Essays on leadership, governance, philanthropy, and strategy. Exploring the messy real-world challenges of aligning structure with purpose.
The Conversation Underneath
When Harbor House finally shifted its fundraising, it didn’t start with a new appeal or a better OBBBA webinar. It started with three people in a room asking what the organization is really for over the next decade, and who needed to be part of that answer.
Honoring What They Actually Cared About
When a founder dies, the family conversation that follows is rarely about strategy. It’s about loyalty, grief, and a question that sounds like clarity but functions as a wall: What would she have wanted?
When Story Isn’t Enough
Every organization runs on an implicit sequence: something comes first, and everything else follows from it. Most of the time that sequence operates below the surface of strategy and governance, invisible until something goes wrong.
Beyond Stakeholders: How a Helpful Term Became a “Non-Word”—and What We Might Say Instead
The modern business sense of ‘stakeholder’ was strategic and practical; yet, it became a ‘non-word’—a term so broadly applied that it no longer tells you anything specific. This clarity matters a lot, because…
Who We Are, or What We Stand For
For nearly two decades, the Whitfield Family Foundation ran like a quiet clock. Then Margaret’s oncologist used the word “aggressive,” and three adult children found themselves at a kitchen table asking a question the foundation had never needed to answer before.
The Architecture Underneath
Most organizations that hit a ceiling don’t have a strategy problem. They have an architecture problem. And the tools most leaders reach for– better people, better assessments, better frameworks– keep pointing in exactly the wrong direction.
The Noncash Giving Opportunity
2.3%. That number– the share of American household wealth held in cash and checkable accounts– should change how every nonprofit approaches fund development. The other 97.7% is in real estate, securities, business interests, retirement accounts, and other noncash assets. Yet,…
The Foundation That Nobody Needed
Why the Best Charitable Planning Advice Is Sometimes "Don't Do This" Charitable giving is not a product of the tax code. This seems obvious when stated plainly, but over the past century,...
Decoupled Giving: How Modern Philanthropy Disconnects People from What Truly Moves Them
On the cognitive architecture of charitable purpose and why institutional philanthropy works against human motivation Christina still remembers the winter her mother kept their car packed in case...
The Biggest Problem with Modern Philanthropy… is ‘Philanthropy’ Itself
When we speak of “philanthropy” today, we often mean something quite different from what the word originally described. And from what humans have actually always done. In many distinct yet...