Is the end of what you're pushing down the column rounded? If you're using a stiff wire, for example, then double back the end about 1"-2" but don't flatten the "eye" completely flat, leave it rounded.
A rounded end is more likely to rise up and pass over an obstruction, rather than to butt up against it.
Twirling the wire is another tactic, using LIGHT pressure to continue pushing.
I spent more than three (>3) decades running wires (from 20-22 ga to 500MCM) so to paraphrase a popular insurance commercial: I know a thing or two, because I've done a thing or two!