Ryan Holiday, The Obstacle Is the Way is one of several popular sources now that urges the Stoic wisdom, premeditacio malorum. In brief, do not make a major decision until pausing to consider the most horrible possible results.
We often do decision postmortems that can haunt us for decades after the effects of the decision are known. But a more useful analytical technique is the premortem. Of course, after a premortem, we run the risk of overly weighting that possible result. However, for certain, we do not want to overlook that possibility entirely. Many of you are familiar with Taleb’s “black swan”. But failing to do a premortem is even worse than ignoring the possibility of the black swan because in that situation you have not even considered what your black swan might be.