Inversion: The Mental Model That Fixes 80% of Bad Decisions

Why We Default to Forward Thinking

When faced with a problem, our instinct is to ask: “What should I do to get the outcome I want?” This is forward thinking. It feels productive. It generates action items, roadmaps, and plans.

But it has a blind spot. Forward thinking assumes you know what success looks like well enough to chart a path toward it. Often, you don’t.

The Power of Thinking Backward

Inversion flips the question. Instead of asking “How do I build a great data team?”, ask “What would guarantee my data team fails?” The answers come faster and with more clarity:

• Hire only for technical skill, ignore communication ability
• Let everyone pick their own tools with no shared standards
• Never define what “done” looks like for a data project
• Shield the team from business context

Now avoid those things. You won’t have a perfect team, but you’ll avoid the most common failure modes.

Where Inversion Shines

Career decisions. Instead of “How do I get promoted?”, ask “What behaviors guarantee I stay stuck?” Working in isolation, avoiding hard conversations, never shipping anything visible, waiting for permission instead of taking initiative.

Parenting. Instead of “How do I raise a confident kid?”, ask “What would destroy a child’s confidence?” Constant criticism, never letting them struggle, comparing them to others, dismissing their feelings.

System design. Instead of “How do I build a reliable data pipeline?”, ask “What would make this pipeline fail in production?” No monitoring, no alerting, no retry logic, no documentation of upstream dependencies.

The Stoic Connection

The Stoics practiced this 2,000 years ago. They called it premeditatio malorum, the premeditation of evils. Marcus Aurelius would start each day imagining everything that could go wrong. Not to be pessimistic, but to be prepared.

Charlie Munger, Warren Buffett’s long-time partner, put it simply: “All I want to know is where I’m going to die, so I’ll never go there.”

Making It Practical

Next time you’re stuck on a decision, try this exercise:

1. Write down the outcome you want
2. List 5 things that would guarantee failure
3. Check whether you’re currently doing any of them
4. Stop doing those things before adding new initiatives

The surprising result: removing failure modes often gets you further than adding success strategies. Subtraction beats addition more often than we think.