I Put AI on My Face. Did It Change How I Connect With People?

An experiment in technology, trust, and the uncomfortable relationship between capturing a moment and actually living it.

I bought AI glasses. AND I’LL HAVE THEM ON AT SUMMIT!!!

Or, more accurately, I decided I wanted to put artificial intelligence directly on my face and see what happened.

Which is a pretty interesting decision for someone who has spent the better part of this year writing about trust, authenticity, human connection, and the growing sea of sameness created by technology.

I talk about AI constantly. I speak about it at conferences. I encourage marketers and business leaders to experiment with it. I've built presentations around the idea that adopting AI requires a fundamental shift in how we think, not simply learning how to write better prompts.

But I've also been pretty vocal about something else.

Technology should make us better at being human. Not give us another excuse to stop trying.

So when I started considering Meta's AI glasses, I found myself having a surprisingly uncomfortable conversation.

With myself.

Because apparently, even the woman who encourages everyone to challenge conventional thinking has a few things she needs to challenge about her own.

And that brings us to an experiment I never expected to conduct.

The Woman Who Won't Stop Talking About Trust Just Bought a Wearable Camera

There's some irony here. I've written about why you can't fake trust anymore. I've questioned whether we can actually measure trust. I've challenged the idea that producing more content automatically creates more influence. I've argued that relationships are built through genuine curiosity, meaningful conversations, and showing up for people without immediately calculating what you're going to get in return. And now I'm considering walking into those same conversations wearing a camera.

Fantastic.

Here's the thing. I genuinely love technology. I love discovering new ways to work, exploring what AI makes possible, and challenging people who insist on doing something a certain way simply because that's how they've always done it.

But I also believe we have a responsibility to question the technology we're so eager to adopt. Especially when that technology has the potential to fundamentally change how we interact with other people. I'm not particularly interested in becoming someone who talks about authentic human connection while secretly recording every interaction for a future LinkedIn post. And I'm definitely not interested in turning every person I meet into a potential content opportunity. Which raises an uncomfortable question.

At what point does documenting your relationships start interfering with actually having them?

Are We Experiencing Our Lives or Just Collecting Evidence That We Lived Them?

I spend a ridiculous amount of time traveling.

Conferences. Speaking engagements. Podcast recordings. Airports. Hotels. Networking events. Dinner with people I've known for years and people I've only just met. There are incredible moments happening all around me, and I genuinely enjoy sharing them. But I've started wondering how much of my life I'm experiencing versus how much I'm documenting.

And I don't think I'm alone.

We've created an entire culture around proving that we were somewhere, accomplished something, met someone important, or participated in an experience worth sharing. We photograph our meals before we eat them. We record concerts while watching them through our phones. We interrupt conversations because someone said something that would make an incredible social media post. And somewhere along the way, we started confusing visibility with value.

I've built a career around community, relationships, and the opportunities that come from putting yourself in rooms with interesting people.

Some of the most meaningful conversations I've ever had happened after the conference ended, when the microphones were off and nobody was thinking about an audience. Those conversations weren't valuable because someone recorded them. They were valuable because nobody needed to.

So here's my first concern about wearing AI glasses.

If capturing everything becomes effortless, will I eventually forget that some things are worth keeping to myself?

Trust Is What Happens When Nobody's Recording

Let's talk about consent. Because I think this is where the conversation gets particularly interesting.

When I host a podcast, my guests know they're being recorded. When I speak at a conference, the audience understands that someone might be filming. When Kate and I create content together, we're deliberately sharing something with an audience. There's an agreement. But what happens when I walk into a networking event wearing glasses that could potentially record the person standing in front of me? Even if I'm not recording, they might wonder whether I am.

And that matters. Trust isn't exclusively about what you're doing. It's also about whether the people around you feel comfortable enough to be themselves.

I've spent years building relationships where people feel comfortable challenging me, disagreeing with me, sharing their experiences, and occasionally saying things they would never repeat on a public stage. I don't want someone wondering whether our conversation is going to appear in tomorrow's LinkedIn feed. And I certainly don't want anyone feeling obligated to participate in my experiment simply because they happen to be standing next to me. My responsibility doesn't disappear just because a piece of technology makes something possible.

Just because you CAN capture a moment doesn't mean you SHOULD. That might be the most important rule of this entire experiment.

You Can Embrace Innovation Without Giving It a Free Pass

Now let's address the elephant in the room.

Meta.

I have questions about the company behind the glasses. Its approach to privacy, its business practices, and the enormous amount of personal information technology companies can potentially collect deserve scrutiny. And purchasing a product is, at least to some degree, financially supporting the company that makes it. That's something I'm not going to pretend doesn't matter. But here's where my philosophy on technology comes into play. I don't believe curiosity requires unconditional endorsement.

I can explore artificial intelligence while questioning the companies developing it. I can recognize the incredible opportunities technology creates while being deeply concerned about its consequences. In fact, I think we SHOULD be doing both.

One of my biggest frustrations with conversations about AI is how quickly people retreat into opposing camps.

Either AI is going to revolutionize absolutely everything, or it's going to destroy creativity, eliminate meaningful work, and fundamentally damage society.

Meanwhile, the questions that actually deserve our attention get buried underneath the arguments. What problems are we solving? Who benefits? What are we giving up? And are we making these decisions intentionally, or simply following whatever technology companies tell us is the next big thing? Those are questions every business leader should be asking. Not just about wearable technology, but about every AI investment they're making.

Being AI-forward doesn't mean being AI-blind. And if I'm going to encourage other people to experiment, I should be willing to examine the consequences of my own experiments.

The Real Experiment Has Nothing to Do With the Glasses

Here's what I find most interesting about this entire situation.

I'm not particularly concerned about whether the glasses take great pictures, whether the AI assistant answers my questions correctly, or whether the technology makes traveling more convenient.

I'm curious about whether they change my behavior.

• Will I reach for my phone less?

• Will I spend more time looking at the world instead of a screen?

• Will capturing a spontaneous moment become easier without interrupting the experience?

• Or will I start looking at everything around me as something worth recording?

There's a pretty significant difference between those outcomes.

And I suspect the answer has less to do with the technology than it does with the habits I've already developed. That realization extends far beyond wearable AI. Think about how we're currently using artificial intelligence in marketing. We're celebrating how quickly we can produce content, automate workflows, generate campaigns, and create personalized experiences. But how often are we asking whether any of those improvements actually make us better at connecting with customers?

• Are we having more meaningful conversations?

• Are we understanding our audiences more deeply?

• Are we creating experiences people genuinely appreciate?

• Or have we simply found a faster way to produce more of the same?

I've said it before, and I'll keep saying it.

Efficiency isn't the same thing as effectiveness. And neither automatically creates connection. Maybe the real experiment isn't whether AI glasses change how I experience the world. Maybe it's whether I can use AI without allowing convenience to dictate my behavior.

Not Everything Needs an Audience

This is the part I'm personally wrestling with. I'm someone who genuinely loves building things, creating experiences, meeting people, and sharing ideas. AMBUSH ON AIR exists because I believe interesting conversations deserve to happen outside conference hallways and private networking circles. I want to amplify interesting voices. I want to challenge conventional thinking. I want people to walk away from something I've created with a different perspective.

But I'm also learning that not everything I experience needs to become something I create.

Sometimes dinner is just dinner. Sometimes a conversation is simply an opportunity to understand another human being. Sometimes spending an afternoon with my family, watching my nephew score three hockey goals, or sitting on the couch with my dog is enough. There's no content strategy required.

No personal branding opportunity.

No audience.

And no reason to document something simply because I have the ability to do so. For someone who has spent much of her career creating momentum, that's a surprisingly important distinction. I'm learning that fulfillment doesn't always have to produce something. And perhaps that's the biggest challenge these glasses present. Not whether I can capture more of my life. But whether I can become more intentional about which parts of my life I choose to capture.

My Rules for Putting AI on My Face

I'm not interested in conducting an experiment without establishing a few boundaries.

And I think those boundaries are worth sharing because they apply to considerably more than a pair of glasses.

First, consent isn't optional. If I'm recording someone, they should know about it and agree to it. Having access to technology doesn't give me permission to make decisions about someone else's privacy.

Second, technology doesn't get to interrupt meaningful human connection. If I'm having a personal conversation, building a relationship, or spending quality time with someone, the glasses can be turned off. The person standing in front of me deserves my attention.

Third, convenience doesn't excuse a lack of accountability. I'll examine the privacy settings, understand what information I'm sharing, and continue questioning the company behind the product. Purchasing technology doesn't mean surrendering my right to criticize it.

And finally, I want to experience more than I document. If the glasses genuinely help me stay present, fantastic. If they encourage me to turn every experience into content, they've failed my experiment.

These aren't particularly revolutionary rules.

But imagine what would happen if we applied the same thinking to every AI tool we introduced into our organizations.

Imagine evaluating technology based on the human experiences it improves instead of exclusively measuring how much time it saves.

That would be a much more interesting conversation.

The B2B Rebellion Might Start With Taking the Glasses Off

There's something wonderfully contradictory about building a personal brand around curiosity, trust, and challenging conventional thinking while questioning whether you should wear a pair of AI-powered glasses.

But I don't think contradictions are necessarily a bad thing.

Sometimes they're evidence that we're actually thinking.

We should be able to embrace innovation without abandoning our values. We should be able to question technology without being afraid of it. And we should be able to experiment without assuming that every experiment needs to become a permanent part of our lives.

I'm not going into this expecting to prove that wearable AI is incredible or terrible.

I'm going into it with questions.

And I'm giving myself permission to change my mind.

Because the entire point of curiosity is being willing to discover something you didn't already believe.

So, did putting AI on my face change how I connect with people?

I don't know yet.

This is the beginning of the experiment, not the conclusion. And I'm not going to manufacture an answer simply because it would make a better ending.

What I do know is that I want technology to create more opportunities for genuine human connection, not fewer.

I want to remember the conversations, not just have recordings of them.

I want to experience the moments, not simply collect evidence that they happened.

And I want the people around me to know that when I'm looking at them, I'm actually paying attention.

Because the most valuable thing I can bring into any room isn't artificial intelligence.

It's my own.

And if the technology on my face ever makes me forget that, I'll take the damn glasses off.

Welcome to the B2B Rebellion. PARTY ON. AMBUSH.