Actually, I struggle with that one a lot. I struggle with perfectionism, when a dose of “good-enough”-ism would really help.
My experience with markets has taught me that you just have to accept that you are ultimately making the best decision within a reasonable time frame based on incomplete information, and that diversifying your decisions limits your vulnerability to random events while allowing a competent thought process to accumulate over a large number of decisions over time.
It’s not as big an issue as it used to be, but it helps to have competent coworkers to interact with.
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The other thing is that I while I write good stuff, it sometimes can take a while to write it. That’s because I refuse to force people to read something I wouldn’t want to read myself. As Hemingway said: “It’s easy to write, you just sit down at a typewriter [keyboard] and BLEED.”
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Another weakness of mine is that I frequently mistake how dumb the rest of the world tends to be. I figure if something is obvious to me, it must be obvious to everyone, and it turns out that that’s just not true. It’s probably because as a child, I was surrounded by some of the smartest minds around, and I was always behind them (heck, I was a kid, and they were Ivy / OxBridge type professors!), but the feeling stayed all my life. A good friend who grew up 50 miles away from me is also wicked smart, but he knew that everyone around him was dumb and so he developed the ability to just run with what he thought, knowing that it was likely better than any advice he could get from those around him. He’s not a billionaire, but he’s done pretty well for himself.
There’s a reverse version of that where I’m confused about something and other people seem so clear about it. I wonder what it is that they know or think that makes them so clear. In retrospect, it’s often because they only see part of the picture, and I’m seeing a bigger one - i.e. they can’t see the confounding issues that I see. But because they seem so confident, I figure they must have done better analysis. I’m sure that’s a major behavioral bias one could write about if it hasn’t already been, and the basis for confidence games and con-men. If it doesn’t have a name, I’ll call it “bcha-bias” - take that, bchas!
That’s one reason that I need to bounce ideas off of other people in order to figure out if they are worth pursuing. I wish that after generating them on my own, I could just have the confidence to go out and put them on. That’s a challenge for me, and why I like to work in teams.
This is also one reason that I focus so much on portfolio construction techniques. In my mind, this is the tool that allows me to go ahead and put ideas on, knowing that there’s a mechanism for risk control in the portfolio construction.
OK, so now you know more about me.