Hair Flipping Up and OutQ: I'm a man who likes to wear his hair kind of long and I also cut it myself. Once my hair reaches a certain length, it tends to flip up and out at its ends in the back, whereas I would like it to either lie straight or curve inward a little. What can I do about this problem?
A: This sounds like a combination of styling issues and cutting technique. In most cases, to ensure the hair curls under, the inner layers - the layers of the hair closest to the scalp at the neckline - are slightly undercut (cut slightly shorter than the layers above them) thereby encouraging the hair to curve inward.
Apart from that, the hair can be styled to help ensure straightness. You can use styling product, such as hairspray in conjunction with a flat iron to smooth the curves into a flatter configuration (just be sure to let the pressed segments of hair cool before you comb through them or you'll just defeat your intended purpose). You could also use a round brush in combination with your blow dryer to style the hair to curve under gently in the back as desired.
The main thing will be to practice these styling techniques until you're comfortable with them and can create the look you desire.
Undercutting or inverse layering
Flat iron styling
How to blow dry hair