Expectations Kill
Jul 2025
A friend told me during a phone call that he just hopes things go well. I don't work that way; I told him I don't really do the whole "hope for the best" thing. I'm more of a "plan for the worst" person.
I said: "I never hope for the best, the best it’s never real and if it does happen then it’s a bonus. Expectations kill."
Expectations create a strange blindness. Once you lock onto how something should go, you stop noticing the signals in front of you. You miss what's actually happening and keep pushing a plan that no longer fits the situation.
Take Jake, a red team engineer who worked with me on ACG. He was sent to assess the physical security at a facility in an unstable region of the world. His briefing described lazy guards and predictable patrols, so he expected an easy job, where he would get in, document the gaps, get out. The guards turned out to be former military contractors with serious hardware, and the facility was a front for something far darker. Jake noticed the mismatch but stuck to his original plan anyway, because that's what he had prepared for. He "hoped for the best". By the time he realized the intel was wrong, he was already inside and compromised. His extraction turned into a real crisis, and he made it out only because his backup team stayed ready for a different reality than the one they had planned for.
Planning is essential. Expecting a single outcome is not the same thing. Planning means preparing for several scenarios, while expecting means betting everything on one of them. Run through the worst cases in your head before you're in them, so you recognize the warning signs when they show up. Map your approach, know your objectives, and understand your environment, but stay ready to adjust the plan the moment reality contradicts it.
Red team your own plans.
Always keep an escape plan, in a Red Team operation, a business decision, or a hard conversation. Know how you're getting out if things go wrong. Expectations can get you killed. Options keep you alive.