I find the more I do this challenge the easier it gets. On day 10, I parted the hair in 3/4 on the front and a 1/4 on the back. I split the back below the left ear and began rolling from left to right in continuous motion until I got to the forehead. The same motion is repeated on the left side — rolling towards the forehead. The tips are crisscrossed and pinned underneath.
Usually I will put a hold pin to keep the roll in place while rolling the other side. And wouldn’t you know it, I forgot to take one of them off this time. You can see it peeking on the top image. Ooopsy!