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Decisiveness Improves When Mistakes Stop Threatening Your Identity

Chris WilliamsonJoe HudsonChris WilliamsonWednesday, November 4, 20264 min read

Joe Hudson argues that a bad decision is not simply one that fails to deliver its immediate goal; it may be one that gets you what you wanted by compromising who you want to be. In a conversation with Chris Williamson, Hudson says fear, resentment and repeated requests for reassurance can signal that you are overriding your own judgment. He also argues that decisiveness improves when being wrong no longer feels like a threat to your identity, making it easier to act, learn and choose again.

A decision can succeed at its immediate goal and still fail you

Joe Hudson questions the usual test for a good decision: whether you got what you wanted in the moment. Getting the cigarette, the money, the job or the person you were pursuing may feel like success. But the more useful question is whether getting it actually gave you what you wanted over the following week, month, year or decade.

That difference matters when a goal is bought by compromising yourself. Hudson’s example is simple: wanting a cigarette and not getting one can be the better decision. The outcome alone does not tell you whether the choice was good. What matters is whether pursuing it took you away from the person you wanted to be.

Hudson offers a warning sign: fear in a choice makes it less likely that you will get what you want. When fear is driving the choice, it may be unprocessed—not that fear itself is bad. He illustrates the point by contrasting a fearful request for a donation with presenting the cause as worthwhile.

The more fundamental warning, though, is a sense that you do not like how you are being in the situation. That signal can be hard to notice if you have spent a long time overriding it.

Resentment can point to where you have stopped holding a boundary

Chris Williamson presses the practical problem: what if someone has ignored that internal signal for so long that they can barely hear it? Hudson suggests looking back over the past week, month or two and asking where you felt something was wrong but did it anyway. Another place to look is resentment.

Hudson’s explanation is that resentment can follow repeated self-abandonment. If you do something you do not want to do often enough, he says, you may come to resent the person asking. In a marriage, resentment may reflect one person failing to hold a boundary: trying to keep the other happy or un-angry, walking on eggshells, or accepting criticism to keep the peace.

Hudson also suggests asking where, over the past week, you were not the person you wanted to be. He cautions that looking fully at the answer can bring an “ego collapse.”

Advice is useful; reassurance can shift responsibility

Joe Hudson makes a strong claim about repeatedly seeking reassurance: each moment of needing someone else to confirm that a decision is okay involves some degree of self-abandonment. Asking for approval, he says, amounts to “I don’t know what’s right for me, but you do,” and shifts responsibility for your happiness onto the other person.

Chris Williamson raises the obvious objection: this could sound like a reason never to listen to anyone, even a trusted friend who knows you or has relevant expertise. Hudson rejects that interpretation. Listening to other people is a source of wisdom; the distinction is between hearing their perspective and needing their approval.

His test is whether you can say you feel good about doing something without turning to someone else to ask whether it is all right. A confidant can offer perspective, but Hudson’s concern is looking to that person for permission rather than listening to what they think.

Decisiveness improves when being wrong stops threatening your identity

Joe Hudson links decisiveness to a stable sense of self. People confident in their identity, he says, are more decisive because a wrong decision is less likely to feel like a threat to who they are.

That also changes the value of speed. In business, Hudson says, making decisions can be better than concentrating on getting each one right. He contrasts making ten decisions a day while trying to ensure each is correct with making a hundred and learning from the results. A decision lets you test a thesis against reality: act, see what happens, and use what you learn to choose again. Waiting for the perfect marketing plan, by contrast, means you are not yet running an experiment or learning from an audience.

The barrier is often the identity attached to the decision. Someone who sees themselves as an action-taker may find it easy to move. Someone who has been punished for mistakes may feel compelled to get every choice right. Hudson describes a person who was still being reminded at dinner of a mistake made six years earlier; that history can make a new decision feel like a test of personal worth.

Chris Williamson offers a line he attributes to “George”: he would rather be high-conviction and wrong than low-conviction and right. Hudson agrees, reasoning that a wrong choice made with conviction will be recognized sooner, allowing the person to learn sooner.

Hudson describes conviction and openness as compatible. He says he is willing to be wrong without treating it as a threat to who he is, and that he needs conviction to take action.

The distinction running through Hudson’s advice is between a choice that compromises you and a choice that tests a thesis. Fear is a signal to process, not by itself a reason to avoid acting; a decision can be made with conviction while remaining open to what it teaches you.

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