Following the end of his war service, on 4 March 1921 Caldicott, at the age of 21, sailed from London aboard the
British India steamship SS
Nevasa for
Mombasa,
Kenya Colony. However, by 1925 he had returned to England, and on 2 October 1925 departed Southampton aboard the
Union-Castle steamship RMS
Briton for
Cape Town, to settle as a tobacco farmer in the
Umvukwes District of
Southern Rhodesia. In 1943–1945 Caldicott served as the President of the
Rhodesia Tobacco Association. In 1945 he married Evelyn Macarthur, who had two existing children, and they had a son together, Michael John Caldicott. In 1946 he was elected President of the
Rhodesian National Farmers' Union until 1948, which gave him a prominent platform for elected office. ==Southern Rhodesia Legislative Assembly==