Do you remember before the internet entered the “dot com” era

Did you ever make a “home page” by hand?

I did. The experience is seared in my memory.

We’re talking late 1995, if memory serves.

Hand-coded HTML in BBEdit.

Uploaded via Fetch to my ISP’s server.

A personal site, for no real reason other than… it felt kinda cool.

I was late to meet some friends. One of them asked, “Why were you late?” I told them: “I was making my home page.” They blinked, skeptical. “Why would you ever want to do that?”

At the time, all I could do was shrug: “Dunno. Kinda cool, I guess?”

I’ve learned since then to pay attention to that feeling. When something feels curiously “cool,” when someone responds with a dry “why would you ever want to do that?” — that’s often the sign I’m onto something.

That instinct is the beginning of speculation. Of creative exploration. Of imagination doing its work.

Which brings me to this other question:

What are the KPIs of speculation?

It’s a strange question. But a vital one — especially in a commercial context where performance is the currency of legitimacy.

KPIs are structure’s way of making things legible. They’re how we track, optimize, prove value. They tell us: Are we growing? Are we efficient? Are we hitting targets?

But what if the work isn’t about targets at all? What if the goal is to explore what doesn’t yet exist?

Can we measure imagination?

Is it the number of prototypes made? The number of conversations sparked? Perspectives shifted? Futures explored?

Did an artifact travel beyond the room it was made in? Did it provoke debate? Did it lead, however indirectly, to strategy or product? Did it help a team rehearse for a world that hadn’t arrived yet?

Did it make an organization more resilient — because it had learned how to navigate ambiguity?

None of this fits neatly into a spreadsheet. But the effects are real.

We’re entering a terrain where the old rules don’t apply. Some call it AI. Whatever it is, it’s new, it’s vast, and it’s not going to wait for us to catch up.

Sitting here in my studio, surrounded by artifacts of imagination, I feel it clearly: We need to cultivate the capacity to invent what doesn’t yet exist. To do it joyfully. But also rigorously. Accountably. Even measurably — if we’re bold enough to imagine what those measures might be.

We need to ask: Do we carry old ideas into new terrain? Do we let structure flatten imagination?

Or do we let ourselves be beginners again? Tinkering. Prototyping. Making home pages for no reason at all. Just because it feels… kinda cool.

Speculation is not blue-sky indulgence. It’s a way of sensemaking. A way to grasp what feels ungraspable.

It’s how we explore the field of fragments — not to solve, but to understand.

And yes, we need ways of knowing whether that exploration matters. Ways to sense if we’re moving in meaningful directions.

So let’s reframe the KPIs.

Not productivity. Not throughput. Not efficiency.

Those are metrics for the known world.

Speculation lives in the not-yet. And if productivity measures the past, speculation measures possibility.

The organizations that invest in this capacity will be the ones shaping tomorrow’s categories — not struggling to catch up to them.