Jackson was born at Duddington, Northamptonshire on 5 March 1878. He enrolled at the Slade School of Art in 1893 where he studied alongside fellow students Wyndham Lewis, Orpen, Gertler, Nash and Nevinson. He left the Slade in 1899 in order to travel to Canada, USA and Mexico, spending three years in Italy.
In 1911, he joined the Army. Upon the outbreak of the First World War, his battalion was sent to France. He was captured in 1916 and was held at various German prisoner of war camps, largely at Schwarmstedt in Saxony. Whilst in captivity he befriended the poet Frederick William Harvey, for whom Jackson executed the drawing that decorates the front cover of Harvey’s biographical work, Comrades in Captivity.
The Imperial War Museum contains two paintings by Jackson. These works, along with several others, were displayed in the exhibition, ‘The Nation’s War Paintings and other Records’ that toured British cities between 1919 and 1920.
In 1918, a few days after the end of the war and just three weeks after his return to England, he married the Hon. Hildred Mosley.
Jackson moved to Westleton, Suffolk, where he continued to paint and began wood carving. Jackson exhibited at the Royal Academy, the International Society, Walker Art Gallery, London Salon and the New English Art Club.
Jackson was heavily involved with Walter Francis Crittall’s ‘Sole Bay Group’ in the early 1930’s, which became popular with many of the leading artists of the time.