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Sitting in the Messy Middle

Eric Crews
|
9.11.2025
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I was trying too hard.

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That's what a friend of mine told me. "Stop talking about what you're going to do," she said. "You don't actually know how you're going to fix this."

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“You have to sit in the messy middle.”

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She was right.

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***

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We all deal with uncertainty, in our personal lives and especially right now in our businesses.

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Uncertainty is uncomfortable to say the least. Most of us want the feeling of control, even if that control is an illusion.

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We problem-solve.

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We set goals.

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We craft solutions.

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The thing is, when you're in the messy middle, there are no shortcuts to the solve. There's only going through the process.

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Some challenges need space and time to unfold.

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As a person who biases toward action, I find the messy middle unpleasant. It’s taken me a while to understand what it truly means to live there. And to recognize I can’t force the time and place of an outcome I’m looking for.

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***

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How do you know you’re in a situation where the best thing you can do is just chill?

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Well, for starters, nothing else seems to work particularly well.

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AI is a timely example. Right now, so many organizations are trying to figure out what their AI strategy is and what value AI can bring to their companies. As a culture, we're probably in the messy middle of figuring out what role AI will actually play in our lives going forward.

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You can educate yourself. You can get support. You can run experiments.

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You can invest in AI, but the technology is developing right alongside your plans, which means that what's possible is still unknown.

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Can’t change it. Have to learn to live with it.

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***

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Most of life is uncertain. My preferred approach is to act otherwise.

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But occasionally, I take my friend’s advice.

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I focus on the facts I know but don’t jump to too many conclusions.

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I set goals based on the outcomes I want but don’t hold them too tightly.

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I try to move forward but don’t create false urgency or set unrealistic deadlines.

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And I deal with the discomfort—usually with exercise and time outside.

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If you’re facing a situation right now that feels beyond your control: welcome to the messy middle.

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Call out the uncertainty. Watch and observe. Maybe do nothing at all.

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The eventual outcome might surprise you…and could be better than what you thought was possible.

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