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Ocean Pines GM John Bailey talks first week in new role

(Sept. 21, 2017) New Ocean Pines Association General Manager John Bailey was busy during his first week of work, getting to know many of the 160-plus association employees, meeting with the board of directors, touring the facilities and sitting in advisory committee meetings.
On Monday, Bailey, also known as “JB,” took time out of his schedule for an interview with the Gazette.
Bailey, 52, joked he was a “tax-deduction baby,” born on Dec. 31.
He grew up in Roanoke, Virginia and attended Averett University, then called Averett College, in Danville, Virginia, where he majored in history and minored in music and religion. His father was a preacher.
“I was raised a preacher’s kid and the original plan was to go to seminary and follow in my dad’s footsteps, working in the church,” Bailey said. “Other doors started opening that piqued my interest in politics and government, and I went in that direction for a while.”
Bailey moved to Washington, D.C. and enrolled in American University, planning to focus on foreign policy. He switched gears and instead finished with a master’s in public administration from George Mason University.
After college, he got married and moved to Richmond, Virginia, where he started working for Keep Virginia Beautiful Inc., a nonprofit environmental organization with a 30-member board of directors.
There, he learned the importance of making a good first impression.
“People have a limited window of opportunity to make an impression upon people who are looking to move to [an area] or are looking to open a new business or relocate a business. You have very few moments to make an impact, so you want to pick your front door,” he said. “That’s one of the things that I want to pursue here, in Ocean Pines. We have two gates and we want to make them stand out.”
Bailey next worked as the county administrator in rural Cumberland, Virginia, but left to pursue an earlier passion – golf.
He played the sport in high school and college, and found work at the pro shop in the Lake of the Woods homeowner’s association in Locust Grove, Virginia. Bailey later became the assistant golf pro at the Evergreen Country Club in Haymarket, Virginia.
Again, his plans changed.
“I had another child on the way and, if you know anything about the golf world, you get the young bucks out of college and you can pay them little or nothing and work them 60 hours a week,” Bailey said. “When you’re in your early 30s and you’ve got one kid and another one on the way, you just can’t compete. So, I went back into management. More headaches, more stress – but more money.”
Bailey was named assistant general manager at Lake of the Woods and took over as general manager within six months. He stayed there for eight years.
Boise Cascade – the same company that originated Ocean Pines – created the gated Lake of the Woods community of roughly 4,000 homes. Bailey said the community has a similar composition, similar amenities and many of the same trends – including a large population of “snow birds” that spend half their time in Florida.  
“I realized that once you understood the skeleton of Lake of the Woods, you understood the skeleton of Ocean Pines,” Bailey said.
He was also the general manager of the Brandermill development in Richmond, Virginia for three years. He said the community also had about 4,000 homes, with a population near 13,000. Most recently, Bailey was the general manager of the Skyline Plaza condominium association in Falls Church, Virginia.
Bailey had some familiarity with Ocean Pines because he and his wife, Meredith, spent part of their summer vacations there during the last six years. His brother and sister-in-law both live in Ocean Pines.
The announcement came in July that, following a nationwide search, Bailey would be the new general manager. When he was first introduced to the Ocean Pines public, on Sept. 11, he told those in attendance he had wanted the job for some time.
“To be blunt, it was at the beach,” he said with a laugh. “To be able to live and work while you’re at the beach was one thing.”
Bailey said the amenities and programing in the Pines were “just amazing.” He remembers getting the Ocean Pines Activity Guide and bringing it back to his staff Brandermill and Skyline.
“I always said, ‘this is it.’ You want to follow an example, you look at Ocean Pines,” Bailey said. “I was telling a couple of the staff the other day, ‘you may not know it because you’re here, you’re living it, but from the outside looking in, Ocean Pines has it going on.”
After spending his first week getting a closer look at the operations, Bailey said there was “a lot of opportunity” in the community.
“There’s a lot good and there’s some stuff we need to fix – and that’s OK,” he said. “It’s a large population and whenever you have that many people in one place, all interested in a lot of different things – everybody has different opinions and different viewpoints, and you can’t keep everybody happy all the time.
“I think the board recognizes that and I think most people recognize that. You just want to be consistent and fair,” Bailey continued. “You want to try new things and sometimes they work and sometimes they don’t, and to not make it personal.”
Bailey said he was aware Ocean Pines has something of a reputation for drama.  
“With that many people and as big as we are, you’re going to have a little drama from time to time. It’s just a matter of moving on,” he said. “I think everybody’s on board with that, and there’s tons of opportunity for interesting and new and good things.”
He said his focus, in the immediate future, is on improving food and beverage operations, drainage, and general administration.
“Not to say that there’s nothing else out there – there’s plenty – but certainly the food and beverage aspect … has obviously been a financial burden and a really bad one this year,” he said. “We’ve got to change that around.”
As for the somewhat infamous nature of Ocean Pines politics, Bailey again said “there’s not an entity out there that doesn’t have its share of drama from time to time.”
“That’s whether it’s an HOA, a town, a city, a county, a church – I grew up in the church and I saw a lot of drama there,” he said. “Any time you have people you’re going to have a little bit of that. It’s just a matter of managing it and saying, ‘OK, this happened’ and moving on.
“Obviously, I’ve read the papers – comments good, bad and indifferent – and yeah, there’s been some drama,” Bailey continued. “I accepted and I showed up, and I’m still here. You deal with what comes.”
Bailey said his father used to have a plaque in his office that paraphrased a famous Mark Twain quote, “I … have known a great many troubles, but most of them never happened.”
“As soon as I get moved, I’ll find it and put it in my office,” he said with a laugh.
Bailey said he meant to joke, while addressing the Ocean Pines community on Sept. 11, that “everybody’s right 100 percent of the time.”
“And everybody would’ve laughed and known that’s just not going to happen,” Bailey said. “There’ll be times when people will be mad at me and I won’t be happy with some of the things that happened, but you’ve just gotta deal with that and move on. ‘We’ve disagreed on this one – let’s see if we can agree on the next topic.’”
He said Ocean Pines, for the most part, is well run and is one of the safest and nicest places to live in the state – if not the country.
“The staff and the residents need to know that – sometimes you get so close to it, you don’t know how good you have it,” he said. “As far as programing and activities – we are the ‘it.’ You’d have to search high and low, nationally, to find an entity that has more programing and activities of a diverse nature and age groups as we do in Ocean Pines. And, we get to do it at the beach.”