Your Best Philanthropy Lesson May Have Happened at the Beach
By: Leslie Gross, Senior Advisor
What if the most powerful giving strategy you never planned happened at a crab table overlooking the Chesapeake Bay?
I grew up spending summers in two very different places– a private community in Annapolis, MD and a small town in East Texas. Both shaped my philanthropic values more than any conference, curriculum, or formal training ever has.
That’s why I work in family philanthropy today.
I will come back to the specifics. But first, a question for you:
What are your children learning about giving this summer — not from what you say, but from what they see?
Because summer vacation may be the most underrated tool in family philanthropy. And most families never use it intentionally.
Why the Next Generation Is Learning Right Now — Whether You Plan It or Not
Here is what the research shows.
The Dorothy A. Johnson Center for Philanthropy and 21/64 found that next gen donors are not waiting for retirement to form their philanthropic identities.
They are doing it now.
They learn best not through instruction, but through experience — by doing, observing, and being part of something real.
The developmental path a young donor takes has a lasting effect on:
- How they think about wealth and responsibility
- What causes they ultimately commit to
- Whether giving feels like obligation or identity
That identity formation starts earlier than most families realize.
If imposter syndrome and self-doubt are barriers for adult philanthropists — and they are, as we explore in You Belong at This Table — the antidote is often rooted in childhood experiences that made giving feel like something that belongs to you.
A family governance conversation matters. But it matters less than a child watching a grandparent show up for someone, year after year, without being asked.
That is what summers are for.
What Makes Vacation Uniquely Powerful
Normal life is full of friction. Work, school, schedules, screens.
Vacation removes that friction.
It creates sustained, unhurried time together — exactly the conditions under which values form and identity takes root.
Research on family vacations and legacy consistently finds that shared experiences during unstructured time are among the most formative for children.
Not the planned lessons. The incidental ones.
Which brings me back to those two summers.
On the Chesapeake. I spent summers at Arundel-on-the-Bay, a historic private Black community in Annapolis, MD. By the 1950s it had become a gathering place for professionals and civic leaders who built something extraordinary on their own terms. Congressman Parren Mitchell — Maryland’s first Black congressman — was a summer resident. So was Alex Haley.
The civic and the personal were never separate there.
Some of what I learned happened at a table, cracking crabs overlooking the Bay, listening to adults talk about their neighbors and their obligations.
My Great Aunt Delores — a scholar and civic leader — was one of those adults. Her commitment to service lives on today in a scholarship in her memory at Coppin State University.
My grandfather, Theodore, was a proud Baltimorean and American Red Cross Volunteer of the Year. While in the city, he took me on his volunteer rounds across town, which always included ice cream and rides for the Perky Hornets –– a local muscular dystrophy bowling team.
He never called it philanthropy. It was just Tuesday.
In East Texas. My summers were spent in Cass County. My maternal grandmother was rooted in the Leek Creek Freedom Colony, a community founded by formerly enslaved people who built their own church, school, and cemetery.
My grandmother Claudia would entertain former students who dropped by from her tenure as principal at the local Rosenwald School.
I remember sitting in her kitchen, shelling peas, and understanding without anyone saying it directly -– what my grandmother gave them was a lifelong dedication to service.
None of it was designed as a philanthropic education. All of it was.
Three Ways to Use This Summer Intentionally
You do not need a formal program. You need a few deliberate choices.
1. Visit somewhere connected to your giving.
If your family foundation supports education, visit a school it funds.
If your giving has a community of faith at its center, worship there together on the road.
If your philanthropic history has a geography, go to it.
NCFP research on next gen engagement finds that concrete, place-based experiences are what move giving from abstraction to commitment. Heritage travel — the kind that connects your family’s values to a place — is among the most powerful forms of next gen engagement.
2. Volunteer together — even once.
Theodore Gross’s volunteer rounds were not framed as service learning.
They were just what happened on Tuesday mornings. But they shaped a lifetime of values in the grandchild who rode along.
GlobalGiving’s research on family philanthropy finds that even a single volunteer experience during a family trip can serve as a lasting reference point.
One morning at a food bank. One visit to an organization your foundation supports.
The memory tends to stay — and so does the sense of belonging to something larger than yourself.
That sense of belonging is what we explore in Who Do You Trust?, our piece on how philanthropists build the peer trust that sustains a lifetime of giving.
3. Let the next generation make a real decision.
Not input. A decision.
GlobalGiving and NCFP both find that giving young family members genuine decision-making authority — over even a modest amount — accelerates philanthropic identity in ways conversation alone cannot.
On vacation, this can be as simple as: here is $100. Where should our family give it, and why?
Let the youngest person at the table argue for their choice.
Then give together.
Research on meaningful family traditions suggests that rituals repeated across years build the scaffolding of family identity. A giving ritual on vacation — even a small one — can become the thing your children replicate with their own families.
What Your Children Will Actually Remember
Delores Hunt’s legacy is a scholarship.
Claudia Pruitt’s legacy is in the former students who still came to her sitting room, carrying what she gave them through a Rosenwald School in a Freedom Colony in East Texas.
Theodore Gross’s legacy is in how his granddaughter built her career.
None of this was a philanthropic program.
It was summers.
Cerulli Associates projects that $124 trillion in wealth will transfer to the next generation through 2048. That transfer will be shaped not only by estate plans and donor-advised funds.
It will be shaped by what the next generation believes about wealth, service, and responsibility.
Those beliefs form early.
They form in places where families slow down, pay attention, and live their values out loud.
Your children will not remember the conversations you had about your giving strategy. They will remember the summer that taught them — without a single lecture — that service is what your family does.
Start Here
Your family does not need a retreat or a governance framework to build a philanthropic legacy this summer.
You need a crab table.
A kitchen table.
A Tuesday morning that becomes a ritual.
Grant Philanthropic Advisors works with families to build multigenerational giving strategies that translate across generations — from the founding generation to the grandchildren who will carry the work forward. The work starts earlier than most families think, and often in places far more ordinary than a boardroom.
Connect with GPA to start the conversation.
About Grant Philanthropic Advisors:
We’re an independent firm helping clients to focus and maximize their philanthropy—in turn, strengthening the fabric of our communities. Founded in 2019, we help donors move from responsive patterns of giving by assisting clients to identify values and become more strategic in their philanthropy. Our goal is to help donors to become more effective as change-makers. We work with foundations (large and small staff teams), donor advised fund holders, multi generational families, individuals, philanthropy supporting organizations and corporations to design philanthropic strategies.