After the end of the Second World War, Shepherd, together with his wife Allison, went to Singapore as an employee of a British trading company.

Later Shepherd purchased majority shares in the firm of Fielding, Brown and Finch working in Malaya and Singapore.

When Shepherd first joined the House of Lords its membership was entirely composed of hereditary peers with a large inbuilt Conservative Party majority.

He thought there was too much unnecessary ceremony and in 1971 argued that those entitled to vote in the Upper House be restricted to regular attenders.

After the Labour victory in the 1964 general election, he became Captain of the Honourable Corps of Gentlemen-at-Arms and Government Chief Whip, House of Lords, a post he held until 1967 when he became Minister of State at the Foreign and Commonwealth Office.

During his tenure at The Foreign Office, Britain was busy shedding Empire and he was very involved in the new constitutions of colonies becoming independent, including Fiji.

In November 1975, Harold Wilson caused controversy within the Labour Party by sending him to represent the UK Government at the funeral of General Franco.

After the surprise defeat of Harold Wilson's Labour government in the 1970 general election, Shepherd worked for Rudy Sternberg's Sterling Group.

He tried to persuade the Conservative government not to privatise the company, warned of the disappearance of loss-making rural services and frequently clashed with the Transport Secretary Nicholas Ridley.