On an earlier post, I’d mentioned that insecurity can be a good thing. I don’t know that insecurity in itself is a good thing, but as a symptom, it’s not a bad one. People strive, I believe, for a sense of security. What I hope to convey is that I think it’s a poor goal – a false one – while the ability to project security & confidence is a good thing, developing an internal sense of security is actually a step in the wrong direction.

Donald Rumsfeld got mocked for this quote:

“[T]here are known knowns; there are things we know we know.
We also know there are known unknowns; that is to say we know there are some things we do not know.
But there are also unknown unknowns – the ones we don’t know we don’t know.”
—Former United States Secretary of Defense Donald Rumsfeld

While I’m no fan of Rumsfeld’s, I like this quote a lot (though not in the original context), and I think it was sad that this is what he was maligned for.

When you start out at something, you know you don’t know anything. At least, you should know that, because if you don’t, you’ll never learn anything.

As you gain experience in that thing, you begin to feel more confident. You know some stuff. You know what you know, and you feel good about it.

After a while, as your knowledge of that field expands even further, you begin to realize – at least if you’re in an interesting field doing interesting things – that it’s incredibly difficult, and that experience matters. You realize the scope of the things that you have left to learn. You know what you don’t know, and more importantly, how far you have to go before you understand it.

Then, there’s the phase where you realize that even when you absolutely master your field, when you are the expert that other experts seek out, that there is a whole system of events that you cannot control, you cannot understand, and in many cases, you have no impact on. Some of this, maybe you know. You may know that you’re more likely to like someone who hands you a hot drink than a cold one. You may know that you’re more likely to make a higher estimate after reading the number 501,208,281,291 than the number 4. And you may know that even if you know these things you can’t affect their impact on you. Those are still part of the known unknowns. But in that vein – if those are the known unknowns, trying to imagine what the unknown unknowns are is like looking into the mouth of madness. And while these examples may seem ludicrous, the point is that in almost every endeavor, there are things like this – things that are almost impossible to anticipate, but will have a dramatic impact on whatever it is you’re doing.

How’s that relate to being insecure?

There’s a level of expertise you reach, I think, where you can make excellent calls. You can have good judgment to deal with new situations, and you can have enough experience that you have a whole toolbox in your pocket to deal with situations like those you’ve encountered before. But in any field that involves some level of complexity, things quickly spiral beyond the point where that system can be completely contained in one mind. So you know there are things that you don’t know. And you know there are things you can’t know. People who make decisions in that space who are confident and assured don’t know they don’t know those things.

I’m not saying that you have to be wishy-washy, or that you have to project that insecurity. I think a good leader will project a calm, steady presence, and make decisions with authority. But I don’t think those people make those decisions with security that their decisions are the right ones. They’re just the best that they can do with the resources available. At some point, those are the only kinds of decisions you can make. No one makes the right decisions all the time, they just make the best decisions they can.

So while you ideally shouldn’t project your internal insecurity, you should feel it. You should internalize it, be aware of it, and understand what you have control over and what you don’t. It will help you remain flexible, because you will always remember that you may have to be adaptable. So to me, a little insecurity isn’t a bad thing. You make the best calls you can, you learn from your mistakes, and you move on.

I hope you’re insecure.

Because then it means you’re doing interesting things – and that the results may be even more interesting than you expect.