Does Anyone Else Feel Like They're Winging It Now?

I have been doing this job for a decade, and for the first time in a long while I regularly feel like I am making it up as I go. Not in a panic. Just a low, steady sense that the ground I stood on for years has shifted, and the confidence I used to have was partly the confidence of knowing how things worked.

I do not think I am the only one. I think a lot of us are nodding along in meetings about AI-native delivery with a calm face and a private feeling of, does anyone actually know how this is meant to work yet? Nobody says it, because saying it feels like admitting you have lost the plot, when really it is just an honest description of the year.

I want to be careful not to dress this up as a crisis. I am not overwhelmed, and the work is getting done. It is more specific and stranger than that: a competent person, good at their job, quietly aware that a chunk of what made them good has an expiry date they cannot read. That is a new feeling for a lot of us, and it does not have a tidy name yet.

Experience is a library of "last time this happened, here is what worked." Mine was full. Estimates, review rhythms, how long things take, what a healthy project feels like. A good chunk of that library got quietly outdated in about a year, because the tools underneath it changed what is true. My instinct for how long a thing takes is calibrated to a world that is being retired every few months.

So I am running on a mix of old instincts that still apply and old instincts that quietly do not, and the hard part is that they feel identical from the inside. That is the real disorientation. Not that I do not know anything, but that I cannot always tell which of the things I know are still true.

You cannot tell from the inside which instinct is which, because a wrong instinct feels exactly as certain as a right one. That is the whole trouble with instinct. It was built to save you from having to think, and it does its job just as confidently when the ground it learned on has moved. So the reliable move now is to trust it a little less and check it a little more, even when it is quietly sure it is right.

There is a strong pull to perform certainty about all this, especially if people look to you to have a handle on delivery. Admitting you are partly improvising feels risky. But I have started to think the performance is the more dangerous option, because it stops you doing the one thing that actually helps, which is staying openly curious and checking your assumptions instead of trusting them.

The people I have watched handle this year best are not the ones with the most confident take. They are the ones comfortable saying "I am not sure yet, let us find out." They treat their own experience as a strong hypothesis rather than a settled fact, and they are right more often for it.

It helps, oddly, to say it out loud. The first time I admitted to a team that I was not sure how something should work anymore, the relief in the room was obvious. Everyone had been holding the same quiet uncertainty and assuming they were the only one. Certainty performed is contagious, and so is honesty, and only one of them helps you actually work out what to do.

Winging it, if you are honest that you are doing it and paying attention as you go, is not the same as being lost. It might just be what learning looks like when the thing you are learning keeps moving under you. The alternative, pretending the old map still fits perfectly, is how you walk confidently into a wall.

I have made a kind of peace with it. Some weeks I know exactly what I am doing. Some weeks I am running a careful experiment and calling it a plan. Both are fine, as long as I can tell which is which and do not dress the second one up as the first.

What has changed, really, is that I have stopped expecting to feel settled. For most of my career, competence felt like a growing certainty. Now it feels more like staying alert, holding my own experience loosely, ready to be shown that a rule I relied on has quietly expired. That is a less comfortable way to work. It might also be a more honest one, given how fast the thing underneath us keeps moving.

So, genuinely, not rhetorically: is it just me, or are a lot of us quietly winging it right now, and would we all be a bit better off if we just said so?