So far in my rather short life I met two kinds of people; those who regret, and those who don't. I honestly think a life without regret isn't a life worth living; to me it means a life of no risks (because you can't win them all). Those who don't regret seem to be kidding themselves at this point in my life; perhaps someday I'll think otherwise.
I quit when I feel I can't push further; in anything. Or in a spurt of self-confidence. For instance, if in a situation where I have been in an obvious rut, but stay out of convenience and safety, I will often go through times when I'll find no reason to push myself and in those times where I do I tend to shed my unwanted baggage (sometimes by quiting a job, relationship, friendship, school, etc) I tend to only quit after lots of time and thinking though.
__________________
EX: Whats new?
ME: I officially love coffee more then you now.
EX: uh...
ME: So, not much.
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