Dearon graduated from the University of Kentucky J. David Rosenberg College of Law. During law school, Dearon worked with the Volunteer Income Tax Assistance (VITA) program, helping prepare income tax returns for low-income, disabled, and limited English-speaking individuals. He also served on the College of Law Honor Council. Prior to joining Circeo Law Firm, Dearon was a staff attorney for the Honorable Kimberly N. Bunnell of Fayette Circuit Court, 9th Division, where he conducted extensive legal research, managed the civil docket, and completed first-round opinion drafting in district court and administrative agency appeals