John S.H. Guest was born in Burton-On-Trent, England in 1873. He began his career in education when he won a scholarship to Cambridge University, where he obtained a Master’s degree in modern history at Corpus Christi College. He started teaching in Yorkshire, but sought greater challenges and, in 1901, took a teaching position at Upper Canada College (UCC) in Toronto, Canada. One year later, he became headmaster of the Preparatory "Prep" School (Junior School) at UCC.
In 1906, John married Gladys Walker daughter of Sir Edmund Walker. Together they had four children, David (class of 1925), John (class of 1929), Elizabeth "Betty", and Katherine "Kitty".
Encouraged by his father-in-law, Sir Edmund Walker, Guest began the enormous responsibility of organizing and founding a preparatory school, and in April 1911 ground was broken for the School House (now Colley House), with Guest personally overseeing all aspects of construction. In the fall of 1911, the Appleby School (now College) opened to receive twenty-nine students.
Guest quite literally ‘built’ the school, comprising School (later Colley) House, the principal’s residence, the Chapel, the barn, and several buildings that no longer exist. Beyond the bricks-and-mortar contributions, he also established Appleby’s foundations, recruited the staff, designed the academic curriculum, established moral and spiritual principles for the boys, fostered a challenging sports program, and looked after the business management of the fledgling institution, even seeing it through the significant financial challenges of the Great Depression. He also saw the establishment of the Appleby Old Boys’ (now Alumni) Association in 1920, and the Appleby Women’s (now Parents) Association in 1928. Over Guest’s tenure, Appleby grew from twenty-nine students to ninety students, from one building to nine buildings, and from five employees to fifteen.
John Guest retired on June 25, 1934, having served as Appleby’s headmaster for 23 years. He had always been skilled with his hands, and pursued his interest by building furniture for his children and grandchildren.
Guest died on April 13, 1953.