From what I understand, you are a left foot forward rider. You cut out on the port side on your heels, which means you will be approaching the wake on your toeside. On the starboard side, you are cutting out on your toes, which means you will approach the wake on your heelside.
Your issue is with your toeside edge. Most beginners have issues with this edge. This drill is invaluable for improving your toeside edge.
Learn good technique before you start ingraining the bad habits.