Steve Jobs, Aristotle, and the Questions AI Can’t Answer for Us

In 1985, Steve Jobs imagined a day when a student could do more than read Aristotle.

Jobs was speaking at Lund University in Sweden, long before smartphones, search engines, or the AI tools we use every day. His hope was that someday we might capture the underlying worldview of a great thinker like Aristotle within a computer, so a future student could ask him questions and get answers.

It sounded futuristic then, but that future is here today.

We can open an AI tool and ask it to explain Aristotle, compare him to another thinker, or respond in a way that tries to reflect his philosophy.

That doesn’t mean we’re talking to Aristotle. We’re talking to a machine-generated synthesis, built from writings, interpretations, and patterns available to the model. Worth remembering, especially in a minute.

Jobs saw computers becoming more than storage devices. He saw interactive learning companions that could move us from consuming information to questioning it, testing our understanding, and entering into a dialogue with the past.

So, I ran a little experiment. I asked an AI tool to respond as if it were Aristotle, drawing on his known writings and philosophy, then I asked three questions…two about leadership, one about relationships.

Here’s what I learned, before you even read the answers. The AI handed me answers that sounded wise. It couldn’t do anything with what the answers asked of me. That work stayed mine, every time. Keep that in mind as you read the three exchanges below. Each quote is the AI’s synthesis, in Aristotle’s voice, not a historical record of what he actually said:

Question 1: Aristotle, what makes someone a good leader?

A good leader must first be governed within himself. He cannot guide others well if his own desires, fears, and ambitions are disordered.

Leadership is not merely a matter of authority or skill. It is a matter of virtue. A leader needs practical wisdom to judge what should be done, courage to do it, justice to give others what they are due, and temperance to restrain his own appetite for power, praise, or comfort.

The good leader does not seek the good of himself alone. He seeks the good of the community entrusted to him.

That answer sounds about right. Confidence, drive, decisiveness, and the ability to win can carry a person a long way. But without character or virtue, those same strengths eventually start working against the people they’re supposed to serve.

Whether it’s true of me is a separate question.

Question 2: Aristotle, how should a leader make decisions when the right answer isn’t obvious?

In uncertain matters, the leader needs prudence. No rule can fully replace wise judgment, because human affairs are too varied and particular.

The prudent person considers the purpose of the decision, the facts of the situation, the people affected, and the likely consequences. He also considers his own motives. A decision can appear reasonable while still being driven by pride, fear, anger, or vanity.

Good judgment is formed over time. It comes through experience, reflection, correction, and the habit of choosing what is noble rather than merely what is easy.

Most leaders want clarity. We want the right answer to announce itself. The spreadsheet, the policy, the consultant, the precedent that makes the decision obvious.

Unfortunately, difficult decisions usually live where the information is incomplete, the tradeoffs are real, and the consequences land on people who are more than names on an org chart.

But, he asks an even harder question. What’s happening inside me as I make this call? Am I deciding from courage or fear? Justice or favoritism? Humility, or the need to be seen being right?

AI can organize the options. It can summarize the arguments. It can show me possibilities I might have missed.

But it won’t clean up my motives. That responsibility remains with me.

Question 3: Aristotle, what makes a friendship or relationship worthy of trust?

The highest friendship is rooted in virtue. Some relationships exist for usefulness. Others exist for pleasure. These are not necessarily bad, but they are fragile because they depend on what the other person provides.

A deeper friendship is different. It is based on willing the good of the other person. Such a relationship is steady because it rests on character, not convenience.

To be worthy of trust, a person must be truthful, faithful, and committed to the good of the other. A trustworthy relationship helps both people become better than they would be alone.

We understand relationships of usefulness. Work relationships, customer relationships, networking relationships, even friendships that lean heavily on shared convenience.

But, are we willing the good of the other person? Do we want what’s good for them, or only what’s useful to us? Do we want them to become better, or only to make our life easier?

Seeing this short exercise, I think Mr. Jobs would celebrate how close we’ve come to his 1985 vision. We have more access to information than any generation before us. We can retrieve facts instantly, summarize books in seconds, compare ideas across centuries before lunch.

That’s amazing!

Yet the more powerful the tool gets, the more responsibility shifts back to the person using it.

Ask Aristotle about leadership, and I have to ask whether I can govern myself.

Ask him about prudence, and I must examine my own motives before I decide.

Ask him about friendship, and the real question is whether I’m willing the good of the other person or just protecting what’s useful to me.

AI tools can generate answers. Wisdom starts when we let those answers question us back.

The machine can help us ask Aristotle a question.

It can’t make us become the kind of person who can live the answer.

Photo by Bernard Gotfryd, circa 1984

Pursuing Tranquility of Order

Peace is often defined as the absence of something.

The absence of conflict. The absence of noise. The absence of pressure. The absence of the next problem.

But peace is less about absence and more about order.

I recently heard peace described as tranquility of order, a phrase with roots going back to Augustine. In City of God, he wrote that “the peace of all things is the tranquility of order.”

This doesn’t suggest that peace only arrives when every problem has been solved, every relationship has been repaired, every task has been completed, and every loose end has been tied off.

That version of peace is impossible to sustain.

Life keeps moving. There’s always another hurdle to clear, another obstacle to navigate, another decision to make, another issue waiting around the corner. Just when we think things are finally settling down, something changes.

The pursuit of peace isn’t the pursuit of a trouble-free life.

It’s the pursuit of a rightly ordered life.

Priorities in the right order. Relationships in the right order. Responsibilities in the right order. Ambition in the right order. Rest in the right order. Attention in the right order.

That kind of peace doesn’t just happen to us.

We create it when we decide what deserves our attention and what doesn’t.

We create it when we stop letting every urgent thing pretend to be the most important thing.

We create it when we clean up a workspace, finish a lingering obligation, repair a strained conversation, or finally admit that something has been taking up more room in our life than it deserves.

We create it when we make the next good decision, even when everything around us is still imperfect.

I’ve always found real satisfaction in this kind of work. A confused or stalled project. A messy process. A cluttered schedule. A team that needs direction. A home project waiting for the right next step. A piece of land slowly shaped into something useful and beautiful.

There’s something deeply rewarding about creating enough order for people to breathe again.

That doesn’t mean controlling everything. In fact, the best kind of order often requires us to hold things loosely, leaving room for the unexpected, and trusting that people, plans, and possibilities are better tended than controlled.

Order, at its best, creates room for life.

It clears enough space for thought. It creates enough structure for trust to build. It gives people enough confidence to move. It helps us see what belongs, what doesn’t, and what needs attention next.

And then, occasionally, we experience it.

A quiet morning. A settled room. A finished project. A table full of people we love. A trail cleared through the woods. A plan that starts to come together. A day where the pieces seem to fit, even if only for a while.

Those moments may not last forever, but they remind us what we’re aiming for.

Pursuing tranquility of order is the steady work of arranging our lives around what is good, true, useful, loving, and worth carrying.

When life feels too overwhelming to arrange all at once, we can start small. The next right step, the next honest action. The next one thing that brings even a corner of our life back into order.

We won’t always get it right.

There will always be disruptions. There will always be pressure. There will always be something that knocks our papers off the desk just after we get them stacked.

But we can keep returning to order.

We can return to our priorities. We can return to our responsibilities. We can return to the people we love. We can return to the work that has been entrusted to us. We can return to the kind of person we’re trying to be.

Peace isn’t found by escaping the noise.

It’s built, little by little, when we keep putting the most important things back where they belong.

Photo by AO NURA on Unsplash – There’s more to this peaceful image than it appears. Growing. Cutting. Drying. Raking. Baling. Each step in its right order. Each making the next possible, leading to this image. The work isn’t finished. Those bales still need to be moved and stored.

But we can enjoy this. The proper order. A moment of tranquility.

Exiting the Tomb of Pessimism

“We must strive to exit our tomb of pessimism.”  I heard this phrase echo through the Cathedral during the Easter Vigil homily, a little over a week ago. 

As Catholics, we celebrate the resurrection of Jesus Christ every Easter…His triumphant exit from the tomb, three days after his crucifixion.

In a much smaller way, we have a daily invitation to cast off our heavy shroud of negativity.  To exit our tomb of pessimism. 

To break the shackles of hopelessness and redirect our thoughts toward a brighter horizon.    

If everything great begins with a thought or an idea, imagine channeling this power toward an optimistic future, filled with amazing possibilities. 

It’s easy to stay in this tomb of our own making, looking through the bars at all the people out there who are clearly happier, more successful, and have all the things we yearn for.    

The truth is none of them matter.  They have no impact on us…except to show us some possibilities, some ideas, and some pathways that worked for them.    

We have the power to rewrite our own narrative, to pivot our lives toward a more hopeful outlook.  The choice is ours alone. 

Escaping the tomb of pessimism demands courage and resolve. It requires us to confront our deepest fears and insecurities, to challenge the status quo of negativity that has held us captive and kept us comforted for so long.

Yet, it is only by confronting these challenges that we can find the promise of transformation.  Only through the struggle that we can discover a new sense of purpose.

Will you remain ensnared in the confines of pessimism, or will you seize the opportunity to step into the light, and walk away from your tomb of pessimism?    

The choice is yours.

Choose wisely.

p/c – Jelle de Gier – Unsplash

Navigating Fear…A Personal Guide to Freedom and Growth

Fear is like that well-meaning friend who occasionally oversteps boundaries. It’s a survival instinct, a leftover trait from our ancestors who needed it to avoid becoming someone else’s lunch. It can guide us toward wise choices and help us steer clear of danger.

Our imagination, on the other hand, is a bit of a storyteller, especially when it comes to tales that can hold us back. With all our experiences and secrets tucked away in our minds, our imagination can whip up some remarkably dreadful future scenarios. And our lizard brains? They thrive on responding to fear.

Fear is undoubtedly real. The fear of failure, loss, embarrassment, injury, loneliness, helplessness, and death can have profound impacts on our thoughts and actions. However, if we recognize, understand, and confront these fears head-on, it will be like flicking on the lights in a dark room – suddenly, the monsters lose their scariness.

By acknowledging that fear is a living part of us, we can take steps toward asserting our control over it. Fear shouldn’t be in the driver’s seat. 

“Yea, though I walk through the valley of the shadow of death, I will fear no evil: for thou art with me; thy rod and thy staff they comfort me.” – Psalm 23

We aren’t alone in this journey of conquering fear. We have a loving God, supportive family, and caring friends to help us face our fears. They can offer a broader perspective and lend a hand when we need it most.

Life is a rollercoaster of unknowns, and fear hates rollercoasters. Instead of fearing the unknown, befriend it. New ideas, experiences, and relationships? Embrace them as opportunities, be curious, and let the adventure unfold.

Life is rarely easy, and sometimes truly terrible things happen to us. But, fear should be the backseat driver, not our navigator.

“I must not fear. Fear is the mind-killer.

Fear is the little-death that brings total obliteration.

I will face my fear. I will permit it to pass over me and through me.

And, when it has gone past, I will turn the inner eye to see its path.

Where the fear has gone there will be nothing. Only I will remain.”

–Paul Atreides in the novel Dune, by Frank Herbert

Photo: Why hot air balloons? Well, taking a ride in a hot air balloon would not be possible if we let fear make the decision. I’m happy to report the balloon ride was amazing!

I have one favor to ask:  If you find this information useful, please forward and recommend it to someone else.  Thanks!