What Was Your Most Frequent Mistake?

To further the riff on advice giving and receiving: Suppose you had the opportunity to ask a really successful person one question and you had to choose between:

  • What was you biggest mistake?
  • What was your most frequent mistake?

Most people ask for the “biggest”. Most people, in my experience, tend to ask for extreme examples to try to understand someone. “What was your most embarrassing moment?” is another common one.

Me? I’d prefer to learn what mistake a successful person committed over and over again before mastering it, rather than their one large lapse of judgment. Though I see the other perspective: if somebody successful committed the same mistake over and over, maybe it isn’t a very important mistake.

In any case, how you ask questions makes a difference. How many times do you think Warren Buffett has been asked the eminently stupid question, “What is the single most important characteristic / habit / lesson / whatever to being successful?” If I could ask Buffett just one question, I would ask about his most frequent mistake, or perhaps what he regrets not doing when he was at my stage in life.

(hat tip, once again, to Eliezer, for sparking this)

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