The Struggle With Skepticism

I will admit that I admire skeptics. I look up to guys like Robert Shiller, who first pointed out the tech bubble, then for an encore pointed out the real estate bubble. Despite all of the pundits who talked about structural changes in the economy, how things are different, Dow 36000, stocks as less risky investments, etc, Shiller held his ground. From my perspective though, it doesn't seem like anyone decided to start listening to him after 2000. Warren Buffett was the same way - lambasted in the late 1990s as too old school, even though he turned out to be right. He's simultaneously worshiped as one of the world's greatest investors, and despised for being a value, buy and hold kind of guy in an age when quants rule wall street. It's sort of paradoxical.

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It has just been my experience that when I get to the core of any idea, person, company, or organization, I almost always find that it has been overhyped. As a result, skepticism is my natural starting position.

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In the early days of the web, I was always the guy responding to chain emails with links to Snopes or Urban Legends. And now, with this blog, I've been critical of "wisdom of crowds," of Google's strategy and stock price, the book "Good to Great," and lots of other things people on the web seem to love. Sometimes I turn out to be right, and intellectually it always feels good, but it's always a pretty lonely vindication. The next time I turn negative on something, no one says "better listen to Rob…"

You see, people really prefer positive people. People need hope, and that is why it sucks to poke holes in the stuff they believe. Our delusions are very dear to us. We want to believe that there is at least the small possibility that Bill Gates really will send us $1000 for every person we forward an email to, and we don't like it when someone tells us it isn't true.

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So I find myself in a perpetually uncomfortable position. I feel compelled by the virtue of intellectual honesty to say what I think, even if I disagree, yet I know that people don't want to hear disagreement. And, I know that if I turn out to be right (obviously, I'm not always right, but I do have a very good batting average), it will probably cause bitterness more than anything else. So what's a businesspundit to do? That's why I prefer to keep to myself as much as possible. The less time I spend around people, the less they ask me what I think.

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The point of it all, I guess, is that sometimes I just wish I could turn off the skepticism. But on the flip side, I feel like I've avoided many of the problems that I've seen others experience because I am skeptical. As a result, I have this simultaneous pride and disgust for my skeptical leanings. It's weird. What I really want is just to do something day to day where that aspect of my personality can come through and be an asset. I just don't what that is.

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Skeptics who go against the popular theories and are right belong in financial markets. Go work for a hedge fund. Be a trader. If skepticism is that much of you, the entrepreneurial route may not be enough to satisfy.

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Your skepticism is probably best characterized as “critical thinking” in other circles, a unique and immutable skill that has and will continue to bring you success. Keep it up.

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I think that you miss the point with your comment that “people like positive people.” While that may be true; it’s tangential. The important point is that nothing happens if people always say no. It’s the person who says yes who gets things done; and generally they are saying yes in the face of nay-sayers.

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I further assert that the final score in life is not how many times someone was “correct” but rather how much they accomplished. In the end, it’s not about being “right”. It’s about making things happen. I’d rather be right on a “yes, lets do it” 1 time out of 10 than right on a “no, lets not do it” 9 of 10 times.

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Now that’s not to say that every idea is a good idea or that there is not a place for healthy skepticism. But it is to say that a skeptical mindset can really get in the way of accomplishing things.

As a final comment, my personal advice to everyone is to know your bent and then “go for the no.” That is, if you are naturally a “no” person, you should consciously spend time looking for the “yes” reasons. If you are naturally a “yes” person, spend time looking for the “no.”

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The tough thing is while no is usually the right answer, it is the question that is usually wrong. One has to search for the correct question which can be answered affirmatively. Entrepreneurs often end up stumbling over it when they pursue their misguided objectives, which is why yes can be correct even when it is wrong.

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