When they returned to public and private schools the next year, she was invited to teach Classical Studies to grades 7–12 at Highlands Latin School, where she designed courses on Homeric epic, Ovid's Metamorphoses, Herodotus' Histories, and Plutarch's Lives of the Noble Greeks.

After a sabbatical in 2004 devoted to study and writing of broader scope, including an adult study on Tolkien’s Lord of the Rings and Dante’s Divine Comedy, Ms. Cassady returned to Highlands Latin in 2005 to teach the history and literature of Rome, incorporating the history of Judaism in the Classical period and the emergence of Christianity. Using Will Durant’s Caesar and Christ as a primary text, she integrated readings from classical authors such as Polybius, Livy, and Tacitus.

By 2006, Ms. Cassady had come to recognize an unmet need in Louisville for classical education in a college-preparatory tradition that is appropriate to students of any faith or philosophical stance.  She joined like-minded scholars in founding Classical Studies Institute and Louisville Classical Academy, its program for students in grades 3 - 12.

Ms. Cassady brings a broad experience of civic life to the Academy.  As an attorney admitted to the KY Bar in 1984, she has been in private and administrative practice.  When she found her children in overcrowded Oldham County schools in the 1990's, she founded the parent group whose petition drive spurred a special election on the issue, heightening public awareness which led to the construction of new schools. For most of the next decade, Ms. Cassady was a partner in Capital Link, a lobbying firm in Frankfort, where her clients included Apple Computer, the Kentucky Association of Marriage and Family Therapists (KAMFT), Dupont Pharma, and M.A.D.D.  In 2001, KAMFT honored her with its Distinguished Service Award for her work in passing its licensure legislation.

Ms. Cassady remains a member of the Kentucky Bar, and she serves on the Board of Directors at Central Bank of Jefferson County, for which she maintains continuing education in law and banking. She is a member of the American Classical League, the Kentucky Association of World Languages, and the Kentucky Classical Association.  In the spring of 2007, she was invited to take part in a Colloquium in Sante Fe, New Mexico on Institutions and Liberty:  Federalism, the Separation of Powers, and the Establishment of Liberty in the Constitution sponsored by the Liberty Fund and moderated by Gordon Lloyd of Pepperdine University.   The experience inspired the Foundations course on constitutional debates in American history that she will offer in the 2009 - 2010 schedule.