According to George Will, “Pessimism has its pleasures. Ninety percent of the time you’re right, and ten percent of the time you’re delighted to be wrong.”

That’s how I go through life.

What made me a pessimist? Nature or nurture, perhaps? (Should I blame my parents’ genes or their parenting skills?) Decades defending litigation, which forced me perpetually into a defensive crouch? (If that’s the reason, then plaintiffs’ lawyers must be optimists.) Or my preferred explanation: Keen observation of reality, coupled with endless experience, naturally breeds pessimism.

As an outside lawyer, my pessimism meant that I presumptively expected the worst (or, at a minimum, the least) from colleagues, opposing counsel, clients, and courts. Those folks generally performed precisely to my expectation, reinforcing my pessimism.

As an in-house lawyer, how does pessimism infuse life?

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