As I transition from my role as board chair of the Nathan Cummings Foundation (NCF) to consulting with other families full time, I’ve been reflecting on what aspects of my identity and approach to leading my own family’s foundation I can apply to my next chapter.
I realized in my time as chair that an unexpected third identity was at play: that of the middle child. The best traits of middle children—bridge builder, innovator, observer—were critical to my ability to navigate my family in childhood and to find success as the leader of a family foundation. As a stereotypical middle child (my sister is a doctor, my brother a lawyer), much of what helped me navigate my family growing up has served me well into adulthood, both personally and professionally. I always say family philanthropy is part politics, part psychology, and I believe those are the same ingredients that make a middle child thrive.
Today, philanthropy is up against ever compounding challenges: a great wealth transfer already underway, inequality that has moved from troubling to destabilizing, and coordinated attacks on the very freedom of foundations to act in accordance with their values. The traits of a middle child are something we can all learn from.
During my seven years as board chair of NCF, I had the privilege of putting these characteristics to work—guiding the unanimous decision to shift 100 percent of the foundation’s assets into mission-aligned investments, launching its first program-related investment (PRI) strategy, and leading the organization through multiple leadership transitions. I’m now applying all of that learning as the founder of the aptly named philanthropic advisory firm, Middle Child Philanthropy.
The Middle Child’s Playbook
So what does the middle child playbook actually look like in practice, and what can it offer a field navigating such a complicated reality? Three traits rise above the rest:
1. The bridge-builder
Middle children learn to connect across difference: up to older siblings, down to younger ones, and sideways to whoever else is in the room. For philanthropy, that means spanning generations of donors and grantees, but also building lateral relationships—across foundations, across funding families, across silos that have calcified for too long.
During my tenure as chair at NCF, we spent a lot of time and energy breaking down silos across the organization with an emphasis on organizational efficacy. We also value the importance of collaborations with other organizations, both philanthropy-serving organizations and other funders, with a focus on the need for transparency in philanthropy.
2. The innovator
Unencumbered by the inheritance of the eldest or the indulgence of the youngest, the middle child often forges an entirely new path. They find footholds where there aren’t any. In philanthropy, that’s the permission to do things differently, such as deploying all assets—not just grants—and reimagining what it means to use a foundation’s power fully, beyond the grantmaking dollars.
At NCF, we have shifted to a totality of assets approach where we look at the impact of our impact investing portfolio, grantmaking portfolio, PRI carve out, and communications when we measure success. Having the same key performance indicators across all of our assets helps us see if we’re actually moving the proverbial needle where we want to be moving it to.
3. The observer
Middle children survive by watching. They learn early what makes each family member tick—what they need, what they fear, what moves them. That deep relational intelligence—earned through attention, not assumption—is exactly what philanthropy needs to be a true partner to the communities and movements it funds, rather than just a check-writer who thinks they already know the answers.
We have always considered NCF to be a learning organization and own the fact that we don’t have all of the answers. As a foundation, we don’t believe it’s about having answers, rather it’s about asking the right questions. When we underwent our last five-year strategic planning process, we went on a listening tour that included interviewing grantee partners, other social movement leaders, and our own staff and board members to develop a clear and targeted focus on racial, economic, and environmental justice.
Avoiding the Pitfalls
We can’t talk about middle children without acknowledging some of the less flattering stereotypes. But it turns out, those have something to teach us in philanthropy too.
1. The people pleaser
As the peacemaker, sometimes middle children can fall into the role of trying to make everyone happy.
We had to take a long hard look in the mirror at NCF to see that, while we were doing good things, we were doing too many good things. As institutions that want to do good, it’s easy to fall into the habit of saying “yes” to such a broad range of issues and areas of focus that you lose sight of your impact goals. And to make an impact, sometimes you have to zero in and streamline.
2. Identity seeker
All too often, the middle child is overlooked, which can lead to a real question of identity. By facing identity at an early age, middle children often develop very adaptable and unique personality traits.
Family philanthropy isn’t a science, it’s an art. With a background in theatre, I have a deep understanding of the human condition which is always my greatest strength in working with families. Every family is its own unique world, and it’s impossible to understand a family’s worldview without understanding what makes their world go round.
It’s important that foundations have a shared institutional identity, and at NCF we underwent significant values work under my leadership to reach consensus on just that. By creating space for voices and opinions to be heard, we were able to create a cohesive, shared identity that doesn’t represent the individual but the collective.
Closing Thoughts
Families are complex, messy, and unique. Middle children have a way of finding space for themselves and carving out a foothold when there isn’t an obvious one given. My Grandma Buddy called me a “stemwinder,” by which she meant I was both the glue that held the family together, and had successfully wound my way in and out of relationships and situations on all sides of the family—and we were stronger for it. When you say ‘middle child,’ everyone knows what you mean. It’s complicated. And that’s family philanthropy in a nutshell. It’s complicated.
The views and opinions expressed in individual blog posts are those of the author(s) and do not necessarily reflect the official policy or position of the National Center for Family Philanthropy.