First of all, I disagree. The future will be cool, at least in the long term. What it won't be is weird, in the sense of people wearing spacesuits in their living rooms. The bizarre visions people have traditionally had of the future (and which, demonstrably, haven't come true) seemed to focus largely on superficial stuff (clothing fashions, which are highly unpredictable but have a long-term mean-reversion) and to exaggerate. That doesn't mean that the world hasn't changed, and won't change, in profound ways.

Yes, the pleasures of life (wine, music, books, sex, spiritual experience) don't change all that much and therefore we use a lot of old technologies in daily life, so it can appear like there's nothing new... but there will be more people able to afford them, and they will be much less impeded by the stupid shit that clogged up peoples' lives in pre-technological times. Just to continue Taleb's example: in the 21st century, a lot of people get to drink wine of (by historical standards) exceedingly high quality. Three millennia ago, wine existed but the vast majority of people never got to drink any.

Many of the modern applications that have managed to survive today came to disrupt the deleterious effect of the philistinism of modernity, particularly the 20th century: the large multinational bureaucratic corporation with “empty suits” at the top; the isolated family (nuclear) in a one-way relationship with the television set, even more isolated thanks to car-designed suburban society [...]

I'm going to stop there with the quote. His point is valid, but I think there's something missed when people rip on suburbia. Yes, it's outmoded and wasteful and somewhat ugly, but the Levittowns were a lot better than the "company towns" of early-industrial hell, and those were a lot better than being a serf on a medieval enclosure, in a time when it wasn't uncommon for a peasant to have his head cut off by a knight (knights were more like warlords than the noble paladins of romance). People tend to compare the experiences of average people now against those of an elite in the past and conclude that things were better, but that's not fair. The 1800-era analogue of a bored suburbanite of 50th-percentile social status (only one car!) was not an English baron, but someone who started work at seven in the coal mines.

People rip on suburbia now because it's outmoded, but it wasn't always this way. Urban freeways are called "parkways" because the vision of Robert Moses (in hindsight we say, "That fucker!", but he was very respected in his time) was for them to be park-like roads for an automotive elite. In the 1920s, suburbia was very much in. The suburban lifestyle, with lots of driving, was designed for the rich and handed down, over a couple of decades, to the working classes in a watered-down form. The result now, almost a century later, is that "suburbia" is no longer cool because the low-quality suburbs of the poor have killed the image of the concept.

Oddly enough, has anyone ever noticed how rich people suburbs aren't called that? The Hamptons isn't "suburbia". The Woodbury towns out there are "charming little towns" rather than suburbs, because the rich people who live there have enough time to make zoning rules that keep a quaint little street or two alive. These people aren't morally superior for having houses in high-price towns that still have walkable main streets as opposed to "suburbs". They're just richer.

One thing I find interesting is that Ted Kaczynski (Unabomber) wrote an essay about technology and alienation, while most of his complaints were of the industrial-era society, not the technological society we evolved into. He was miserable because, in spite of his extreme intelligence and adept writing, he had no real influence in a world run by corrupt corporate institutions. So he went out and killed people in order to effectively force the New York Times to publish his rant. If he had waited 15 years and not killed people, he would have had the public access and attention he craved. He might have trolled a bit, but no one would have died. Technology was just about to solve many of the problems that had him so upset-- that he blamed on industrial society.

My view of technology and progress is that it's nearly monotonic in "goodness", but that the old humanity we're now trying to distance ourselves from is quite tenacious and willing to use technology toward pre-technological purposes, and so the long-term convergence toward democracy that we'd like to see doesn't come nearly as fast as we'd like. For example, one might like to believe that, in an electronic world, old-style industrial pressures like taking orders from managers, showing up in an uninspiring white-box office during certain hours, and writing TPS reports would vanish... but human nature is a certain way and power likes to maintain position, so the transition is actually taking decades rather than the hours that it "should". The result of this is that the technological push toward a better world appears to collapse into an unsatisfying half measure and people end up having to use technology in uninspiring ways (e.g. getting to write code, but still having to take orders from non-technical executives or "product managers"). That's not technology's fault. That's an artifact of humans being slow to improve themselves.