Holbrook Jackson was born in Liverpool, England, on New Year's Eve, 1874. After rudimentary schooling, he worked as a clerk, while freelancing as a writer. Around 1900 he was in the lace trade in Leeds, where he met A. R. Orage. Together, the two men founded the Leeds Arts Club. At that time Jackson was a Fabian socialist, with a penchant for Nietschze.

Later, Jackson and Orage moved to London. In 1906, shortly after arriving in the capital, they founded the Leeds Arts Club, which split from the Fabian Society, whose interest was more economic and political. In 1907, Jackson and Orage bought The New Age, a struggling Christian Socialist weekly magazine, with finance from Lewis Wallace and George Bernard Shaw.

In 1908 Jackson left The New Age, and also began a relationship with Orage's wife. From 1911, he took an editorial position on T. P. O'Connor's T.P.'s Weekly, a newspaper with a strong literary focus. He took over as editor in 1914, and later bought the publication, converting it into the literary magazine To-Day. Around this same time, Jackson, founded the Flying Fame Press, beginning a long association with small press and the worlds of typography and book collecting

Jackson was a prolific author, publishing numerous works in the areas of biography, literary scholarship, memoir, philosophy, and history. Amongst his better-known works are Bernard Shaw (1907), William Morris (1908), Great English Novelists (1908), The Eighteen Nineties (1913), Romance and Reality (1911), All Manner of Folk (1912), Southwest ho! and Other Essays (1914), Occasions (1922), The Anatomy of Bibliomania (1930, 1931), The Fear of Books (1932), and The Reading of Books (1946). Jackson died on 16^th June, 1948, aged 73. Today, he is best remembered as a proud bibliophile and aphorist.