Why doesn't anything work anymore?

October 8, 2025

I’ve officially reached “old man yells at cloud” age.

Despite the constant influx of news and advertising around the evolution of technology and how it’s revolutionizing every aspect of our lives, I find myself absolutely fucking floored at how little things work on a daily basis anymore. Yeah, I’m getting older (I’ll be 40 in a few weeks!), but didn’t think I’d enter this phase so soon. Yet here I am, forced into it by the almost universal lack of care combined with the glut of disdain for customers tech companies have today.

I know about the theory of enshittification. Beyond all of that, though, it’s truly astounding how bad it feels like everything technology-related has gotten. A small sampling from the past few days:

• Sendgrid constantly times out under simple operations e.g. filtering some data in an analytics view. Sendgrid also randomly gets stuck in a login/logout loop with no remedy available other than to switch to an incognito tab or reopen my browser.
• Chrome’s “reopen all last tabs” completely ignores tabs in tab groups if there are more than one tab in the group (what the fuck else would there be in a group?!?). Which… results in most of my tabs getting lost after being forced to restart Chrome for updates.
• My van’s USB port works maybe 60% of the time for connecting my phone and using CarPlay. Zero rhyme or reason as to when it will or won’t work.
• My smart TV is dumb as hell. It sometimes won’t even turn on, defaults to different inputs depending on the day, randomly restarts, etc. It’s terrible.
• Universal Audio plugins completely forget they’ve been authorized no matter how many times they’ve been authorized.
• iCloud flat out just doesn’t sync quickly or reliably.
• Facebook (which I try to avoid as much as possible) refuses to load a feed on Safari on desktop—likely intentional friction to push me to the mobile app, but still.
• Slack fails to load messages unless restarted after my laptop connects to a new network e.g. when I’m working from a coffee shop.
• Instagram suggests following the same people over and over, no matter how many times I dismiss them. Sometimes showing them immediately again after dismissing.
• All of Apple Music.
• MacOS Tahoe and iOS 26 🤣

I’ve worked in the tech industry for close to two decades at this point. I’ve seen how difficult it is to build quality products, but I’ve also seen that it can be done. It just feels like no one gives a shit anymore, beyond a handful of independent devs and small shops. It’s wild.

I’m not proposing any real solution other than encouraging people to care more, but I know anyone who reads this blog likely isn’t in a position of power to enforce care in their companies. The ones who could create change only care about the usual destructive forces: shareholder value, growth at all costs, and their own net worth. So I’m just here to rant because I need to exorcise some anger.

I guess I just wanted to shake my fist at some clouds. The ones outside are beautiful, so iCloud, AWS, Azure, etc. will have to do the job here.