Philanthropy helps families avoid shirtsleeves-to-shirtsleeves challenge

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 wealthcreating 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-toshirtsleeves” 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, MultiGenerational 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

Nonprofit of the month:

New Legacy Charter High School New Legacy Charter High School is a new public school for pregnant and parenting teens and their children, opening in Aurora this fall. The school combines a rigorous academic program, parenting education, wraparound support, and a focus on health and wellness. Impacting two generations at a time, the school is founded on the belief that young parents are motivated, responsive, and resilient when provided with the right supports.


Bruce DeBoskey is a Colorado-based philanthropic strategist working with The DeBoskey Group to help businesses, foundations and families design and implement thoughtful philanthropic strategies and actionable plans. He is the president of the Colorado Philanthropic Advisors Network, a teaching fellow with Boston College’s Center for Corporate Citizenship and a frequent speaker at conferences on philanthropy.