This is hardly an original observation. It was made to brilliant effect 50 years ago by Jane Jacobs in The Death and Life of Great American Cities. That book was the product of her campaign to stop Robert Moses, the city and state public works executive, building the Lower Manhattan Expressway, an elevated highway that would have enabled motorists to speed directly from Queens to New Jersey via the Williamsburg Bridge and the Holland Tunnel. In the process, it would have destroyed the character of the area through which it passed.

Jacobs explained, through meticulous observation, how the life of cities is the product of multiple, unplanned social interactions. The density of urban living, far from being an evil, is the source of its vitality. Short streets divided into many blocks lead residents and visitors to take a multiplicity of routes and acquire a variety of experiences. Jacobs explained why the planned cities of the world such as Canberra, Brasília, Chandigarh and Letchworth Garden City are so boring. And her readers were told how the expressways Moses had built had damaged the life of the outer boroughs of New York.

Jacobs won her battle – the Lower Manhattan Expressway was abandoned. But she also won a much larger war. Moses, perhaps the most powerful man in New York for half a century, was finally ousted in 1968. The bulldozers that razed Penn Station were halted before they reached Grand Central. The ramifications extended far beyond that city. Within a decade, the era of modernist architecture was over. Town planning became more modest in conception and incremental in execution.

If unplanned social interactions are the key to a vibrant city, they are also the key to a vibrant organisation. I do not suppose Yahoo’s Marissa Mayer ever met Jane Jacobs, and the technology executive might have found little in common with the community activist. But there are clear analogies between Yahoo’s retreat from home teleworking and Jacobs’ rout of the town planners.

The enthusiasts for the virtual organisation, like the designers of the planned city, seek to impose a structure of rational organisation on a system they understand only imperfectly. Teleworking is the equivalent in cyber space of the corridor of offices, each with its own closed door. Modern office architects have abandoned the corridor in favour of open spaces where communication does not require the deliberation involved in opening an office door, picking up a telephone or sending email. “Communications and collaboration will be important, so we need to be working side-by-side” – the memo is Yahoo’s, the sentiment is Jacobs’.

Jacobs aroused the ire of town planners, who thought their schemes would usher in a rational world populated by the happy faces seen in architects’ drawings. Yahoo faces similar criticism from technophiles who find it difficult to distinguish a Facebook friendship from a hug. People such as Roy Kurzweil, the inventor of optical character recognition and speech-to-text processing. His latest book, How to Create a Mind, carries in its subtitle the immodest promise of “the secret of human thought revealed”.

Mr Kurzweil argues that human thought is based on recognition of a finite number of patterns. It follows that machines can – and soon will, in 2029 to be precise – replace human intelligence. All that is required is a suitably large encyclopedia of recognisable patterns. Town planners similarly thought they could list the functions required for a city and fit each in well-ordered places. Like Moses, Mr Kurzweil has some insight into human thinking and the requirements of modern life, but not enough. Jacobs’ approach was more finely tuned to the nuances of everyday behaviour. A walk around the parts of downtown Manhattan where she lived and which she loved reveals the failures of imagination of the planners of yesterday and today.