Ashley commenced his articles at Dawes & Vary Solicitors in Kyabraym, Victoria in 2000. Once admitted his practice became quite varied and included a large volume of Magistrates' Court appearance work. Ashley frequently advised and prosecuted on behalf of a local water authority, Goulbourn Murray Rural Water. These matters involved prosecuting individuals for use of the authorities' water resources in contravention of section 288 & 289 of the Water Act 1989.
Whilst employed by Dawes & Vary, Ashley also represented clients in criminal matters, personaly injury claims and commercial disputes. In 2002 his career focus shifted slightly more towards corporate and commercial matters. During his remaining time at Dawes & Vary he conducted and appeared in disputes involving; insider trading, insolvent trading, claims against company directors, claims against publicly listed companies, claims made under the Trade Practices Act and claims in contract.
In November 2003 Ashley signed the Bar Roll. His practice has been wide and varied and he has appeared in most state and federal Courts within Victoria and also both jurisdictions.