Between Meetings & Meals — Episode 015
The best technology sends you back into real life
Lately, I’ve been thinking a lot about the loop between real life and the digital world.
How moments, conversations, ideas, and even chaos move from IRL → Digital → IRL.
And maybe the best technology isn’t the stuff that keeps us trapped behind a screen… but the stuff that helps us get back to real life a little faster.
The Pour
Clay Shannon was the wine of the week.
We opened it Friday night while watching the Spurs game, and from the very first sip, we both stopped and looked at each other a little.
It was that good.
Not overly bitter, really smooth, and the finish just kind of lingered in a way that made it memorable. I don’t have the proper wine vocabulary for it yet, but it immediately stood out from most of the bottles we’ve had recently.
It’s probably the most memorable wine we’ve had in the past month.
Definitely one we’ll buy again.
And honestly, that moment felt very on theme for this week.
A simple Friday night at home. A basketball game on in the background. Good conversation. Good wine.
Nothing flashy.
Just real life being good for a couple hours.
The Table
Last Friday, we had a friend over to the house to watch the Spurs game.
We opened the bottle of Clay Shannon and settled into one of those conversations that just drifts naturally all over the place.
We talked about work.
Family.
Kids.
Wine.
Life.
AI.
Random stories.
Just a really good conversation.
And something I’ve noticed over the past month or so is that this blog keeps unexpectedly showing up in real life.
Sometimes a friend will bring up a wine I recommended.
Sometimes someone references an AI tool or lesson from an episode.
Last night at my son’s golf banquet, even his coach mentioned something from the blog.
And every single time it catches me off guard.
Because on my side, this mostly just feels like numbers on a screen.
I don’t really know who’s reading it.
I don’t know who’s paying attention.
And honestly, with my inconsistency lately, I’ve still been beating myself up a little for not posting as regularly as I wanted to.
But hearing those moments in real life always reminds me that this thing exists outside the screen.
That’s been the coolest part.
Something happens in real life.
It becomes digital.
Then somehow it circles back into real life again through conversations and connection.
And even if all this blog does is provide a little value, a recommendation, an idea, or just some entertainment for somebody… honestly, that feels pretty meaningful to me.
The Edge
I’ve been spending a lot of time lately inside Claude Cowork and honestly, it’s changing the way I think about work.
The live artifacts, scheduled tasks, skills… all of it has started making certain things feel dramatically easier.
Not easier in a lazy way.
Easier in a “I’m no longer avoiding this because it feels overwhelming” kind of way.
One example that blew me away recently was organizing large folders of documents.
Normally, if you had a folder with a hundred random files in it, you’d have to open each one individually, read it, understand what it is, create a naming structure, organize folders, move things around manually… it’s tedious.
With Claude Co-work, it can look through all of them at once.
It understands the context, identifies patterns, asks questions about how you want things organized, and helps structure everything in minutes.
That kind of thing used to feel like an all-day task.
Now it feels approachable.
And the more I use tools like this, the more I keep thinking about this loop:
IRL → Digital → IRL.
Something from real life enters the digital world.
The digital world helps organize it, improve it, simplify it, or create something from it.
And then ideally… it comes back into real life in a better form.
Less stress.
More clarity.
More time.
Better conversations.
More presence.
That’s the part I’m becoming most interested in.
Not just saving time.
But what we actually do with the time we save.
The Lesson
I wrote something about this a long time ago called Building a Digital Brain, and I feel like I’m still refining that idea in real time.
The better these systems get, the more important it becomes to understand where the line is.
What belongs in the digital world?
What belongs in real life?
And how do you make the two work together instead of competing against each other?
Because I don’t think the goal is to live more digitally.
At least not for me.
The goal is to make real life better.
To reduce friction.
To organize chaos.
To spend less time stuck in tedious work and more time being present.
If AI is supposed to save us time, then eventually we have to ask:
What are we doing with the time we get back?
For me, I think I’m trying to turn that time into richer IRL experiences.
Better conversations.
More moments around the table.
More creativity.
Less stress carrying things mentally all the time.
That loop has become really interesting to me lately.
IRL → Digital → IRL.
And honestly, I think the best technology should always send us back toward real life.
If this resonated, the newsletter is where it continues — one honest email at a time.