In 1908 and 1909, he visited his brother in Sydney then in 1912 joined him, then enrolled in the Royal Art Society School to study drawing and painting under Dattilo Rubbo alongside fellow students Grace Cossington Smith, Norah Simpson and Roy de Maistre.
A review in the Sydney Morning Herald described his work as "daring," displaying "a splendid audacity" and a "spirit of modernism.
Wakelin needed to work in England to keep his family and obtained employment with “Hopwoods and Cinads advertising agencies.
An example of his work, exhibited in 1944 at the Macquarie Galleries, the reviewer describes Wakelin as having an exploring temperament and "one of our most forceful painters.
[11] He was an affable, sociable man of considerable attainments in fields other than painting - he read widely and had a fine bass voice, with a repertoire from popular songs and Gilbert and Sullivan to Mozart and Bach.
More personal subject matter included his daughter Judith, his wife Estelle, Roland Jr., and close friend and fellow artist, Douglas Dundas.