
The Big Win
What ten thousand sunflowers taught me about AI, culture, and the work the sector keeps trying to skip
Articles
Essays on generosity, responsible AI, trust, and the future of social impact.
Latest writing
Essays on generosity, responsible AI, and the future of the nonprofit sector.

What ten thousand sunflowers taught me about AI, culture, and the work the sector keeps trying to skip

The nonprofit sector has learned to describe AI fluently. That is exactly the problem.

The greatest threat to generosity is not distrust. It is the shrug.

What my grandfather understood about apathy, and what it has to do with the energy behind every AI prompt

A thoughtful response to Nan Ransohoff’s important piece on AI, wealth and the future of philanthropy

What the economic theory of competition, the Industrial Revolution, and the tool open on your screen reveal about the sector that had the antidote all along.

Why the next decade will reward the thing AI cannot make.

What we lose when the fundraiser isn’t there.

Why the Biggest Threat to Your Organization Isn’t AI - It’s a Lack of Vision

On curiosity, overwhelm, and the discipline of knowing when to stop.

On the Weight of Knowing What’s Coming - and the Grace of Saying It Out Loud

Leadership, humility, and the cost of looking away.

Agentic AI and the Next Nonprofit Operating System
Earlier writing
Seven essays from Nathan’s earlier article archive, preserved here with direct links to the original publications.
March 2025 · 7 min read
What it means to protect human agency, connection, and purpose as intelligent systems become part of everyday life.
January 2025 · 6 min read
A year of gratitude, reflection, and appreciation for the people carrying nonprofit missions forward.
October 2024 · 6 min read
Lessons from The Sorcerer’s Apprentice for leaders learning to work with powerful new tools.
October 2024 · 6 min read
Why responsible and beneficial AI is a nonprofit imperative, especially as adoption accelerates.
August 2024 · 6 min read
How curiosity becomes a practical superpower for learning, leadership, and adaptation in the AI age.
August 2024 · 6 min read
A choice leaders face when efficiency and human value appear to be in tension.
May 2024 · 6 min read
The nonprofit sector’s imperative to move from abstract ethics toward responsible and beneficial practice.