From growing up on several different army bases in the Philippines to becoming the director of the Upper School here at Saint Stephen’s, Mrs. Anna Conn has been through a lot.  

Conn’s parents were both teachers overseas at Department of Defense schools, which meant that she and her brother moved around a lot, living on Air Force and Navy bases in the Philippines. but something unexpected happened when she was 13, an event that turned her life upside down.

“When I was in junior high, in 8th grade, we had a volcano erupt,” Conn said. “So we all evacuated.”

From there, Conn’s family to move to Seoul, South Korea, where she finished up junior high and high school. Following that, her parents moved the family to Japan for a few years. However, even after all this moving around the world, she ended up living in Bradenton.

“My grandmother lived on Fontana,” Conn explained. “Even wherever we were, we always came back to Harbor Hills.”

Conn explained that she lived in Bradenton for a year when she was a kindergartener, attending Saint Stephen’s, where she got a small glimpse into what the school was like.

However, Conn didn’t always want to pursue a career in education. Because of her parent’s military careers, Mrs. Conn thought she wanted to join the air force and be a doctor.

“So I went to Eckerd College, and I took all my classes,” Conn said. “I mean, everything from standing and saluting to boot camp… then I realized I didn’t want to do that.”

Conn ended up majoring in math and minoring in finance, not pre-med, and she got a job at Merrill Lynch for a few years and thought she wanted to be a stockbroker. However, she decided to change her mind completely and went back to Graduate school for education. Although she only attended Saint Stephen’s for a short while at a young age, she decided to interview at the school but unfortunately didn’t get the job. 

“When it was time to get a job,” Conn said. “I came down and I interviewed here and, believe it or not, the first time I did not get the job.”

After this rejection, Conn worked at Bradenton Preparatory Academy for a year before finally getting the job here at SSES.

Even after the original denial, Conn wasn’t discouraged.  A big part of her personality is a positive attitude. Anytime someone walks into the school and sees her standing in front of the main office, there’s always a warm and welcoming smile on her face. To stay in this mindset, Mrs. Conn has a certain belief system she goes by.

“Why waste energy being negative?” Conn asked. “There’s just absolutely no reason to dwell on it…If something bad happens, you can definitely kinda feel all the feelings. But then you gotta pick yourself up and just keep going.”

This mentality is something that Mrs. Conn offers to all of her students in the Upper School. When speaking about her core values, she wishes that she could get that message across to every student and wants to be remembered by it.

“I think I’d love for my students just to remember me always welcoming them through my door,” Conn said. “Whether they’re having a rough day, they want to tell me good news, or they got in trouble, I always want them to think I can always go to Mrs. Conn no matter what.”

Although Mrs. Conn has had a lot of stops and detours on her journey, she found her home here at Saint Stephens’s.