Portrait of a Graduate: Steven Stillman ’02

Steve Stillman ’02 is Academy at the Lakes’ oldest living graduate – and at just 31 years old, he’ll be holding on to that title for quite a while. He remains involved with the school today as the president of the school’s budding Alumni Association.



Stillman’s first experience with Academy was as a young child. He attended Academy as a pre-schooler, and would return years later as a high school student.

“After attending a couple high school programs, and with difficulty finding the right fit, my family reached out to Academy once again,” said Stillman.

The high school had just recently opened at the time, and after considering the successful pre-school experience, the Stillman family decided that Academy would be the best choice for them.



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Stillman is a member of the 2002 graduating class – a class that consisted of only four graduates including himself.

“While some might be put off by the idea of a small class size, to me the situation couldn’t have been more perfect,” said Stillman. “The student-to-teacher ratio was basically 1 to 1 at the time, which resulted in an above average amount of interaction with teachers. For me, this was motivating, as my previous inability to find the right ‘fit’ came as a result of feeling lost in the proverbial crowd.”

“Sure, it was impossible to get lost in the crowd and our social experience was predetermined, but that was exactly what I needed.”



“[Academy gave me] a second chance to succeed,” said Stillman. “While many go through high school already achieving that [perfect] fit, or acquiescing to a fit, others progress feeling out of place, and that was me.”

Instead of accepting inevitability and being unhappy, Stillman challenged his environments, moving around to a couple of different schools and figuring out what was, and was not, working for him.

“The initial draw of the Academy was its close proximity to home and student-to-teacher ratio, though attending the school opened my eyes to so much more,” said Stillman. “The faculty was outstanding, togetherness existed amongst students, and campus was growing and evolving – all of which helped to develop a culture that promoted learning, excitement, motivation, fun, and thought. That is what I was looking for and, ultimately, is what molded me into who I am today.”



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The culture and environment fostered by the school helped to motivate Stillman to question and learn, preparing him for life after Academy.
Upon graduation, Stillman attended Harvard University, where he earned a Bachelor of Arts in Humanities/Linguistics. Following his time in Cambridge, he worked for four years as a stock broker before eventually returning to school. He would go on to receive a Master of Science degree in Information Systems Security at the University of Florida, and has been working as an Information Security consultant for the last two years.
With all the success he’s had, Stillman still believes that people should focus on finding the programs that work best for them.

“While some might do well in a public school environment with lots of students and established traditions, others might prefer smaller class sizes and developing new traditions,” he said.

It’s all about finding the right fit, and following Stillman’s example by flourishing once you do.


As a fully-accredited college preparatory school, Academy offers a challenging curriculum with a wide range of core and elective choices, including Advancement Placement and Honors tracks. Learn more or schedule a tour.


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