After a brief stint as a civil servant with the Inland Revenue and HM Customs and Excise,[2][3][4] Loveday was recommended by his former headmaster and joined the Royal Naval Air Service (RNAS) on 17 March 1918 as a probationary flight officer.

[2] On arrival in South Australia, Loveday worked on the pastoralist William George Mills' property, Millbrae, near Nairne in the Adelaide Hills.

In 1922 Loveday obtained a 15 acres (6.1 ha) horticultural block at Renmark near the Murray River in the northeast of the state, and became engaged to Mills's youngest child, Liza "Lizzie" Hilliary.

The farm turned out to be unworkable as an ongoing concern, and Loveday relocated, working as a haulage contractor mainly around Clare in the Mid North of the state.

His service in World War I meant he was entitled to a soldier-settler block and took up land at Cungena inland from Streaky Bay on the Eyre Peninsula.

The land Loveday took up was marginal, and he and his family lived in a basic iron and timber house while he cleared 1,400 acres (567 ha) of Mallee scrub on which to grow wheat.

Drought and depressed grain prices made his situation difficult, and he became president of the local branch of the South Australian Wheat Growers’ Protection Association and secretary of its Eyre Peninsula section.

Loveday, as a staunch advocate of equality, started a staged process towards pay equity for women teachers, including 'accouchement leave' and other means of reducing discrimination were begun.

However, his inept handling in 1966-67 of the (John) Murrie case—involving a Darwin primary-school headmaster who publicly complained about the lack of experienced teachers at his school—angered many in the teaching profession.