Dealing With Tech Stack Regret

It's uncomfortable to realise a tool I helped choose is causing trouble. The temptation is either to defend it for too long or decide everything needs replacing immediately.

I'd rather identify the actual difficulty first. Is the problem the tool, our use of it, or a requirement that changed? Sometimes a local fix is enough. If we do need to move, a gradual route is usually easier to fit around the work the product still needs.