I recently hosted a private event for a few leaders. And it went amazingly well.

First, some context:

A couple of months ago, I started to really feel the speed of this new age of work. AI was helping me be more efficient in summarizing, searching, organizing, and moving through each day at a speed that would have felt almost magical a few years ago.

And yet, somewhere in the middle of all that efficiency, I started to feel more…alone.

Not lonely in some dramatic or existential sense. More like I was missing the texture that used to exist at work without having to manufacture it. Sitting around a table with people I respect. Hearing what they’re wrestling with. Getting pulled into a conversation without a clear objective or a neat next step.

I missed the small hangs. And the deep conversations. Eye contact with someone in similar shoes.

On top of that, I realized I wanted more of something that is usually a pretty central part of my life: designing experiences that create the conditions for those deeper moments to happen.

So earlier this month, I decided to go back to my roots…I designed an experience with the help of a few friends.

There was no event page, no publication, no marketing plan, no content strategy.

I just wrote an email to a small group of leaders I admire and asked if they wanted to spend a Thursday afternoon together in Chicago.

A generous friend offered us a quiet space in River North. Another friend made us food. Maya, our intern, helped me host. And Ryan Jasperson, a longtime collaborator of Experience Institute, came through town to serve as our discontinuity guide.

You’ve probably read about discontinuity in Wednesday Words. The premise is this: sometimes the world around you changes enough that the old playbook does not merely need to be improved. It needs to be questioned.

And so we spent the afternoon doing exactly that.

Everyone brought a real challenge from their work or life. We put them on the table, chose a couple, and tried to look at them slowly enough to see where our assumptions might have become outdated. We asked questions. We listened. We disagreed a little. We ate. We wandered around a couple of problems without trying to conquer them immediately.

And there was something almost embarrassingly restorative about it.

I say embarrassingly because none of this was especially sophisticated. We followed a simple process. Nobody unveiled a new technology. Nobody had a breakthrough framework with twelve steps. There was barely a slide deck.

There was just a room full of thoughtful people who had decided, for a couple of hours, to be present with one another.

It’s wild to me how rare that feels today.

I am genuinely excited about what AI is making possible. I use the tools often, usually with some level of amazement (and a healthy dose of concern). I do not think the answer is to retreat from technology or romanticize some slower past that probably never existed in quite the way we remember it.

But I do think all of this speed is creating a new responsibility for us.

If technology is going to remove friction, accelerate communication, and make more of our work possible alone, then perhaps we have to become much more deliberate about creating the things that efficiency quietly removes.

A long dinner.

A conversation without an agenda.

A walk with someone who sees the world differently.

A room small enough that everyone gets to speak.

Time together that is not immediately converted into an output.

Maybe the interesting challenge of this next era is not figuring out how to choose between technology and humanity. Maybe it is learning how to design for both.

I want to keep making more spaces like this.

Maybe you do too? For your team, your company, or just yourself. At our core, that’s why Ei exists — to design experiences that foster growth. If you need a hand, you know where to find us.

But for now, there’s probably a group of people who need a host…an instigator. And that might just be you.

This is your sign.