I haven't grown my hair long since I was about 12 years old. I've had the fade / disconnect look for a few years and figured it was time to finally try something dramatically different. My ultimate goal for my hair style is the top knot aka man bun, but it's a long process.
When you grow your hair out you will hit many stages of growth where it's difficult to style your hair. It helps to have a little perspective on what to expect and how to handle the issues. We call these stages of growth - the penis stage. Where no matter what you do to your hair, it'll just look like penis.
Don't worry about that, have some fun and play around with it at different lengths. Think of it as a new hair style every month until you get to the length you want.