Gentry High finance teacher reflects on over 30 years at high school


With over 31 years in the Indianola School District, Gwendolyn Milton guided students toward the right path and now retirement is the next step for her.

She has been a part of Gentry High School through nine principals and nine superintendents.

“Although I have traveled to many countries and worked many jobs, one of the most enjoyable jobs was working for 20 years as Office Manager at Gentry High School” said Gwendolyn Milton.

After realizing the importance of teaching financial responsibility, Milton made her way into the classroom.

She believes her greatest accomplishment was making the transition from Office Manager into a teaching role, because it enabled her to teach students about financial literacy.

“Education, I believe, is the key to a successful life, and financial literacy is a lifetime responsibility” said Milton, who most recently served as Academic Advisor and Financial Literacy Teacher at Gentry.

Whether as office manager or teacher, Milton touched the lives of countless students over the years.

Kiyona Crawford met Milton in 2012 during her senior year at Gentry High School. Milton was a senior coordinator for Crawford’s graduating senior class and also one of her teachers.

“I was privileged to be able to have her as a teacher inside and outside of the classroom” said Crawford. “She taught me financial literacy and also how to prepare for life after high school coming into adulthood. During the brief two school semesters I’d known her, she became my mentor. I admired her passion for teaching and how she effortlessly conducted business at Gentry and within the school district.”

Milton has received many awards and recognitions, including Gentry High School Teacher of the Year Award in  2012-2013 and Indianola Chamber Educator of the Year in 2013.

Milton believes it is important to maintain relationships with students.

“She was a very active faculty member,” said Crawford. “Whether it was facilitating after-school activities or being a senior coordinator, every role she had at Gentry she conquered. As a teacher, mentor, and individual she gave a lasting impact on anyone she encountered.”

Not only did Milton leave a lasting impact on students but also her co-workers.

“Working with Mrs.Milton for the past thirteen years has been an awesome experience,” said Lora Dean, Guidance Counselor at Gentry High School. “She was a mentor to myself, she’s guided me and she has shown me so much, and I’ve gained a wealth of knowledge from working with her. She’s like a second mom to me.”

Over the years Milton has been many different things to many different people and has played many different roles within the walls of Gentry High School.

Milton was born and raised in Cleveland. She is an alumna of Mississippi Valley State University (Bachelor of Science degree in business administration), University of Southern Mississippi (Master Teachers of Economics Endorsement)  and Delta State University( Master of Arts in Teaching Secondary Education).

“Say what you mean and mean what you say. Be fair and consistent with people” were the words of advice Milton had for whomever fills her position in the future.


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