The Inner Work of Asking (Part 3): Do We Trust Generosity?
They told me I owed them nearly $2,000 and needed to pay it immediately.
I had been working at the nonprofit for only three months. The organization had mistakenly failed to deduct the cost of my health insurance from my paychecks. They now wanted the full amount back, and I didn’t have the money.
I called my sister in tears. She listened, helped me calm down, and suggested that I ask the organization to set up a repayment plan I could manage. That was my plan.
The Inner Work of Asking (Part 2): Relationship to Mission
I remember sitting across from a couple who were poised to make a significant gift to the LGBTQ+ organization I was serving. Their child was queer. They had tremendous capacity and had already invested generously in organizations advancing LGBTQ+ rights.
Yet somehow, instead of talking about our work, I found myself talking about wilderness, the importance of children spending time outdoors, and Richard Louv's then-new book, Last Child in the Woods.
I did eventually make the ask, and they made a generous gift. By every outward measure, it was a successful donor visit.
But as I drove home, I couldn't shake the realization that the conversation which had come most naturally wasn't about the mission I represented. My heart had wandered somewhere else.
I still believed deeply in LGBTQ+ equality and justice. What had changed was where I felt most alive. I found myself increasingly drawn to conversations about connecting people with the natural world and protecting the places that had shaped my own life.
That meeting became one of the first clues that it was time for me to discern what was next. That experience taught me something I still believe today: fundraising is at its best when it flows from genuine conviction.
The Inner Work of Asking (Part 1): Our Relationship to Money
Fundraising often gets framed in terms of strategy, campaigns, donor pipelines, and metrics. Yes, those things matter. Yet the people who seem most effective and most sustained by the work over time are often those willing to engage at a deeper level.
Beneath the tactics, something quieter and more profound is unfolding.