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

But for me, for now, the friction is what I’m looking for. 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 combinin... See more

It occurs to me, much later than it occurred to the archivists, that we have never possessed such a complete and damning record of our past interactions. I can tell you every college scholarship I never got. Every sale at The Gap for the past 18 years. Every flight I’ve ever taken, anywhere in the world. Most grocery lists, news alerts, heartbreaks... See more

According to iCloud, I have more than 23,000 photos and almost 2,000 videos resting somewhere on Apple’s servers. I have tens of thousands of songs liked somewhere in Spotify. How much is jotted down in my Notes app? How many conversations do I have stored in Messages, in WhatsApp, in Signal, in Twitter and Instagram and Facebook DMs? There is so m... See more

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

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