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Erik Van Alstine

Author. Leadership strategist. Expert in Perceptual IntelligenceTM.

Worst. Lesson. Ever.

This Whitey Bulger story is excerpted from my upcoming book, Automatic Influence: New Power for Leading Change, which will be published September 8, 2016. Click here to read the introduction and first chapter! Also, please help me help others by sharing this!


My last blog entry was about the difference between our experiences and the lessons we draw from them. Experience isn’t the same as wisdom, which is why the world is filled with old fools.

Consider how James “Whitey” Bulger, the Boston mobster played by Johnny Depp in the film, Black Mass, teaches a lesson to his young son Douglas. Douglas had punched a classmate in the face. Now, at the dinner table, it’s time for the father-son talk.

“Hey buddy, I need you to listen very carefully to what I’m saying because there are lessons again and again throughout your whole life,” said Bulger to his son. “You gotta learn from these things, right?”

He pauses to make sure Douglas is listening. “It’s not what you do,” he says, slowly, “It’s when and where you do it.”

He pauses again. “And who you do it to…or with.”

Whitey pauses again to let it sink in. Then he delivers the most important part. “If nobody sees it,” he says. “it didn’t happen.”

Douglas’ mom is horrified. “Jimmy, he’s six. You really think that’s the best thing to be telling your kid?”

“Yeah,” says Bulger.

That may be the worst advice. Ever. But notice that it’s a “lesson” drawn from experience. There’s a big difference between our life experiences and the lessons we draw from them. And while no one draws them out quite as badly as Bulger, there are all sorts of terrible draws.

We need to be careful who we listen to.

Watch the Scene

Here’s the scene from the film. It would be interesting to sort out the right and wrong lessons here, because while the lessons are mostly horrible, there’s enough truth to candy-coat the poison. What do you think?

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