This presentation will go through various steps on how students can bridge the gap between academia and becoming a penetration tester. This will include a breakdown of certifications, career fields to take on before getting in the industry of penetration testing, what to expect, and speed bumps and roadblocks that students can expect to see in their journey. In addition, the talk will go over various high-level road maps based on career paths, academic journeys, and other situations that will allow viewers to create their own roadmaps to becoming penetration testers.