make mistakes of ambition

on overthinking

The ego likes to believe that it can prevent risk & uncertainty. There’s a myth among intelligent people that they can outthink everyone else, and even outthink reality. Smart people are taught from an early age that cleverness is their greatest strength, their secret weapon, and the solution to all problems.

This belief grows when we observe the mistakes of others. There is so much thoughtlessness in the world, which leads to much unnecessary pain. Observe the critical commentary around anyone who takes a visible risk: “these people are idiots. They don’t know what they’re doing. They haven’t considered the second, third, fourth-order effects.”

The thoughtfulness argument has merits. If people were more careful, they would avoid a great deal of suffering. We need the ambitious to be more thoughtful, but we also need the thoughtful to be more ambitious. As with any belief about the world, there is a grounded version and an ungrounded version: a conscious version and a shadow version.

The conscious belief: “with careful thought, I can avoid unnecessary suffering.”

The shadow belief: “with careful thought, I can avoid all suffering.”

The first belief is true. The second is not. There is no avoiding suffering in life, even if you control every variable. If you’re trying to do something bold in the world, like building a business or creating art, then the probability of suffering increases. To be ambitious is to court suffering.

From the outside, it’s easy to tell when someone is in the grips of the shadow belief. They hesitate. They overthink. They get stuck, especially when faced with choosing between two bad options. Choosing between the lesser of two evils violates the shadow belief, because the ego insists there must be a way around. There must be a safe path.

What’s more, it becomes a question of identity. If I can’t find the right answer, I’m just not smart enough. If I can’t avoid suffering, I’m not good enough. What an extraordinary belief to hold! And yet so many of us do. Not only are we put into a world where suffering is inevitable, but we also believe that experiencing suffering makes us lesser. “If I’m not smart enough to find a way to avoid suffering, then that means that I’m not good enough, which means I’m going to experience even more suffering in the future.” Thus we’re set up for a spiral into despair.

It happens. People get destroyed by their own beliefs about reality. The temptation here is to rationalize our way out of the shadow belief. But you can’t think your way out of overthinking. You can’t just say, “Okay, I accept that suffering is inevitable; I will now incorporate that into My Inherent Smartness and all will be well.”

No. Your body needs to learn to integrate a paradox: suffering is safe to experience. Making a decision that you regret is safe. Making a bad decision out of a lack of forethought is safe. To escape the shadow belief, you need to feel that in your bones.

Niccolò Machiavelli:

“All courses of action are risky, so prudence is not in avoiding danger (it’s impossible), but calculating risk and acting decisively. Make mistakes of ambition and not mistakes of sloth.”

And from the biography of John Boyd, an American fighter pilot:

“There are two kinds of mistakes a student pilot could make when delivering bombs or rockets: “pussy errors” and “tiger errors.” Pussy errors are the result of coming in high, shallow, and slow: the pilot is tentative. Tiger errors are the result of coming in low, steep, and fast: the pilot is overly aggressive. Nobody wanted to be known as the pilot who committed pussy errors.”

All courses of action are risky. We only have a preference between what kind of risk we engage with: ambition or sloth, tiger errors or pussy errors.

The paradox: we must accept that there is no safety, and feel safe in that. Overthinking is just one symptom of a hypervigilance in body & mind. Hypervigilance is an attempt to keep you safe from harm, and there’s constant potential for harm, just by being alive. To be alive and to not be hypervigilant is an extraordinary achievement, when you think about it, and that’s the choice that we’re presented with.

How do we reconcile with this paradox? How do we actually feel safety & certainty when there is no real safety & certainty? By realizing that our sense of safety does not come from an external source. Safety is an internal experience, and it can come from within. It must come from within.

To stop believing that our cleverness will save us, to uproot the shadow belief that we can & must avoid suffering, we must feel, at a visceral level, that we can access a sense of safety, no matter what. The prerequisite to that confidence is a practice of creating a sense of safety within ourselves.

Practice is the key word here. The ego wants to immediately solve the problem by saying, “Okay, I will now choose ambition over sloth every time.” Not going to happen. But we can start to lean into tiger errors, and to see if we can help ourselves feel safe in the act of doing so. What does safety feel like in our body? How can we access & create that experience even when taking risks? When we do so, what happens on the other side? What does courage feel like, and how can we practice that feeling over and over?

That’s no small act. To pursue courageous action, to embrace the uncertainty & inherent risk of reality, to create the love & belonging & safety you seek within yourself, in the face of terror of mortality… I think that’s the highest calling of a human being.

As you embrace this practice, you will notice the limits within you. You’ll notice the places where it’s impossible to feel safe, where your body clenches and grips around that shadow thesis, where it refuses to let you take a step. You’ll notice where the hyper-vigilance overrides every other thought. If we get caught in trying to “solve” our own fear, then we’re right back in the ego’s domain.

Can you relax into your overthinking, rather than trying to get it to relax? Can you embrace courage not as a solution to fear, but as its companion?

With love,

Scott

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