"The nice part about being a pessimist is that you are constantly being either proven right or pleasantly surprised"
About this Quote
Will’s intent is partly self-portrait, partly permission slip. As a journalist - and a conservative columnist famous for treating politics as a running audit of human limitations - he’s speaking from a profession trained to anticipate failure, hypocrisy, and unintended consequences. The subtext is that optimism is a luxury belief, a kind of psychological leverage that can wipe you out when reality calls in the debt. Pessimism, by contrast, pays dividends: accuracy when institutions disappoint, and a small, almost childlike delight when they don’t.
What makes the sentence snap is its rhetorical judo. “Nice part” reframes a traditionally grim stance as the more comfortable option. “Constantly” hints at a world that reliably underperforms - not occasionally, not tragically, but as a steady baseline. And the punchline is the bargain it offers: you get to be right without trying, or happy without expecting to be.
Context matters here. Coming out of late-20th-century American commentary culture, Will’s quip doubles as an ethos for punditry itself: forecast gloom, claim vindication when things go south, and treat any improvement as evidence of your reasonableness rather than your cynicism. It’s funny because it’s true - and a little uncomfortable because it might also be a business model.
Quote Details
| Topic | Optimism |
|---|---|
| Source | Later attribution: Essential Quotes for Scientists and Engineers (Konstantin K. Likharev, 2021) modern compilationISBN: 9783030633325 · ID: PIogEAAAQBAJ
Evidence:
... The nice part about being a pessimist is that you are constantly being either proven right or pleasantly surprised . -George Will , 1994 If you keep saying things are going to be bad , you have a good chance of being a prophet . -Isaac ... |
| Cite |
Citation Formats
APA Style (7th ed.)
Will, George. (2026, February 8). The nice part about being a pessimist is that you are constantly being either proven right or pleasantly surprised. FixQuotes. https://fixquotes.com/quotes/the-nice-part-about-being-a-pessimist-is-that-you-61534/
Chicago Style
Will, George. "The nice part about being a pessimist is that you are constantly being either proven right or pleasantly surprised." FixQuotes. February 8, 2026. https://fixquotes.com/quotes/the-nice-part-about-being-a-pessimist-is-that-you-61534/.
MLA Style (9th ed.)
"The nice part about being a pessimist is that you are constantly being either proven right or pleasantly surprised." FixQuotes, 8 Feb. 2026, https://fixquotes.com/quotes/the-nice-part-about-being-a-pessimist-is-that-you-61534/. Accessed 24 Feb. 2026.









