I attended a program that was part of Chicago Ideas Week last week called “Lessons: The Choice Is Yours.” Among the amazing speakers (for example, the founders of bothchange.org and Defy Ventures), the program concluded with an appearance from Malcolm Gladwell, the noted New Yorker writer and author of many books like Outliers andThe Tipping Point. Malcolm (is it wrong to pretend that we are on a first-name-only-basis?) spoke about his current book, David and Goliath. (Full disclosure: I haven’t read it yet but plan to in a nanosecond when my Kindle app magically grabs it from cyberspace after I click “buy” on Amazon.)

The David/Goliath story has always been one that has resonated with me, perhaps in part because I reach 5’2″ on a good day, don’t look much older than 12 (thank you L’Oreal for hiding my gray) and I’ve often felt that I am underestimated by my (usually taller) adversaries. I am also a consummate lover of the underdog, as David has come to be known in conventional wisdom. Also, in recent years, we have equated the firm I helped found (small litigation firm using alternative fees) with the Davids of the world, so much so that when we updated our website earlier this year, we created a home page with a picture of a slingshot and the phrase: “David won. We litigate against Goliaths every day.”

Imagine my confusion-then-turned-glee when I learned that Malcolm’s proposition is that David, clearly the faster and more nimble player replete with a sling and some rocks in his pocket, was indeed not the underdog after all. How could we have thought otherwise for so long? Of course he wasn’t! Goliath, though big and lumbering, was also weighed down by heavy armor and wielded weapons designed for close combat. A sword, a shield, etc. Why? Naturally, because that’s the way it had always been done before. But David was not part of the army, knew nothing of those long-established traditions, and thus had no preconceived notions about the expected way to fight. Instead, he had his sling and some rocks and a different way of fighting. And this proved fatal to Goliath.

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