Remember that hair grows forever, it doesn't stop. If you go out on a limb, drastically change your hairstyle and end up hating it, it can always be changed to something else, another style or color. Talk to your stylist to see if they have any fun celebrity hairstyles for you. You never know, they may have a style that they have been dying to try on you, but never had the opportunity before. Most hairdressers won't try to push a new style on you (nor should they), but if you ask, they love to share their creative side.
When an individual that has medium length or long hair and is just is out of ideas for how to style it then the perfect solution is the ponytail. It has many advantages such as keeping the hair off the face and looking neat and tidy without a lot of work.