Expectations Kill

I was talking with a friend the other day about worst-case scenarios, and he said he just hoped things would never go south. 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. It's just how I'm wired. I'd rather think through what could go wrong ahead of time and have at least some kind of game plan ready in my head. I like being prepared rather than crossing my fingers.

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.

You know that feeling when you're waiting for something to happen exactly the way you pictured it? Yeah, that's where things usually go sideways.

I've learned the hard way that expectations are basically just disappointment in a fancy package. The moment you lock yourself into how something "should" go, you're setting yourself up for a world of hurt. And it's not just about hurt feelings - these rigid expectations can lead to some seriously bad decisions.

Here's the thing - expectations aren't just about being let down. They create this weird blindness where you can't see opportunities or adapt when things shift. You become so invested in Plan A that you forget there's a whole alphabet of other options. You get tunnel vision in a tunnel of your own making.

When you expect something specific to happen, you stop paying attention to what's actually happening. You miss the signals, ignore the feedback, and push forward with a strategy that might be completely wrong for the situation you're actually in.

This is basically guaranteed to go wrong - the only question is whether it'll be a quiet failure or a full-blown disaster.

The alternative isn't to be pessimistic or give up on goals. The focus should be on staying flexible and keeping your eyes open. Go in with a direction, not a destination carved in stone. Be ready to pivot when reality shows up with different plans.

Because reality always wins, and it rarely sends an RSVP.

Take Jake, a red team operator who worked with me back in the day on ACG, he was deployed to assess physical security at a facility in a... let's call it an "unstable region". His intelligence briefing painted a picture of lazy guards, predictable patrol routes, and standard corporate security protocols. Jake expected to waltz in, document some vulnerabilities, and extract cleanly.

But when he arrived, those "lazy guards" turned out to be former military contractors carrying serious hardware. The facility wasn't some sleepy corporate office - it was a front for something much darker, with surveillance tech that made his gear look like toys from the 90s. Instead of recognizing he'd walked into the wrong kind of operation and aborting, Jake stuck to his original infiltration plan because that's what he'd prepared for.

Even though he knew better than to take intel at face value, he planned based on his "expectations" of the situation. For some reason, he decided to roll the dice and assume everything would go according to the briefing - which is basically just gambling with extra steps.

By the time he realized his intel was garbage, he was already inside and compromised. What should have been a quick recon turned into a nightmare extraction under "real conditions". Jake made it out, barely, but only because his backup team ignored their own expectations and came in prepared when the situation went sideways.

Expectations kill. You have to keep your options open.

I'm not saying don't plan. Planning is crucial. But there's a difference between planning and expecting. When you plan, you're preparing for multiple scenarios. When you expect, you're betting everything on one outcome.

Use your common sense and the power of visualization to run through what could go sideways before it actually does. Picture the worst-case scenarios in your head until you've got some kind of muscle memory for how you'd react. If Jake had spent time visualizing what a hostile facility actually looked like instead of just assuming his intel was solid, he might have recognized the danger signs before walking into a trap.

Plan carefully, absolutely. Map out your approach, know your objectives, understand your environment. But also know that the moment you make contact with reality, that plan is probably going to need some serious adjustments. Maybe all of them.

And always - always - have an escape plan. Whether it's a Red Team operation, a business venture, or just a difficult conversation, know how you're getting out if things go south. Because expectations kill, but having options might just keep you alive.