Rich Hickey is a proponent of "hammock-driven development." He's the antithesis of the Zuckerberg "move fast and break things" culture. If you're considering a breaking change, then maybe it's a good idea to hang on to it for a while until you've got a clearer picture of what you're doing. Then maybe you can aggregate a bunch of breaking changes into a partial (or total) redesign and ship that as a new product.
Yes, sometimes you may end up with the Python 3 scenario. But I think that's the right place to have a philosophical debate, rather than between only the insiders who participate in the decision to merge the breaking change.