This newsletter is a hand-written reflection on an in-person conversation. You can watch the video or listen to the audio here.
I drive a 1985 Land Cruiser. It’s rough on gas and incredibly slow, but it’s really fun to drive around, and people often comment on the classic vintage color.
Last week I drove through the school drop-off with the windows down because it was a beautiful morning. The principal of the school happened to be helping direct traffic, and as the line slowed, I stopped right in front of him. He eyed the Land Cruiser and said, “Driving something like that, you need to go do something awesome today, like rock climbing or mountain biking.”
Without thinking about it, I immediately responded:
I’m actually going to go sit alone and talk to AI all day.
His face slowly twisted into a shape that suggested equal parts disappointment and concern, but before I could attempt a recovery, the line started moving and I drove off towards the office. Where I proceeded to talk with AI, mostly alone, for most of the day.
Will AI make us lonely?
That less-than-quick-witted car line exchange bothered me for several days, and I figured out that it wasn’t because of what the principal might think of me; it was because what I said was the truth.
For me and an increasing number of my professional peers, AI has changed work dramatically. We build, chat with, and dispatch AI agents every day, for hours.
Social media, big promises, and loneliness
Social media’s promise is in the name: stay more connected with other people. But that isn’t playing out. CDC data shows that nearly a third of adults reported feeling lonely.
The causes are deeper than just social media, as Robert Putnam pointed out half a decade before Facebook made sign-ups public, but research shows that the dominant experience for many people on platforms like TikTok is consumption. A Pew study found that the top 25% of TikTok posters generate 98% of content, and almost half of users had never posted.
No one questions whether social media algorithms are designed to keep users engaged, but it turns out that engagement is an isolated experience.
AI can increase isolation, too
AI has similar contours to social media: the entire experience is designed to keep us engaged, but we talk with ChatGPT and Claude alone, on our phone or computer.
Agents can give us significant leverage in our work, but that often means we need to work with humans less than we did previously.
A woman on my team writes and publishes a monthly report for our company, and with agents, she can perform deep research, query data from databases, and validate findings, all by herself. Other people are still involved in the process, but on her own, she can do the same work that would have previously required two or three people and multiple meetings.
That kind of leverage is powerful, but is it always good?
Empathy over efficiency
It’s likely that AI will become more collaborative over time, but in the current state, the form factor is designed around the individual. Our tools shape us, especially the ones we use every day, so it’s important to step back and ask whether the way we use AI is improving our human relationships or taking us down a path that will make us more lonely and atrophy our relational skills over time.
One person might be able to do the job of three people now, but human empathy is still the most powerful and important part of our work, no matter what we do.
Watch or listen
You can watch or listen to the conversation that inspired this newsletter. Watch the video below, or check out the audio on Spotify or Apple Podcasts.


