When the gelato lady in Sicily put her towel down, stepped from her shop and applauded, Ray Chiaramonte knew his singing could be more than just a passing interest. • Chiaramonte, the executive director of both the Hillsborough County City-County Planning Commission and the Hillsborough County Metropolitan Planning Organization, rediscovered his gift 10 years ago when he went to Sicily with his cousin Jim Callan and Jim's wife Rosanna Esalino, a Sicilian native. • Sure, he spent time singing in church choirs and during his teens, did some rock 'n' roll singing with a garage band. But he had never had an audience quite like this. • Esalino was scheduled to give a concert in the town square and she asked Chiaramonte if he would sing. With a little prodding, he fashioned a version of Frank Sinatra's My Way. When the gelato lady, not known for generous compliments, gave her approval, Chiaramonte became planning policy wonk by day, song stylist by night. • Chiaramonte, who performed at the county's monthly food truck rally at Joe Chillura Courthouse Square on April 11, recently shared his thoughts about singing and planning with Tampa Bay Times columnist Ernest Hooper.
When I saw the news about you singing at the park, I thought it was a different Ray Chiaramonte.
I haven't been singing that much since I took on the second job, but Joe Chillura asked me to do it. He came out to the park that day, which was really nice. I really enjoyed it and I need to do it more. It's a great stress-reliever.
So what happened when you got back from your big debut in Sicily?
My cousin and his wife were living in Colorado Springs, but they came here for the Italian Festival in Ybor City . . . and ended up moving here. We got some jobs singing and learned some songs. My first night I got $20 to sing at Roma's in Ybor City. I ended up pretty much having a regular singing gig at Rigatoni's until it closed. Then when I took on the second job (with the planning commission), I kind of decided I was too busy to do it all the time.
You must be thrilled to finally tap into your singing desires.
Sometimes I can't even believe it's true. I've always like to sing, but I'm kind of shy about it. I remember the first time I performed at Roma's I was shaking. It was something I wanted to do all my life, but I don't get nervous anymore. When I came back from Sicily, I decided to take voice lessons from a guy named Blake Leopold in Hyde Park. That helped me out a lot.
So I understand you pattern your singing after Frank Sinatra?
I don't specifically try to imitate him. I love his songs, but I try to do it the way I like to do it. Sinatra and I have the same birthday, and one side of his grandparents come from that same part of Sicily as my grandparents. But I once read that the strength of his singing is that he does it with such ease it's almost like he's talking. It's very natural. I want to be sincere and believable, so I try to sing more like who I am. I like the more modern interpretations, like Michael Bublé — a little jazzier and a little more modern.
So is there any synergy between your singing and your role as a planner?
Singing gave me more confidence to do public speaking. In that sense, it reinforces and makes me more outgoing. I'm less nervous about public speaking. At a national conference, I once gave a presentation to planners about going out of their comfort zone. It was a 4 o'clock session so there might have been someone about to doze off. So I started by saying, "I'm going to do something outside of my comfort zone, and I sang a cappella the first couple of lines of Michael Bublé's song, Feeling Good. I think doing that did get their attention. They didn't expect something so unexpected at such a serious conference, but it gave me a good intro into my topic, which was going out of your comfort zone. In that sense, it has helped.
Can you explain the roles of the planning commission and the MPO?
The planning commission is the main agency and the MPO is a subset of it. We have 12 staff members as part of our 42-member staff who are under contract to be MPO planners. The main role of the planning commission is long-range land-use planning. The MPO was created to do transportation. They operated somewhat separately because the MPO's mission was to make sure federal dol-lars were being spent on things the community wants. Back in the 1960s, the interstate highways just plowed through cities with no significant input from those cities. But in 1966, the mayor of San Francisco said, "You're not putting the interstate through this historic district in San Francisco." As a result, the MPO was created to give local communities a voice in federal projects. With the state lessening some rules, the planning commission and the MPO can operate with the same timetable. We're going to do the update of land use and the transportation plan together — it's called Plan 2040 — and have it done by the end of the year.
What's the biggest challenge with your dual roles?
The complexity of politics in getting things done. What I love about Hillsborough and Tampa is all of the different players involved. You have to create alliances of very different people who want the same things. It's very interesting and exciting but also very difficult. I feel very strongly that we need a modern transportation plan but we have to get the right plan and projects the majority of people can support and pay for. It's something I think about a lot: How we can make that leap forward.
Sunday Conversation is edited for brevity and clarity.