Through much trial and error, I taught myself how to cut my own hair when I was still in high school. I like to style it my own way so I knew what I wanted. Messed myself up a few times, so my dad would fix it or I'd just cut it even shorter. If you keep short hair, it shouldn't be hard to learn how to cut it yourself. The guards on the shears do most of the work for you. If you keep medium length hair, then it's more difficult since you have to know how to work with scissors but you can also cover up your mess up easier if you style it correctly.
I slick it back with pomade, then comb and blow dry it to give it some volume, then hairspray it to make it stay.