On Expectation

Box of Amazing enters its tenth year

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Friends,

We are creatures of expectation.

We expect flying cars and colonies on Mars. We expect that by now we would know what we are doing. Expectation is a kind of waiting. You wait for something to arrive, and then it does, or it doesn’t, or it arrives and goes wrong.

The Metaverse arrived. It flopped. Everyone who expected it didn’t know what to do when the future showed up broken. Including Meta. The people who were paying attention saw the gap between promise and reality. They didn’t expect. They watched.

That’s the difference. Expectation waits for arrival and attention accepts that arrival may not come, or may come sideways, or may come and mean nothing. Or be a disaster. Attention is the harder posture because it doesn’t promise resolution.

Nine years ago I chose attention over expectation. I didn’t know that’s what I was doing. I just started writing about things I didn’t understand, hoping that the writing would teach me what I thought. I recount this every year.

I think very deeply about whether it’s all really worth it. And the balance of whether I am doing it for myself or others. It’s because of others, that I find clarity in doing this for myself.

As Box of Amazing enters its tenth year, I want to talk about what happens to the people who watch closely for a long time. Not what AI has become. What we become while watching it.

There’s a belief I held for years, and I suspect you hold it too. If I stay close to the technology, I’ll stay sharp. Read the papers. Follow the launches. Keep proximity. The assumption is that vigilance equals readiness. That watching closely is the same as learning.

It isn’t.

Proximity can accelerate the very thing it’s meant to prevent. The closer you stay, the faster your frame hardens. You stop being destabilised by the thing you once found strange.

The mid-2010s felt different because I was still confused. I used the wrong words. I asked obvious questions. I stayed with ideas longer because I couldn’t shortcut them. The friction was the learning. Friction is my favourite word these days.

Today I write faster. I know the vocabulary. I can move from question to draft without the detour through uncertainty. That efficiency is real. But so is the loss.

I notice it in small moments now. A draft that comes together faster than it once did. A conversation that assumes a shared baseline of machine assistance. The absence of certain skills that no longer get practiced because a shortcut exists. The commitment is pressing the return key.

None of this obviously announces itself. It accumulates and builds, by noticing, bit by bit, action by action. Until you don’t notice it any more and it becomes the new normal.

We start as observers and become optimisers. We trade the posture of learning for the posture of deploying. The shift feels like progress. It often is. But it has a cost we rarely name.

I see it in myself and in others.

Here is the mechanism as I see it. Our attention hardens into expertise, and expertise filters out surprise. The longer you watch something, the more efficiently you process it. Efficiency is useful. But efficiency is also a kind of closure. You stop asking whether your frame is right once it starts working.

And here is what makes it worse. Optimisation is not neutral. It selects for speed over destabilisation. Every time you process faster, you remove a little more of the friction that would have sharpened your judgement. Fluency feels like mastery. Often it is just pattern-matching at speed.

This is the drift from observer to optimiser. It happens to everyone who stays long enough. And it happens faster to those who stay closest. The risk isn’t that we become bad at noticing. It’s that we become good at noticing only what we’ve already learned to see.

Nine years into writing about AI, I can tell you what matters faster than I could in 2016. But I’m less certain I can tell you what I’m missing. The early confusion protected me from premature confidence. That protection is gone now. This doesn’t rebuild cleanly later. You can’t re-enter confusion once you’ve optimised your way out of it. The neural pathways have been paved. The shortcuts are load-bearing.

I sometimes wonder about the path I didn’t take. That Sliding Doors moment.

A decade is long enough to foreclose other lives. I could have gone deeper on one thing instead of wider across many. I could have spent those hours becoming someone who knows one domain completely instead of someone who patterns across several incompletely.

What did I get instead? Layers I couldn’t have planned. A way of seeing that only comes from refusing to settle too early. A book I couldn’t have written nine years ago because I hadn’t done the writing that would give me the thoughts.

And smaller things. A smile here when something lands. An “oh, I get it” there. The occasional groan at a bad joke. Evidence, faint but real, that the bet mattered to someone other than me.

Did I take the right bet? I don’t know. That’s not false modesty. It’s the honest answer when you’ve chosen one path and can’t see the others anymore.

Someone told me recently that my writing has become more philosophical. I think they meant it as a compliment. I’m not sure it is one. If you uploaded every article I’ve shared in this newsletter, everything I’ve written, every note and half-formed thought, AI could probably chart my path through the decade. It could determine who I’ve become. I can’t, not fully. I’m too close. I’m inside the sum, not above it.

What I know is that I’ve read widely and understood narrowly. The reading didn’t give me answers. It gave me layers. And the layers didn’t clarify. They complicated. Maybe that’s what philosophical means. Not understanding more, but understanding less, with more care.

Always be learning. Always be curious. That’s the mantra I hold. But curiosity without integration is just accumulation. The newsletter gave me both the gift and the problem. I learned constantly. I don’t know what it adds up to. Maybe that’s the point of learning in a field that is always changing: the accumulation of “aha moments” with no end in sight.

A decade is longer than it sounds.

My kids grew up thinking I had this weird hobby that no one else’s parents had. Towards the end of the week, Dad disappears to write about robots. They never said it like that, but that’s what it was. A strange ritual in a house full of ordinary ones.

People I loved died in that decade. People who might read my work one day were born. We survived COVID. Survived it and then, somehow, moved on as if survival were the same as resolution. We watched the elections and wars that felt like juncture points in human history. We lived through power shifts that historians will name cleanly but that we experienced as fog.

I don’t know what era this is. I know it has a shape, but I can’t see it from inside. We are mid-chapter, mid-sentence, mid-gesture. The clarity will come later, or it won’t.

All while, every Sunday, I sent out an email.

That’s not heroic and I’m certainly no hero. It’s just what I did and what I do. The one fixed point while everything else moved. A small stubbornness against the current. Probably useless. Possibly not. And maybe a bit weird, but I choose this weirdness.

Sometimes I wonder if I’ve written anything at all, or if I’ve just been a slave to the algorithm.

Every article I read was recommended. Every link I followed was served. The reading list that made me wasn’t chosen. It was curated by systems optimising for engagement, not understanding. I became the person those inputs created. And now I can’t remember which ideas I found and which ones found me.

Maybe it doesn’t matter. Maybe the difference between chosen attention and captured attention is smaller than I want it to be.

And what about you? Are you still here, really here? Do you feel something when you read this, or are you skimming, thumb moving, harvesting a phrase before you move on?

I’m not asking to accuse. I’m asking because I don’t know anymore what reading is becoming. Whether the person on the other end of these words is still the kind of reader who stays with a sentence, or whether that reader is already historical. A figure future generations will study the way we study scribes before the printing press.

The monks copied texts by hand for centuries. Every word was labour. Then Gutenberg arrived, and within a generation, the craft was obsolete. Not because the scribes were wrong. Because the economics changed.

What if attention is the craft being automated now? What if the careful readers are the scribes, and we don’t know it yet?

Pompeii knew Vesuvius was a mountain. They didn’t know it was a volcano. Or they knew and had normalised the risk. When it erupted, some were found mid-gesture. Eating. Arguing. Reaching for something on a table.

We might be mid-gesture right now. Future historians might find us frozen in the scroll, thumb still moving, not looking up.

I started this newsletter because I thought I couldn’t write a book. I didn’t know how to write. I didn’t have the ideas. I had curiosity and confusion, and I had the willingness to think in public before I knew what I thought.

In the tenth year of Box of Amazing, I’m finishing that book. Not about the technology. About how we survive it. What accumulated over a decade wasn’t prediction or foresight. It was the slower thing. A way of seeing that only comes from staying in the difficulty long enough.

The writing has been arduous. It still is. But I have thoughts now that I didn’t have before. They came from the friction, not despite it.

Calcification needs a counter-practice. Here is mine.

Once a month, I read something I’m confident I’ll disagree with. And I write down one place it might be right that I’ve been wrong. It kills me a little, but it’s the right thing to do.

Not just exposure to disagreement. Admission of error, even if only to myself.

It is not comfortable. That’s the point. Observation is a discipline, not a credential. The moment you stop being surprised, you’ve shifted from learning to confirming. The only way back is to manufacture the confusion you’ve optimised away.

Nine years ago, AI felt distant. A vocabulary forming at the edges. Today it feels domestic. Familiar. Almost manageable. A bit like a new pair of slippers.

That familiarity is the achievement and the danger.

The bet I made in 2016 wasn’t on a technology. It was on the discipline of paying attention before knowing what to look for. That discipline still matters. But it requires something I didn’t anticipate. The willingness to stay a beginner even after you’ve become an expert.

Expertise is what you gain. Surprise is what you lose. The question for the next ten years is whether you can hold both.

Stay Curious - and don’t forget to be amazing,

Rahim

PS. If your organisation is grappling with how AI is reshaping work and leadership, I speak and advise on this.

Rahim Hirji Author, SuperSkills (2026) | Keynote Speaker | Advisor

Building human capability for the AI era.

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