To draw it that way you have to break a bond, which isn't really an accurate representation of hyperconjugation, but it predicts the right effect. In your carbocation example, notice that you would also make a R+, which you left out, so in the same sense in the radical case you would make a R. and the double bond.
In the case of an electron donating group you get another (real) resonance structure where the radical is on the heteroatom, e.g. R2C(-)-O.