The Struggle With Skepticism

A comment on an earlier post asked if I would round out my time here by writing more about some personal experiences and insights. I'll try my best, and I'll start with the aspect of my personality that is at once my greatest source of both joy and pain – my 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.

I don't have a negative outlook on life… seriously, I don't. 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.

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.

Most importantly though, there are social consequences. Just about everybody I know reads Fred Wilson (as well they should), and everyone knows he is a very smart dude and very successful. So when I see him write that the WSJ should be free, but feel compelled to post the opposite, I figure my stock goes down a little in everybody's book. Multiply that by 20 more popular bloggers and you understand one of the reasons I don't want to blog any more. Half of what I want to write is to disagree with someone that everybody looks up to. As this blog has grown, I've felt more and more like I should hold back on criticism of popular ideas to avoid losing readers. I prefer to criticize ideas that are more acceptable to criticize, so I have tried to stick to those.

20 Hidden Ways Business Professionals Struggle With Pain

I got an email today from Techdirt Insights stating that I had won several hundred dollars for a top answer to the question "What's the Secret to Mobile Social Networking?" The last one I answered I won as well, "Wall Street Wants To Know What Google's gPhone Is All About…." The odd thing here is that if you asked anyone who knows me who you should talk to about trends in mobile social networking or the gPhone, my name probably wouldn't come up, yet I've won almost every Techdirt analysis question I've answered. At first I thought it was a fluke, and there just weren't very many participants, but it turns out that isn't true. The questions have a very good response rate. But how can I beat out all these other guys who are writing about how the gphone is the future and if Google does it, all the other mobile companies should just give up now? Those are the kinds of memes that seem to be popular on the web.

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.

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.