Hardest thing I've done? That's pretty debatable. And it's so long and complicated, I don't really feel like explaining it at midnight. I'm sure no ones cares either. :P

I've had a lot of bullshit happen in my life. Though a lot of my college experience and the retarded internet mob vs me (series 1 and 2). We're obnoxious to deal with but that can be chalked up in hindsight as just a long waste of my time, and some of it was probably my fault even if it was entirely consistent of altruism = suffering.

Middle school certainly was one of my lowest points in life, probably caused me more problems while giving me no actual benefits in the process. But, I'd argue that wasn't "middle school" itself. It was the kids, adults and my parents that made that a miserable experience. Nor was it my decision to go to it.

Though I guess this wasn't either, Hospital/Slowly Dying for about a week at 18. That wasn't fun, am I'm still technically going through it, because it's a lifetime problem...But again, "done" sort of implies your choice in my eye vs. experienced.

So, now there's two (I can think of currently.) that was a "choice" that was the hardest thing to deal with and caused the most problems.
There's one year where I let my roommate's brother's not be homeless and paid the fucking price for it. But though I'd consider that the worst year of my life in general.

But the hardest thing I probably did, was take my parent's threat head on and move out on my own at 19. To attempt to condense in a tolerable size chunk. Parent's threatened to have the cops arrest me, if I didn't move out in 2 weeks time. During this time, just got out of early college, so no money (aside what I had) no job and they would do nothing for me. Unlike most people, I wasn't a pussy and took it as a challenge.

Moved out in less than 1. Not a single irl friend of mine could help nor family member (or honestly even tried.) Sold everything I had to scrape some money together. I got an online friend/stranger I hanged with a few times to drive me to point A. (So assholes, be nice to strangers on the internet. Might actually come in handy if you ever deal with real problems in your life.)

Finding a place to live/move in one week already sounds pretty impossible in hindsight. But I did, moved into the ghetto. Only learned the place was roach infested later. In under a few months, I was mugged 10 times, harassed daily by someone, had a restaurant pulled so much shady shit for the sole purpose of making me not go there. (lawsuit worthy stuff) Was stalked and followed by people, had several people threaten to kill me and/or burn my house down. Assaulted, had my phone stolen several times. And I lived of 50 bucks a month for all purchases, not including the rent. Had no transportation. No real outside help. And I cut of my depression medication that my parents were forcing me to take, cold turkey. Then I lived with psycho recovering crack addict instead. Had money stolen, more verbal abuse, more assault and some more death threats. And in a single day, lost basically every single thing I had from 18 years. All gone. And I also couldn't take medication, that I basically needed to live. (not the sad pills. :P) And that's just what I remember at night and not including lesser important details and ignoring the endless search for a job that never came. I can certainly say I was alone as I possibly could be which I can guarantee you was the worst part. (because at least my other bad years had a cat.)

And, for good measure the only two things I had worth anything, I both lost at the end of this fun time. I had money coming my way, and my dad decided to tell me he'd steal it all and nothing could be done. Thankfully that didn't happen and I was finally able to get out of it. Wasn't a year, so that's why it wasn't my worst year. It was long enough. :/ (also in hindsight, comment is long and this was shorter than I could of made it.)

THe hardest thing I ever did was leave the man I had been completely in love with for 23 years and start over. I took only what I could fit in my minivan and left everything else, including my 18 year old daughter. She opted to stay and try to take care of her dad. I got in my van and drove to Alabama to a friend I had met online. After deciding that we were compatible in RL and not just as internet friends we got an apartment together. My daughter came down three weeks later and moved in with us. Friendship became love and my friend and I got married two years later.

He took a job driving over the road and became hateful and jealous of my being home. He would call 10-20x a day just to scream at me about everything that annoyed him. This was on top of 22 years of not appreciating me and verbal abuse. My kid was an adult and I finally decided I had had enough. Not one person, not even my sister that I am ridiculously close to had any idea. Sometimes you have to stand up for yourself and this was the only way I could do it.