Where do you often place your room for error in the house of risk? That is, how do you prefer to err when you guess on anything, for fun or when planning? Do you tend to overshoot, underestimate, alternate, something other?
Err on the side of caution is the conventional wisdom we are given for how to manage risks. It’s good advice, but not great advice. I have seen far too many situations where erring on the side of caution kept us from taking sufficient risk to do what was needed, because we were focused on some other risks rather than the risk of not doing enough that should have been the primary risk to manage. This is especially true for decisions to help on a societal level, but could apply just as well to individuals. To that end, I rephrased that cautionary advice about erring to be more inclusive, more caring, more human. After all, how much do you think would people mind if you had erred, and had over cared, as a result?