Chesterton Academy Grad Grateful For Classical Education


If the secret of life is learning to say “thank you” better, the education of Grace O’Connor has been a lesson in gratitude.

“I’ve been to many different kinds of schools,” O’Connor explained. “Private, public, all-girls, Catholic, homeschooling - the best school is the one that pursues the true, good and beautiful.”

As a 2020 graduate of the Chesterton Academy in Annapolis, O’Connor developed an appreciation for the school’s classical curriculum.

“Through the Great Books, we tackle problems that are in the world today, that other schools are afraid to talk about,” said the 18-year-old Severna Park resident who lived in Virginia, California and Hawaii before moving to Maryland. “The Socratic method allows for civil conversation and personal growth. Everyone is treated like an adult. No subject is off limits.”

Much of her education has taken place outside the classroom. In the summer of 2019, she lived in Calcutta, India.

“It’s called the City of Joy - one of the poorest cities in the world. A place of material poverty and spiritual prosperity,” O’Connor said.

Working with the Missionaries of Charity founded by Saint Teresa of Calcutta, O’Connor became even more appreciative of what she has.

“I’ve been in rich places. And in the poorest of poor places,” she said. “I’ve tried to find happiness in sports, self-image, the party scene, success. But an obsession with superficial things is making my generation isolated and fearful.”

In the summer of 2018, O’Connor walked the Camino de Santiago, also known as the Way of St. James, leaving behind all electronic devices.

“Social media creates a world that doesn’t exist,” she said. “I had to break out of that. Leave behind the Instagram feed.”

At the end of her 100-mile pilgrimage, she visited the tomb of St. James in Galicia, Spain, ending her journey with an epiphany.

“I found my authentic self in Christ,” said O’Connor, who is a member of St. John the Evangelist Catholic Church. “Not in chasing self-improvement or self-promotion, or a virtual definition of success.”

In 2020, O’Connor’s vocation of gratitude continues. For the foreseeable future, she plans to work with the Servants of the Lord and the Virgin of Matará, a Catholic religious community. Her work will be hands-on as she serves the poor, the sick and the elderly. Despite the excitement surrounding next steps, O’Connor’s thoughts continually return to her classical, Catholic education at Chesterton Academy.

“Abiding joy comes from seeking the true, the good and the beautiful,” she said. “Serving others. Serving God.

“I was headed down a bad, self-centered road — cynical, meaningless, destructive. I am so grateful to Chesterton Academy for creating an environment of growth, thought and joy!”


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