At 17, Boylan entered the Society of Jesus. During his studies ill health led to his being sent to Australia, where he taught at St Aloysius and Riverview in Sydney. He then returned to Ireland where he was ordained a priest and appointed to the Irish Messenger office as editor (the circulation increased from 75,000 to almost 300,000). Much to his delight, after two years in that office, he was sent back to Australia in approximately 1907, where he became prefect of studies at Xavier College, Melbourne, a position he held for about ten years.
Boylan's well regarded novel Heart of the School is set at Xavier. Generally classified as a children's book (e.g. Muir, vol.1 (1992), 873), Boylan himself describes it as 'not primarily written for young boys and girls. I would describe it as a book about boys for grown-ups'. He edited Madonna and Messenger of the Sacred Heart 1918-1949 and was also Rector of St Patrick's College East Melbourne 1919-1921. He also wrote a number of Australian Catholic Truth Society pamphlets, including Factors in National Decay [191-] and The Inquisition in the Light of Historical Perspective (1932). In October 1953 he died at the Jesuit house at Pymble, NSW, where he had lived since 1949.