Ready was the son of Colonel John Tobin Ready and the grandson of John Ready, former Lieutenant Governor of the Isle of Man. Educated at Wellington College, Ready was commissioned into the Royal Berkshire Regiment as a second lieutenant on 5 December 1891. He was promoted to lieutenant on 28 July 1894, and was part of the Kitchener Expedition to defeat the Mahdi in Sudan 1898–99, taking part in the battles of Atbara (April 1898) and Omdurman (September 1898).