In their new vacation paradise, the Lilienthals quickly became uncomfortably aware of the disparity between their nearest neighbors’ wealth and fame and the year-round inhabitants’ poverty. In fact, the contractor they hired to build an extension to their home told them how needy a nearby elementary school was; he knew of the school’s problems because his wife is the principal.

"It got us thinking about vacation homeowners in Second and Third World countries, and how those countries could benefit more from their largesse than some of their pet projects back in the States," Peter says. He and Sallie, at the principal’s invitation, attended a weekly faculty meeting at the Anguillan school, where they asked the teachers what sort of items would improve their classrooms. Though they didn’t specify a figure at the outset, the Lilienthals had in mind a modest initial donation of roughly $10,000. To their surprise, the teachers’ wish list was even more modest—fans for the classrooms, new light bulbs, new linoleum.

"I was a bit taken aback," Peter says. "I said, ‘No, I want you to think really big.’ It took a while to draw them out. Finally, they said if they got some computers and printers, that would be huge." A computer in every classroom was more what the Lilienthals had in mind. They did not talk through all of the details, such as whether the school’s power supply could actually accommodate that many devices, but they soon found out that setting up an ambitious giving plan in a remote spot creates its own complications.

The Lilienthals had in mind a modest initial donation of roughly $10,000. To their surprise, the teachers’ wish list was even more modest—fans for the classrooms, new light bulbs, new linoleum.

Members of the school staff agreed to create a list of names and contact information for other prosperous vacation homeowners in the community so they could start a fundraising drive and presumably boost their giving program. Staff members were confident they could obtain names through contractors on the island. According to Peter, this is the way things are done in Anguilla, and he knew better than to interfere with a cultural more and try to take on the task himself. Besides, the Lilienthals wanted the recipient of their philanthropy to be a local partner with the ability to take care of operational details.

But months passed before they heard anything more about a list. "We made up our minds that if they weren’t enthusiastic enough to take the next step and do something, then we weren’t going to push it," Peter says.

The Lilienthals’ experience is not uncommon among would-be patrons who become frustrated, according to Prudence Brown, a research fellow at the University of Chicago’s Chapin Center for Children and coauthor, with Leila Fiester, of a 2007 report, Hard Lessons About Philanthropy & Community Change From the Neighborhood Improvement Initiative. "In many community-change efforts," Brown says, "the community wants to start out with a stop sign, a cleanup drive or something that seems very modest and with little potential to transform the neighborhood." Those initial proposals may strike philanthropists as inconsequential baby steps, but, in reality, they are valuable tools for giving each party a chance to get to know and trust the other, Brown adds. "If you dismiss what the community wants, you’re already demonstrating a kind of disrespect and prioritizing your own needs as a giver over that of the institution or community."