On my morning bus into town, every teenager and every grown-up sits there staring into their little infinity machine: a pocket-sized window onto more words than any of us could ever read, more music than we could ever listen to, more pictures of people getting naked than we could ever get off to. Until a few years ago, it was unthinkable, this cornucopia of information. Those of us who were already more or less adults when it arrived wonder at how different it must be to be young now. ‘How can any kid be bored when they have Google?’ I remember hearing someone ask.

The question came back to me recently when I read about a 23-year-old British woman sent to prison for sending rape threats to a feminist campaigner over Twitter. Her explanation for her actions was that she was ‘off her face’ and ‘bored’. It was an ugly case, but not an isolated one. Internet trolling has started to receive scholarly attention – in such places as the Journal of Politeness Research and its counterpart, the Journal of Language Aggression and Conflict – and ‘boredom’ is a frequently cited motive for such behaviour.

It is not only among the antisocial creatures who lurk under the bridges of the internet that boredom persists. We might no longer have the excuse of a lack of stimulation, but the vocabulary of tedium is not passing into history: the experience remains familiar to most of us. This leads to a question that goes deep into internet culture and the assumptions with which our infinity machines are packaged: exactly what is it that we are looking for?

‘Information wants to be free’ declared Stewart Brand, 30 years ago now. Cut loose from its original context, this phrase became one of the defining slogans of internet politics. With idealism and dedication, the partisans of the network seek to liberate information from governments and corporations, who of course have their own ideas about the opportunities its collection and control might afford. Yet the anthropomorphism of Brand’s rallying cry points to a stronger conviction that runs through much of this politics: that information is itself a liberating force.

This conviction gets its charge, I suspect, from the role that these technologies played as a refuge for the Californian counterculture of the 1960s. Brand himself embodies the line that connects the two: showing up to meet Ken Kesey out of jail in the opening of Tom Wolfe’s The Electric Kool-Aid Acid Test (1968) – ‘a thin blond guy with a blazing disk on his forehead… an Indian bead necktie on bare skin and a white butcher’s coat with medals from the King of Sweden on it’ – then creating the Whole Earth Catalog, the bible of the back-to-the-land movement, or, as Steve Jobs would later call it, ‘Google in paperback form’.

Before there was a web for search engines to index, Brand had co-founded the WELL (the ‘Whole Earth ’Lectronic Link’), a bulletin board launched from the Whole Earth offices in 1985. Its members pushed through the limitations of the available technology to discover something resembling a virtual community. At the core of this group were veterans of the Farm, one of the few hippie communes to outlast the early years of idealism and chaos; in the WELL, these and other paisley-shirted pioneers shared their experiences with the people who would go on to found the Electronic Frontier Foundation in 1990 and Wired magazine in 1993.

This line from counterculture to cyberculture is not the only one we can draw through the prehistory of our networked age, nor is it necessarily the most important. But it carried a disproportionate weight in the formation of the culture and politics of the web. When the internet moved out of university basements and into public consciousness in the 1990s, it was people such as Brand, Kevin Kelly (founding editor of Wired) and John Perry Barlow (founding member of the Electronic Frontier Foundation) who were able to combine the experience of years spent in spaces such as the WELL with the ability to tell strong, simple stories about what this was and why it mattered.

information took the place of LSD, the magic substance whose consumption could transform the world

The journalist John Markoff, himself an early contributor to the WELL, gave a broader history of how the counterculture shaped personal computing in his book What the Dormouse Said (2005). As any Jefferson Airplane fan can tell you, what the Dormouse said was: ‘Feed your head! Feed your head!’ The internet needed a story that would make sense to those who would never be interested in the TCP/IP protocol, and the counterculture survivors gave it one – the great escapist myth of their era: turn on, tune in, drop out. In this new version of the fable, information took the place of LSD, the magic substance whose consumption could transform the world.

The trouble is that information doesn’t nourish us. Worse, in the end, it turns out to be boring.

A writer friend was asked to join a pub quiz team in the village where he has lived for more than half a century. ‘You know lots of things, Alan,’ said the neighbour who invited him. The neighbour had a point: Alan is the most alarmingly knowledgeable person I know. Still, he declined politely, and was bemused for days. There can be a certain point-scoring pleasure in demonstrating the stockpile of facts one has accumulated, but it is in every other sense a pointless kind of knowledge.

This is more than just intellectual snobbery. Knowledge has a point when we start to find and make connections, to weave stories out of it, stories through which we make sense of the world and our place within it. It is the difference between memorising the bus timetable for a city you will never visit, and using that timetable to explore a city in which you have just arrived. When we follow the connections – when we allow the experience of knowing to take us somewhere, accepting the risk that we will be changed along the way – knowledge can give rise to meaning. And if there is an antidote to boredom, it is not information but meaning.

If boredom has become a sickness in modern societies, this is because the knack of finding meaning is harder to come by

There is a connection, though, between the two. Information is perhaps the rawest material in the process out of which we arrive at meaning: an undifferentiated stream of sense and nonsense in which we go fishing for facts. But the journey from information to meaning involves more than simply filtering the signal from the noise. It is an alchemical transformation, always surprising. It takes skill, time and effort, practice and patience. No matter how experienced we become, success cannot be guaranteed. In most human societies, there have been specialists in this skill, yet it can never be the monopoly of experts, for it is also a very basic, deeply human activity, essential to our survival. If boredom has become a sickness in modern societies, this is because the knack of finding meaning is harder to come by.

It is only fair to note that the internet is not altogether to blame for this, and that the rise of boredom itself goes back to an earlier technological revolution. The word was invented around the same time as the spinning jenny. As the philosophers Barbara Dalle Pezze and Carlo Salzani put it in their essay ‘The Delicate Monster’ (2009):

Boredom is not an inherent quality of the human condition, but rather it has a history, which began around the 18th century and embraced the whole Western world, and which presents an evolution from the 18th to the 21st century.

For all its boons, the industrial era itself brought about an endemic boredom peculiar to the division of labour, the distancing of production from consumption, and the rationalisation of working activity to maximise output.

My point is not that we should return to some romanticised preindustrial past: I mean only to draw attention to contradictions that still shape our post-industrial present. The physical violence of the 19th-century factory might be gone, at least in the countries where industrialisation began, but the alienation inherent in these ways of organising work remains.

When the internet arrived, it seemed to promise a liberation from the boredom of industrial society, a psychedelic jet-spray of information into every otherwise tedious corner of our lives. In fact, at its best, it is something else: a remarkable helper in the search for meaningful connections. But if the deep roots of boredom are in a lack of meaning, rather than a shortage of stimuli, and if there is a subtle, multilayered process by which information can give rise to meaning, then the constant flow of information to which we are becoming habituated cannot deliver on such a promise. At best, it allows us to distract ourselves with the potentially endless deferral of clicking from one link to another. Yet sooner or later we wash up downstream in some far corner of the web, wondering where the time went. The experience of being carried on these currents is quite different to the patient, unpredictable process that leads towards meaning.

The latter requires, among other things, space for reflection – allowing what we have already absorbed to settle, waiting to see what patterns emerge. Find the corners of our lives in which we can unplug, the days on which it is possible to refuse the urgency of the inbox, the activities that will not be rushed. Switch off the infinity machine, not forever, nor because there is anything bad about it, but out of recognition of our own finitude: there is only so much information any of us can bear, and we cannot go fishing in the stream if we are drowning in it. As any survivor of the 1960s counterculture could tell us, it is best to treat magic substances with respect – and to be careful about the dosage.