Leadership, AI, and the Danger of Outsourcing our Humanity

We’ve been canoeing and traveling the Boundary Waters Canoe Area for years, long before GPS became a standard tool.

In wilderness travel, one of the most critical skills you develop is reading a map. But here’s the thing: map reading is a misnomer. You’re not just reading paper or tracing a route — you’re using the map to make sense of your reality. You learn to read the landscape: the curve of the shoreline, the rise of the hills, the direction of the wind.

A map isn’t meant to pull your head down; it’s meant to lift your eyes up. It sharpens your awareness, deepens your presence, and teaches you scale and distance. It’s easy to get stuck in the map — but that misses the point.

When the pandemic hit and everything closed down, the Boundary Waters became a popular “safe” vacation. Suddenly, people with all kinds of outdoor experience were heading into the wilderness — and many brought GPS.

Curiously, GPS often made them worse travelers. It gave them the comfort of certainty, but at the cost of attunement. Instead of noticing the land and learning the cues, they followed the blue dot. They didn’t have to engage, so they didn’t.

This is where the concept of cognitive offloading matters.

Cognitive offloading is when we shift mental work onto external tools — like writing something down so we don’t have to remember it, using a calculator, or relying on AI to draft, summarize, or analyze for us. It can be a huge boost to efficiency.

But here’s the catch: offloading doesn’t just reduce effort; it creates distance.

Kenneth Burke once wrote that humans are “separated from [their] natural condition by instruments of [their] own making.” Every tool we build — even the most powerful — puts a layer between us and the world we lead in.

And here’s the deeper cost: when we offload too much, it’s not just our cognitive skills that erode — it’s our relationaland emotional skills.

We become more efficient, yes — but also less textured. We stop hearing the quiet cues. We lose the felt sense of the room. We manage tasks instead of stewarding relationships.

As Sahil Bloom put it this week in his excellent newsletter: “People are more efficient and productive, but lose a sense of texture, meaning, or purpose in the work. They have unwittingly optimized the life out of their life.”

Oliver Burkeman calls this the cost of “frictionless” living — a way of working and leading that trades richness for speed, and depth for surface. We save time but lose weight. We get more done and feel less grounded doing it.

So how do we keep AI from making us less present, less connected, less human?

Here are four places to start:

Identify your non-negotiables. What parts of your leadership can’t be offloaded without cost? Relationship-building? Listening? Strategic judgment?

Use tools as amplifiers, not replacements. Let AI support the work, but keep human hands on the tasks where your insight matters most.

Stay context-aware. Ask: What am I no longer noticing? What am I no longer engaging with directly?

Rebuild your “map-reading” muscles. Step away from the tools sometimes and navigate by your own attention — even if it’s slower or less efficient.

In leadership, as in wilderness travel, the goal isn’t just to reach the destination. The goal is to understand the terrain.

What parts of your work remind you to lift your head up and truly notice?