Mr. Christopher Olley Retirement Announcement

Headmaster Mr. Christopher Olley

Dear Chesterton Families,

With both sadness, and gratitude for his dedicated service, we would like to announce that our Headmaster, Mr. Christopher Olley, has shared his plans to retire within the calendar year.

Our board of directors has begun the process of gathering a pool of potential candidates to serve as Mr. Olley’s successor. Mr. Olley has graciously agreed to continue serving as Headmaster for several months until a candidate is selected.

While we are saddened by his upcoming departure, we wish him all the best as he prepares for a new chapter in his life. His retirement will mean more time to spend with his wife, Jane, his children, and his granddaughter, Layla Jane. Mr. Olley will also make time for biking, fishing, and coaching the Chesterton Academy girls basketball team.

Mr. Olley’s career has been marked by his passion for education and his commitment to our Catholic faith. Mr. Olley joined Chesterton Academy in 2018 as executive director and was appointed headmaster in 2021.

 “I can’t thank Jay Ward and Dale Ahlquist enough for giving me the gift of Chesterton,” Olley said. “The faculty and staff has made Chesterton Academy a national model for Catholic Classical schools. I consider myself lucky to have partnered with such outstanding servant leaders. The students and parents made my time at Chesterton Academy the most rewarding experience in my career.”

We are so very grateful for the profound impact Mr. Olley’s leadership has had on our school. His long-term vision, decisive direction, thoughtful stewardship, and team-based approach have been valuable assets to our success.

Mr. Olley has over 40 years of experience as a teacher, coach, and school administrator, touching the lives of many young people during the course of his tenure.

Please pray for Mr. Olley that he would enjoy a smooth transition and a joyful retirement. Please also pray for the guidance of the Holy Spirit to help us find his successor. Lastly, please continue to pray for Chesterton Academy, as we carry out our mission to raise up the next generation of saints.

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