He worked unhappily as an underwriter at Lloyd's in London for thirteen years before some of his sketches were accepted for the periodical The Sovereign.
At the Daily Mirror, Haselden originally started with political cartoons, but soon settled into his trademark style of gentle, conservative social commentary reflecting on middle-class fashions and manners.
During World War I, Haselden established a popular reputation with his only truly sustained attempt at political caricature, the adventures of "Big and Little Willie", a satirical comic strip[1] mocking Kaiser Wilhelm and his son, the Crown Prince.
Haselden often lampooned social and technological trends of the time by making bold predictions about how the future would transpire, including fashion,[2] camera phones[3] and feminism.
His work drew praise from celebrities including Margot Asquith, Stanley Baldwin, Paul Nash, Walter Sickert.