A group of former students, current students, educators and seasoned infosec professionals discuss how to bridge the educational gaps whether starting out in infosec or pivoting into a new infosec specialization. We will touch on resources that current students can leverage, the transition into working in infosec, and ways that the infosec industry can help foster new practitioners. Additionally, we will shortly explain the paths we took and how we dealt with the obstacles we faced. We then evaluate these problems to find room for improvement in the industry and give our perspective on what either side could do to make the transition more seamless.