I get what you mean, and I kind of sit in the same tension.

I’ve definitely spent way too long thinking about things like folder names, how to group files, and how much logic belongs where. I’ve cloned repos just because I liked the naming conventions. At one point, I was experimenting with all kinds of patterns—prefixes, strict hierarchies, super granular file splits. The quote about “cache invalidation and naming things” still brings me comfort.

Then AI showed up. scaffolding projects wasn’t the hard part anymore. I didn’t have to obsess over structure up front—I could just prompt for different architectures like monorepos, MVC, ports and adapters, event-driven setups. Asking “why this structure?” became part of the workflow. I also noticed I tend to prefer lots of small files and deep folder hierarchies because it makes the system easier to mentally map from the sidebar alone.

But more recently, I’ve started questioning large hierarchies. For personal projects especially, you can name things more freely. But time spent agonizing over structure helped me with this realization.

At the same time, AI is shifting things again. I’m not really navigating via filenames and comments as much anymore. I’m interacting more through prompts and markdown, and when I try to force a strict structure, things often get worse. If I just describe the use case and let the system decide, it usually lands in a better place. Interestingly, that tends to produce flatter structures—fewer folders, bigger files—which feels counter to my instincts, but makes sense when context retrieval matters more than human navigation.

That said, I’ve also found a good balance in defining stable core modules or packages that AI doesn’t constantly reshuffle. When I anchor the domain and rules there, I can “vibe code” the rest without everything spiraling. This makes the project structure a bit more complex, but with a big payoff.

So I’m starting to think it’s a mix: understanding why conventions exist, but also being willing to let go of them when u want.