Scattered clouds

We were sitting on the beach, watching clouds gather over the water. As I described the latest updates made to several AI tools we frequently use, and their attempts to help users organize their digital lives, I couldn't help but notice the irony: as more of our world moves to "the cloud," our lives are actually getting more complicated and cloudier. The promise of cloud computing was meant to simplify everything–our files, communications, and creations would float effortlessly in the digital ether, accessible from anywhere. Yet each new solution seems to bring its own complexity.

Cloudy skies ahead

This reality was punctuated by my experience earlier that morning with ChatGPT's new Project feature. What promised to be a simple way to organize conversations turned into a puzzle of limitations: chats that had been started with custom GPTs couldn't be moved into Projects, forcing users to choose between organization and functionality. Those who've built workflows around custom GPTs now face an awkward choice: abandon their custom GPTs and try reconstruct their workflows in Projects, or keep using them and miss out on the incredibly helpful new folder organizing feature.

While ChatGPT's limitations are just one example, this fragmentation extends far beyond chat interfaces. I've been struggling to organize my AI-generated images across various platforms, each having its own unique organizing system (if it has one at all). Despite similar underlying needs, each platform has developed its own approach to filters, folders, and filetypes. The result? No consistent way to manage growing libraries of digital creations across different services.

Music's Cloudy Lessons

The large music platforms offer both hope and warning about our cloudy future. While there are tools like TuneMyMusic to sync music libraries and playlists between platforms like Spotify, Apple Music, YouTube and Tidal, they're more of a patch than a solution. Songs vanish without warning when licensing agreements expire, leaving holes in carefully curated playlists. Those of us who create music or maintain libraries of rare recordings face even greater challenges, forced to pay additional ongoing subscription fees just to maintain access to our own content across devices.

The Fragility of Cloud Platforms

Perhaps most concerning is the ephemeral nature of cloud services themselves. Platforms shut down, get acquired, or pivot to new formats with alarming regularity. For example, in just a couple weeks from now InVision, once a popular professional prototyping tool, will be shutting down and all user files will disappear forever.

We're repeatedly faced with a digital dilemma: spend hours backing up and migrating our data, or let go of years of original and carefully curated content and start fresh. The very tools that promised to free up our time now demand regular maintenance just to preserve what we've created.

Finding Peace in Digital Impermanence

I wish I had clear solutions to offer. Beyond the obvious but time-consuming approach of downloading and routinely backing everything up—essentially defeating the purpose of cloud solutions—there's no easy answer. Perhaps there's wisdom in pursuing a kind of digital zen: acknowledging that like the clouds floating by high above the beach, our digital lives have become fluid and ever-changing. We can build our castles in the cloud, but we should remember that they, like their sandy counterparts below, are subject to the tides of technological change.

Looking back at those gathering clouds over the water, I realize we probably should have seen this coming. The promise of the cloud was always a bit of an illusion. After all, real clouds are beautiful but inherently unstable, shifting and dissolving as conditions change. Our challenge now is learning to find peace in that impermanence while protecting what matters most.

Images generated with Midjourney. Editing assistance provided by Claude 3.5 Sonnet and ChatGPT-4o with Canvas.