Why are esters meta directors? Can't the carbonyl donate electrons into the ring? I'm having trouble understanding why an ester is a meta directing/deactivating group.

I'm not talking about an ester with its oxygen bound to the ring, like an acylated phenol. I mean the R group is bound to the ring and the alkoxy group is bound only to the carbonyl carbon.

It seems to me like the pi electrons in the carbonyl pi bond could be pushed down and delocalized into the ring. Why is this not possible?
As your concept oxygen gets positive charge and that leads to least stability which is as follows: