How do you decide when a redesign is actually worth it vs. just polishing what you have?

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Been going back and forth on this for our product for a while now.

We've had the same core dashboard layout for almost 2 years. It works, users aren't complaining, but it also doesn't feel "current" anymore compared to newer competitors. Part of me wants to do a full redesign, part of me thinks we're just chasing trends and should focus on fixing actual usability issues instead.

Some signs I keep going back and forth on:

Conversion/retention numbers are stable, not dropping so it's not really broken
But onboarding feedback keeps mentioning the UI feels "dated" compared to competitors
A full redesign is expensive and risky (relearning curve for existing users), but staying stagnant for too long backfires eventually too

Curious how others think about this. Do you wait for actual metrics to drop before redesigning, or do you treat "feels dated" feedback as a real signal on its own? Also curious if anyone's done a phased redesign (small structural changes over time) vs. a full rip-and-replace, and how that went.

We've written a bit about when a redesign is actually justified vs. not as part of our SaaS design work, but genuinely curious what's worked (or backfired) for others here.

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