Not saying it is right or wrong, but a lot of the upsetting changes for existing users are for the benefit of new users.
Also, "users" are "people" and the average adult lifespan (18-78) is around 60 years. That implies that the time for the "new users" to become half of the user base is around 30 years, so what does that say about how often it makes sense to do this?
But suppose you're right. Then the solution is competition. Don't take away the old thing, provide both. If the new users want to use the new thing and the old users want to use the old thing, great.
And then if the new users still want to use the old thing you've got a pretty good red flag that you messed it up.
That doesn’t add up at all... you’re implying that users are gained and lost at exactly the same rate, consistently, over a span of at least 30 years.
It doesn’t invalidate your other point about competition, but it’s a flawed argument to base any reasoning upon.
The point at which "new users" are the majority of the user base never even happens.
Your new UI might be garbage, but there's no red flag here. A new user will likely need to make use of tutorials, troubleshooting, and other help online; most or all of which will be based on your old UI (and possibly coupled with comments like, 'Don't use the new UI, it's trash. Here is how to switch...'). Having been such a new user, I only pick the new UI when forced or when it's clearly better; the former being the more common case.
Sure, you can make your official documentation use the correct UI (or design your UI in such a way that the documentation can be agnostic—but then what is this big change that makes lives better?), but unless your documentation is very good, people are still going to need to reference all these other sources.
Recently ran into this issue when submitting an app to Google Play. New interface didn’t even match up to Google’s own instructions. Frustrating.
As well it should. Because now things that used to take three seconds will take 15 minutes for a month until you learn the new interface.
The designer will respond that yes, but then once you learn the new thing it will take two seconds. And if you save one second twice a day then you'll have made back that 10 hours you spent learning the new thing in less than 50 years!
Except that they're going to change it again in less than 50 years.
And that's assuming that the new design is actually better and not just different or worse, because also, this:
https://news.ycombinator.com/item?id=25950351
Rule of thumb: If the new thing isn't better enough to cause people to switch to it voluntarily without any prodding or the removal of the option to use the old thing, it isn't better enough to be worth it.