Jackson attended MacKillop Catholic College on the NSW Central Coast, where he completed his HSC. Following the completion of his schooling, Jackson decided to take a working gap year, during which he worked at both Wyong Rugby Leagues Club and BAX AV.Following his gap year, Jackson enlisted into the Australian Regular Army as an officer cadet, training at the Australian Defence Force Academy (ADFA). During his time at ADFA, Jackson partook in both military training (encompassing field craft, weapons and tactical training, as well as personal, unit and subordinate administration) and University study through the University of New South Wales. Jackson studied a Bachelor of Arts, majoring in Politics and English. Following completion of his time at ADFA, Jackson moved to the Royal Military College at Duntroon, the Australian Army's Officer Training institution, where he completed 6 months of the 12 month long course, before deciding to pursue a different and challenging career, outside of Defence.In the interim between leaving Duntroon and commencing his civilian career, Jackson was assigned to Defence Legal, where he worked as a Senior Research Assistant inside the Office of Defence Special Counsel. His duties here included management of a small team and the wider office environment, both general and specific researching tasks culminating in the construction of detailed reports for senior management, and providing a point of contact for both military and civilian stakeholders to liaise through.