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If I have to err, it’s on the side of assuming the worst…

“If I have to err, it’s on the side of assuming the worst. This way, if I’m wrong, I can always apologize. Or send flowers. You err on the other side, the flowers will be coming to you.” quote by Barry Eisler
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““If I have to err, it’s on the side of assuming the worst. This way, if I’m wrong, I can always apologize. Or send flowers. You err on the other side, the flowers will be coming to you.””

Barry Eisler

About This Quote

This interpretation was drafted with AI assistance. It is one reading of the quote, not the author's own explanation.

Assuming the worst prepares you to apologize and make amends, turning mistakes into opportunities for reconciliation.

In simple terms: Expecting the worst lets you apologize and fix errors.

Key Takeaway

Adopt a cautious optimism to manage errors.

Themes

responsibility apology optimism

Mood

reflective pragmatic

Type

advice philosophical

When to use this quote

  • customer service
  • personal relationships
  • leadership

Key Concepts

ethical behavior conflict resolution

Questions to Reflect On

  • When is it better to assume the best?
  • How do you balance caution with optimism?
A Different Perspective

Over‑cautiousness can breed negativity.

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