Think backwards to move forward.
Inversion
Instead of asking 'how do I succeed?', ask 'what guarantees failure?' Inverting the problem surfaces risks you'd otherwise miss.
The direct path to success is not always the clearest one. Inversion asks you to flip the problem: instead of 'how do I make this work?', ask 'how would I guarantee this fails?' The obstacles you identify backwards are the exact ones blocking you forwards.
The method
Take your goal. Invert it completely — articulate the conditions that would guarantee the worst outcome. List every way you could make it fail. Then flip back: are you currently doing any of these things? Are any of these risks unaccounted for in your plan?
Charlie Munger on inversion
Munger built his entire investing philosophy around it: 'Invert, always invert.' He'd ask 'what would make Berkshire fail?' not 'what makes it succeed?' This surfaces blind spots that forward-looking optimism systematically hides. Most plans are too optimistic. Inversion forces honesty.
The asymmetry of failure
Success has many paths. Failure often has a few highly predictable ones. Identifying the few reliable failure modes is far more tractable than mapping all possible paths to success. Fix the failure modes and you've eliminated the most probable bad outcomes — often more valuable than optimising the upside.
In engineering leadership
Before a launch: don't just ask 'what needs to go right?' Ask 'what would cause an outage in the first hour? What would cause this to silently return wrong data for 3 weeks? What would cause us to not notice until customers complain?' Those three questions alone find more issues than a forward-pass review.
In practice
Planning a new hire? Invert: what kind of person would definitely fail in this role? Someone who needs heavy direction and your team can't provide it. Someone who'd be bored at this scale. Someone whose values clash with how you give feedback. Now screen for the absence of those things — not just the presence of skills.
TL;DR
Ask how to guarantee failure, not how to guarantee success. Surfaces risks optimism hides.