It would happen while he was volunteering at Project Homeless Connect — one-day, one-stop events that corralled crucial social services under one tent.
"My job was to say, 'Come back next year' — thinking that was uplifting," Dippy recalls. "But you'd see the devastation in their faces."
No valid ID means no job. No real housing. No government or military benefits. For the displaced, nothing's more valuable than a name. Without proof of identity, they're worse than homeless.
Dippy had seen enough. He pressed his case with a coalition of Orlando churches that was considering a proposal to give homeless people $10 to get an ID.
Handing out money's the easy part. What homeless people really needed, he insisted, was help navigating the maze of bureaucracy.
"It was me opening my big, fat mouth," he says.
But that big mouth led to the creation of IDignity, which has given new urgency to beating a simple but underappreciated problem for the homeless — identity. Dippy coined the name and is now the full-time executive director and organizer of monthly events designed to restore identification.
Where more ballyhooed projects have faltered, Dippy's project has quietly helped thousands traverse the frustrating complexities of recovering identity documents, which leads to meaningful and sometimes life-changing assistance.
That's why Dippy has been named 2010 Central Floridian of the Year by the Orlando Sentinel's editorial board, a 28-year-old annual tradition that recognizes the contributions of an individual or a group who make a difference.
"He represents all that is good and compassionate in each of us and in our community," says Ray Larsen, executive director of the Central Florida Commission on Homelessness, which has awarded IDignity two grants. "He is committed to making sure that the homeless and very poor have a friend and ally and help."
Dippy, 41, prefers to heap praise on the government agencies that provide support at the events, and the IDignity volunteers, one of whom he salutes each month with a "golden ticket" to signify the hope their efforts give to the homeless.
But ask anyone and they'll tell you Dippy's the glue.
"Behind that friendly, good-natured persona is one tough leader," says Bill Warren, the Reedy Creek Improvement District administrator who became a Dippy mentor after serving as an IDignity volunteer. "By that, I mean he doesn't give up. That passion inspires others to stick with it."
Share and share alike
Other, higher-profile efforts have shared that passion, but with less success. Larsen's commission, christened nearly three years ago, had the sharpest captains of industry aboard and an audacious plan to raise millions and end homelessness within a decade. But it ran aground financially, before a recent partnership with Heart of Florida United Way. Likewise, when the economy hit bottom, the bottom fell out on plans for a $2 million full-service homeless drop-in center backed by downtown churches.
In their wake, IDignity's success might seem unlikely, considering it's a grassroots movement with a shoestring budget — $193,000 in 2010 — that relies almost soley on volunteers and couldn't afford to pay Dippy a salary until last January.