I’ve always been a fan of breaking things down to figure out how they work—sometimes that means disassembling old electronics, other times it means turning a question on its head. That’s where inversion comes in.
Inversion is this strange, elegant mental model—popularized by Charlie Munger but rooted in the mathematical mind of Carl Jacobi—built around a simple idea: if you want to solve something, try solving the opposite. Don’t just ask, “How can I succeed?” Ask, “How might I fail?” Then avoid those failures.
This flipped way of thinking has helped me untangle everything from tricky team dynamics to gnarly security architecture. It’s not magic. It’s just honest thinking. And it’s surprisingly useful—in life and cybersecurity.
Everyday Life: Living by Avoiding the Dumb Stuff
In personal productivity, inversion’s like having a brutally honest friend. Don’t ask how to be productive—ask what makes you waste time. Suddenly you’re cancelling useless meetings, setting agendas, trimming the invite list. It’s not about optimizing your calendar, it’s about not being a dumbass with your calendar.
When it comes to tasks, the question isn’t “How do I get more done?” but “What distracts me?” Turns out, for me, it’s that one open browser tab I swear I’ll close later. Close it now.
Even wellness gets better when you flip the lens. Don’t chase the best workout plan—just ask “Why do I skip the gym?” Too far away, crappy equipment, bad timing. Fix those.
Same with food. I stopped keeping junk in plain sight. I eat better now, not because I have more willpower, but because I don’t trip over the Oreos every time I pass the kitchen.
Inversion also made me rethink how I spend money. Don’t ask “How do I save more?” Ask “What makes me blow cash unnecessarily?” That late-night Amazon scroll? Canceled. That gym membership I never use? Gone.
Relationships: Avoiding Trust Bombs
In relationships—especially the ones you care about—you want to build trust. But instead of obsessing over how to build it, ask “What destroys trust?” Lying. Inconsistency. Oversharing someone’s private stuff. Don’t do those things.
Want better communication? Don’t start with strategies. Just stop interrupting, assuming, or trying to fix everything when people just want to be heard.
Cybersecurity: Think Like the Adversary
Now let’s pivot to my day job: security. Inversion is baked into the best security thinking. It’s how I do architecture reviews: don’t ask, “Is this secure?” Ask, “If I were going to break this, how would I do it?”
It’s how I approach resource planning: “What failure would hurt us the most?” Not “Where should we invest?” The pain points reveal your priorities.
Even in incident response, I run pre-mortems: “Let’s assume this defense fails—what went wrong?” It’s bleak, but effective.
Want to design better user behavior? Don’t pile on password rules. Ask “What makes users work around them?” Then fix the root causes. If people hate your training, ask why. Then stop doing the thing that makes them hate it.
The Big Idea: Don’t Try to Be Smart. Just Don’t Be Stupid.
“It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.” — Charlie Munger
We don’t need to be clever all the time. We need to stop sabotaging ourselves.
Inversion helps you see the hidden traps. It doesn’t promise easy answers, but it gives you better questions. And sometimes, asking the right wrong question is the smartest thing you can do.
Would love to hear how you’ve used inversion in your own life or work. Leave a note or shoot me an email. Always curious how others are flipping the script.
* AI tools were used as a research assistant for this content, but human moderation and writing are also included. The included images are AI-generated.
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