# Why is ester more reactive to nucleophile than carboxylic acids?

I was given just this statement at face value, but I think it refers to nucleophilic reactions where the carbonyl is the electrophile.

From what I understand, the $$\ce{-OR}$$ in ester is more electron donating inductively than the $$\ce{-OH}$$ in $$\ce{-COOH}$$ (due to the alkyl groups in $$\ce{-OR}$$). So this should make the carbonyl carbon less positive, making it a weaker electrophile, making it less reactive no?

The resources I read say that it's because the $$\ce{-OR}$$ is a better leaving group than $$\ce{-OH}$$. But alkoxide ($$\ce{RO-}$$) is a stronger base than hydroxide ($$\ce{OH-}$$), so why would it leave first?