Freedom hurts. Get a helmet.

"Could I have done more with my day? Was that the best essay I could have written? Was hot asphalt really the best place for a midday make-out session?" 
Regret, possibly one of the most biting of emotions, seems like an obviously negative emotion. People speak gleefully about life without regret, people take pride in putting painful experiences behind them. I'd like to make the wingnutty claim that it is not. I'd, seemingly insanely, like to postulate the opposite. I believe every pang of regret, every time the phrase "what if" tries to crawl out of your chest with its dull, searing claws, is a moment of true beauty. 
Let's start with choice. It is, simply put, what all of us fight for. The liberty to live how we want, love how we want and consequently, fuck up our lives however we choose. Choice is freedom; freedom is life. Freedom doesn't guarantee happiness anymore than oppression manages to discourage rebellion. What it does guarantee is that the external hurdles to happiness: the cops, landlords and voyeuristic politicians will be gone. If any of you can say that those have been responsible for all of the problems in your life, I skeptically offer you the sincerest pity.
So, what then? If freedom isn't automatic happiness, why fight? If our choices can leave us miserable and broken, why not give them up? I fight because I know that those moments, the ones that leave us wishing we could take everything back, are the same moments that can make us ecstatic. The night that ends with our head in a toilet could have been the party we tell stories about for years. The community garden that ended with a shouting match and a field of rotten produce could have been a vibrant source of life and beauty. The moment a lover's words turn you into a walking scab could have been a kiss that sent you soaring.
Imagine this on a societal scale. Imagine the potential wonder we humans are capable of. Sure, we can and will fuck up. Sure, a lot of fights will be lost and a lot of ideals abandoned. But I'd take the sweet sting of regret over the cold, crushing tedium of lives in the world we were tossed into. I know it's a cliched sentiment, but hurt really does beat feeling nothing at all. Strap on a helmet and put on a party hat, because this world of choice is going to be a roller coaster, but who doesn't love those? 

May want to bring a barf bag.