I doubt it. xkcd has been hitting it out of the park consistently of late, and he's been experimenting more and more with radical new projects. I think it'll be a while before he gets tired of cartooning.
That's why I said "_why-like proportions". It will be unexpected and shocking. I know its a bold prediction, but this kind of whimsical genius seems like a most unstable isotope.
The difference between Watterson and Munroe is that Watterson made far more money but didn't have a ton of control, whereas Munroe probably makes less money but has far more control. Part of that is down to sheer popularity. Watterson is worth several hundred million dollars according to reports, whereas Munroe likely makes at most a few hundred k a year. Which is still very respectable, but not quite in the "fuck it, I'm retiring" impulse zone as Watterson's wealth is. Also, Watterson was fairly disconnected from his fans and the primary interaction of his work were the ongoing struggles with his syndicate masters. Whereas Munroe's main interaction related to his work is directly with his fans, which also directly provide his income (through merch sales, mostly).
So there's very much less reason for Munroe to get frustrated with the process and stop. Watterson got tired of the bullshit and decided he'd had enough. If Munroe gets bored of doing the strip I suspect he'll just move on to some other project, which will be equally public (like what-if).
>xkcd has been hitting it out of the park consistently of late
I haven't checked it in a few years since it was getting so bad, so based on this I went and looked through the most recent dozen or so comics. Can you point to some of these home runs? Because all I saw was the same inane observations without adding any insight or thought or a joke or anything. I'm honestly not just trying to be contrarian, I just can't see how his recent work is in any way different from the last 3 years.
