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)

9 comments on “What Was Your Most Frequent Mistake?
  • Awesome reframing of the question, and it could probably bring some unexpected, honest, helpful answers.

    The only thing I would counter to that is that really successful people seldom make the same mistake over and over again (once they become conscious of it, of course). They profit from their mistake, iterate, and then move on.

    Learning what mistakes they committed over and over again, may tell you less about the mistake and more about their personal learning mode, and their mistake-positive attitude or lack thereof.

    While it would be the second question I posed to a model of excellence (such as Buffett), I would rather learn the biggest mistake he or she made because: a) they’ve probably spent a lifetime monitoring the mistake, decoding it, practicing it, and making it useful to themselves, so it’s specific and measurable to the person seeking advice; b) the person will probably modify the feedback from the mistake to suit your own situations, thus ensuring it’s realistic and relevant to you; c) they’ve spent more time being totally honest about the mistake, seeing how it fits into the service of their overall mission, than hiding it or disregarding it (whereas if they committed the same mistake over and over again, they would probably have reservations about revealing that).

    It’s a great question to ask, provided you could get some honest answers.

  • Very eloquently put.

    One definition of the word ‘insanity’ is doing the same thing over and over again hoping to achieve a different result.

    My most frequent mistake wasn’t necessarily one action that I took time and again. It was a character flaw – pride and ego – that led me to become obsessed with trying to have it all and do it all. At those points in time I was so driven to get ahead I ignored the importance of friends and wise counsel. I thought I could do it all on my own.

    Needless to say, I was wrong on all counts, but figured it out and corrected that repeated mistake.

    By the way … it was also my biggest mistake.

  • Ben,

    You can’t make the point without begging the question…

    What was YOUR most frequent mistake?

    Now that you’ve gotten everyone curious about the subject, perhaps you’d like to offer your insight.


  • My most frequent mistake is not asking for exactly what I want, and being disappointed when I don’t get it.

    Far too many of us believe that others can read our mind. They can’t. And we shouldn’t blame them for this shortcoming.

  • Ben,

    I definitely have to agree with you about the question you’d ask Warren Buffett, but I think I’d lean more towards the question regarding what he wishes he would have done at our age.

    Obviously, the question of “what is the single most…?” cannot be answered so briefly, therefore the answer you receive will be of little value and hardly beneficial, but that’s what most people are looking for all the time, a quick simple fix to everything. On top of that, you’re hardly helping yourself to stand out when you ask the same ‘scripted question’, but if you were to ask something not so common there is a bigger chance that he (or anyone for that matter) would remember you for asking this question (especially if it catches them off guard).

    As far as the most frequent mistake question, I think that’s highly geared to each individual and is not necessarily something that you may be able to learn from or try to apply to your own life, but it would be a very interesting tidbit of information to know (or it could be more valuable, just less likely).

    Either way, I think both of those questions are very well thought through and I feel like they both would give you a great inside (not from a typical viewpoint) into whomever it happens to be that you are asking!

  • I am with David.

    Frequent mistakes (of a homogeneous variety) indicate a weak arousal system. (S)he is not fully awake or is insensitive to incoming signals – a psychological sleep walker. Yet successful they got because they figured their limitations early on, probably hired a good set of filters to pore over each decision and bridged the gap. Good enough.

    So the question could as well be –”let’s hear about your limitations…”

  • Ben, excellent and insightful post.

    If I had to answer either question – the answer would be the same. I hired friends.

    I would never recommend it to anyone. I don’t care how long you have known them. I have had “Friends” steal from me, sabotage my business for their own comfort and give less than adequate performance.

    I have done this with people I have known since childhood and folks I considered to be like family. I can be pretty cynical, but I always have a weakness for friends.

    Take it from me – the two do not mix well.

  • Very insightful post, Ben? If i were given the choice to ask only one question (besides the 2 choices you gave), i would ask, “What drives you everyday?”. Because it tells me what mind-set or thought process has brought the person to his current level and (2) whatever drives him today is the culmination of all the past mistakes, achievements, confusions etc. In essence that tells me about the strong “cable” that he has become, which is woven of thousands of “threads” of habits, mistakes and doubts.

  • Hi Ben,
    I’m a newish reader to your blog. Its a pleasure to read it, I like how you write. As for this question, I don’t know whether my most frequent mistake would be interesting, but it has been trying something other people said I shouldn’t/couldn’t do without necessarily thinking through how I would approach the problem first. Essentially, figuring things out as I went along. On the bright side, thats led me to become really good at learning on the fly, and I’ve come upon some pretty amazing opportunities that way. One that may be a pertinent one happened in my freshman year: I wound up as the only undergraduate researcher in a particular professor’s lab, partly because I was told that he didn’t take undergrads and decided to apply. Profs are really nice, and even though it seems unlikely to happen to you, don’t get intimidated because they’re a nobel laureate or something…they LOVE talking about their research, and they’re there to teach. Just go for it. Hope your fall is treating you well in socal.

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