Henry Edmund Holland left school when he was 10 and worked on a farm, until he was apprenticed to the Queanbeyan Times as a compositor at the age of 14. Five years later, Holland moved to Sydney, where he met Annie McLachlan at a Salvation Army meeting and married her the following year. In 1892, working intermittently as a journalist, Holland joined the Australian Socialist League. He co-founded the Socialist newspaper in 1893, which underwent several name changes over the next few years, finally becoming the Sydney-based People in 1900. In 1896 Holland was sued for libel and, unable to pay the fine, was jailed for three months.
Holland became more involved in socialist politics, being instrumental in notable strike actions, and standing unsuccessfully for several parliamentary positions. During this period, Holland edited the Grenfell Vedette, and then the Queanbeyan Leader in 1905, before returning to Sydney to start the International Socialist Review for Australasia. His involvement in the Broken Hill strike of 1909 led to him being jailed for sedition.
In 1912, Holland made a lecture tour of New Zealand, and becoming involved with a miners' strike, stayed on to edit the Maoriland Worker, before being imprisoned for the second time for seditious language. In 1916, he played a key role in the beginnings of the New Zealand Labour Party and was elected to the House of Representatives in 1918. He was made chairman of the Parliamentary Labour Party in 1919, and held this position until his death.
In addition to his journalism and social commentary, Holland wrote numerous pamphlets on local labour issues and international politics. He wrote one book of poetry, Red Roses on the Highways (1924).