A transition from a penetration testing to a red team state of mind can be a challenging one. This presentation intends to provide guidance, resources, and insight into how to become a red team operator. Looking into tools and strategies to help build out successful engagements. Ensuring actions conducted by you and your fellow operators are documented. How to configure infrastructure in a "real world" manner and ensure it is protected. Remembering that we are testing technology, but most importantly, people. Keeping a level of fairness to provide the blue team with tactics, techniques, and procedures (TTPs) which can be identified, contained, and remediated. Understanding the "pyramid of pain" and why OPSEC is important. Ensuring you have the right points of contact and have the ability to stop an escalation before it gets too "serious" someone needs to be there to prevent a lot of "on calls" being woken up for a simulation. Lastly, while we want to research and explore new TTPs and be stealthy we need to ensure that at the end of the engagement the red team has learned something but most of all the blue team has grown and feels positive in their abilities.