Steve Filosa spent twenty years running Prep@Pingree, a scholarship, academic enrichment, and jobs program in Essex, Massachusetts. The program's premise was simple and counter-cultural: serve kids through long-term relational commitment rather than high-altitude, short-term intervention. Not something that scales. Something that works. By design, Steve built it to replace himself. Eventually, he did.
What came next surprised him. He expected to help other organizations build more Prep at Pingrees. He didn't expect that a significant part of his practice would turn out to be working with donors — people with resources to give and no one to think alongside them about how to give intentionally.
Six years in, Steve talks about uncertainty in a way that doesn't come from a framework. It comes from experience: starting a program in 2001 under enormous national headwinds, committing to something again at fifty with no safety net, and discovering both times that the net appeared.
In this conversation: what he didn't anticipate about building Prep@Pingree; why he thinks TFA-style interventions tend to serve their participants more than the kids they're there for; what changed in the final decade that made handing over the keys feel like relief; what the hardest thing to teach a board is; what year six looks like compared to year one; and what "peace" actually means when you've stopped needing to have all the answers.
IN THIS EPISODE
The Principal Uncertainty is a podcast by George Laufenberg. It's not about finding solid ground — it's about staying oriented in open water.
