Wisdom in the Age of AI

AI Can Think. But Can It Know What Matters?

A few weeks ago, I dumped a bunch of strategy questions into ChatGPT.

Within seconds, it had generated a bullet-pointed roadmap, complete with objectives, milestones, and a neat little process for goal-setting.

It was kind of like having a second brain. A sparring partner. A way to stress test my ideas and fill in gaps.

But I didn’t end up using a single thing from what it spit out, even after a bunch of iterations (though it helped with my brainstorming).

The plans and ideas looked ungrounded, rushed…kind of like an over-eager college grad version of myself trying to prove I knew everything before I’ve had enough time to actually learn.

The conversation on AI often centers on how it will improve speed, scale, and optimization.

It’s about how quickly you can get something done, how much you can produce, how many steps you can skip.

But what actually gets lost with speed, when we rush to answers?

The word Wisdom is derived from the Old English words wis (“of a certainty, for certain”) and dóm (“statute, judgment, jurisdiction”).

Wisdom is much more about judgement: WHAT to do, vs. how to do it.

Wisdom feels slower. Messier. It comes not just from what we know, but from what we’ve lived.

From the passing of time. From making the wrong decision and learning the hard way what that costs.

From the embarrassment of overreaching, the joy of choosing well, the heartbreak of regret.

There’s also an embodied aspect to wisdom. It’s not purely intellectual. Wisdom lives in how we relate within a web of the whole. It considers the system, the roots, the ripple effects. As leaders, whether in organizations, communities, or our own lives, many of us are trying to make decisions that don’t go against our values, that align with a deeper truth about what it means to be alive right now. To live and work in a way that honors first principles.

Wisdom isn’t about generating eight strategic plans in under ten seconds.

It’s about discerning which (if any!) of those eight are actually worth pursuing.

For me, wisdom doesn’t usually emerge while I am hunched over my computer, in the 3 minutes between back to back meetings.

It arrives on a walk outside. In the shower. In the quiet moment after I’ve stepped back. It asks me to slow down and listen—first to my own gut, and then to something deeper.

So the question I’ve been holding is this:

Will AI deepen our wisdom—or make us more reliant on fast answers and convenient outputs?

There’s a version of the future I hope for: one where AI creates space for wisdom to emerge.

Used well, AI could become a tool, not for replacing our judgment, but for refining it.

A way to unburden the busywork so we can focus on what only humans can do: discern, connect, choose with care.

AI may give us answers; wisdom knows which questions are still worth asking.