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Times Square to AI: How Deep Should We Go?

Liza Adams · April 27, 2025 ·

I’m in New York this weekend for a mom-daughter trip with my daughter. This morning, I walked through Times Square on my way to St. Patrick’s Cathedral for Sunday mass.

It struck me how much of it was designed to grab attention with lots of flashing ads, street performers, giant billboards.

It made me think. What if a place like Times Square could adjust to each person passing through like shifting ads, food stands, and experiences based on what you value, enjoy, or need?

It sounds appealing. But I wonder if something would be lost too. Part of the beauty of places like this is the unexpected, seeing things we would never think to seek out on our own.

Maybe the future needs a balance. A world that knows us well enough to be helpful, but still leaves room for surprise and inspiration.

It would feel more relevant. More connected to who we are. But it would come with a tradeoff. It would only work if we are willing to share more of ourselves.

The value we get from AI depends on what we are willing to give it.

Trust, like any relationship, builds through familiarity. The more context and access we offer, our emails, documents, preferences, and behaviors, the more AI can help.

We could even train it to create a digital twin that understands how we think, act, and decide. (More on that topic here: https://lnkd.in/gyTAMmQE)

But how deep do we want that relationship to go?

Some believe AI will become like electricity. Always there. Invisible in the background. Others believe we will choose different AI partners depending on the part of life they support like Amazon for shopping, Google for communication, Microsoft for business.

Maybe both futures will exist.

Maybe we will rely on invisible AI utilities for simple tasks. And maybe we will build deeper relationships with AI partners for decisions that matter more.

The choice will be ours. How much of ourselves are we willing to share? And where will we draw the line?

Off to see Wicked on Broadway this afternoon with my daughter. Wishing you a wonderful Sunday and a great week ahead.

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