The study of historical linguistics raises numerous questions regarding what counts as change, where it takes place and what processes affect the type of changes that are observed. These questions can sometimes take on a seemingly paradoxical nature, occasionally making it look like changes are something that cannot be studied. Little over a half a century ago, Weinreich et al. (1968) set out to propose a model of language and language change that was intended to deal with – or avoid! – contradictory assumptions which had been causing problems within historical linguistics (Weinreich et al. 1968:98, 150). Despite this, many of the issues can still be found in the present-day literature of language change. In this paper, I look at and evaluate some paradoxes that have been prominent within discussions of diachronic syntax. I conclude that many of these issues are terminological in nature and that they are in fact not specific to syntax at all. I furthermore suggest that some assumptions need to be taken with a grain of salt and, in some cases, reevaluated based on what we know about language transmission and change.