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He was trained as an engineer and worked as both an agricultural and motor engineer before he married in 1939. Before his wedding he bought the narrow boat Cressy and fitted it out as a floating home on which to cruise the inland waterways. He planned to make his living as an author but the Second World War soon disrupted this course.
His account of his voyage before the war was published in 1944 in the book Narrow Boat and generated tremendous interest in the country's much neglected canal network. Robert Aickman read the book and wrote a letter to him suggesting the formation of a society to campaign for a new waterways world, an idea that had not occurred to Rolt who was by nature a private man. However he enthusiastically embraced the proposal and at the inaugural meeting of the Inland Waterways Association (IWA) in 1946 he was appointed Honorary Secretary. Soon a comfortable friendship was established not only between Tom and Robert but also included their wives Angela and Ray, a relationship that involved cruising on Cressy together and staying at the Aickman's Gower Street flat.
As time progressed Tom became less satisfied with the demands placed on him by Robert's ambitious programme of campaign cruising and lobbying for the IWA. He felt that the time demanded of him was difficult to balance with the need to earn his living as an author he also felt that Robert was taking insufficient account of his views. Tom had the idea of holding the first IWA Rally of Boats at Market Harborough in 1950. Robert took up the idea and went further making it into a Festival of Boats and organised many land based activities. Before the festival was held in August the break between the two men occurred. The final straw had been a disagreement over the IWA policy of fighting for every mile. Tom had aligned himself with a group who proposed prioritising IWA efforts or as Robert saw it "keeping some waterways and letting others go".
On 11 October 1950 the matter came to a head in a meeting at the Imperial Hotel in Birmingham where Tom and the other "heretics" were defeated. Tom and many others left the IWA over this policy split. For Tom it was a particularly sad time as his twelve year marriage to Angela also ended. She went to join Billy Smart's Circus as assistant ring master and Tom went on to run the Talyllyn Railway Preservation Society.
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