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strategy

Thought architecture, systems thinking, and frameworks that guide decisions. Less theory, more pattern recognition.

How I Used One AI to Train Another: A Tactical Reset in Data Architecture and AI Tooling Strategy

How I Used One AI to Train Another: A Tactical Reset in Data Architecture and AI Tooling Strategy

Like most devs experimenting with AI tools, I’ve found myself juggling multiple platforms, APIs, and half-understood schemas to build things faster. Sometimes it works. Other times, it works against you.

The Lost‑Phone Test for AI: Could Your Org Still Function Tomorrow?

The Lost‑Phone Test for AI: Could Your Org Still Function Tomorrow?

Dropped phone, lost life. Same test applies to corporate AI: if your copilots vanished tomorrow, would work even slow down? The “Lost-Phone Test” exposes integration gaps and makes the case for a Chief Intelligence Officer to weave tools into real workflows.

It’s Time for the CIO 2.0

It’s Time for the CIO 2.0

Most AI conversations start in the wrong place — with tools, not capabilities. What’s missing isn’t another pilot. It’s a new executive role: someone to steward how your organization thinks, learns, and evolves.

The Human Loom

The Human Loom

You don’t have to be the thread. Or the pattern. Just be the thing that lets it all come together.

The Spotlight Isn’t the Stage

The Spotlight Isn’t the Stage

A shiny idea isn't strategy. This post digs into decision hygiene: the discipline of thinking beyond the spotlight, and seeing the systems, ownership, and scope your choices actually live inside.

The Real Work Is Reading the Signal

The Real Work Is Reading the Signal

The complexity isn’t in the tech—it’s in the noise. This final post in the Commerce Drift arc explores why reading the signal is the real skill behind every good commerce strategy.

When Custom Isn’t Better: The Burden of Bespoke

When Custom Isn’t Better: The Burden of Bespoke

We romanticize personalization. But sometimes the problem isn’t lack of choice—it’s too much of it. Especially when we’re not sure what we really want.