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The first time

We expect most things to work right the first time. On the face of it, this isn't the wrong way to go about things. We're not saying we want things to work right, just that we expect them to. It's ok if they work wrong.

Except we never think they work wrong. We think if something didn't work right, it didn't work. It failed. So what we're really saying when we expect things to work right the first time, is that we're okay with them failing.

What happens when we're risking a lot on something that has huge potential, but can also fail spectacularly? We shift goalposts just a little. This time, we really hope it will work. We spend a lot more time planning, we try to predict all the things that go wrong and try to make sure they don't, we expect weekly, daily updates on what's happening so we can keep up with every small thing that affects it. We micro-manage the shit out of it. We think it's ok, because we're counting on this one.

And then it fails. Our wonderful idea dies before our own eyes.

Most often, we pick up the pieces and move on. Sometimes, we do a post-mortem. Most post-mortems tell us either that we did the wrong thing, or that we went about it the wrong way. Knowing this after we've failed makes it hard for us to go back at it again. We pick something that's just a little less risky, even if the payoff is not as big as our previous idea. We move on.

Sometimes, we don't move on. We believe in our idea strongly enough that we go at it again. This time, we don't go about it the same way. We do some things differently. We reduce the scope, we de-prioritize the parts that are too risky - the ones we didn't foresee before.

How many times are we prepared to do this? Most high-risk ideas with great potential die at least 3 times before they get anywhere.

What if, instead of counting it to work the first time, we give it our best, but we go at it not as if we're solving a problem but as if this is our first attempt to learn more about the problem? What if the post-mortem is the real goal of the exercise?

When Elon Musk says,

Instead of putting landing legs on the booster and the ship, we're going to catch them with a tower, to save the weight of the landing legs. We're talking about catching the largest flying object ever made, on a giant tower with chopstick arms.

He's proposing to do something that has a huge payoff, but also something that can fail spectacularly. So how does he go about it?

This probably won't work the first time.

He's expecting to do it more than once. He believes in the idea, to be sure, and he is fully committed to it. You can tell he isn't going to scope it down when it doesn't work right the first time, because he's doing it to learn how he can do it better the second time.

The post-mortem is the goal.