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1. I wish I'd had the courage to live a life true to myself, not the life others expected of me.
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It's not all it's cracked up to be.
I mean, sure, great, if you're into that sort of thing. Chances are you'd have just wound up feeling nervous and uncomfortable a lot of the time. Plus, you have to ask yourself who this you that you're supposed to be being true to actually is. Chances are, you got it right the first time, and the true you is driving a bus in Esher, rather than sipping green tea in an ashram in Kerala.
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3. I wish I'd had the courage to express my feelings.
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And if you had, you'd be sitting here thinking "Wow, I wish I hadn't been so loud and tiresome. Maybe if I'd kept my mouth shut I wouldn't also be regretting having lost touch with all my friends in point #4."
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5. I wish that I had let myself be happier.
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You can slag off vegetarians all you like, but no cow has ever gone to the abbatoir thinking this.