Moving in the rain

Oliver Burkeman, writing in his newsletter The Imperfectionist, reaches back to a book title that stopped me: Rabbi Alan Lew's This Is Real and You Are Completely Unprepared. Burkeman's point, characteristically, is not to alarm. Uncertainty, he argues, is not a temporary inconvenience. It is our basic state of existence. We are never ready. Not really. And waiting until we are ready is, in the end, just another way of not beginning.

It made me think about our work at Milestones.

And about the tension I sit with whenever I describe what career strategy work actually does. The language we use: clarity, tools, confidence, taking control, can sound, if you read it in a certain light, like a promise to resolve uncertainty. To get you ready. To eliminate the fog.

Well, yes and no.

We cannot conjure certainty where none exists. I am not entirely convinced that any honest career strategy work could, or should, promise that. The future remains unwritten. The economy shifts, organisations change, the role you were confident about six months ago disappears. None of that stops because you have done some careful thinking.

But what I have come to see is that clarity and certainty are not the same thing. And the confusion between them is, I suspect, at the root of a great deal of professional paralysis.

A client said it plainly after going through the Milestones process."I now have more clarity. I may not be more certain about the future, but I am certainly more confident." That formulation is quietly precise, for it names something important - that you can hold genuine uncertainty about outcomes whilst still being clear about your values, your priorities, and the direction you want to move in. Confidence, in this sense, is not the absence of doubt. It is the ability to act meaningfully in spite of it.

Lew's title This Is Real and You Are Completely Unprepared might sound like a provocation. And at one level it is. But I think it is also a kind of permission. If being unprepared is the normal human condition, then unprepared is not a reason to wait. It is simply the weather.

We don’t change the weather. Instead our job is help you decide where you want to go. And to do that with enough honesty and rigour that you can start moving, even in the rain.

I wonder sometimes whether that is a less exciting proposition than clients expect. Perhaps. But my experience is that most people, once they have the clarity, don't need the certainty anywhere near as much as they thought they did.

If you want to explore what that kind of work looks like, you can find out more at Milestones or give me a call.