Interesting Confusion

Like every human being on Earth, I am not immune to bias. Despite putting a lot of effort into recognizing mental tricks, logical fallacies, and decision-making noise, I am perhaps 10% better than the average person at reducing the impact of those things on my decisions.

And that’s pretty good! Honestly, if we all got 10% better at making decisions the compound effect would probably make the world unrecognizable. So I’m not complaining!

But I always look for novel ways to trick my brain into freeing itself from all the chains that bind our thinking. And one interesting way I’ve discovered is to put myself in situations where I don’t know enough to be biased.

You see, if I know anything about a topic, then I probably have at least some opinion on it. I recognize that my opinions could be wrong, but it’s still a base point that my thinking will emerge from. Likewise, if I already have a positive impression of a person’s intelligence overall, I’m likely to weight the things they say with more belief than if I heard them from someone who I thought wasn’t very smart.

(To a certain degree the intelligence of the speaker is a rational thing to use as one piece of evidence towards a statement’s truth, but it shouldn’t be the only thing and you should be very careful about it – most people aren’t “generally smart,” they’re knowledgeable in specific areas. Einstein actually said a lot of dumb, definitely wrong things about topics that weren’t physics, but because he’s the universal avatar of “smart people” in most folks’ imaginations, they take everything he said as gospel. Don’t do that!)

So what I’ve done lately is just find interesting-seeming writing written by people who I don’t know anything about, on topics I don’t know anything about, just to start puzzling through it and see what I can absorb. I can’t tell if I’m reading utter nonsense or the next great work of genius that will define our time. I don’t know if I’m standing in the presence of a true master or entertaining a crackpot. It doesn’t matter! In any case, I learn something.

The fun of this is that I have no “skin in the game,” no preconceived notions about any factor, and no agenda for my learning. So bias is pretty much at a minimum, at least in as much as it can be with our particular kinds of brains. I am often confused, in a fun way. My ego is in zero danger, so while I can get confused, I never get frustrated.

This is good practice for learning. Try it, and then remember what it feels like. Then when you find yourself doing something else that looks like learning and should be learning, see if it feels the same. Do you feel confused but interested, psychologically safe and curious, mind changing and possibilities swirling? Or are you nodding along, saying “uh huh, that’s what I always thought” and feeling righteous?

Because that second one? That’s not learning.


There’s a little mental game I like to play when I find myself forming an opinion, making a big decision, or investing intellectually in a particular belief. I like to ask myself: “what would make me believe otherwise?”

If I can’t think of what would make me change my mind, then I back off from formalizing the decision. I’m not ready. I’m being emotional, irrational, and biased. It’s one thing to say, “I have this opinion because I believe it’s true,” but it’s quite another to say “here is the specific evidence I would need to believe the opposite.” Most of the time, we’re not prepared to do that.

Fair Thee Well

[I know it’s “fare thee well.” It’s a gimmicky pun.]

I’ve noticed that most people are way more concerned about being treated fairly than they are with being treated well – or with just having a good life in general.

Furthermore, this mentality often seems coupled with a dire short-sightedness. People who are extremely concerned with “fairness” tend to only look at the fairness in a single encounter or exchange, even if that means huge sacrifices in potential upside elsewhere.

For instance, imagine you’re a shopkeeper, and a semi-regular customer is a dollar short on his $21-dollar purchase. You’re within your rights, of course, to refuse the sale and/or demand the extra buck. But doing so, while focusing on fairness, may easily lead to a marked decrease in that customer’s loyalty or desire to do business with you. You could lose a customer entirely, plus maybe others who witnessed the exchange or hear about it later. Meanwhile, spotting that guy the dollar could be a cheap way to buy a lifetime customer (who may even just hand you back the extra dollar the next time he sees you, as often happens).

That doesn’t mean there aren’t a thousand possible exceptions or counter-reasons in the above scenario; as in most things, context matters here. But it’s a demonstration of how caring about getting a “fair deal” can actually mean you get a very bad deal.

The You That You Want to Be

Somewhere out there is a version of you that is just waiting for you to become it. That version is happier, more successful, more fulfilled, healthier.

Many people envision this, but they think that the pathway to that version of themselves is full of secret twists and turns, and if they just discover what they are, they’ll be able to become this happier, successful, fulfilled and healthier version of themselves.

The pathway is more obvious. In order to get to that person, you have to become happier, more successful, more fulfilled, and healthier. When you’ve done that enough, you’ll be them.

And that person has still another version of themselves that they want to be.

You live and die every day. There are no moments you get to keep, no plateaus to conquer and hold. This is one of those truths where you can either fight it and be miserable your whole life, or you can embrace it and already be halfway to the version you want to be. But you can’t change it. Life only stops exactly once.

Worry Not

Lots of people worry about stuff. It’s a pretty natural part of the human condition. Yet often we carry worry around like a weight, stressing us out and hurting us, and yet we don’t change a thing about our behavior. It’s just pointless stress.

Often when I hear about someone’s worries, I’ll ask them this question: “Imagine you found out that the thing you were worried might happen was instead guaranteed to happen in 3 months. What would you do differently in those three months?”

And people usually tell me a whole host of things they’d do. Things that they, of course, are not doing right now.

So if they were certain of something, they’d act in preparation. But only being worried it might happen causes a bunch of stress but no behavioral changes.

And here’s the real kicker – usually the changes described by the person in the hypothetical scenario are all upside. In other words, there’s no reason not to do those things just because the potential event might not manifest. Worried you might lose your job, so you save money and look for a better one. Turns out you don’t lose your job? Oh no, you saved money and improved your industry knowledge for nothing!

In fact, not only does the guaranteed negative event cause people to plan better, in most cases it actually causes them to stress less!

Think about that. A negative event that might happen causes a bunch of stress and no action. A negative event that definitely will happen causes only a small amount of stress and a bunch of positive actions taken to mitigate (or even take advantage of!) the event.

This is like a superpower. As soon as you find yourself going around in the worry circle about something, just shift gears. Say it absolutely will happen, plan accordingly, and live your life. Don’t let the spikes that happen steal months from you.


When you topple a really, really big tower – even if the tower was full of bad people – it can fall on good people who had nothing to do with it.

The taller the tower, in fact, the farther away the rubble can fall. People who didn’t even know the tower was there could be hurt.

I’m not saying that you should never attempt to eliminate bad things. We should tear down bad towers, for sure. But lots of people get very, very zealous about what they perceive to be the bad towers (and of course, they’re not always right), to the point where they don’t even consider that there could be people standing in the fallout zone.

If you seek to help good people more than you hurt bad ones, you’ll generally be more likely to make the world a better place. “Bad people” are only bad if they’re hurting folks, so if you’re focused 100% on hurting bad people and never even thinking about the good people you want to help as a result, then you’re no longer acting from a place of justice. Just hatred.

Lean Machine

How much of your personal environment is truly necessary to your functioning and happiness?

In the pure survival sense of the word, you don’t need a car, or a phone, or a computer. In a really strict and not terribly helpful definition of the word, they’re luxuries. But even though they can be used for leisure-related things, they sure don’t feel like luxuries. They feel like the cost of entry into the modern society that surrounds us.

I’ve always accepted that… sort of begrudgingly. Phone, car, computer – I don’t like being squeezed or forced, so if I have to buy those things in order to unlock the tremendous benefits around me, I’ll do it with the barest investment I can make. I have always bought extremely inexpensive, stripped-down versions of those items. I’ve never bought a new car in my life (for all sorts of reasons they’re terrible investments), and my phones and computers are always whatever version has the fewest bells and whistles.

Those are obvious examples, but I think in general we build this machine around us to navigate modern life, but then we often overdo it and build on more features than are necessary. Everything you have an account for, every subscription service, every organization where you’re a member. Some of these are the end goal – you may have a season ticket to your favorite team’s events because you like to go. But others are means – everything from your metro pass to your subscription to a video call service is part of your Modern Machine.

Not only can there be a lot of bloat if you let this get away from you, but the more you build it, the more it can look like a cage. You build all these tools and frameworks around you and suddenly they’re funneling you into a very specific kind of place, or job, or activity, or lifestyle. You outsource your freedom to things that are supposed to give you more of it.

The modern world has a lot of advantages. I’m no proponent of isolationism (except in reasonable, cleansing bursts, anyway) or completely disconnecting from society. But I am a proponent of being deliberate about your choices, and only taking exactly as much as you need, without yielding anything you don’t want to lose.

If You Get Lost

If you ever get lost in the woods, build a house. Now you’re not lost anymore – you’re home.

My life is, in many ways, is radically different than it was just a handful of years ago. Sometimes I look around and I don’t recognize it. I’ve gained a lot! I’ve lost a lot. Things have changed.

Plant a flag. Grow some roots. Build a house. Whatever it takes to make the place you are into the place you should be.

I am not at all good at this. I’m a fixer, not a settler. If I had lived during the frontier days of America, I think I would have had a major problem – the allure of what was over the next hill would always have been more attractive than whatever land I was supposed to build a farm on.

Exploration is good. Ambition, drive, adventure – all good. But there’s a balance; the other side of the scale. A place to return to. Even if we’re not talking about a physical one.

It Would Have Bit You

My father used to say that if I found something I was looking for in what should have been an obvious place: “If it was a snake it would’ve bit you.”

Assume the obvious, at least as a starting point. Sometimes we come up against a problem and we assume that just because no one has solved it yet, that the solution must be complex or difficult. But maybe not!

Start with the obvious place. The easy solution. It might not work – but it rarely takes long to check the obvious, so you’re not out much effort. But if you skip that step, you could spin your wheels for a long time before you realize to come back to it.

Don’t get bit.