In his early years, Proudfoot helped his father in the shop by performing tasks such as filling blue bags with sugar. During the 1930s unemployment in Crook approached 40% and Proudfoot became familiar with the problems of retailing in a poor community. He was educated at a local council primary school but failed the 11-plus examination in spite of sitting it one year late after being "held back" a year. Subsequently, at age 14, he was sent to stay with two maiden aunts who ran a boarding house in Scarborough where he attended Scarborough College, an independent school. After gaining the school certificate Proudfoot joined a Durham accounting practice as a trainee.