[5] Ole returned to Estonia in 1918, when his country became independent, and worked as a theatre designer, teacher of drawing, art critic and as of 1923, as a professional artist.
This group was able to organize a whole series of exhibitions dedicated to Cubism experimentation, although Ole himself never became totally non-figurative, retaining a strong link with the material world.
Their work was primarily distinguished by modest geometricized abstraction and decorative colourism suggested by Synthetic Cubism, rather than by explorations of simultaneity or collage.
As a consequence to Ole's first study trip to Paris, the cubist severity of form vanished and he preferred to depict large figurative compositions, dramatically staged, with soft planes and colours and nuanced pastel tones.
As a consequence to the German occupation of Estonia during World War II (1941–1944) and fleeing the Soviet occupation of Estonia (1944), Ole left as a refugee to Finland in 1943, where he continued to paint portraits of personalities of Finnish cultural life, such as the ones of the linguist Lauri Kettunen and of Viljo Tarkiainen, biographer of Aleksis Kivi, and landscapes.
However, fleeing the Continuation War between Finland and the Soviet Union in 1944, Ole moved to neutral Sweden and became a Swedish citizen in 1951.
During those trips Ole's sensibility experienced a new type of light, powerful natural forms, contrasts of colour and structure, of rocks and water found on fjords.
Such works, particularly their expressionist dynamism of colour, have a definite influence of other Nordic artists, such as Edvard Munch, Ernst Josephson, and Akseli Gallen-Kallela.
[12] During the late 1960s and early 1970s Ole's style underwent a new and unexpected metamorphosis, returning to a cubist simplification of forms and gentle planes and motives, moving from landscape painting towards figurative compositions.
The result of this last change can be noticed on Ole's self-portrait of 1979 Autoportree, on the 1988 Motiiv Stockholmist (English: Motif from Stockholm), and on the 1991 Uue pesa ehitamine.