On Clarity, And the Discomfort it Brings

There’s a peculiar relief that comes from ambiguity. The meeting that trails off without a clear next step. The project that sits, not quite begun, because someone else has yet to decide. Even in the most purpose-driven work, you can feel it: a hunger for strategy, but a quiet dread of what real clarity demands.

After an offsite, the air was thick with feedback, some honest and fair, some circling the edges of discomfort. I kept thinking about the effort we all put in, the hours of preparation, the pre-work and strategic research, the AI images that landed in the wrong way. The “what could be better” boxes filled faster than the ones about what worked.

If you’ve led long enough, you know this territory. The harder you try to hold the group, to meet every mood, to absorb the static in the room, the heavier you become. At some point, you find yourself carrying more than just the outcomes, you carry the reluctance, the old doubts, the collective longing for someone else to make it all easier.

It’s tempting to double down on empathy, to keep smoothing the surface, hoping the mood will lift. But the truth is, there are moments in every system and team, family, even self, when what’s needed is not more empathy, but more clarity. And clarity is deeply, unsettling.

Because clarity means naming the real challenge. It means seeing the risk, the gap, the truth that “this isn’t working,” or “this change will hurt,” or “we can’t keep going like this.” It means making a call on direction, on boundaries, on what will no longer be tolerated, and accepting that, for some, it won’t be welcome.

A post that John Cutler released this landed hard. It said, “Strategy equals clarity, and clarity can be one of the most unsettling and existential things someone can have.”

Not because clarity is cruel, but because it asks us to step into responsibility. It asks us to accept that, even with all the frameworks and systems we build, someone will have to choose, to risk, to hold the discomfort.

There’s a line from T.S. Eliot that John quoted:

They constantly try to escape From the darkness outside and within By dreaming of systems so perfect that no one will need to be good. But the man that is will shadow The man that pretends to be.

We build systems and feedback forms, strategy decks and processes, not to avoid being good, but sometimes to avoid being the one who decides. The one who owns the discomfort, who moves anyway.

What I’m learning (again, and again) is this: empathy is a tool, but it isn’t a cure. Systems can support us, but they can’t spare us from the work of judgment, risk, and honest presence. Clarity, real clarity, will unsettle. That’s how you know it’s working.

You can’t empathise your way out of a system that’s stuck in avoidance. And you can’t systemise your way out of the need for courage, virtue, or choice. In the end, it always comes down to someone seeing things as they are, naming what needs to change, and moving, sometimes through the discomfort, not around it.

If you’re holding that space right now, you’re not failing. The weather is what it is. Your job isn’t to absorb it all. It’s to keep the mission in view, make the call, and let the system feel the shift.

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Thanks for the inspiration John.

-Layla