Lisa Taylor, a 34-year career educator in the Upper Keys, is retiring at the end of June from the Monroe County School District. She and husband Jeff, who is retiring May 28 from his position as a project manager with the Ocean Reef Community Association, are embracing a new chapter in life.
She has served the past 13 years as the principal of Plantation Key School, seeing the school through a multiyear design and construction of a new campus, post-Hurricane Irma repairs to the original facility during the same time and a global pandemic. She is ready.
“What really sealed the decision was spending this spring break at a lakeside inn in Mount Dora,” Taylor said. “We realized we could do this for the rest of our days.”
“We all thought she was superwoman,” said school board member Sue Woltanski, who was president of the PKS-Parent Teacher Association during Taylor’s first year. “A first-year principal and intimately involved in the design and construction of the new school, she didn’t miss a beat. She had a vision, she knew what she wanted for her students and her fingerprints are all over that school. It is her legacy.”
“She has this amazing ability to see the uniqueness that is in each child,” Woltanski said. “This has been instrumental to my daughter and to many other students over the years.”
Taylor was a student teacher under several Monroe County educators including Anne Dunn, retired Key Largo School teacher and lifelong Tavernier resident.
“She was really born to be a teacher and she became an exceptional leader,” Dunn said. “She was always mature beyond her years.”
Keys Weekly sat down with Taylor during the second-to-last week of school, a busy time of end-of-year activities, to talk about her career and what retirement might look like (The conversation has been edited and condensed for clarity).
How long have you lived in the Keys? My family and I were snowbirds from New York, outside of Buffalo. Starting when I was in the fifth grade, during the school year we lived on a boat in Plantation Yacht Harbor, then we would return to New York for the summers. I graduated from CSHS in 1976.
How did you get into education? It took me a while to find out that education was for me. I went to Florida Keys Community College (now College of the Florida Keys) and earned my AA degree. I attended Miami-Dade College and then found my way to Florida International University where I earned a bachelor’s degree in elementary education. I started student-teaching at KLS at the start of the 1992-93 school year, when 1,200 displaced Miami-Dade students came to Monroe County for their schooling after Hurricane Andrew devastated South Dade.
I earned a master’s of reading from FIU in 2004 and a second master’s in leadership from the American College of Education in 2010. I was also a middle childhood generalist national board-certified teacher from 1999-2019, one of my greatest professional accomplishments.
Who were your mentors? Oh my, I’ve had so many. Frankie St. James and Annette Martinson saw leadership abilities in me. Margy Liscio was one of my supervisory teachers when I started out. She offered a real-world perspective of the child and classroom. She was amazing. Anne Dunn was another teacher I worked with as a student teacher. Her daughter Erin became my daughter’s first babysitter and now her children are attending PKS.
I don’t know what I would have done without David Murphy and Blake Fry (both former Coral Shores principals) when I came to PKS. They guided me my first year, at a time when I was the only administrator here. There was no assistant principal support and they answered the phone every time I called.
Another great mentor is Jessica Olefson with the Keys Children’s Foundation. She taught me about honoring people’s honor, seeing how much they could afford and then providing assistance in a way that doesn’t cause embarrassment. She also taught me how to ask for funding and the importance of grant funding. I have become a grant-writing queen.
Any memorable moments that stand out? Watching each child grow over time. I was especially worried about the too-busy boys and the super-shy girls, but I saw them grow and find themselves. They become their own person and find their way.
Probably about 30 years ago, one of those busy boys I was so worried about made me a little stuffed red apple that he sewed himself. I’ve kept that with me ever since as a reminder the students eventually find their way. That student, Chris Mendez, is now a human resources specialist with the district serving the Upper Keys.
Proudest achievement as a teacher? Seeing the light bulb go off in a child’s eyes when they finally comprehend a concept being taught. That joy has never subsided.
Proudest achievement as a principal? Our third child, as my husband coined it, refers to the new PKS campus. He was in it with me every step of the way. I was as proud as any new parent when the campus finally opened in January 2019.
Most difficult time as a teacher? I’ve had more than a few but a couple stand out. When 9/11 happened, I had a child in my third grade class whose father was a U.S. Air Force pilot. The student was falling apart throughout the day until word was received that his father was alive.
Another significant time impacted me both professionally and personally. One of my dear friends and colleagues was fatally shot by her husband, who then killed himself. One of their three children was in my class. Jeff and I actually welcomed those kids to our home for about six weeks.
Most difficult time as a principal? The death of a student of which we experienced a few. There is just nothing you could really do except grieve together and act together as a community for the long term supporting the grieving family.
How do the challenges today compare to when you first started? The challenges today are so different from when I started. We had more freedom in what and how we taught. While standards and expectations changed over the decades, we continue to grow based on what society tells us we need. We keep up with the requirements to be successful, focusing on the student and their sweet spot to success.
What about artificial intelligence? I use it to be more efficient in my job, yet I don’t think kids are ready to use it effectively. We need to teach them the right ways to use it and know how and where to use other sources of information to verify information.
Tell me about the transition from the classroom to administration? I loved it because I felt I was affecting more students and I had great mentorship. The families and community are so connected to our school and that makes the job even better.
What advice would you offer to your successor? I’ve worked with Maida Court for nearly 10 years and say to her, don’t forget to have fun. Keep looking for the high spots throughout the day. There are so many great things happening; don’t get bogged down in the hard stuff.
What does your retirement look like to you? We don’t quite know yet. We’ve been too busy to reflect or make plans. We do have a family reunion in Buffalo soon and there are many trips we’ve talked about over the years. I want to learn how to just be.
I plan to be very involved in many community partnerships, including Upper Keys Rotary and the Islamorada Chamber. I am really looking forward to supporting organizations that have school and community connections. I also am on the boards of the Early Learning Coalition for Miami Dade and Monroe Counties and the Florida Association of School Administrators.
Anything you’d like to add that wasn’t asked? Yes, how much my entire family has supported my career. Jeff, my husband of 41 years, has been very supportive and always encouraged me to follow my heart. My kids still help when I need them for an event or project. My mom and siblings have been supporters for everything I needed from babysitters to cheerleaders to participating in many activities related to my work so we could all be together making memories.
