[Cross-posting this essay from 2020 by request.]

I am not an “optimist”. Well, not exactly. Though I sing the praises of progress in these essays, and though I paint a bold vision for the future, I have hesitated to apply that term to myself. I have said that I am “fundamentally” optimistic, or a “paranoid optimist”; or I have reached for constructions like “short-term pessimist, long-term optimist”. But none of these are quite right.

In my discussion with Tamara Winter and Trevor McKendrick on optimism, the three of us converged on a formulation that I think resolves the paradox: descriptive vs. prescriptive optimism.

Descriptive optimism is the expectation that good things will happen, that an outcome will be positive, that the trend is in the right direction. It is a belief about the world.

Prescriptive optimism is the decision to work to make good outcomes happen. Whether lighthearted or desperate, cheerful or grim, it is a commitment to action and effort.

Descriptive optimism, for me, is highly contextual. It is situation-specific. I am mildly optimistic about our efforts against coronavirus. I am fairly pessimistic about US politics.

Prescriptive optimism is deeply philosophical. It is a belief about the nature of life, intelligence, and agency. It is a moral attitude, a way of living.

Descriptive optimism is determined by the external facts, but prescriptive optimism is an internal choice.

Descriptive optimism on its own can lead to complacency, Panglossianism, and other cavalier attitudes—progress as coasting. Prescriptive optimism calls for boldness, courage, and vigorous effort. When the two are combined, they call for expansive, ambitious plans. When prescriptive optimism is combined with descriptive pessimism, they together call for grit, determination, and fighting spirit.

The French writer and Nobel laureate Romain Rolland captured it in a passage later echoed by the Italian Marxist Antonio Gramsci, when he wrote of

this intimate alliance—which for me makes the true man—of pessimism of the intelligence, which penetrates every illusion, and optimism of the will. It is this natural bravery that is the flower of a good people, which “does not need to hope to undertake and to succeed to persevere,” but which lives in struggle over and above suffering, doubt, and the blasts of nothingness because his fiery life is the negation of death.

This has been distilled to a motto: “pessimism of the intellect, optimism of the will”. I am a pessimist or optimist of the intellect according to facts on the ground, but I am ever an optimist of the will.

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I like this distinction.

Recently I talked with someone about something and was asked whether I'm optimistic, and I answered something to the effect of "Not to make a self-refuting prophecy, but I think things will work out well at the end. We just have to make turn out that way and not get complacent". So I was both descriptively optimistic and prescriptively optimistic, though my descriptive optimism was conditional on other people being prescriptively optimistic and doing what needs to be done. Perhaps you can call that conditional optimism - I'm optimistic about X conditional on Y. Though that raises the question of whether you're optimistic about Y.

P.S: In the part where you quote Romain Rolland it's not clear that you're quoting him and not Gramsci (I had to enter the link to find out), could be made clearer if you put the Gramsci part in parentheses.