Ali Abdaal recently posted a video in which he shares his "anti-wasteman" system for making progress on his bucketlist. A key feature of the system is asking the question "How surprised would I be if I failed in this goal?" and then "What are the top 3 reasons for this failure?"
Anything that can go wrong, will go wrong.
The idea is to imagine whatever you're planning has already happened, and that it went really badly (or really well), and then asking yourself what happened. You can make this visceral by thinking up scenarios like:
- The day after launch, you open up a news website and see terrible (or fantastic) headlines about your product. What do they say?
- You see your assistant walking towards you with a terrified (or delighted) expression on their face. What are they about to tell you?
And so on. You then adjust your plan to avoid these failure modes (or take advantage of the success modes) until you feel very surprised at the thought of the plan failing.
There's something about simulating hindsight which makes anticipating consequences much easier than relying on foresight. Murphyjitsu is probably one of the most useful techniques I learned at CFAR, and has become something I use routinely in a variety of situations.
For example, when checking a job candidate's references I always ask:
- If I made this candidate an offer, and 6 months later I told you it worked out great, why would that be?
- If I made this candidate an offer, and 6 months later I told you it hadn’t worked out, why would that be?
Of all the questions I ask, these always elicit the most insightful answers, and often even the referees are startled by the things that come to them.