When the Reminder Needs a Reminder: Overengineering, Simplicity, and the Hidden Cost of Complexity

Christina Guerrier

16 Apr 2025 — 2 min read

There’s a certain satisfaction in automating the repetitive.

A few weeks ago, I decided to build a recurring reminder system for my team. Just a lightweight ping before our weekly meetings to make sure everyone remembers to upload their documents. Nothing fancy. Just a nudge.

At first, I was delighted with myself. Automating these nudges meant I didn’t have to remember to send them. Or worse, forget to send them.

But then, I started thinking—what if someone’s out on PTO? Or what if the meeting falls on a holiday and gets shifted? Or if a team isn’t scheduled to present that week?

So I tinkered.

I added conditions.

Then added exceptions to those conditions.

And before I knew it, I was halfway down a rabbit hole of branching logic and escalating complexity. A system meant to save me time was now costing me energy. Worse, it was still brittle—one small shift and the whole thing risked breaking.

That’s when I stopped and asked myself: What’s the actual job to be done?

It wasn’t about accounting for every exception. It was about making sure people were prepped for their moment at the table. And more importantly, that I wasn’t the blocker.

I started out trying to be clever—layering in logic to account for PTO, shifting due dates, and nudge timing. But somewhere along the way, I realized: I didn’t need all of that. Our schedules were already predictable enough. So I simplified the system—ditched the fancy logic—and built something light and practical.

It worked. And it took half the time.

The Operator’s Temptation

If you’re like me—an operator at heart—your instinct might be to anticipate every edge case. You want things to run smoothly, predictably, at scale. But there’s a fine line between building a resilient system and overengineering one.

Sometimes, the pursuit of perfection gets in the way of progress.

Sometimes, a simple reminder is better than a sophisticated one that never lands.

What I’m Taking Forward

Build for the 80%. Solve for the common case first. You can layer exceptions later—if you really need them.
Let it breathe. Try the simpler version first. See how it performs before adding complexity.
Keep the goal in sight. A clever solution is only clever if it still solves the problem.

Final Thought

Operations isn’t about showing off the most elegant system.

It’s about enabling people to do their best work, with clarity and ease.

And sometimes? That means putting down the logic tree and picking up a post-it.

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