Guido is not asking Python to live without a dictator. Guido is asking Python to learn how to live without Guido, so that Python may outlive him.
This is a tale as old as time. Apple lives on with only memories of Steve Jobs. The United States lives on with only memories George Washington.
For some inspiration I'd recommend listening to the track "One Last Time" from the Hamilton musical:
"One Last Time" - Hamilton At The White House #ObamaLegacy
Original Broadway Cast Recording on YouTube
Original Broadway Cast Recording on Spotify
I think that remains to be seen.
I'm sure there's more you could have written, why hold back?
I could be wrong, and I don't follow Apple closely, but the impression I get from longtime Apple fans is that the last few years have been a stream of mild disappointments.