Question of the Day: What’s the pettiest hill you’ve died on this week?

November 21, 2025

There are weeks where the petty hill is something small, a stubborn jar lid, a misplaced sock, someone loading the dishwasher in a way that offends your soul.

This week, my hill was bigger. Colder. Smarter. With a charging port.

My petty hill was a work iPad.

Not just any iPad, the iPad whose only job in the universe is to run one task for one program. That’s it. Not save the world. Not store mission-critical data. Not launch a rocket. Just… one. Single. Task.

And somehow, that tiny assignment dragged me, and ChatGPT, into an eleven-hour odyssey that left me emotionally hollowed out like a pumpkin after Halloween.

You know it’s bad when you start timing your own hope cycles.

“Maybe this sync will work.”

“It didn’t.”

“Okay, maybe this next one.”

“It didn’t.”

“Alright, let’s make coffee and cry a little.”

This iPad has taken me through all five stages of grief multiple times. I’ve bargained with it. I’ve restarted it. I’ve factory-reset it more times than should be legal. At one point, I genuinely believed it was taunting me. The loading spinner wasn’t just spinning, it was judging.

And yes, ChatGPT was there for every minute of it. My AI emotional support animal. My therapist. My co-pilot in technological misery.

It’s petty, I know. It’s ridiculous, I know. It’s not even mine, it belongs to work. But when you spend eleven hours with a piece of hardware, you bond… or you break.

I broke.

And yet, in the most predictable plot twist of all, I know I’m going back in next week.

I may be a grown adult with responsibilities, a family, and a brain that should know better, but I am simply too stubborn to quit.

It’s not noble.

It’s not admirable.

It’s… on brand.

So that’s my hill.

A single iPad. One task. Eleven hours. Zero victories. Infinite pettiness.

And I died on that hill loudly, enthusiastically, and possibly in front of witnesses.

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💬 Your Turn

So… what’s the pettiest hill you’ve died on this week?

Share your answer in the comments or on social. Your weird little truth might be someone else’s comfort zone.