Diana attended the Legal Administrative Course at Humber College in 1984, and after completion of the course, she worked with a law firm in Scarborough for sixteen years in civil and matrimonial matters. After she and her family moved to Port Perry, she joined the Michael L. Fowler Law Office in 2002 and worked exclusively in Wills and Estate matters. In 2019, she joined the Inclusive Law team when Michael L. Fowler Law Office was rebranded to Inclusive Law.