[2] He was educated at Rossall School, before matriculating at Magdalen College, Oxford, where he studied mathematics.
[1][3] Osborn worked for a period under W. E. Henley on the National Observer, alongside J. M. Barrie and H. G. Wells.
In 1895, owing to ill-health, he travelled to Canada for a year's holiday, but ended up staying until 1900.
[3] The majority of Osborn's journalistic career was spent as literary editor of The Morning Post, which was later absorbed by The Daily Telegraph.
[2] In addition to his newspaper work, Osborn was also an accomplished author,[2] writing books on a wide range of subjects, including Greek and Roman civilisation and the Middle Ages.