Cheryl Doolittle has been a treasured member of the Pine Crest School community since 1986.
Beginning her career at Pine Crest as a chemistry teacher, Ms. Doolittle retires as the Upper School Dean of Scheduling and Student Activities. In her current role, she is an integral part of the Upper School administration, working with alumni Joseph Walters ’95, Upper School Head, Krista Promnitz ’97, Assistant Upper School Head and Dean of Student Services, and former science department colleague Glen Pierson, Upper School Assistant Head and Dean of Students.
Upper School administration dressed as characters from the board game Clue for Halloween 2017. From left to right, Jessie Metzger, Glen Pierson, Krista Promnitz ’97, Joseph Walters ’95, and Cheryl Doolittle.
We sat down with Ms. Doolittle to find out what is next for her as she approaches her retirement.
The Magazine (TM): When did you begin working at Pine Crest?
Cheryl Doolittle (CD): I moved to Florida after teaching and coaching in New York for 10 years. I was teaching at a local high school when a coworker, Maureen O’Sullivan, came to Pine Crest and interviewed for a biology position. Jim Byer, then Upper School principal, said they needed a chemistry teacher. So I interviewed with Mr. Byer, Mr. McMillan and Doris Schmick, the AP Chemistry teacher and the Science Department Chair and was fortunate to begin in September of 1986.
After my first year, my husband was transferred to California for two years, and when I returned to Florida, Doris Schmick retired, and I became the AP/Honors Chemistry teacher.
TM: When did you begin working as an administrator?
CD: While in the classroom, I helped with a few administrative tasks and Student Council. Eventually, I taught one less class and took on more responsibilities in the office. I became a full time administrator in 2014.
TM: What is your favorite thing about being an Upper School administrator?
CD: That is such a hard question! I think our teamwork is my favorite thing. We [the Upper School Administration] bring many great experiences and opportunities to students, and that is a result of working so well together. We have had a lot of opportunities to be creative and to enact change by pooling our talents.
Working with the Honor Court is a real privilege. You see a very different side of students when they are in this role. They are caring and deliberate when they are trying to make good judgments about their fellow students who find themselves in awkward circumstances.
I also like the puzzle solving aspect of student scheduling. It is an annual brain teaser — to give everyone what they want and make it work for them, and for the Upper School.
TM: What is a favorite memory you have of your time at Pine Crest?
CD: Coaching the math and science team in the late 90s is one of my best memories. I enjoyed the projects we worked on and the academic competitions. My students demonstrated creativity and resourcefulness in solving the challenges of the engineering design competitions and science olympiads as well as plenty of competitive spirit.
TM: What has been your proudest moment as an educator?
CD: I would say the proudest and also bittersweet moment is sitting at graduation each year watching my students graduate. I am very proud of them and sad to see our time together come to an end.
Christopher, Thomas ’13, and Cheryl Doolittle
TM: What will you do next?
CD: I have a bunch of half-baked ideas! One thing I will do is finish the fixer upper my son and I bought in Daytona. I would like to travel; I have a list of places I would like to see in the United States and Europe.
TM: Do you have any advice for a new faculty member to Pine Crest?
CD: Take what you do best, capitalize on that talent, and make it your hook in the classroom. We are a culture of students, faculty, and administrators who appreciate people who have unique talents. Every faculty member should cultivate that strength or interest that sets them apart.
TM: Is there anything else you would like our community to know?
CD: I will have a Facebook page now that I am retiring. So if you want to reach out, I would love to hear from you!
