Jean Thompson, new Head of School of The Island School on Boca Grande, has never had a bad day in her 18 years as educator since graduating college in 1994.
At least not so anyone - students or colleagues - would know it. She has an infectious laugh, a ready smile and a glass-half-full attitude others appreciate.
"One of my fellow teachers as I was leaving Hebron Middle School, said 'I'm waiting for Miss Thompson to have a bad day,' " Thompson said in relating the anecdote with a trademark smile.
Article Photos

Jean Thompson, Head of School of The Island School
Thompson comes The Island School well qualified.
Previously a mathematics teacher and elementary summer school coordinator at Laurel Nokomis School and a high school mathematics teacher in the Hillsborough County School District and the Anchorage School District in Alaska, Thompson was assistant to the chief financial officer of the Tampa Bay Buccaneers in 2001 in her only hiatus from education work.
She's been an assistant principal of Heron Creek Middle School in North Port since 2007, following two years as coordinator for assessment, curriculum and instruction at HCMS. This will be the first time Thompson is the head of her own school.
Fact Box
Jean M. Thompson at a glance
Birth date: Sept. 25, 1970
Occupation: New Head of School of The Island School on Boca Grande
Begins: July 1
Education: bachelor's degree in secondary education and mathematics from the University of Maryland, master's degree in educational leadership from Nova Southeastern University, attended the Leadership Academy of the Sarasota School District and studied the Art of School Leadership at the Harvard Graduate School of Education.
Awards: 2009 University of Florida Distinguished Educator and the Sarasota County Assistant Principal of the Year. Teacher of the Year at Heron Creek Middle School in 2006 and the Anchorage, Alaska, Middle School of Science in 1998.
Selected to present to U.S, Secretary of Education Richard Riley in 1998 and nominated for the ASCD Outstanding Young Educator Award in 2006 and BP Teacher of Excellence Award in 1996.
Residence: Englewood
Hometown: Clarksburg, Md.
Family: Husband, Billy Thompson, a 747 pilot for Southern Air, and a Golden-doodle and a Labra-doodle
Hobbies: Avid runner and triathlete who enjoys fishing and sailing.
The official start of the new school year is July 1 although she has been busily soaking up knowledge from her predecessor, Rosa Ramos. Here's her cheery outlook on the future of The Island School:
QUESTION: How did you learn of the Island School opening?
ANSWER: I had gone online to look at sunrise services the Saturday before Easter and the first article I looked at said head of school retiring. I really wasn't looking to leave my current school or Sarasota County at all but something just struck me. That's very interesting. I need to find a little more information about it.
Q: What was so interesting to you?
A: I knew one of the teachers who worked here (Melissa Ellsbury) and having a small school where I could personally know all of the kids and their families, and really be a part of the community, was very interesting to me. That's one of the biggest things I'm excited about.
Q: You attended the last Island School Board meeting of the season with your rsum in hand. Had you already decided to apply?
A: I thought I'm at least going to come and see the school, meet the board members, give them my rsum and let them know I am interested. And one step led to the next.
Q: Before coming to Florida you taught in Alaska. How did you stand the cold?
A: I loved it. Loved it! Loved the outdoors. We fished all summer long for salmon. Our dogs were named Sockeye and Coho at the time. In the winter we'd hook them up and ski-tour with them on cross-country skis. They'd be harnessed and hooked to my waist and we'd go flying through the trails. (laughs).
Q: Are you a marathon runner?
A: Half-marathons but I usually do shorter distances.
Q: What are your first-year goals as Head of School?
A: Have a real good understanding of the students, the staff, the board and the community and parents. Then work on building on the foundation we already have here.
Q: I didn't hear anything about Florida Comprehensive Assessment Test scores in there. Is that part of the equation?
A: Yes. They really toughened them this year. They did.
Q: Was that a necessary step for Florida student academic improvement?
A: Umm, we have to continue to challenge ourselves and our children so they continue to grow. I know that's the test everybody looks at and our kids have to be competent and do well and that's the bottom line. But that's one day. I do think we need that assessment to be sure we are on track and we are holding ourselves and our students to high standards.
Q: Do you have educational role models?
A: I have been very fortunate to have had a lot of great mentors in my life. Dr. Keith Taton, my first principal in Anchorage, Alaska, just saw a talent or a spark and continued to push me into open doors and to give me opportunities and to have experiences. Wendy Katz in Sarasota County had a big influence as director of Leadership Development. When I got my job as assistant principal Jerry Kaplan was my mentor; they paired us with retired mentors in the community as someone to talk to once a month. He asked such insightful questions that would really make me sit and reflect. Jerry and Jeffrey Mordock is another mentor. Oh, one more: Dr. Bill Bolander, my current principal, who just always encouraged me and has kind of been pushing me out of the nest.
Q: What will be your leadership style?
A: I think I come with excitement, a smile, and enthusiasm. I tend to look at the positive in everything. Not afraid of hard work. I push myself to excel, my staff and my students.


