I have very, very few regrets. This might be my biggest one. I try to live and act in a way that precludes me from regretting anything later on. For example, if a girl breaks up with me, I’ll often keep trying and trying to get back together with her. Sometimes I know I’ve crossed the line of being annoying, but it’s t0tally worth it.
Whether we get back together or not, I never have to think to myself later, “Man, I wish I had tried just a little bit harder with her. Maybe then it would have worked out.” I have a clear conscience, I can go on my way with zero regrets, and I never really have to think about it ever again.
Earlier today I tried to think if I had any regrets at all, and I eventually found one. It’s something I haven’t thought of in about 8 years. At the time I was 17 and still living with mom and dad in Beijing. It was the summer either before or after my senior year of high school. And when I say senior year of high school, I actually mean what under normal circumstances would have been my senior year of high school. I was “homeschooled,” which mean that I pretty much just wandered around Beijing and did whatever I wanted. Best year ever.
Anyway, it was the summer of 2003 or 2004, and I was dating a girl. We had been dating for about a year and we were madly in love or whatever (remember, I was 17). She went back to the States for the summer with her family. I was heartbroken.
Dad had to go work in the Philippines for a few months that summer, and mom was going to go with him. They gave me the option of coming with them or heading back to America. But it was a no-brainer. I *had* to go back to America to be with my girlfriend. We loved each other. I couldn’t bear to spend any more time away from her. I missed her.
So sitting here at my desk at 25 and single, I can say that my biggest regret in life is not living in the Philippines for a few months when I was a teenager. I feel pretty good about that.
I forgot about Girlfriend as soon as I got to college (I don’t regret that), and now I think she’s going to nursing school in Arizona. I’m a struggling entrepreneur and have given away most of my possessions over the past few months. The goal was to fit everything I own into a carry-on bag so that I could easily pick up and leave if I ever got the urge to go somewhere… like the Philippines.