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Sometimes I think the obstacle is a lack of confidence in my own judgment, a reluctance to conclude “Yes, this is indeed better than that” without some external reassurance. Maybe even a refusal to take responsibility for deciding.
It’s easy to measure a life in years or accomplishments or accumulated wealth, harder to measure in joy or satisfaction or making the world a better place — at least while I’m engaged in it, though these are the most meaningful measures for assessing a life once lived.