I shaved my head when I was 20 and it was the most liberating thing I've experienced. I had almost waist length hair. I felt so free and it was amazing to see my actual head for the first time. I had freckles and small birth marks I didn't know I have. I honestly loved how it felt the night after I shaved it with a razor. But you're right, growing it out was so difficult. So many awkward phases. I want to shave it again at least one more time. Maybe for my midlife crisis.