Haven't had a hair cut in 6 years, I don't plan on getting one.
People always ask when I plan to cut my hair, some are even shocked when I say I don't want to.
Is there any way you need your hair to be cut before growing it out? I was letting it grow quite long, but it started looking silly due to the different initial lengths (longer up top, shorter on the side). In the end I got it cut and it looked way neater again.
Find a stylist you trust, tell them you want to grow your hair out. They'll help you get an initial shape, and while it's growing, it's still important to get trimmed up. It takes time, and in the middle stages can look a little messy, but it all comes together in the end.
Also remember a little bit of styling can go a long way during those awkward lengths. Sometimes it really is all in how you wear it.
my grandmother used to threaten to cut my hair while i slept and she’s dead now. coincidence? yeah