A friend of mine from Coro, Joe, was telling me a story about his family. His wife is a busy executive and Joe often plays Mr. Mom. Their mornings are hectic and frenzied scenes where getting ready for work, feeding the kids, and getting everyone out the door in a timely way is the goal. Pretty typical setting for most families. His wife is cooking some eggs, Joe is tending to the one year old and the 4 year old son chimes in, "Dad, what's a hard-on?" Multi-tasking Mom overhears and wheels around and expounds, "WHAT did he say Joe?" And proceeds to lecture Joe about the evils of TV and their responsibility to monitor what he is watching and gets off on a good rant. Joe holds up his hand to his wife and says, "Wait!" Joe turns to his perplexed son and asks "Why do you ask? And where did you hear these words?" Mom has her arms folded and is IMPATIENTLY glaring at Joe. His son replies nonchalantly, "On Winnie the Pooh," and goes back to eating his cereal. "Really, Winnie the Pooh?" Joe queries. Joe sneaks a glance at his wife. His son continued, "Yeah, I just wanted to know why Rabbit is so hard-on Tigger."

A couple of days ago, I met Charles Collier from Harvard. He is a much sought after speaker on family philanthropy, how to engage families of wealth in legacy and estate planning. He was addressing some of the well-healed donors with whom I work. His book Wealth in Families is a great primer for families to have these conversations, especially in how to engage the next generation or two. His lessons apply to all families and to our lives in general. He poses many WHY questions. Questions that will create "break through" moments, questions that help families understand who they are and what they want. 

• Why are we involving you, our children, in our estate plans?
• Why is philanthropy important to this family?
• Why do we care about legacy? 

Collier also wants the family to understand HOW the family made money, what values and struggles it took to achieve their success. Having a series of family meetings around the future of the family triggered by estate planning will yield great benefits. 

The idea of constantly asking ourselves and the people we care about around us break through questions is essential. When we ask ourselves WHY we are doing something or why this is important, we have to reflect and evaluate the path we are on. When we ask WHY of others we help them pause and reflect too. The WHY question used judiciously can be very helpful in finding the truth. Besides, WHY does Tigger bounce so much? 🙂

Thanks for reading. John