In Python it took 10 years, and even now you can't get companies to migrate, because why make developers do the work when application still can be used. Many places will probably start the migration in 2020, which shows that giving 10 years head start was a mistake and all it did was create FUD and division in the community.
The Python 3 immediately picked up for new projects after announcement that 2.7 will no longer have new feature and only bugfixes in 2015. Industry will wait for the last moment when all support for 2.7 will be ceased in 2020.
The proper way make a major breaking change like python did is to provide a bridge between the two versions, so you could import 2.7 modules from 3.x applications, and even the other way around. As of today there is still no such thing.