A way to prop up this kind of humility is to keep score. Use a decision journal. Write in your own words what you think will happen and why before a decision. Refer back to it later. See if you were right, and for the right reasons (think Bill Belichick’s famous 4th down decision against Indianapolis in 2009 which summarizes to: good decision,... See more
When stumped by a life choice, choose “enlargement” over happiness. I’m indebted to the Jungian therapist James Hollis for the insight that major personal decisions should be made not by asking, “Will this make me happy?”, but “Will this choice enlarge me or diminish me?” We’re terrible at predicting what will make us happy: the question swiftly... See more
So practice making fast decisions. Accept the risk and emotional labour involved in doing so. Course correct when you make mistakes and don’t get pregnant unless you really want to.
The best way to manage the myriad decisions of the modern age is by employing “philosophical razors,” so-called because they shave away options, simplifying choices.
A very small subset of your decisions are one-way doors. Non-reversible portals into bad realities. These ones should take you more time. They require more information.