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One common occurrence during mid-life is an increasing tendency to look back. For me, this introspection was triggered ceremoniously as the clock struck midnight on my 40th birthday. Given that the average man lives until his early 80s, I had reached my halfway mark.

This topic surfaced recently during a meetup with friends over drinks. Someone posed the question of regrets as a roundtable discussion. My friend in his 50s immediately responded that he wished he had taken up more challenges. Though I was already into my third glass of red wine and not entirely clear-headed, I understood we were talking about career regrets – a common theme.

This notion of regret had been on my mind even before the meetup. I had recently watched a K-drama called “18 Again,” where the lead characters fall in love during college. The male protagonist wants to continue his basketball career, but his girlfriend becomes pregnant. They drop out to start a family, and he takes on various jobs to make ends meet. However, he constantly looks back on the basketball career he could have had if he’d made a different choice at 18. Mysteriously, he gets the chance to be 18 again and live a different life.

The plot reminded me of “The Family Man” starring Nicolas Cage. In that film, the main character chooses career over love and lives to regret it, until he’s given a glimpse of how life could have been had he chosen differently. That movie left a deep impact on me and remains one of the few I’d rewatch given the chance.

For those unfamiliar with regret, let me explain. Regret is an aversive emotion focused on the belief that a past event could have been changed to produce a more desirable outcome. It involves imagining how life might have gone differently, often leading to self-blame and guilt. Regret is inherently negative, making us feel worse by focusing on past mistakes or missed opportunities. It requires mental time travel, comparing actual outcomes with imagined alternatives. Studies show that 83% of people occasionally look back and wish they had done something differently.

I probably spend 83% of my days regretting. What if I had studied harder and made it to a local university? What if I had the maturity to better manage my first relationship? What if I had worked harder when I was younger on my first business venture?

Regret is a painful emotion that can lead to feelings of disappointment and guilt. Persistent regret can negatively impact mental health, leading to anxiety and depression. Perhaps that’s why I often feel like a perpetually depressed soul.

In my most frustrated moments, I’ve even wished I didn’t have children, imagining all the free time I’d have for myself. There’s a common theme here: we think something is missing, often triggered by our current experiences.

As I write this at Amped Trampoline Park, accompanying my child to a playdate, a part of me wishes I could be anywhere else. How I long for the life of a single person! But obviously, that’s not possible. The toothpaste is out of the tube, so to speak. Facts are facts, whether we accept them or not.

I find solace in Naval Ravikant’s perspective on why comparing ourselves to others is unnecessary. If we prefer someone else’s life, we’d need to embrace everything about them, not just the parts we envy. We can’t cherry-pick the best aspects of different people’s lives – that idealized version simply doesn’t exist.

Importantly, the path we’ve chosen, rightly or wrongly, has led to all the good things we have in life right now. I likely wouldn’t be a published author if I hadn’t failed in my past businesses and careers. And those failures might not have occurred if I’d been a straight-A student, lacking the impetus to take risks as an entrepreneur.

For all the regrets my friend and I may have, we also have the good things that came with our choices. I can’t imagine my life without my children or the people I’ve met along this unintentional timeline.

Ultimately, the cards have been dealt, and ruminating on a better hand changes nothing. Driving while constantly staring at the rearview mirror will only lead to a crash. We only live once, so it’s best to play the hand we’re dealt and enjoy the rest of the journey.

Look straight ahead, embrace the present, and stop dwelling on what could have been. And perhaps, it’s time to stop drinking so much at meetups too.