The Lost Generations

Every generation worries about the one that comes next. But in a world changing this fast, perhaps the more interesting question is not whether new generations can adapt, but what adaptation actually means.

I hear organisations wondering how to attract them, retain them, motivate them, bring them back to the office or develop them into leaders. Behind these questions sits another one, rarely stated quite so directly: how do I get this new generation to adapt to the world of work?

It sounds reasonable. Until I started wondering whether the question itself might be the problem.

A STEP BACKWARDS?

A few days ago, I came across a LinkedIn post about young people buying iPods again. Not because an iPod is technologically superior to a smartphone, obviously, but precisely because it does less. No notifications, no endless feed, no algorithm deciding what comes next. Just the music you chose to put on it.

There is some substance behind the anecdote. Earlier this year, Axios reported that US eBay searches for the iPod Classic had increased 25% between January and October 2025 compared with the same period a year earlier, while searches for the Nano were up 20%. More recently, ITV reported that searches for classic iPods had risen 31% in the UK between January 2025 and January 2026.

Under the post, I wrote: "What looks like technological regression may actually be cultural progress. The question isn't why Gen Z is going back to iPods, but what they're trying to leave behind."

What struck me wasn't that they were going back to the iPod. In a way, I wasn't surprised at all. My reaction was closer to: here we are.

For some time, I've had the feeling that something is shifting in our relationship with the constant noise surrounding us: more content, more notifications, more recommendations, more things competing for our attention. So seeing young people deliberately choose a device that removes most of that noise didn't feel like nostalgia or a step backwards. It felt strangely contemporary.

A generation that has grown up with permanent connectivity may not experience less connectivity as a loss. Choosing a device that does less can also mean choosing what gets in.

The iPod wasn't interesting to me as a comeback. It was interesting as a signal of what a generation might be trying to leave behind.

WHO IS SUPPOSED TO ADAPT?

It made me notice a similar assumption in the way I hear new generations discussed at work: the system is fixed, the generation is the variable.

The workplace, hierarchy, career ladder and definitions of ambition or success are treated as the reference point. A new generation arrives and the question becomes how successfully it can adapt to them.

Except the system isn't fixed. AI is transforming work. The economics of housing have changed. A pandemic disrupted formative years. Smartphones and algorithms have profoundly altered the information environment. The people entering adulthood today aren't simply witnessing these transformations from the outside. They are being formed by them, just as previous generations were formed by a different set of conditions.

Deloitte's 2026 Global Gen Z and Millennial Survey offers an interesting glimpse into this. Based on more than 22,500 respondents across 44 countries, it found that only 25% of Gen Z respondents prefer fast career progression and rapid promotions. Forty-four percent prefer steady progression, while 21% would consider moving laterally, or even taking a step back, for the right opportunity.

It would be easy to interpret this as declining ambition. Yet 76% of Gen Z respondents say they are interested in pursuing senior leadership roles at some point in their careers. They haven't necessarily abandoned ambition. They may simply be questioning the version of ambition previous generations built around it.

Technology reveals something similar. Nearly three quarters of Gen Z respondents in the same survey already use AI in their day-to-day work, while 30% believe their organisations aren't prepared for the changes AI will bring.

The iPod and AI aren't contradictory signals. If anything, I find their coexistence revealing. The same generation can embrace one of the most transformative technologies of our time while deliberately stepping away from other technologies that no longer serve it in the same way.

Perhaps that isn't resistance to progress. Perhaps it is a different reading of progress.

WHEN RESISTANCE BECOMES INTERESTING

Around the same time, I came across the work of Miguel Aubouy, entrepreneur and co-founder of DOJI an organisation dedicated to understanding and teaching the mechanisms of innovation.

He makes a distinction I find useful here. Improvement operates within the logic of an existing system: it makes what already exists better. Innovation, in his view, introduces something the existing system wasn't designed to accommodate. This is why he argues that genuine innovation often encounters resistance, including from the organisations supposedly looking for it.

I don't think resistance automatically means progress, nor that every generational disagreement should be romanticised as innovation. But Aubouy's distinction made me look at generational friction differently.

A generation that accepts every premise inherited from the previous one can certainly improve the existing system. Reinventing it requires something else: the willingness to question what everyone else has stopped questioning.

What if some of the behaviours previous generations interpret as a refusal to adapt are actually signs of adaptation to conditions that have already changed?

THE PROBLEM WITH EXPERIENCE

This is where the question became uncomfortable, because it turned back on me.

I have spent more than twenty years working inside organisations, brands and creative businesses. That experience is valuable. It has taught me how organisations work, how careers develop and how decisions get made. But experience also gives me a map, and that map was drawn in the world in which I learned to navigate.

The problem isn't age. Nor is it that new generations somehow possess an innate understanding of the future. The issue is more subtle: previous generations were shaped by the world that brought us here, while new generations are being shaped by the world that's emerging.

Neither perspective guarantees wisdom. But they aren't the same perspective.

And because previous generations still occupy many of the positions from which organisations and institutions define what is normal, successful or desirable, there is a risk that experience becomes more than a source of knowledge. It becomes the standard against which everything new is judged.

I can then confuse my experience of how the world worked with an understanding of how the world works.

HISTORY RHYMES

A few days later, I heard Jimmy Carr discussing the future. He referenced Neil Howe's The Fourth Turning, a controversial theory proposing recurring generational cycles in history. I wouldn't take those cycles as historical law, but Carr used a phrase that connected with what I had been thinking: "History doesn't repeat, but it rhymes."

What interested me wasn't the idea that history follows a predetermined pattern. It was the simpler observation that generations aren't shaped only by what previous generations teach them. They're shaped by what happens to them.

Someone who came of age before the internet wasn't formed by the same information environment as someone who never experienced a world without it. Someone who encountered AI halfway through a career won't experience it in quite the same way as someone encountering it before that career has even begun.

Different worlds produce different ways of navigating them.

Carr ends his reflection with a deliberately provocative prediction: "We're going to have some fucking heroes on our hands in 20 years."

Maybe. But I wonder why I should wait twenty years to look for them.

THE LOST GENERATIONS

The people who will shape what comes next are already being shaped by the conditions around them. Some of their behaviours will turn out to be mistakes. Some of their rebellions will lead nowhere. Some of the ideas previous generations built will prove remarkably resilient. An iPod revival certainly doesn't prove that a generation has understood the future.

But culture rarely announces a transformation clearly enough for everyone to recognise it at the same time. It leaves signals: choices that initially seem irrational, questions that irritate the people who stopped asking them, and sometimes conflict between those whose worldview was shaped by what exists and those whose worldview is being shaped by what comes next.

For years, organisations have asked how new generations will adapt to the world they inherit. I am beginning to wonder whether that question contains a blind spot: the assumption that the world they inherit is also the world they will inhabit.

Perhaps this is why the expression Lost Generations has started to mean something different to me.

Not because new generations have found all the answers. And not because previous generations suddenly have nothing left to teach them. Quite the opposite. But the generation with the most experience of the previous world isn't necessarily the generation best positioned to understand the next one.

Maybe being lost isn't about not knowing where you're going. Maybe it's about knowing exactly where you're going, without noticing that the world around you has changed direction.

Perspective Shift #04 · What Makes Us Human