Gambling With Your Friends to Stay Honest

Here’s a habit I have which I hate, that you might be able to relate to. A friend might say that he thinks that a Zodiac boat goes really slow. I then reply that I’m not sure, but I think they’re quite fast. As we go back and forth, I become more and more convinced that I’m right. My unstated goal has nothing to do with discovering the truth, but it has everything to do with convincing my friend that I’m right.

Often times he’s in the same position, not totally sure how correct his position is, but determined to get me to believe him. If there’s a more useless way to spend time than these sorts of arguments, I haven’t discovered it yet.

It’s not difficult to figure out why we do this. We all want to seem smart, and a good way to seem smart is to be right all the time. Including this time, dammit. And like any habit that’s fueled by the ego, this habit is a good one to put on the chopping block for execution.

Around 2005 I had hired a few people to help me with my online gambling business. One of these guys was named Andrew. He also thought that he was right all the time. But a more notable commonality we had was that we liked odds and we liked betting.

So we bet on everything. If a given day passed without us betting on something, it was a fluke, not to be repeated soon. An average day played host to four or five bets, ranging from ten to one hundred dollars.

“I think the restaurant is still open.”

“I’m pretty sure it’s not.”

“Want to bet?”

The answer was ALWAYS yes, it’s just a matter of terms. A restaurant’s hours might be a twenty dollar bet with even odds. More specific bets might have different odds. If he, for example, thought that he could make a 7 letter scrabble word out of a random collection of seven letters that he spotted somewhere, I might give him two to one odds to try to induce him to bet.

He and I aren’t friends anymore, so our betting is done. My guess is that we ended up close to even in the end. The idea of the bets wasn’t to try to earn an income off the other person, it was to create a sense of accountability. We were reckless when we first started this, but when you know you’re likely to be financially challenged on any statement you make, you consider things more carefully. You aren’t as enticed by hyperbole.

In the beginning, I remember betting when I KNEW I was wrong, just because I didn’t want to admit that I said something I hadn’t really thought about. Lose twenty bucks a couple times for dumb things like that and you stop saying them.

We started to take each other’s statements more seriously. There was a penalty for guessing incorrectly, so you could generally count on the other person to make a good guess. We also became good auditors of our own confidence. Instead of insisting that something was so, I’d say that I thought that there was at least a 33% chance it was so, knowing that he would offer me a two-to-one bet on it to compensate for my odds.

None of my friends now like betting as much as I do, which is a shame. I still get a bet out of them once in a while, but weeks pass in between them. It always strikes me as a little disingenuous when we’re in a heated argument over something and the other person won’t bet, though. You’re willing to try to convince me, but aren’t willing to stake twenty dollars on your opinion? All the bluster in the world doesn’t give me the same assurance that an Andrew Jackson might.

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Sorry I forgot to post Wednesday. I get inordinately confused about the date/time in the US when I’m in Japan. I have a bunch of friends here right now, too, so I’ve gotten way behind in pretty much everything.

Photo is of Brian, Toby, and Michiru in Tokyo. I have a ton more photos, as do Todd and Michiru, but I haven’t put them up yet. Will do it as soon as I have half a day to sit around.

I sprained my ankle the day before the trip and it’s still in bad enough shape that it’s stopping me from doing everything I want to do. But I’ll tell you this: ace bandages help a LOT. Surprised!


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