If It's Not a Hell Yes -- It's a No
We should avoid entering the trap in which the cost of planning exceeds the cost of making the wrong decision (this is exactly what the parable illustrates). Another example of this is bikeshedding, in which far too much time is spent debating trivial issues. In these cases it would be better to pick arbitrarily to minimize time spent deciding. (View Highlight)
If it's not a hell yes, it's a no. If a decision is required, flip a coin.
Another case in which planning can be overdone is when the cost of planning is incommensurate with the potential benefit. For example, most would agree that it doesn’t make sense to spend four hours researching the best place to have lunch. That’s because the difference between the average choice and the best choice is not likely to be so significant as to make the time spent worth it (and, in any case, even after four hours you might not pick the best choice). You could spend a few minutes and get an outcome almost as good. (View Highlight)