You ever feel like the world’s just not set up for honest people? Like, if you play it straight, you get steamrolled, but if you bend the rules, you get ahead? That’s what The Penguin (2024) hits on with that line: “The world ain’t setup for an honest man to succeed.” And look, I get the reaction—people hear that and think, Well, guess I’m screwed then. But that’s a victim mindset, man. Flip it. Invert it. Think like Charlie Munger.
For those who don’t know, Charlie Munger was Warren Buffett’s right-hand man, a brilliant investor, and one of the sharpest minds in decision-making. One of his big mental models was inversion thinking—instead of just asking, How do I succeed?, ask, How do I fail? Then, avoid those failure points, and boom—you’re already ahead.
If you’re an honest person, your biggest risk isn’t the system—it’s the people around you who know how to exploit your honesty. So let’s use some AI and critical thinking to ask: How could I be set up to fail just by being too honest?
Let’s say you’ve got a coworker who knows you’re always truthful. They could throw you under the bus because they know you won’t lie to defend yourself. Or a friend who knows your financial situation could guilt-trip you into bad deals. A relative could twist your words, knowing you won’t deny something just to save face.
The real trick here is to use LLMs (Large Language Models) to think through these scenarios ahead of time. If you’ve ever used ChatGPT, Copilot, or Gemini, you’re already using an LLM—it’s just a powerful AI that helps you process information, generate ideas, and anticipate outcomes. You can use these tools to generate prompts that simulate real-world situations, predict risks, and prepare for them. That’s the power of inversion—don’t just think about success, think about failure and reverse-engineer a way to avoid it.
But here’s where it gets even better: Personas. If you really want to fine-tune these prompts to your situation, create personas that reflect the types of people in your life. Think about your boss, your best friend, your business partner, or even that sketchy relative. What do they know about you? How could they use that information to trip you up?
By creating different personas, you can craft hyper-personalized prompts that expose blind spots in your relationships. You don’t just think about how someone could take advantage of you—you can see it from their perspective. That’s a serious edge in a world where being naive gets you crushed.
I put together 12 powerful prompts that help you identify where you might be vulnerable because of your honesty. And if you use personas, you’ll get even sharper insights. Check them out. No excuses. Protect yourself, play smarter, and don’t let the game play you.
12 Prompts for Inverting the “Honest Man’s Dilemma”
- If someone wanted to use my honesty against me at work, how would they do it?
- What does my closest friend know about me that could be used to manipulate me?
- How could a business partner take advantage of my straightforward nature?
- If I were too honest about my finances, what’s the worst way someone could exploit that?
- How could my past mistakes be used against me if someone wanted to sabotage me?
- What’s a situation where my refusal to lie could put me in a tough spot?
- How could a dishonest landlord, bank, or employer use my honesty to their advantage?
- If I were in a negotiation, how could being too open weaken my position?
- What kind of social situations make it easy for people to take advantage of honest individuals?
- How could a relative use my sense of family loyalty against me?
- If I had to defend myself in a dispute, how could being too transparent work against me?
- How can I recognize when someone is trying to exploit my honesty and what’s the best way to counter it?
AmpedThink 