Best times is when users give feedback and I can react on it. When users are complacent and quiet, it's also opportunity to innovate where it's not always obvious.

Building tools, apps, services that you use yourself, what you want and need, is the ultimate driving force for innovation. When the product is a result of an employment at a corporation, this driving force is reduced or lost. Open source projects run by corporations shows this issue, the Bitpay wallet is good example of this. Maintained primarily by employees who change over time.