But, then, ultimately, we get to this somewhat stark moment of conviction – a decision without certainty but with some level of instinct and belief. The work you’ve done is a big input, but then, I find there’s something else, too. It’s some combination of understanding, excitement, experience, gut, and fear. And this process repeats throughout our... See more

First, become able to feel conviction even in the face of high uncertainty. Second, learn how to weigh your options so hard that by the time you've picked the best available action, no part of you has an urge to go back into "deliberation mode" until you encounter new evidence or ideas that would have changed the result of your deliberation. Third,... 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 ge... See more