By his early twenties, Ashton had become a well-known figure in the local media and newspaper companies, writing music, literary and art reviews.
Ashton had never worked as a full-time artist; however despite this, in 1938 he won the Sydney sesquicentenary prize for landscape drawings.
Ashton was, as well as an artist, a musician who had been known to entertain guests and lodgers at his Mosman house; it was because of this that the suggestion of forming the first Sydney String Quartet was put forward.
While attending his father's art school, Ashton began a relationship with Mary Ethel Roberts (died 18 December 1945), whom he married on 24 January 1908.
[4] A month after his wife's death, Ashton resigned from The Sun in order to devote his time to painting and reading, and to be closer to his family.