy families, thoughtful, facilitated communication around values, world views, 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.

This column originally appeared in the Denver Post, August 16, 2015.  It is reposted here with permission by the author. 

About Bruce DeBoskey

Bruce DeBoskey, J.D., is a Colorado-based philanthropic strategist working across the U.S. with The DeBoskey Group to help families, businesses and foundations design and implement thoughtful philanthropic strategies and actionable plans. He is a frequent keynote speaker at conferences and workshops on philanthropy. More information at or @BDeBo.

Check Also

Use Your Whole Brain to Improve the Way You Live Your Life

Rob Schware, a Whole Brain Living Coach, discusses the paradigm created by Jill Bolte Taylor to understand thoughts and emotions, offering tools for a more controlled, enjoyable life.

Opinion: A Middle East Quiz for Pundits & Protesters

Moshe Phillips criticizes American commentators for lacking historical understanding of Israeli affairs and perpetuating misconceptions about Zionism and Israeli policy.