There’s this thing they do often in cartoons like Roadrunner, where the character runs off a cliff and just keeps running straight through the air as if they were running on flat ground. It’s only upon realizing they are flying that the character falls.

What if they never looked down?

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I have a few friends who I can rely on to look down all of the time; to be skeptical and cynical. It doesn’t matter what I send them, they’ll always poke holes in it. There’s always something wrong. There’s a reason it won’t work. It could be a blueberry pie recipe and they’d tell me that the pan recommended is incorrect and thus will result in a subpar pie. Know the vibe?

And then I have another category of friends. For these people, life seems to be on easy mode. It’s almost like they aren’t even trying. Partly this is because most of them are effectivists. But I think partly it’s because they believe they can fly. Like they just don’t look down. While my skeptic friends say well, that would never work because Y, my easy-mode friends have not even considered Y. If Y happens then maybe they would consider it. But there’s no reason to consider Y until it happens, in their view. Why look down if you’re already flying.

This reminds of me when I meet people who say things like, “I want to do [thing], but in order to do [thing] I first need to accomplish X, Y, and Z.” And then a week later I meet someone who is doing [thing] but has not done X, Y, and Z. What gives? Well, I think the former person is looking down and thinking of the reasons they might fall. And the latter person is just flying.

Of course this kind of thinking can lead you down all kinds of bad paths, too, and I think that some of the world’s very successful tech founders are good (or actually, bad) examples of it. There is such a thing as toxic optimism. If you are building rockets or super powerful AI, perhaps you should have some skeptics in the room. Some down-lookers.

But in life? In relationships? In getting the job (or jobs) you want? In moving to the beach of your dreams? How much do you really gain by looking down? How real does gravity need to be?

Sure, if you try something (like starting a company) on a whim there will be people who think “wow, what a lack of self-awareness.” And if you end up succeeding they will attribute your success to pure luck or to delusion or use it as some example of why society is broken or whatever. Maybe some of the time they will be right. But I think it’s worth asking whether you would rather be the person flying weightless in the sky, or the person on the ground pointing.

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Over the past couple of years I’ve realized that one of the traits I value most in people (above ‘taste’ and ‘ambition’) is earnestness. I like it when people are earnest, when they do their best to take things sincerely and seriously. When they give it their all.

I think there is a lot in common with earnestness and not looking down. In some sense, in both of these things you are saying: “well, what if things could be good”. You are choosing optimism. When a friend comes to you with an idea, instead of defaulting to the 100 reasons why it might be bad, you first consider: what if I took this at face value? And what if it worked? Without earnestness you eventually end up as the sort of person who criticizes everything but never actually makes, or does, anything; you are the worst of the Reddit and Hacker News comment sections, you are the forever cynic. You are always looking down, always making sure you aren’t risking anything or breaking any rules, and you aren’t, but also, you’re walking.

Wouldn’t it be nice to fly, sometimes?

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