Pierneef resigned as lecturer and became a full-time painter in 1923, due to differences of opinion regarding the curriculum with the Department of Education.
Pierneef visited South West Africa (now Namibia) from 1923-1924, where he sketched extensively for paintings that would later be completed in his studio. These would later be considered some of his best works.
Despite his successes, he was experiencing some financial difficulties, and had to resort to other jobs to make ends meet.
During one of these, an advertising project to sell the land around Hartebeespoort dam, he met his future second wife, a Dutch woman named May Schoep. Pierneef divorced Agatha in 1923 and married May in 1924.
The couple visited Europe from 1925-1926, where Pierneef promoted his art and also studied the newest art movements.
He also held a solo exhibition in the Netherlands, where his Bushmen drawings drew great attention.
In 1927 Pierneef's daughter was born and he held a very successful exhibition of 86 of his works in Pretoria.
However, during his solo exhibition the following year, he had some abstract modern works on display, which were very badly received, compelling him to revert to his old style.
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