Working in The Transforming

Working without a crystal ball

A lesson in uncertainty from a New York City psychic

Drew Weilage · June 24, 2026

"You dumb piece of shit."

Yoooooo.

It's the kind of statement that makes you turn your head on a New York sidewalk—a little less surprising coming from a very direct New York mother, a little less awful landing on a 17-year-old who'd clearly made some poor choices in recent days.

But what made it unconscionable is that it was coming from a psychic.

Here's a woman whose entire profession is built on knowing what's coming. People pay her good money to sit across a table and find out what their future holds. And here she was telling on herself—she didn't see her own son's choices coming, didn't know until it was already done, found out the same way the rest of us find out everything: after the fact, too late to do anything but yell about it on the sidewalk.

You can hear lots of interesting things on New York City sidewalks. But it's rare to come across an entire lesson on uncertainty on your way to happy hour.

Say "uncertainty" in a meeting these days and everyone nods, because everyone's feeling it, and hearing about it, and reading about it. But then what? If uncertainty is our reality, what next?

Couple thoughts.

Let's get precise on what we mean by uncertainty.

Uncertainty is a psychic's empty crystal ball. It is the absence of knowing what's coming next. And "not knowing" is famously irritating to humans.

Vaughn Tan is a go-to uncertainty expert, and here is the distinction he draws between risk and uncertainty: risk is when you don't know what's coming, but you know the odds. A coin flip. A confidence interval. A weather forecast. There's a number to hold onto.

Uncertainty doesn't give you a number. No odds. No model. No actuarial table. None. Your brain can do something with a coin flip. It has nothing to do with uncertainty except feel it.

And boy are we feeling it. Like everyone. At an intensity we haven't felt before.

Because the more tangled and interconnected a system gets, the more it produces actual uncertainty instead of garden-variety risk. One part moves, three other parts you never touched move with it, and nobody could've modeled that going in.

That's not theoretical. That's everything you experienced at work and at home and out in the world during the pandemic. And there are pandemic-equivalent events happening right now.

There's a lot going on: what AI can actually do, who holds power globally, whether the thing you're looking at is even real, whatever is happening with the economy.

And yes … to the eagle-eyed observer—this moment isn't all that different from any other moment in history. We've always been on the precipice of life-changing events no one saw coming. Humans have never had certainty about the future. Plague, famine, war, a bad harvest before anyone understood crop rotation. Uncertainty isn't a 2026 condition. It's the human condition.

What's different is the density of it, and the speed. Past generations had long stretches to recover between disruptions. That gap has disappeared. And there's a layer that genuinely is new: it used to be that you didn't know what would happen next. Now you sometimes can't even trust what's happening right now—this video, this quote, this "news" story.

We're also more exposed. Every disruption everywhere, all the time, in your pocket. Outside your front door. Around the corner at work. That's real too.

We don't need a functioning crystal ball to know futurist Kevin Kelly is right: Uncertain Uncertainties—uncertainty, sustained and compounding—aren't going anywhere. "In other words," he writes, "We have a sustained, extended period of uncertainty. Not just a few years, but a decade or more."

The work playbook—the org chart, the five-year plan, the way decisions cascade down from the top—was built for managing risk. Not for Uncertain Uncertainties.

Organizational decision-makers, who often sit at the top of the hierarchy, are reckoning with uncontainable uncertainty. The outcome of that reckoning is The Transforming—"the always-happening, always-unfolding state of change in your job, and the continuing result of market forces far beyond our control."

This leaves the organizational decision-makers in the same position as the psychic. A little exposed.

Since at least after World War II, the C-Suite had a job something like the psychic's: read what's coming, build the strategy, manage execution, and then catch the disruption before it reached the rest of the org. And it mostly worked—not because they could see the future any better than a psychic can, but because disruption used to move slow enough, and far enough apart, for someone up top to absorb it before it became your problem.

That's not holding. Not because the people running things got worse at their jobs. Pour one out for them, honestly—Boards of Directors, Wall Street, their own employees still expect them to know what's coming … in a moment when nobody can. The environmental uncertainty has finally outrun what any one person, or any layer of management, can catch and hold. The whole thing's getting exposed, the same way the psychic told on herself.

So if you're feeling like you don't have direction in your work, or you don't know what's coming next, or you're bracing for whatever decision from up above is about to land on you—yeah. That's uncertainty.

All of this means we might need a different orientation to the uncertain reality we're working in. Uncertainty hits us as a social threat, which we still need to settle to do our best work, but when the impact of uncertainty is environmental, universal, and ever-present, we need something more like a different perspective.

That reframe arrives in an essay by Martin Shaw: what if we swapped "living with uncertainty" for "navigating mystery?"

As Shaw puts it: "Navigating mystery humbles us, reminds us with every step that we don't know everything." Not the C-Suite. Not the consultants with the five-year plan. Not the psychic. (Not us, either.)

Mystery doesn't carry uncertainty's baggage—none of the overconfidence that pretends to know, none of the anxiety that comes from admitting you don't. It's quieter. Easy to miss if you're not paying attention.

Navigating mystery turns uncertainty from something you feel into something you do.

"Is AI going to take my job?" Not yet. Use it and find out what it's truly good at, and what's still yours. Then go do more of that.

"Do we have a plan?" Nope. That doesn't mean you can't start making sense of what you're looking at.

"Is that rumor true?" Perhaps. But you can ask where it came from before you decide what to do with it.

None of us are working with a functioning crystal ball. Not the people running your org and making decisions about the work. Not the psychic, despite what she charges for the sit-down. Not us.

No need to manage that uncertainty. Better to navigate the mystery.