A Small Problem That Wouldn’t Stay Small

My iPhone stopped letting me send texts by voice.

Which shouldn’t matter. Except I drive a lot, I’m required to be hands-free, and suddenly a basic function had become a daily failure I couldn’t ignore.

So I did what you’re supposed to do. I called Apple Support.

Nancy answered from Bangladesh. She was patient, methodical, clearly working from a checklist. We spent an hour toggling settings, checking permissions, rebooting. Then she escalated me to her manager, David, calling from Canada.

David was good. Warm, sharp, experienced. He walked me through deeper resets, consulted colleagues, ran through a longer checklist. Eventually, we landed on the nuclear option: factory reset, reinstall everything one app at a time.

When the Fix Doesn’t Stick

We reset the phone. Siri worked. We started reinstalling apps. Everything seemed stable.

Then, a couple of hours after we hung up, it broke again.

I stared at the phone, that same quiet failure. No warning, no clear trigger. Just… gone.

I emailed David, frustrated. Not angry at him — just at the situation. I had followed every instruction. Twice.

Then I reset the phone again. This time on my own.

I went slower. More methodical. One app at a time, testing Siri after each installation, making sure it held before moving on.

By the time I went to sleep, I had a stripped-down phone and a working Siri.

I woke up the next morning.

It wasn’t working again.

That’s a particular kind of frustration. Not the heat of crisis, but the cold irritation of a problem that should be solvable and keeps slipping away.

That’s when I turned to AI. Not for an answer, but for something rarer: a thinking partner.

Thinking Out Loud With a Machine

I opened a conversation with Claude and started talking through the problem out loud. Not “fix this,” but: here’s what’s happening, here’s the pattern, here’s what doesn’t make sense.

It pushed back. Suggested hypotheses. Abandoned them when they didn’t hold. Helped me see gaps in my own reasoning.

We started narrowing.

The overnight failure mattered. That pointed to something syncing, not something I was manually installing.

Then I looked at my contacts.

I had 11,743 contacts. Over years, across multiple accounts — iCloud, several Gmail accounts tied to different parts of my life — it had become a kind of digital attic.

Claude suggested the volume might be overwhelming Siri’s indexing.

That didn’t quite hold. So we refined it: not just volume, but structure. Six separate accounts syncing simultaneously. Duplicates. Partial entries. Names with no numbers, no emails — just fragments floating in the system.

I turned off the Google accounts one by one. The contact count dropped from over 40,000 entries to around 4,000.

Then I turned off iCloud contact sync entirely and wiped the local contacts from the phone.

The Relief of a Diagnosis

There’s a particular satisfaction in knowing what the problem is, even before you’ve solved it.

I see this in pastoral work all the time. People often feel relief just having a diagnosis, even a hard one. Because ambiguity is its own kind of suffering. The not-knowing is often worse than the knowing.

Life doesn’t always give us that clarity. We sit with illnesses without names, relationships without explanations, griefs without edges. So much anxiety lives not in what’s wrong, but in the shapeless sense that something is.

But when the problem has a name, the terrain becomes navigable.

Standing there with a phone that worked only when it had zero contacts, I felt that click.

The Limits of Expertise

At 8 a.m., my phone rang. It was David.

The night before, I had sent him a frustrated email when the issue came back. He saw it first thing and called immediately.

This time, I didn’t need him to diagnose the problem.

I told him I had figured it out — that it was the contacts. Multiple accounts, duplicated data, overwhelming Siri’s indexing overnight. I walked him through how I had arrived at it, working it out step by step with what I half-jokingly called my AI mirror, my digital golem.

There was a pause. He was impressed.

And then, because he’s good at his job, he pivoted:

“Okay — so how do we get your contacts back?”

We spent another hour and a half on the phone.

He walked me through iCloud restore options. Sync settings. Different sequences for bringing data back without breaking the system again. We tried to find a way to reintroduce the contacts cleanly.

But we kept running into the same problem: the system could restore the data, but it couldn’t fix what was broken about it.

At a certain point, I had to go. Life doesn’t pause indefinitely for troubleshooting, even when the problem is real.

He encouraged me to call him back later so we could keep working on it together.

But by then, I could see the edge of it.

He could help me get my contacts back.

He couldn’t help me make them usable.

From Restoration to Transformation

So I went back to AI.

I exported my contacts: over 10,000 entries, 15 megabytes of messy data.

Then I had Claude write a Python script to clean it.

Deduplicate. Remove corrupted entries. Strip out empty records. Rebuild something usable.

Fifteen minutes later, I had 3,700 clean contacts.

David, with all his expertise, had been guiding me toward manually merging duplicates in iCloud, one by one. It would have taken hours, maybe days.

The AI did it faster. And better.

David isn’t the villain of this story. He’s a competent professional using the tools he was trained on. His checklist solves most problems most of the time.

He wasn’t incurious. He listened. He adapted. He stayed with the problem.

What he didn’t have was a different kind of tool — or a different way of thinking with it.

Pirkei Avot asks: Who is wise?

One answer: one who learns from every person.

Another: one who sees what is being born.

David had the first kind of wisdom in abundance.

What he didn’t have — and what most of us are still developing — is the second: the ability to recognize that something genuinely new has entered the room, and that the old toolkit might not be enough.

What AI Actually Changes

The gap that’s opening right now isn’t simply between experts and non-experts.

It’s between people who know how to think with AI and those who don’t.

AI doesn’t make you smarter.

It changes how thinking happens.

It turns intuition into something you can test in real time. It lets you hold a complex problem steady while you walk around it, examine it, revise your assumptions without friction.

The skill isn’t having the right answer.

It’s asking better questions, faster. Seeing when something doesn’t fit. Backing up without ego. Trying again.

AI doesn’t replace that.

The Collapse of the Technical Barrier

There’s a term in software right now: “vibe coding.” The idea that you can build working systems just by describing what you want in plain language.

A year ago, that sounded like fantasy.

Yesterday, I used it to clean a broken database in fifteen minutes.

The line between “technical person” and “non-technical person” is dissolving.

Not because everyone becomes an engineer.

Because the definition of what a thoughtful person can do is expanding.

Why This Matters for Spiritual Leadership

I think about this in my work.

Clergy sit with problems that don’t come with diagnostics. Grief without language. Conflict without resolution. Systems that don’t quite work but can’t easily be rebuilt.

We operate with limited time, limited resources, and problems that resist checklists.

The communities that learn how to pair human wisdom with AI capability will be able to do more — and do it more meaningfully.

The ones that don’t will keep running the same playbook and wondering why it no longer works.

The Question of This Moment

The question isn’t whether it’s powerful.

It’s whether we’re willing to learn how to think differently with it.

Rav Kook wrote: Hayashan yitchadesh, vehechadash yitkadesh — may the old become new, and the new become holy.

The old wisdom doesn’t disappear. Curiosity, humility, the willingness to learn — those stay.

But they get renewed.

And the new tools, if we meet them with the right spirit, don’t just make us more efficient.

They expand what’s possible.

That may be the real question of this moment:

Not whether AI is powerful.

But whether we’re ready to become the kind of people who know how to use that power well.

Because in the words of the wise Jewish author Stan Lee:

“With great power comes great responsibility.”

© The Times of Israel (Blogs)