Series: The machine that never sleeps #

1. AI is making us work more
2. AI and the Devaluation of Effort
3. The Myth of AI-powered Sisyphus (Current)

intro #

We live in an age of infinite possibility. We have infinite ways to “stay productive” through infinite tools and infinite ideas. The story we were sold was thus: automate the tedious and amplify your creativity, then use the time leftover for what truly matters. But, somewhere between the promise and the present, we lost the plot.

In Part I, I spoke about how AI is making us work more instead of less as the efficiency trap fills every saved minute with new obligations. In Part II, I explored how frictionless creation cheapened our effort, making beginnings effortless and endings rare.

This third part is about what comes after those realisations, when you finally see infinity for what it is and learn to stop running toward it.

the queue never empties #

One thing I am slowly coming to accept is that the backlog grows faster than you can clear it. There is always another idea worth pursuing, another feature worth building, another framework or language to learn, another essay worth writing. The queue is a living thing, fed by newsletters and Hacker News and the ambient hum of what everyone else seems to be accomplishing.

As I mentioned in the previous essays, AI toxifies this by reality by tempting us with the illusion that everything is within reach. We just need to stay awake a little longer, prompt a little smarter, and automate some more, then we can finally “catch up”.

But, there is no catching up.

For every task completed, ten more take its place. For every tool adopted, another emerges with promises of being even faster, better, and more game-changing (this applies to LLM models, too). The queue is infinite because the tools are infinite. The moment you start using AI to “be more productive”, you expand the very definition of productivity.

That’s not a bug in the system. It’s the defining feature of this era.

the modern Sisyphus #

In many ways, I see parallels between our situation and that of the mythical Sisyphus. In Greek mythology, Sisyphus was punished by the gods to roll a boulder up a hill for eternity, only to watch it tumble back down whenever he approached the summit. In the original story, the punishment was futility, the cosmic joke of effort that could never matter, labour that would never end.

But, in the age of AI, our punishment is subtler and perhaps more insidious: perpetual possibility.

Imagine Sisyphus’ boulder slightly automated - it even sets itself up at the foot of the hill while he supervises. But, the hill has grown taller and steeper, and the horizon gets further the higher he climbs. We are Sisyphus, and every time we think we are approaching the top, we discover that the summit was an illusion. There’s always another hill beyond it.

In this world, it’s not the weight of effort that crushes us, but that of abundance. We are haunted not by the fear of failure, but by the constant reminder that success is just within reach. That somewhere in this infinite domain, there’s a better version of ourselves who chose the right projects, learned the right skills, and built the right things.

the illusion of keeping up #

Of course, these are the stories we tell ourselves to justify the chase. We say that we’re “building skills” or “staying relevant”. That if we don’t keep up, we’ll fall behind, as if there’s some finish line we’re all racing toward.

But, there is no finish line. The technology moves faster than any human can follow. Before you even master one tool, three new ones emerge. As soon as you ship that vibe-coded app, the landscape shifts and it feels outdated.

And AI, for all its promises of freedom, has exacerbated our fear of being left behind. Everyone online is claiming massive productivity gains from using LLMs. And, the result is that no one wants to hop off the treadmill. It runs faster, smoother, and more seductively. The machine never sleeps, never tires, and never questions whether it should keep going.

So, we don’t either.

the weight of could #

What we face is a cognitive abyss deepened by the paradox of knowing you can do anything, but still never feeling like you’ve done enough.

When I sit at my desk in the morning, I’m not confronted by limitations. I’m confronted by a dizzying array of options. In each moment lies a dozen parallel universes of things I could be building, writing, exploring, or optimising. The machine doesn’t judge my choices, it just makes them all seem equally feasible.

The old barriers that used to make choices for me - time, energy, skill, boilerplate - have dissolved. What remains is something harder: pure prioritisation.

The burden of choosing what matters when everything seems possible.

recognising infinity #

What’s becoming clear to me is that the overwhelm isn’t a temporary state that will pass once we “become more efficient”. It’s structural. It’s permanent.

To recognise infinity is not despair, it’s clarity. Infinity has always been there, lurking beneath the surface of human ambition. Everyone is so obsessed with the idea of AI making us more productive because we thought we had finally found a solution for infinity. But it simply fooled us into thinking zero inbox was finally within reach.

What must change, then, is not infinity itself, but our stance toward it. We can look into the abyss, acknowledge its immensity, and then gracefully turn back to the finite.

The small, the local, the unfinished. The things that don’t scale, that won’t be automated. The things that require our particular care and attention.

That is where meaning survives - not in mastering the infinite, but in tending the limited.

the grace of enough #

There’s a concept I keep returning to, one that feels almost countercultural in our moment: enough.

Not in the sense of settling or mediocrity, but in the sense of sufficiency. The radical idea that you can do one thing well and that can be enough. That you can ignore new tools or let fleeting curiosities pass and still feel accomplished.

It’s not about lowering standards or giving up ambition and curiosity. it’s about recalibrating them to work for us in an age of infinite possibility.

Because the old model - do more, achieve more, compound your abilities - assumed scarcity. It assumed that each new skill or tool opened new doors that would otherwise remain closed. But when everyone has the tools and means to open these doors, the question shifts.

It’s no longer “what am I capable of doing?” but “what do I care about enough to do myself with my limited time and attention?”

That’s a tougher question but it may be the only one that matters.

choosing finitude #

If there’s one take away from this series, it’s that we live in an age where there’s a fundamental asymmetry between our tools and ourselves.

They can run forever. We cannot. They can generate endlessly. We must choose where to stop.

This forces us to choose - to pause, to rest, to close the tab, to finish something and let the rest go. This is not a failure of ambition, but the most human act of all. It’s an assertion of values. It’s saying, “this matters more than that. This is worth my finite attention. This is enough”.

It’s a great refusal born not out of fear, but out of wisdom. To stand before infinity and not fall in. To see all the things you could do, and consciously choose to turn away.

the machine that keeps going #

So, yes, the machine will keep chugging along. It will outpace, outproduce, and outlast us.

But maybe that’s not a tragedy. Maybe that’s freedom. Because once you stop trying to do everything, you start to see the quiet beauty of doing something well and slowly.

Because the point was never to keep up or exhaust the infinite.

Sisyphus was punished with endless labour because he tried to cheat death, to extend his life beyond its natural limits. Maybe our version is similar - we suffer from trying to cheat time - with the only caveat being that we’re freed the moment we stop trying to do everything.

The boulder will always roll back down. The queue will always refill.

But you don’t have to push it up again tomorrow.

That’s the grace we’re offered in this age of infinite machines: not the power to do everything, but the wisdom to choose what matters and let the rest remain undone.

The machine never sleeps.

But we can.