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I don't know what to do with my hair.(advise on self cutting)

My hair has gotten pretty long and I have no attachment to that, I just hate getting my hair cut. I have been thinking of buying some clippers and just cutting it myself. Do any of you guys cut your own hair? I just want to be able to have my hair not make me look like a bum without having to go to a damn hair cutting store thing, I don't even know what to call them... If I get a set of clippers can I cut my own hair and have it look like I actually give a damn with out me having to actually give a damn?

I'm at the point where full on pony tail is a consideration in my hairdo. I don't even enjoy having long hair though I usually do. I need help! Do I continue down this long hair road or do I cut it myself? and how do I get acquainted with self hair cutting? I just hate salons and barbershop though I cant tell them apart.... they are all asian ladies who barely speak English, I just want respectable hair with limited fuss.

here is me with short hair:

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and now with long ass hair(most recent photo):

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