Have you ever found yourself caught between the weight of the world that you have inherited and the responsibility of what you’ll leave behind for your children and your children’s children? Recently, I’ve been reflecting deeply on the Hebrew phrase L’dor V’dor—literally “from generation to generation”—which speaks to the sacred transmission of Torah and its teachings, but extends far beyond religious text to encompass the ongoing flow of values, traditions, and our collective responsibility for Tikkun Olam—repairing the world.

This reflection has been particularly poignant as I witness families navigating what researchers call the greatest wealth transfer in modern history—more than $100 trillion projected to move from baby boomers to millennials and Generation X over the next 24 years, affecting everything from family businesses to charitable giving. But beyond the financial capital lies something far more complex and precious: the transmission of values that will shape not just family legacies, but our shared future.

“It is not your duty to finish the work,

but neither are you at liberty to neglect it.”

— Rabbi Tarfon, Pirkei Avot 2:16

What I’m Listening To: Questions That Stop Time

Krista Tippett’s OnBeing podcast recently launched “Hope Portal,” in which she begins by asking two questions that have been reverberating through my thoughts:

“Right now, today, what is filling you with despair?

And what is giving you hope?”

These aren’t casual inquiries. They’re invitations to discover what we’re truly inheriting from this moment in history and what we choose to pass forward.

When I sit with these questions in the context of family philanthropy, I find myself thinking about the young adults I work with who are grappling with inherited wealth while confronting global instability, systemic inequality, and climate change. Their despair often centers on the magnitude of problems they’re inheriting. Their hope is predicated on the unprecedented opportunity to use their resources, creativity, and collaboration in ways previous generations never imagined. Krista emphasizes that none of the great virtues, including hope, are meant to be carried alone. We are called and invited to surround ourselves with others, to look back at what our ancestors have tried and understand what they have learned.

What I’m Learning: Trust as the Ultimate Gift

I’m currently working with second-generation philanthropists whose parents gave them perhaps the most precious gift possible: trust wrapped in purpose. The first generation (G1)’s directive was elegantly simple. They must work together as siblings and do good in this world. Beyond that? Complete flexibility and autonomy.

This past year, I’ve watched this family respond to our current moment with remarkable agility. They’ve given out grants earlier in the year, prepaid on multiyear commitments where partners needed cash flow, and developed a entirely new strategy focused on building engaged, thriving communities by working in partnership with those communities rather than for them. They’ve also leveraged larger funders’ infrastructure, understanding that impact in the world matters more than who gets the credit.

With another client, I’m witnessing similar courage to question conventional approaches entirely. They have invited their family in to share the experience of giving together. They are exploring spending down their donor-advised fund rather than growing it perpetually, and potentially aligning their investments with their values. They are developing an understanding that every dollar, especially those already designated for charitable purpose, can be deployed for repair of the world.

What this shows families everywhere is that values-based guardrails actually enable innovation rather than constrain it. When the “how” is flexible, the “why” can stay constant while responding to changing circumstances.

What I’m Reading: The Weight of What We Inherit

Taffy Brodesser-Akner’s Long Island Compromise has been haunting me with its unflinching portrayal of how trauma and wealth transmit across generations. The novel follows a family decades after a father’s kidnapping, showing how one traumatic event ripples through children and grandchildren in ways both seen and invisible. What struck me most, other than remembering a similar event in my family’s history, is how the family’s wealth—meant to provide security—becomes inextricably linked with their trauma, passed down as both blessing and burden.

This complex inheritance mirrors what I see in family philanthropy: we don’t just pass down values and resources, but also our fears, our silences, and our unprocessed experiences. The characters struggle with a similar quandary that many of my clients face: How do you honor what created the family’s foundation while not being confined by it?

Values transmission isn’t about creating exact replicas of previous generations. Research on multigenerational philanthropy shows that successful families establish what experts call ‘guardrails’ (what remains constant) and ‘open gates’ (what can evolve) so that core principles endure while allowing adaptation to changing circumstances. This requires patience and relationship-building over time rather than assuming immediate alignment.

What I’m Watching: Passion and Pain in Equal Measure

I’ve been completely absorbed again by “The Bear,” (Season 4) which offers perhaps the most visceral portrayal of generational transmission I’ve ever seen on screen. The show explores trauma’s impact across generations, showing how childhood wounds don’t just shape Carmy individually, but get passed down through family systems – from his mother’s struggles to his brother Michael’s addiction and suicide, to Carmy’s own battles with anxiety and control.

What makes the show so compelling is how it reveals trauma gets both inherited and unconsciously reproduced. Carmy doesn’t just receive his brother’s restaurant – he inherits Michael’s coping mechanisms, his way of managing stress through chaos, his belief that love and pain are inseparable. Even the kitchen culture itself carries forward patterns of verbal abuse disguised as excellence, where screaming is normalized as “passion” and emotional wounds are worn as badges of honor.

But Season 4 shows something profound: the possibility of conscious interruption. As Carmy begins to recognize his own patterns and their origins, as he starts making different choices about how to lead and relate to others, we see someone actively choosing what to carry forward and what to transform.

This mirrors what I witness in family philanthropy: the next generation inherits not just wealth and values, but also the founders’ ways of being in relationship, their approaches to power, their definitions of success, and often their unprocessed trauma around money, control, and worthiness. The question becomes not just “What do we do with this inheritance?” but “How do we transform what needs transforming while honoring what deserves to be preserved?”

“And you of tender years can’t know the fears that your elders grew by. And so please help them with your youth. They seek the truth before they can die.”

• – Crosby, Stills, Nash & Young, Teach Your Children

What I’m Witnessing: A Generation Grounded in Values

In my work with families, I see Rabbi Tarfon’s wisdom that we are not free to desist from the work playing out daily. The next generation does not seem to be overwhelmed by the impossibility of “finishing the work”. Instead, they’re energized by the imperative to do their part. The families I work with understand that meaningful change requires more than financial contributions. They leverage their 6 T’s, including social media for advocacy, engage in impact investing, and respond to immediate crises with flexibility that would have been impossible under traditional philanthropic structures.

What strikes me most is how values-driven stewardship naturally responds to the changing world that is inherited. When foundation priorities shift from education and arts to environmental causes and social justice, this isn’t generational rebellion. It’s the same underlying values of equal access, justice and community being expressed through the lens of contemporary challenges.

What I’m Wondering: Your Inheritance, Your Legacy

As we move through this extraordinary moment of wealth transfer and global challenges, I find myself returning to those essential questions:

• What world are you inheriting?
• What are the gifts and the challenges passed down to you?
• What values serve as your North Star as you navigate complex decisions about impact and legacy?
• How might the ancient wisdom of L’dor V’dor inform your approach to engaging the next generation in your family’s philanthropic journey?
• What aspect of “repairing the world” calls to you most urgently in this moment?

The Hebrew tradition teaches us that each generation receives the sacred responsibility of interpretation, of understanding timeless principles through the lens of contemporary challenges. In family philanthropy, this means honoring the values that created wealth while empowering each generation to express those values in ways that address the world they’re actually inheriting.

L’dor V’dor reminds us that we are all links in an unbroken chain. We are recipients of gifts we didn’t earn, stewards of resources we didn’t create, and ancestors to generations we’ll never meet. The sacred work isn’t perfecting the transmission, but ensuring it continues with integrity, courage, and hope.

From generation to generation, circa 1986