October 7, 2026

AI Can Make More Decisions for Us. That Makes Human Judgment More Important.

One of the promises of artificial intelligence is that it will remove friction from our lives.

AI agents will research options, compare prices, schedule appointments, negotiate with companies, book travel, manage recurring purchases, and eventually handle countless decisions that currently consume our time and attention.

Much of that sounds good to me.

I use AI every day. I use it to research, pressure-test ideas, explore strategy, challenge assumptions, and sometimes surface questions I did not know I needed to ask. I am also experimenting with AI versions of my own voice, likeness, and thinking.

So I am not standing outside this technological shift warning people about AI.

I am deliberately pushing AI pretty far into my own work and life.

And the further I go, the more interested I become in a different question:

Where should the boundary of human judgment be?

The real question is not whether AI can choose

Recent work around personal AI agents makes that question increasingly practical.

Companies including Meta and Sierra are working on systems that could allow AI agents to act on behalf of individuals. The technical challenge is figuring out what those agents are authorized to do, what information they can access, and when control needs to return to the human being.

But there is another layer beneath the technology.

Suppose I tell an AI agent:

Find me the cheapest nonstop flight to Chicago that arrives before noon.

That is easy enough. I have already decided what matters. The AI is simply searching more efficiently than I can.

But what happens when I ask:

Find me the best job.

Tell me where my family should live.

Help me decide whether I should sell my company.

Tell me what I should do with the next ten years of my life.

Now the word best starts carrying a great deal of weight.

Best according to what?

Income?

Security?

Status?

Time?

Family?

Faith?

Health?

Meaning?

Service?

Possibility?

An AI system may become extraordinarily good at optimizing toward an objective.

But somebody still has to decide which objectives deserve optimization.

AI may move the choice upstream

This may be one of the most important shifts of the AI era.

We will not necessarily stop making choices.

We may increasingly make choices about how choices are made.

That means deciding what our AI systems are allowed to optimize for, what values they should protect, where efficiency matters, and where it does not.

There is nothing inherently wrong with optimization.

The fastest route values time.

The cheapest purchase values money.

The highest-paying job values compensation.

But a flourishing human life contains things that do not always fit neatly into a ranking system.

Sometimes we pay more because we trust someone.

Sometimes we take the slower road because the experience matters.

Sometimes leaving a job is courageous.

Sometimes staying is.

Sometimes persistence is conviction.

Sometimes it is fear wearing respectable clothes.

AI can help us examine those tensions.

It cannot remove our responsibility for deciding what they mean.

This became personal while I was writing about it

There is an irony here.

When I began developing my recent LinkedIn article about AI agents, the first argument AI helped produce was a strong business story about brand loyalty.

It was good.

And I rejected it.

Not because the analysis was wrong.

It simply was not asking the question I cared most about.

I wanted to know what this technological shift means for human agency.

That small moment captured the larger issue for me.

AI helped execute the assignment.

I still had to decide what the assignment was ultimately for.

That distinction is becoming central to how I think about Pick Yourself For Success in the Age of AI.

For years, Pick Yourself For Success has been about refusing to surrender authorship of your life to employers, institutions, gatekeepers, or other people.

AI introduces a new version of the same challenge.

We can build systems specifically designed to serve us and still gradually hand pieces of that authorship away.

The answer is not to reject the technology.

I believe AI can expand human agency enormously.

The challenge is to use it to enlarge what we can see without automatically surrendering our authority over what deserves to matter.

I explore that idea more deeply in my new LinkedIn article:

Read “AI Can Choose for You. It Cannot Decide What Should Matter.” on LinkedIn

As AI becomes better at finding the road we ask for, our responsibility may move one level higher.

We still have to decide whether that road leads somewhere worth going.

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October 7, 2026

AI Can Make More Decisions for Us. That Makes Human Judgment More Important.

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