Biglaw, In-House Counsel, Partner Issues

Inside Straight: Pessimism Has Its Pleasures

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?

First, my pessimism poses an obstacle for outside lawyers hoping that I’ll retain them. I talk to lots of lawyers, but I hire few. Why? Because I’m able (with some effort) to be civilized when I meet people, but there’s always a voice in my head screaming, “This guy’s inept! Just like everyone else!” The only way for an outside lawyer to shout louder than my inner voice is to demonstrate competence, and it’s hard to get a chance to do that.

You can demonstrate competence by (1) having worked with me in the past, and having proved yourself or (2) already being on my corporation’s preferred counsel list, so you’ve impressed my colleagues in the past, and you’ll naturally be given a chance to impress me.

Other than that, it’s hard to get a chance to prove your competence. What can I say? Life is tough. (I already conceded that I’m a pessimist.)

For lawyers working under my supervision (as associates at a firm, a few years back, or in-house now), however, my pessimism makes life easy. My expectations are so low that it should be no problem to exceed them: “I asked that person to report back on Wednesday. And he did! What a joyous surprise! And his report was comprehensible. That’s a two-fer! This makes my week!”

Deliver stuff on time and right, and you’re an instant superstar in the mind of a pessimist. Maybe life isn’t so tough, after all.

How does my pessimism affect my approach to people for whom I work? “This person — CEO, CFO, head of a business unit, whoever — assumes (appropriately) that I’m an idiot. How can I overcome that presumption? I am going to send this person regular reports, written in plain English, that show that I’m addressing this person’s legal issue intelligently and effectively. Over the course of a relatively short time, this client will think: ‘Eureka! Herrmann may actually be competent! What a pleasant surprise!'” If I manage to pull that off, I’m golden.

Perhaps some people are optimists. (“Ninety percent of the time they’re wrong, and even a blind squirrel finds acorns ten percent of the time.”)

Perhaps optimists prejudge strangers differently than I do. And perhaps, around the edges, one works with optimists differently than one works with pessimists. But I suspect that even optimists wouldn’t be disappointed to occasionally see evidence that their lawyers are handling projects intelligently and efficiently.

I suppose optimists disagree with George Will’s bromide. But surely everyone must agree with this little chestnut that I pulled out of a fortune cookie decades ago and treasure to this day: “He who expects no gratitude will never be disappointed.”

I saved that for decades? What can I say? It’s the pessimist in me.

Mark Herrmann is the Vice President and Chief Counsel – Litigation at Aon, the world’s leading provider of risk management services, insurance and reinsurance brokerage, and human capital and management consulting. He is the author of The Curmudgeon’s Guide to Practicing Law (affiliate link) and Inside Straight: Advice About Lawyering, In-House And Out, That Only The Internet Could Provide. You can reach him by email at

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