Happy 20th Anniversary, Gmail. I’m Sorry I’m Leaving You.

I am grateful — genuinely — for what Google and Apple and others did to make digital life easy over the past two decades. But too much ease carries a cost. I was lulled into the belief that I didn’t have to make decisions. Now my digital life is a series of monuments to the cost of combining maximal storage with minimal intention.

I have thousands of photos of my children but few that I’ve set aside to revisit. I have records of virtually every text I’ve sent since I was in college but no idea how to find the ones that meant something. I spent years blasting my thoughts to millions of people on X and Facebook even as I fell behind on correspondence with dear friends. I have stored everything and saved nothing.

This is an example of what AI, in its most optimistic state, could help us with.

We already see companies doing this. In the Apple ecosystem, the Photos widget is perhaps the best piece of software they’ve produced in years.

Every single day, I am presented with a slideshow of a friend who is celebrating their birthday, a photo of my kids from this day in history, or a memory that fits with an upcoming event.

All of that is powered by rudimentary¹ AI.

Imagine what could be done when you unleash a tuned large language model on our text histories. On our photos. On our app usage.

AI is only as good as the data it is provided. We’ve been trusting our devices with our most intimidate and vulnerable parts of ourselves for two decades.

This is supposed to be the payoff for the last twenty years of surveillance capitalism, I think?

All those secrets we share, all of those activities we’ve done online for the last twenty years, this will be used to somehow make our lives better?

The optimistic take is that we’ll receive better auto suggestions for text responses to messages that sound more like us. We’ll receive tailored traffic suggestions based on the way we drive. We’ll receive a “long lost” photo of our kid from a random trip to the museum.

The pessimistic take is that we’ll give companies the exact words which will cause us to take action. Our own words will be warped to get us to buy something we’ve convinced ourselves we need.

My hunch is that both takes will be true. We need to be smart enough to know how to use these tools to help ourselves and when to put them down.

I haven’t used Gmail as my primary email for years now², but this article is giving me more motivation to finally pull the plug and shrink my digital footprint.

This is not something the corporations did to me. This is something I did to myself. But I am looking now for software that insists I make choices rather than whispers that none are needed. I don’t want my digital life to be one shame closet after another. A new metaphor has taken hold for me: I want it to be a garden I tend, snipping back the weeds and nourishing the plants.

My wife and I spent the last week cleaning out our garage. It reached the point where the clutter accumulated so much that you could only park one car in it, strategically aligned so you could squeeze through a narrow pathway and open a door.

As of this morning, we donated ten boxes of items and are able to comfortably move around the space. While there is more to be done, the garage now feels more livable, useful, and enjoyable to be inside.

I was able to clear off my work bench and mount a pendant above it. The pendant is autographed by the entire starting defensive line of the 1998 Minnesota Vikings.

Every time I walk through my garage, I see it hanging there and it makes me so happy.

Our digital lives should be the same way.

My shame closet is a 4 terabyte hard drive containing every school assignment since sixth grade, every personal webpage I’ve ever built, multiple sporadic backups of various websites I am no longer in charge of, and scans of documents that ostensibly may mean something to me some day.

Scrolling through my drive, I’m presented with a completely chaotic list that is too overwhelming to sort through.

Just like how I cleaned out my garage, I aught to do the same to this junk drawer.

I’ll revert to Ezra’s garden metaphor here: keep a small, curated garden that contains the truly important and meaningful digital items to you. Prune the rest.

(Shout out to my friend Dana for sharing this with me. I think she figured out my brand.)