So, you think you want to be a penetration tester, or you already are and don't understand what the difference between you and all the other "so called" penetration testers out there. Think you know the difference between a Red Team, Penetration Test and a Vulnerability assessment? Know how to write a report your clients will actually read and understand? Can you leverage the strengths of your team mates to get through tough roadblocks, migrate, pivot, pwn and pillage? No? well this talk is probably for you then! We will go through the fascinating, intense and often crazily boring on-site assessment process. Talk about planning and performing Red Teams, how they are different, and why they can be super effective and have some fun along the way. I'll tell you stories that will melt your face, brain and everything in between. Give you the answers to all of your questions you never knew you had, and probably make you question your life choices. By the end of this session you will be ready to take your next steps into the job you've always wanted, or know deep inside that you should probably look for something else. There will be no judgment or shame, only information, laughter and fun.