Establishing a Day of Caring to build engagement

One of the hardest things for any family to accomplish, but especially a family of wealth, is to engage multiple generations in a meaningful way. I’m convinced that one of the best ways to do that is through shared Philanthropy.

In the summer of 1999 my cousins and I ranged in age from 12 – 27. I fell somewhere in the middle, at 19 years old. Those of us who were 16 and older had attended our first Family Retreat the prior year, and were introduced to the concept of our Family Office and all that it entailed. Without delving into too much detail, I’ll simply say that it was overwhelming and exciting at the same time. We were hungry to learn more, and by the summer of 1999 our CEO had helped us come up with an interesting idea: a cousins investment group. It was aimed at teaching us not only about investing but about working together, and though we didn’t know it at the time, just about everything our Family Office dealt with, but on a smaller scale.

Our investment group, 5/4ths Investment Co, went through a lot of challenging times. After all, we were teenagers/young adults, and we had a lot going on from high school to college to first jobs. Though a few of us emerged as more engaged leaders, not everyone was as excited as when we first began. In the summer of 2003, we realized we needed to make a change. In addition to voting for our first ever chairperson, we also started to look beyond just 5/4ths. We asked the board if we could begin planning the family retreats and make them more interesting to us on a personal level.

Throughout the remainder of 2003 and into 2004 we planned. But we felt something was missing. The retreats were, frankly, a bit boring and followed the same pattern every year. A board meeting on Thursday, larger full Family Meeting and 5/4ths meeting on Friday, often supplemented with a speaker chosen by the administrative staff, golf for the adults Saturday, and a closing dinner Saturday night. Though my generation typically spent the day together on Saturday, we wondered if there wasn’t more we could do as a family. And that’s when the ideas started rolling. I wish I could say I came up with the idea that would become a family tradition, but it was actually one of my incredibly creative cousins.

We would do a family Day of Caring. Something that would engage the entire family- all three living generations – and bring us all together in the same space.

Going from an idea to actuality was the larger challenge. What type of work did we want to do? What type of organization were we interested in? Would our grandparents be able to physically do the work? If they were able to do it, would the work be interesting enough to teenagers who liked to move around all day? Would an organization in our area be able to accommodate all of us, and help us find a way to work together, or even be interested in a one day project like this?

Needless to say, we accomplished our goal, and the next retreat and the site of our very first Day of Caring was at The Parental Stress Center of Pittsburgh. We worked on all sorts of projects from planting a new roof top garden, to helping with painting projects that even our grandparents could assist with. Working together in this way brought us closer in a new way – not through financial gain through the meetings, or through food/alcohol as did with the dinners, but bonding over a shared work ethic and doing something for the greater good. To say it was successful doesn’t give it enough justice. The Day of Caring has become an integral part of our family retreats. From the planning, which engages family members who might not otherwise stay engaged, to the day itself, we have helped countless organizations, and more importantly we spend time together and have fun!

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This Content Collection offers tips for investing in your grantees’ capacity to engage volunteers, while also exploring the role of volunteering as part of the philanthropic education for your own family.

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