Great article on redesigning here: http://firstround.com/review/heres-how-asana-won-with-its-product-redesign/
"If the rapid cycle of design trends is the external trigger for a redesign, there’s another internal reason one should be initiated as well: the pace of product development. “It's not just design trends that are moving faster. We’re seeing more functionality and features developed in a shorter time span,” says Goertler. “In a year, you can go from an MVP to a product that’s chock-full of functionality, which, when more features are piled on at top speed, can become untenable. That’s when you hit the limits of your original design. You can’t extend your design system to accommodate new feature development. So it’s time for a redesign. The alternative is to continue cramming everything into an already cluttered UI, which stifles all your feature development work.”
Anyone out there done extensive redesigns of their own original designs?