When 'It Works' Becomes the Problem

Back in the day, I worked on a system built entirely on .NET 4.8, MSSQL Server, SSIS, and Windows Server 2019. Everything was locked into the Microsoft stack, Visual Studio, proprietary VPN tunnels, and tools that only worked on Windows. If your setup wasn’t exactly right, you were out of luck.

The system had been running for years. No documentation. Tons of hardcoded logic. The codebase had evolved into a maze of legacy patterns and patchwork fixes.

The team knew the system deeply. But they’d been working in isolation for so long that no one ever questioned anything. New ideas weren’t welcomed. Suggestions to modernize were ignored. It wasn’t broken so why fix it?

I raised a few flags. I brought up how hard it would be to onboard new developers, how brittle the codebase had become, and how dangerous it was to be so deeply tied to one vendor. The response? Shrugs. Silence. Maybe a polite nod.

That experience taught me a hard but valuable lesson: avoid deep vendor lock-in. Being all-in on a single platform might make life easier in the short term, but it severely limits flexibility in the long run. It makes change harder. It makes hiring harder. And it makes your stack age faster than you think.

The client had no technical background, so they never pushed back. And the team was comfortable. The system still ran. So in their eyes, everything was fine.

But from the outside, it felt like watching something slowly crumble. Not a big issue for now but in the meanwhile technical debt piling up, year after year.

I’ve worked on legacy codebases before. I usually enjoy untangling them. But this one was different. It wasn’t just the code it was the mindset. Resistant to change. Suspicious of improvement.

If there’s a takeaway here, it’s this: just because something works doesn’t mean it’s working well. Stability is not the same as sustainability. And the longer you wait to modernize, the harder it gets.

If I ever catch myself clinging to old tools just because “they still work” I hope someone calls me out (or slaps me).