November 21, 2025
Every now and then, the Thought of the Day and Question of the Day pair up like a buddy-cop duo who definitely aren’t following the department handbook. Today’s Thought is all about knowing when to stop trying, while today’s Question asks which ridiculous hill I’ve chosen to die on this week. And yes, I have an answer. A glowing, battery-powered, professionally assigned answer.
But we’ll get there.
First, the Thought.
Thought of the Day: “If at first you don’t succeed, try, try again. Then quit. There’s no use being a damn fool about it.” — W.C. Fields
W.C. Fields understood human nature better than most philosophers. We all love a good comeback story, sure, but there’s a point where “trying again” becomes “I will not be defeated even if logic, dignity, and the laws of physics oppose me.”
There are plenty of moments where trying again is noble. There are also moments where quitting is the most intelligent, self-preserving thing a person can do.
I had one of those moments this week.
Well… I should have had one.
Instead I chose the “be a damn fool about it” path, and I will fully blame myself for that.
Let’s just say today’s Thought hit uncomfortably close to home.
Too close.
Unsettlingly close.
Because I have spent the week wrestling with something that absolutely does not deserve the amount of emotional energy I gave it.
But that belongs in the Question section.
If you want a warm-up for today’s theme, you might enjoy this earlier reflection about participating in your problems or this one about misfortune testing the brave.
Today’s Thought reminds me that wisdom is often found not in repeatedly trying… but in recognizing when something is simply not meant to be fixed right now.
Which brings us to the biggest “not meant to be fixed right now” moment of my entire week.
Question of the Day: What’s the pettiest hill you’ve died on this week?
Let me set the scene.
There is a work iPad which needs to be configured which is a little more complicated than your personal device.
A simple, innocent, unassuming work iPad that needs to be configured through the work network for one task.
Not ten tasks.
Not a complex workflow.
Not a mission-critical system.
One. Task.
And somehow that iPad has consumed the better part of my waking life.
By my own estimate, and I say this with the resigned clarity of a man who has stared into the abyss, ChatGPT and I have spent about eleven hours together trying to get this one device to cooperate. Eleven hours of syncing, re-syncing, checking profiles, verifying certificates, restoring, rebooting, bargaining, pleading, caffeinating, and experiencing the five stages of grief on a loop.
It has taken me to emotional places I did not know technology could take a person.
And yes, this is the hill I died on this week.
Not a dramatic hill.
Not a noble hill.
Not even a hill with a decent view.
A corporate-issued rectangle flashing “Hello” with every restart and a vendetta.
How petty is that?
Spectacularly petty.
But also incredibly on-brand.
You’d think after eleven hours I’d learn W.C. Fields’ lesson.
You’d think I’d walk away.
You’d think I’d say, “You know what, this can wait until next week.”
And I did.
Eventually. Maybe. I don’t really know yet.
But quitting doesn’t mean the hill wasn’t real.
It was.
And I died there loudly, dramatically, and with ChatGPT as my battlefield medic.
Now it’s your turn:
What’s the pettiest hill YOU died on this week?
Trust me, after hearing mine, nothing you confess will sound unreasonable.
Final Thoughts
Today’s Thought of the Day and Question of the Day felt like a cosmic setup. The Thought told me when to stop trying. The Question asked me why I didn’t. And somewhere between those two lives the truth: I’m stubborn, I care too much, and sometimes I fight battles that don’t need fighting.
But at least they make good stories.
Now tell me yours—
What petty hill did you die on this week?
Leave a comment. I promise, I will appreciate the solidarity.
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