Nobody I've talked to believes Steve Jobs is anything but deathly ill. They're also convinced that Apple will go on somehow -- even if not quite in the same vein. But what if this situation applied not to Jobs but to another technology entrepreneur that I've covered a great deal -- Canonical's Mark Shuttleworth?
I don't mean to be morbid, but when you spend as much time in this industry contemplating things that seem to have a life of their own, it's always a grave shock when real-world morality comes along. So what if for whatever reason, whether ill health or anything else, Shuttleworth was unable to continue leading Canonical? How would they fare, as well as the other Linux variants that look to Ubuntu for guidance?
Much of this seems to come down to two things: 1) whether or not you need someone charismatic and visionary at the helm in an endeavor like this (and to what end), and 2) how hard it is to replace them.
In Apple's case, they needed someone of Jobs's vision to bring the company back from its moribund state in the Nineties. Now that they're on top of a good thing, maybe they don't need a charismatic leader as much as they need someone who can just make wise decisions about what's worth selling. The company has more ingenuity and talent under one roof than any other ten companies put together; they just need to not chase dead ends and they'll be fine.
Canonical, though, I'm not as sure about. They're that much younger and smaller, use an entirely different business model, sell an entirely different kind of product -- and, most important, they have a charismatic and visionary leader in a world where most open source work tends to be anonymous. The collective effort that Linux has nominally been is being supplemented with work being led by someone who has a specific, overarching conceit about how things should work. Anyone can fork a project; not everyone can give it momentum.
So what happens to all of that if he goes away? My worry is that the very specific conceits that Shuttleworth brings to Canonical and Ubuntu are not things that can be easily duplicated by others. Whether or not he likes it or wants it, the man himself is important. Few people are in the position he is, to look down on the whole and say what works and what doesn't.
I believe how Apple handles this will be relevant, since it would serve as a strong model to emulate in itself. Nobody is going to be able to replace Jobs, but I don't think it's impossible for them to find someone with some measure of the same vision.
The same goes for Mark: you can't replace him, but you can certainly find a way to move past him. And if Canonical becomes as much of an institution as Apple, they'll need to find a way to do that: to make it possible for Shuttleworth's vision and energy to be infused, at least to some degree, into successors to the helm.