How do you decide when it’s time to stop using a tool you’ve used for years?

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I’ve used the same task manager for almost three years. It works fine, but every time a new launch shows up here with a cleaner design or smarter features, I wonder if I’m just stuck in a habit.

Last month I tried switching to a newer app for a week. It looked better, but I spent more time moving my tasks and learning shortcuts than actually getting things done, so I went back to my old one.

It made me wonder if loyalty to an old tool is a smart choice or just a fear of the switching cost.

How do you decide when a tool has stopped serving you and it’s worth the effort to switch? Has switching ever paid off for you, or did you regret it?

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sometimes the tool decides for you. google ending gmailify made a lot of people with 4-5 inboxes rethink a setup they used for years. when switching, move one workflow first, not everything in one week. so basically if a tools ins't giving you what you expect as per the new era. for example if an excel software doesn't work with AI, you will start to consider other tools, because now AI is a must feature of these kind of works.