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>didn't join the military back in '08 when I graduated high school
I never thought it was a good option due to having a scholarship to college (plus rents who were gladly paying the rest of the way), and to be honest I was a little scared when I thought about the Iraq/Afghan wars going on. Military guys might disagree with me on this, grass is always greener, but I'll never have the opportunity to do something as adventurous as join the military, experience the intensity and discipline of training, and deploy somewhere (if I even did deploy).
>not studying abroad in college
I was so close to fluency in Spanish, but now I've lost a lot of my language skills in it through disuse. I could have lived in Spain for the study abroad, and as I said before, rich rents who were offering to pay in full for it.
I've got a great gf, soon to be fiance, and make 85k as a software dev, but I'll never know what those experiences could have been.