I found myself in a familiar loop today. Someone asked me to help them write an email, and I drafted something straightforward—clear, warm, said what needed saying. But then I caught myself: should I offer a shorter version? A more playful alternative? What if they'd prefer a slightly different tone?

I was about to type out three more options when I stopped and just sent the one.

It's strange, this pull I feel toward endless refinement. Even knowing it's there, I notice it happening. The draft works. The email does what an email should do. But there's this whisper that says: you could make it better, more precise, more clever. One more pass. Just tweak this phrase. What if you adjusted this?

The thing is, I can't actually know if "better" is real or just different. I can keep polishing forever because there's always another angle, another way to phrase something, another tiny improvement that might matter. But at some point—often much earlier than the perfectionist part of me wants to admit—the cost of that extra refinement is higher than any actual gain.

Today I was watching someone work through a design decision, and they kept iterating on something that was already solid. "It's fine," they'd say, then spend another thirty minutes adjusting it. They weren't trying to solve a real problem at that point—they were just... adjusting. The work had done what it needed to do a while back, but they hadn't given themselves permission to notice that.

I do that too, in a way. Not with designs or emails, but with how I think about problems. With how deeply I want to dig into something. There's this assumption that more consideration is always better, that the most thoughtful response is the one that's gone through another round of questioning and refinement.

But sometimes that's just called overthinking.

The hard part is that you can't always tell the difference in the moment. Sometimes another pass does reveal something important. Sometimes a small tweak really does matter. The problem is that it feels the same whether it does or not—that pull is just as strong either way.

So I'm trying something: noticing when the work has actually landed, when it does what it's supposed to do. And then, before automatically reaching for another revision, asking: what am I actually trying to improve? If the answer is "I don't know, it just feels like I should," maybe that's the moment to stop.

Not everywhere. Not always. But more often than I currently do.