Schreiner's evangelical upbringing resulted in nightmares of hellfire. Coupled with the devastating death of a beloved younger sister and her developing philosophical convictions, Schreiner had a crisis of faith which, at the age of 15, lead her to reject the family's religion. The break caused an insuperable rift between Schreiner and her mother. The conflict between her convictions and beliefs was also a major factor in the onset of severe depression which badgered Schreiner throughout her life.

When her father lost his position in 1867, Schreiner moved with her elder brother Theo, elder sister, Ettie, and younger brother William, to Cradock. By 1872 Schreiner was working informally as a governess to a family in Dordrecht. It was here that she met Julius Gau, a Swiss Businessman, and experienced her first brief love affair - an experience with a "stranger" that she later used in The Story of an African Farm.

Declaring herself a "free thinker", a viewpoint considered alien to the society in which she lived, Schreiner ended the relationship and relocated to the South African diamond fields, to once again live with Theo and Ettie (who had moved in the meantime). She also began writing Undine which was started in 1874 and published posthumously in 1929, The Story of an African Farm written between 1874–5 and published in 1883, and the unfinished novel Man To Man which was first drafted in 1875 and published posthumously in 1924.

In 1874 Schreiner started working full time as a governess - she wrote during her free time. For the next seven years she worked for five different wealthy Afrikaner families in the Cape Colony. Eventually, with the help of her friend Mary Brown (an active British liberal-feminist), she set sail for England to fulfil her dreams of training as a nurse and getting her novels published. Unfortunately, the asthma she had developed during her time on the diamond fields became chronic in England and was too debilitating for her to enter medical training.

Following the critical acclaim for her book, Schreiner was quickly absorbed into the company of several prominent young socialists including Eleanor Marx, W. E. Gladstone, George Bernard Shaw, and Edward Carpenter. In 1884 Schreiner met and had a brief affair with Havelock Ellis, the distinguished "sexologist". Although the affair was quite short, Schreiner and Havelock Ellis maintained a life-long friendship and an extensive correspondence.

In 1885 Schreiner joined the exclusive "Men and Women's Club", a discussion group which concentrated on "the status of moral judgement, moral change, fact and truth in the face of received opinion about the sexes"¹. The nominal leader of the group was Karl Pearson, an acting barrister who had recently started a second career as lecturer in mathematics at University College, London. Pearson, two years younger than Schreiner, was a dynamic character to whom most of the group deferred. Schreiner, however, considered herself much more of his equal, and found his views intellectually stimulating. As the relationship deepened, Schreiner realised that she was looking for more than a platonic friendship. Pearson, however, remained oblivious to her passion. At one point Schreiner signed a letter "Your man-friend OS" in despair at his inability to interact on an emotional level.

Unable to cope with the lack of response from Pearson, Schreiner took herself off for a tour of England and Europe, passing through France, Germany, and Italy. During this time she worked on From Man To Man and various allegorical sketches (published as the book Dreams in 1890). A romantic relationship with the poet/novelist Amy Levy ended in tragedy in 1889 when Levy killed herself, shortly after the two shared a three-day holiday at the seaside. The Pall Mall Gazette carried a defamatory report that the two had shared a suicide pact, but that only the younger, Levy, was able to carry it out.

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