I grew my hair out from pixie cuts several times.  If your hair is not already one length, I'd suggest working with your stylist to get hair trims that will ultimately give you hair that is all one length - without layers.  This can be a challenge, but it is well worth it.

When you struggle with styling your hair, let us know and we might be able to provide you with new styling suggestions to try that will help you get through some of those more awkward lengths.