PROFILE: Kendra Flanagan

December 24, 2015
By Marcy Shortuse

Kendra Flanagan
BY SUE ERWIN – The next time you’re strolling around town on Park Avenue, you might want to stop by the Chamber of Commerce office and say hello to the new Executive Assistant, Kendra Flanagan.
You’re sure to be greeted with a friendly smile.
Kendra spent the first 12 years of her life in Boca Grande with her family, and she spent the summer months in Maine.
“I had a split childhood – we lived in Florida and then we spent summers up north,” she said.
They lived in Boca Grande until she was three years old, and then her parents built a home in Port Charlotte.
“That’s where my home-base was, but I still went to The Island School,” she said.
Her parents, Keenen and Marcia, were high school sweethearts who came to Boca Grande soon after they graduated from high school.
Both worked at various places on the island for more than 20 years, and many locals still recognize their names.
Kendra said her parents worked at places like “The Temp” and “The Inn.”
And that they were well known for being nonjudgmental of others and accepting everyone for who they are.
“They are just great people. They’re really friendly and they’re both very positive and genuine,” Kendra said. “I am proud to be their daughter. They are both so amazing. When some locals hear my last name, people I don’t even know will approach me and tell me how much they liked my parents.”
Kendra attended The Island School until she was 12, and then her parents moved the family back to Maine full time.
There she attended Rockland District High School for four years.
“It actually isn’t a school anymore. I was in the last graduating class of the high school. There weren’t enough students attending, so they combined two schools and renamed it,” she said.
She has one younger brother, Reilly, who is 19. He was born in Cape Coral when Kendra was 3.
“He is my little brother but he is 6’ 6” and he’s like an old soul in a young body. We’re all very close – ridiculously close,” she said with a smile.
Keenen is a PGA Professional who owns a Pro Shop in Rockland, Maine.
Reilly works the grounds at the Rockland Golf Club, where his dad also works.
“He really likes golf like my dad, and he wants to go to school for it down here, but he’s still figuring that out,” she said.
Kendra’s father worked at Riverwood Golf Club in Port Charlotte as a Pro when he lived in Florida.
He will be coming down to Orlando in January to attend golf school for two weeks to re-up his classifications. Then her parents will come to Boca Grande for a week or two to visit Kendra.
Marcia runs a little seasonal restaurant called Sandbagger’s Café, situated just above Keenen’s Pro Shop. She’s had it for nearly four years. Kendra has spent a lot of time helping to keep it running successfully.
The establishment offers snack bar food with items such as hamburgers, sandwiches and salads.
“It’s a great little place. I am very proud of her. She tries to offer a lot of healthy options on the menu and always tries to use locally grown products, because Maine has many different Farmers Markets in the summertime. So we try to capitalize on that,” Kendra said.
Before working at the Chamber of Commerce, Kendra worked at a pre-school in Rockland. She took a course to get certified as a BHP (Behavioral Health Professional) and found herself working one-on-one with special needs students.
“I would pick them up from school and go to their house and spend the day with them and help them with their homework. It was really interesting work,” she said.
She worked mainly with 3-year-olds to 5-year-olds for several years.
“I wasn’t sure if I wanted to make a career out of it. But I did really enjoy it and might go back to school one day for it,” she said.
When she was in high school, she took an EMT class and found it fascinating, but she didn’t feel passionately about pursing it as a career.
“It takes a really special person to do that kind of work. I personally had a hard time separating from it after school. It’s something very close to my heart, but I just fell into a different path,” Kendra said.
Two years ago, in Maine, she started practicing Reiki, an ancient healing technique based on the principle that the therapist can channel energy into the patient by means of touch. She plans to study that in the future.
“I took a few classes on it, but I would like to learn more about it. It’s basically using life force energy to heal the body. It has personally helped me a great deal,” she said.
Kendra does not play golf very much, but has dabbled in the sport. She lost interest during her high school years.
“I haven’t played as much as I should. I know how to play, but I don’t do it on a regular basis. My brother is an amazing golfer; he is really, really good,” she said.
Kendra plans on visiting Maine again for her birthday in June.
Kendra doesn’t have any pets right now, but she hopes to have a dog sometime in the future.
“I love animals, but with moving recently, it would have been very hard to have one,” she said.
It’s a pretty strange coincidence how Kendra ended up living in Boca Grande again 10 years later.
A childhood friend, Nicki Heimann, whom she hadn’t seen in years, was visiting some friends up in Maine when she stopped by Kendra’s house for an impromptu visit.
“I heard someone throwing rocks at my window, and I looked outside and saw it was my best childhood friend, Nikki – and I couldn’t believe it,” Kendra said.
While the two were catching up, Kendra mentioned how much she wanted to move back to Boca Grande, and she asked if Nikki knew of any jobs available there. Nikki told her about the Executive Assistant opening at the Boca Grande Chamber of Commerce, and the rest is history.
“I always wanted to live in Boca Grande again, and I always felt I would come back. I swear the universe just put this together. I just never thought I’d get this lucky. I absolutely love it here. There is something about this place that I have always felt connected to. There’s a special energy that draws you in. This is a beautiful town, and I have a beautiful job.” Kendra said.
She relocated here on November 1 of this year.
Kendra said her favorite thing in Boca Grande is the Farmers Market, and she enjoys going there every Friday. She also is very happy to be so close to the beach, and she enjoys connecting with the people on the island every day.