It doesn't look bad, but for women the haircut is always an indicator for what state she is in (hair in face/ pony cut = insecurity/teen).

Since you're considering to cut off your hair completely, I assume there must have been a significant emotional development in your life. Women tend to make this visible by changing their hair style, aka cut it off. But short hair is usually depending on the shape and looks of the face and in the most cases also a fashion thing. That's why too often it doesn't look good or it looks outdated faster than the hair can grow again.

The solution: You leave them long, perhaps shoulder-long and get rid of the pony and everyone will see you're a "new" woman;-)