The 3 AM Bug That Taught Me More Than My Kid’s Bedtime Story

My son climbed onto my lap around 9:30 with a dinosaur book and asked for “just one more.” I said five minutes. He knew I was lying before I did.

By the time I looked up from my laptop, it was past midnight and he was asleep on the couch with his socks half off, the book open on his chest like a tiny tent. I had been chasing a bug in an agent retry loop. The bug won most of the round. My son won the rest.

The loop that refused to loop correctly

The agent I was building had one simple job: call an API, wait if rate-limited, try again. Textbook. I had written this pattern probably a hundred times for work. This one, somehow, was retrying forever on errors it should have given up on, and giving up instantly on errors it should have retried.

I told myself I would find it in ten minutes. That is the oldest lie engineers tell themselves, right after “this refactor won’t touch anything else.”

Choosing the wrong thing, slowly

Around 11, my wife came out, saw the scene, and just raised an eyebrow. She did not lecture me. She did not have to. She picked up our son, kissed his forehead, and carried him to bed. I mumbled something about “almost done.”

I was not almost done. I was two hours and four coffees away from done. And the whole time, part of me knew the honest truth: I was not staying up because the bug was urgent. I was staying up because I did not want to lose to it.

Eben’s note: The bug was not the emergency. My ego was the emergency.

What the fix actually was

At 2:47 AM I finally saw it. The retry function was checking the error type after catching a wrapped exception, but the wrapping stripped the original class. So every error looked like a generic failure, and my conditions fell through to the wrong branch. A four-line fix. Four lines.

I sat there for a minute, feeling that specific, quiet kind of stupid you only feel alone at 3 AM. The fix was small. The cost was not.

What debugging and parenting share

Here is the thing nobody tells you about bugs like this: they reward a kind of patience that real life rarely gives you room to practice. You have to slow down. You have to read carefully. You have to stop guessing and start checking. You have to accept that the problem is almost never where you first looked.

Parenting is the same, and I am worse at it. When my kid melts down over the wrong color cup, my instinct is to fix it fast, not read the actual error. I skip to the retry. I do not check what was really thrown.

Small things I am trying to do differently

• A hard laptop-closed time at 10:30 on weeknights, even if the code is “so close.” Close is not done, and done can wait until morning.
• When my son asks for one more book, I say yes or no honestly. No more “five minutes” that are actually two hours.
• Before I dive into a bug after dinner, I write down on a sticky note what “good enough for tonight” means. If I hit it, I stop. If I don’t, I stop anyway.
• I try to debug my kid the way I debug my code: read the actual error, not the one I expected.

The part I don’t want to forget

When I finally closed the laptop, I picked him up off the couch. He was heavier than I remembered, in that way kids get heavier every month without warning. He muttered something about the dinosaur and went back to sleep on my shoulder.

I stood in the hallway for a second, holding him, thinking about how the retry loop I had just fixed would probably run a few thousand times tomorrow and nobody would ever notice. And the bedtime story I skipped would also run a few thousand more times, across his childhood, and I would notice every single one I missed.

What I am taking from this

The bug taught me the fix. My son taught me the lesson. Code is patient. It will be there in the morning, broken in exactly the same way, waiting for a clearer head. A six-year-old asking for one more book is not patient, and should not have to be. I am trying to get the order of those two things right, one night at a time. Some nights I will still get it wrong. Tonight, at least, I know which one I want to get right tomorrow.

Tags: #parenting #coding #worklife #aiagents #dailyblog #Eben