James Holden served a six year apprenticeship under his uncle, Edward Fletcher, with the York Newcastle & Berwick Railway. In 1865, he then joined the Carriage & Wagon Department of the Great Western Railway (GWR). From November 1870 to June 1873, he was the superintendent of the Saltney Works of the Shrewsbury & Chester Railway. Eventually he was promoted to the position of Chief Assistant to William Dean at Swindon, before becoming the Locomotive Superintendent at the GER, in July 1885, succeeding T.W. Worsdell.