Transitioning

I thought I had decided that I got my last perm in 2010. However a brief convo with my boss's boss's boss (as in the top boss) lead me to this question:

Well, let me give u the replay then ask the question.
HER: "Oh, your hair was long last week. Now it's short."
ME: It's different every week.
HER: We had a picture in the paper of you over the weekend with the longer hair, which is not to say you don't look nice with shorter hair too, and I thought it was a great picture that they took.

So the question here is, when going natural, am I altering the texture by continuing to press it, or is it better to just let it grow like it wants to and leave it alone?