I’ve Lived Through More Than One End of the World.

What repeated cycles of technological disruption have taught me about survival, judgment, and hope.

I don’t measure my career in job titles or companies. I measure it in moments of significant change.

Over the course of my life, I’ve watched this happen again and again. New tools. New platforms. New ways of making, distributing, and valuing work. Each time, they arrived with the same promise: everything will change. And each time, they did, just not always in the ways I expected.

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This is where I usually ask you to sign up for my newsletter or go read more about how I think about things. But today, especially if you are caught up in the chaos that is the advertising industry, and are now trying to figure out what you will do next, I would ask you to read the whole article. It’s long, so think of it as an investment into your future. And if you know someone that is now trying to figure it all out, send this to them.

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I’ve lived through the rise of personal computing, the early days of Apple, the cultural shockwave of MTV, the arrival of Photoshop, the birth of the internet, the spread of mobile, the dominance of social platforms, and now the public arrival of AI. Each of these moments rewired how we work, how we think, how culture moves, and how value is created. Some collapsed industries. Others created entirely new ones. Many did both at once.

There’s a temptation, especially right now, to compare them. To ask whether AI is “bigger” than the internet, more destabilising than mobile, more dangerous than social media, more profound than anything that came before.

I don’t think that’s the right question.

None of these things is like the others.

There is a temptation, especially in moments like this, to compare technology cycles. To ask whether AI is bigger than the internet, more disruptive than mobile, or more culturally destabilising than social media.

I don’t think that’s a useful exercise.

There is no meaningful way to compare the arrival of Photoshop to the arrival of AI. Or the internet to mobile. Or MTV to TikTok. They emerged from different forces, landed in different cultures, and reshaped different layers of human behaviour. Trying to rank them doesn’t clarify anything. It distorts it.

Technology doesn’t move in a single line. It arrives in waves, each with its own physics, its own casualties, and its own opportunities. To treat them as equivalents is to misunderstand what they demand of us.

But that doesn’t mean they have nothing to teach us.

What is comparable, what does repeat, is not the technology itself, but the human response to it. The patterns of fear, excitement, resistance, overreach, adaptation, and eventual normalisation. The way organisations behave. The way power shifts. The way identity gets tangled up in tools.

That’s where the real learning lives.

What Repeats Every Time the Ground Shifts

Every cycle begins with noise.

The first wave is always loud: bold predictions, inflated claims, moral panic, utopian promises. New experts appear overnight. Old experts are declared obsolete. Conferences fill up. LinkedIn fills up faster. Everyone feels pressure to have a point of view before they’ve had time to develop one.

Then comes fear often disguised as principle.

I’ve seen this in every cycle. People don’t say “I’m scared.” They say, “This will ruin quality,” or “This isn’t real craft,” or “Clients will never accept this,” or “This undermines the profession.” Sometimes they’re right about the risk. Often, they’re really protecting an identity built around a previous set of rules.

Another pattern: tools get mistaken for thinking.

When Photoshop arrived, design didn’t become better by default; it became faster. When the internet arrived, information didn’t become wiser; it became abundant. When social platforms arrived, connection didn’t become deeper; it became performative. And now, with AI, output doesn’t automatically become insight.

Each cycle tempts us to outsource judgment to the tool. Each cycle punishes us for doing so.

And then, quietly, something else happens.

The real advantage doesn’t go to the loudest adopters or the fastest movers. It goes to the people who learn how to integrate the new capability into their existing judgment. The ones who ask not just “What can this do?” but “What should I now do differently?”

They are harder to spot. They’re usually less visible. But over time, they’re the ones still standing.

My Own Throughline (And the Role of Luck)

I want to be careful here. This isn’t a victory lap.

I didn’t predict every shift. I didn’t always move early. I made wrong calls, stayed too long in some places, and left too early in others. Timing and luck played a role, more than we like to admit.

What did change over time was my posture.

Early in my career, curiosity carried me. I wanted to understand new tools, new media, new ways of making things. Later, discernment mattered more, learning what not to chase, what to ignore, what would age poorly. Now, judgment feels like the tangible asset: knowing when to adapt, when to hold, and when to step back and reframe the problem entirely.

Each cycle stripped something away. Certainty. Familiarity. Comfort. And each cycle forced a recalibration: What is my actual value here, independent of the tools?

That question has never stopped being useful.

Why This Moment Feels So Hard

It’s the end of the year. For many people, it’s been a brutal one.

Layoffs. Consolidations. Titles disappearing overnight. Careers that felt stable suddenly feeling provisional. For some, it’s not just professional loss. It’s identity loss. When work has been a source of meaning, structure, and self-worth, disruption cuts deep.

Understandably, this moment feels different. AI operates closer to cognition than previous tools. It touches writing, thinking, synthesis, creativity, things many of us believed were safely human. The speed is disorienting. The breadth is unsettling.

Every generation believes the disruption they face is uniquely destabilising. Sometimes they’re right about the impact. They’re almost always wrong about what it ultimately demands of them.

The Lesson That Outlasts the Technology

Across every cycle, the people who endure—and often thrive—are not the most technical or the most performative. They are the ones who invest in orientation.

They learn how to learn. They separate signal from noise. They resist the urge to tie their identity too tightly to a single tool or role. They understand that speed without direction is just acceleration toward the wrong destination.

Experience, when used well, isn’t resistance to change. It’s infrastructure. It’s what allows change to be absorbed without collapsing the system.

That doesn’t mean clinging to the past. It means carrying forward the parts that still matter: judgment, taste, ethics, context, and the ability to ask better questions than the machine ever will.

A Quiet Note of Hope

If you’re in a period of transition right now—between roles, between identities, between versions of yourself—I won’t offer false reassurance. These moments are genuinely hard. They ask more of us than any keynote or trend report ever will.

But I will say this, with the confidence that only time gives you: Cycles will be lived through. They can even be risen through.

And when the noise fades, and it always does, the people who remain are rarely the ones who chased every new thing. They’re the ones who learned what endures when the tools change.

As we head into a new year, in the middle of another significant recalibration, that’s the lesson I keep returning to. Not a comparison. Not panic. Not nostalgia.

Transition.

It’s slower. It’s quieter. And it’s still the most reliable way I know forward.

One last thought, especially for those in the middle of it right now.

Transition doesn’t arrive fully formed. It’s built slowly, often through moments that feel like setbacks while you’re in them. The cycles don’t just disrupt careers, they train judgment. And if that’s true, then even this moment, difficult as it is, is not wasted time. It’s part of the education.

I’ve been here before. More than once. And I’m here now.

If you’re feeling disoriented — between roles, between chapters, between versions of yourself — and you want a place to think out loud, my door is open. Sometimes what helps most isn’t advice or strategy, but simply being heard by someone who’s lived through a few cycles and come out the other side.

If you reach out, I’ll make the time. Coffee if you’re in Singapore. A call if you’re not. We’ll figure out the rest.

I’ve also written and shared a lot of my thinking publicly, including a book on how to approach AI with clarity rather than fear. Not because I have all the answers, but because writing has always been how I find my own orientation in uncertain terrain. If any of it helps you find yours, then it’s doing its job. DM me, and I’ll happily give you a copy, because in your search for the next thing, AI will undoubtedly be a talking point.

I’ll leave you with something I’ve carried quietly through every transition:

You still have to put feet to prayers.

Hope matters. Support matters. But momentum — even a small, imperfect step — is what changes your relationship with the moment you’re in. The first step is physical. It isn’t easy. But once you take it, the path has a way of revealing itself.

That’s been true in every cycle I’ve lived through.

And I don’t believe this one will be any different.