In a world where winning is everything, regret is seen as a sign of weakness and imperfection. Having regrets has been interpreted as losing in life.

“No point crying over spilled milk.” The metaphor is designed to be so simple, so relatable for children because it’s something we have been told as kids, and it’s something we are supposed to tell our children. Be forward thinking, stop thinking about the past. There’s just one thing wrong about this anecdote. I regret so many things.

I regret trips I never took, bad habits formed, skills not developed, toxic relationships prolonged, things I did, things I didn’t do, words said, words not said. I travel back in time, flip the event several times over and re-examine my options. I give my best guestimate of what could have been by what should have been. It doesn’t matter if it was life changing, an event when I was young or something as seemingly unimportant as a recent purchase. I do it because at the time, I think I made the wrong choices, but only when it was too late. 

When I was young, I had an extreme asthma condition. During my gradeschool days, I was sick for approximately 30% of the time, but I always did okay. I was so small, and quiet and frail, that I naturally turned me into a teacher’s pet. They didn’t mind if I just came to take the test.

Realizing this advantage I had, I thought to do what any kid has thought of. Fake being sick. So my mom woke me up one morning, and I didn’t really feel like going to school, so I told her I was sick and felt an asthma attack coming. It went smoother than I thought, no proof was required, I was told to go back to sleep and the rest of the day was no-class bliss.

The next day, being content with all the cartoons I got to watch, I woke up early to get ready for school. Mom stopped me before I got out and was ordered back to bed. “You might not be well yet,” she said. That one day turned into a tiring whole week of not being sick and doing nothing. When Monday came, I got sick for real. It was camping week, the 3rd or 4th annual camping in a row I’ve missed. And like clock-work, I was always sick for camping. Childhood ruined.

To this day, I’m still not sure if my mom thought I was really sick or if she was just calling my bluff. And not pretending to be sick won’t change the fact that I was going to get sick the week after. I was still going to miss camping, but at least I got to experience the preparation, the “pretending to go, and getting ready” even though I can accurately predict that I will get sick for camping day. I always get sick during fun events and occasions, especially camping. As my sister used to tell me when she gets pissed at me, “you’re allergic to fun, you can’t get excited.”

And that’s the story of how I am technically still a star scout. However we can’t stay in gradeschool forever, and as we get older, our mistakes get bigger, our future regrets deeper.

We’ve always been told, we are defined by our choices. In my head, I go back to those times, and resist. I argue… but that does not define me.

There was a time when I was young and reckless and brave enough to tell myself, “I will not regret anything in life.” 

Back then, I was more interested in winning rather than learning. Looking back, what’s funny is, now I regret not regretting.

I was quite the black sheep when I was young. I started smoking when I was 15. I started hanging out with a new friend, Anne. Every lunch break, we stayed at her friend’s place. That afternoon, we were just lounging in the living room, she handed me a lit cigarette and said, “Come on Jessica, one puff won’t kill you.”

In the days that followed, one puff became one stick, until it eventually became a habit. I will not regret anything. 18 years later, I still smoke, struggling to quit, regretting why I even started. Those days, I told myself, I will not regret this. After all, it’s part of who I will be.

Later in life, I realized I was lying. It was never about discovering who I was or standing up for who I’ve become. It’s about the inability to admit I was wrong. No regrets meant I didn’t have to admit I was wrong, that I should have made a different choice, that I should change.

I’ve done worse things in my life, and they haunt me all the time. They come before I sleep, when I close my eyes, or any other quiet moment, and I shut them by humming a song, or saying “stupid Jessica” out loud.

In a world where winning is everything, and regret is seen as a sign of weakness and imperfection, I don’t feel like a loser in admitting I regret.    

If we live a life absent of any regret, then how will we learn?