This one is more of an uncut journal, maybe an archive in history of my thoughts on AI in 2026. Things are moving so fast that I want to look back on this as a time capsule.
Why I Recorded This at the Lake
I brought you here to the lake, Lake Erie, near my house, because I wanted to share my thoughts on this really rapidly developing technology in a place that has just about nothing to do with technology. Though I’m told data centers do need a lot of water.
I think sometimes we forget when we’re on a screen and we’re seeing development, and some new model came out, and now it can do this, and now it can do this. We lose track of this physical world that we inhabit, which AI can’t feel. It can’t feel this wind and this breeze.
A couple weeks ago, I did a swim across the bay to raise money for a fundraiser. A bunch of people did it and swam a mile across this bay. When I got to the other side, my two young kids met me with signs that said, “Go dada.” Ellie painted this giant blue line. And when I got up off the dock, she said, “Dad, this is the lake. This is you.”
I want to see AI do that.
There are some human elements and souls that cannot be replaced with AI.
The Pope, an Encyclical, and 42,000 Words
The main core thought I want to offer you and myself today starts somewhere unexpected. I am not Catholic. Far from it. And yet the pope recently put out what’s called an encyclical.
Apologies if I butcher this, but my understanding after some research is that an encyclical is not like some random tweet from the pope. These are documents put out as a kind of marker of this pope’s contribution. This one is a 42,000 word document.
I discovered that he did this in a newspaper. I’ve unsubscribed from all digital news and I only get a local newspaper, because I take way more action off of that local newspaper than I do off of any international news that I’ve consumed.
So I find out about this encyclical, and instead of reading the ironic AI summaries all over the internet, I decided to bear down and listen to it. The entire thing. 42,000 words, several hours long.
The guy who read it has a random podcast on Spotify. I just searched it, and it begins with him saying it’s pretty ironic that all sorts of AI readings of the Pope’s encyclical are showing up. That kind of is not the point, to have AI read the Pope’s statement on AI. So the podcaster just goes, “So I’m just going to bear down, and with my humanity and all my imperfections and my coughs and my dog barks and whatever else, I’m going to read it.”
“Where Are We Going?”
There are a couple of things that struck me at the very beginning.
He asked a question that my wife asks every time I come downstairs from the office excited about some new technology. She has a very grounding way, usually over tea, of sitting down and saying, “It’s really cool, Chad. Where are we going?”
Awesome, this thing that used to take you three months now takes you a day. Where are we going?
I think it’s a really good question to ask. As a heavy AI user, I’ve noticed that my biggest self-work is actually pausing and slowing down long enough to decide what it is that I want. If we can create and build and articulate at the speed of thought, what is it that you want to create and build, and why?
Where are we going?
That question is one of the most useful conversation starters you can bring to your team right now.
Dignity
There was an immense amount of philosophical, foundational underpinning in the pope’s encyclical. He used the word dignity over one hundred times.
So my homework for you is to go look up the definition of dignity. Whether you’re religious or not, Catholic or not, I think the word dignity is worth paying attention to.
Here’s what that looks like in practice. As AI can manage my inbox better than Taylor, the chief of staff on my team, it would be undignifying to say, “Hey, Taylor, you’re not good enough.” But it would be very dignifying to say, “Hey, Taylor, good news. You don’t have to do this tedious stuff anymore. You have the gift of being able to connect with people.”
Leaning into Will Guidara’s theme of “unreasonable hospitality”, what are the ways that while the world is zigging very hard toward AI, we can zag?
I think it’s fine to go the AI route, and there are philosophical debates about that. But I think it’s really powerful to zag toward leaning more into intimacy and connection, more toward our own humanity.
Three Buckets for a Better AI Conversation
Here’s my last invitation, and this is just my current best thinking when conversations about AI come up.
I was at a conference recently, and about 20 people were in this way too open discussion about AI. You have people who are like, “It’s using too much energy, we’re going to burn down the planet,” and you should research that, because AI data centers use a lot of electricity (though I suspect this will be a somewhat temporary problem). And then there are other people who are like, “It’s the best thing ever.” So there is a spectrum of polarization.
I think it’s helpful to divide our thinking into three buckets. To have a progressive conversation on AI, I would invite you in any one conversation to touch on all three.
1. The Philosophical
Conversations are starting to emerge about transhumanism, posthumanism, what does a beyond-human look like. These are really big philosophical debates that we as a species get to ponder.
2. The Psychological
We have these little bots that tend to agree with us and pump us up and support us. What does that do when you’re like, “I don’t even have to call my dad and ask for advice on how to be a father, I’ll just ask Claude”? What does the psychology of that mean over the long term? It’s super convenient in the short term. What does that mean over the long term?
3. The Practical
The biggest advocates I’ve seen for AI, and the heaviest users, often haven’t gone anywhere. No progress made. And it’s all under the guise of, “I’m learning. I feel like you have to learn or you’re going to fall behind.”
While that may be true or not, it would be good to pay attention to whether anything you’re doing is actually making a meaningful difference in the world.
Where I Land
These are my extremely imperfect, unfiltered, uncut thoughts in 2026 that might look really stupid or really smart 10 years from now.
Want to discuss this with other folks who lead groups? Register your interest for the Connectors Summit this December, a live experience where facilitators, trainers, and leaders come together to practice, connect, and reset.
I’m Chad Littlefield. Have an awesome day.
