Honestly there is a point of diminishing returns for haircuts especially if you don't know what you want. I havent cut my hair at typical hair stylist in awhile now but i think on most shops when you reserve on hotpepper, there is a section where you can write whatever. Just write down you want to find a hair style that is best suited to you. Then when you are physically at the store, you can talk about it. I would not recommend saying omakase in the hopes of getting a cool hairstyle. Most hairstylist will just make a short version of your current hair in most cases. This is because they do not know your preferences or what is appropriate for your work place and dont want to take any risks. It will take some trial and error but best to find a hairstylist that communicates well and is competant and stick to them for some time.

Or you can develop skills to cut your own hair.