Where AI Ends & Wisdom Begins

Last week, I had the privilege of joining my friends at Brown Rudnick in their Washington, DC office for an AI conference. Incredible minds. A room full of innovators. A skyline view that quietly reminds you how fast the world is changing.

And yet, my biggest takeaway had nothing to do with speed or efficiency or the dazzling potential of the tools being built.

It was one simple truth:

AI will always give you an answer.
But it will never say, “I don’t know.”

Think about that.
A machine that never pauses. Never hesitates. Never questions itself. Never considers consequence.
It just answers.

On the surface, that feels powerful. But as someone who’s built a life, a business, and a philosophy around intentionality, it struck me as the exact limitation that separates artificial intelligence from actual wisdom.

Because “I don’t know” is not weakness.
It is the beginning of honesty.
It is the foundation of trust.
It is the doorway to doing the real work.

When I was younger in my career, I feared those words. I worked obsessively; over-prepared, over-studied, over-armed with information, because I was afraid of being exposed. I was afraid of not having the perfect answer. I was fraid of letting someone down.

And one day, that fear caught up with me.

I was a bank rep. I recommended a fixed annuity to replace a maturing CD. I missed one detail…one I thought I understood…and it cost my client 15 years of liquidity. He confronted me. I had no excuse. I owned it. I tried to fix it, but the damage was done.

He forgave me. He had every right not to.
That moment shaped the rest of my career.

It taught me the value of humility.
The responsibility of stewardship.
And the power in saying, “Let me find out, and I’ll come back to you.”

AI will solve whatever problem it’s given: without compassion, without conscience, and without any awareness of the impact on the human being on the other end of the equation.

But real advisors—real partners—must care.
They must question.
They must verify.
They must be willing to slow down and seek truth over convenience.
Especially when they’re guiding someone’s life’s work and hard-earned savings.

So here’s the reminder the conference gave me…and perhaps it’s one you need today too:

Trust is earned through transparency.
Wisdom is built through humility.
And “I don’t know” is only a weakness if you stop there.

At Intentional, this is the core of what we do.
We combine powerful tools—yes, including AI—with something far rarer:
Human discernment.
Human compassion.
Human responsibility.

If you’re looking for someone who won’t just give you an answer but will walk with you until we find the right one, I’d love for you to explore what we’re building.

Your story deserves nothing less.