Everything is Broken

Foiled by Technology.. Again

After struggling for hours today with a web-building tool, I have come to a clear and deeply scientific conclusion: Everything is broken. Not “a little glitchy.” Not “needs a refresh.” Broken.

I am currently being charged for applications I canceled months ago. Meanwhile, a piece of software—designed specifically to organize people’s availability—was completely unable to… organize people’s availability.

What is happening?

This is not my first rodeo with technological collapse. At my last company, we ran an online fundraising platform used by thousands of nonprofits and schools. Right in the middle of our busiest season, our system broke. Auction chairs and their committees were suddenly staring at disaster, their fundraising goals slipping out of reach in real time.

The VP of Engineering sat in the office next to mine. I remember the grim faces, the stony stares, the eerie silence as he and his team worked the problem. No small talk. No movement. Just the heart-pounding awareness that something had failed at exactly the wrong moment.

That experience taught me something important: Technology is not foolproof. In fact, it is often… fool-adjacent. And now, in a world where companies are increasingly using AI to write their code, it feels like all bets are off.

So what do we do?

Recently, while trying to schedule a meeting, I abandoned all platforms and went rogue. I sent a good old-fashioned email. “Here are three times. Please reply with your availability.”

Old School. And you know what? It worked.

Lately, I’ve been thinking about my mom. Technology often leaves her completely flummoxed—passwords, updates, alerts that sound urgent but mean nothing. I try to help her as do all of her grandchildren when they can. Now I’m starting to feel her pain.

Between the password abyss, the Google drive with countless folders and the relentless parade of “exciting new AI tools,” I am increasingly tempted to walk away from it all.

Make some art. Read a book. Sit in a room with other humans telling stories. Honestly, that sounds fantastic.

Maybe I’ll just retreat to the rehearsal room—where the connections are real and the stories make sense. Even actors, with their fragile egos, are more resilient than the technology we depend on every day

The cast of The Spitfire Grill in the rehearsal room.

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