On Regrets

Dear PiePie,

At your age, I hope you don’t yet have any regrets, especially as Daddy and Mommy are likely making most important life decisions for you. But as you leave the comforts of home and we entrust you with such decisions, you will one day look back on the choices you have made, and that is when regret may come. About things you did. About things you did not do.

Regret, it seems, tend to occur when things didn’t pan out the way you thought they would and, knowing what you know now, you felt like you made a mistake. But this definition of regret is not quite fair.

For one, whether the decision is ultimately successful does not make the choice right or wrong. The world is probabilistic. So you may have made the right decision, but due to luck or whatever unforeseen circumstances, things did not pan out the way you intended. That doesn’t mean you were wrong, nor that you should regret the decision. The outcome should never be the only barometer of the quality of the decision.

More importantly, hindsight is perfect. Looking back, everything appears deterministic, but it is unfair to judge yourself on that. The better way to think about regret might be, knowing what you did then, would you have made the same decision?

The reason to think about regrets like this is not simply to narrow the list of regrets and make yourself feel better (although that’s a really nice side-benefit as well). The main reason is that hopefully, those regrets spur you to make better decisions in the future. But since you will never have the benefit of hindsight in whatever future decisions you will be making, it seems prudent to strip out that ‘advantage” in adjudging whether your decision should be regretted.

Upon reflection, when I look back and think about regrets through this lens, it seems they tend to fall into a few common buckets.

Impulses. In the spur of the moment, it can be difficult to control your emotions or temptations. And in those moments, it is easy to say or do things that you regret almost immediately. Beyond simply better self-control, the most practical way to avoid regrets here is to avoid or remove yourself from situations where your emotions and temptations might get the better of you. It requires self-awareness of your “tolerance” level, but things are so much easier if you are not caught in compromising situations. In the heat of the moment, it is often best to walk away to regain a cool head.

Fear. We tend to prefer options with more certainty, and which are “socially-sanctioned”. It’s safer to follow the grain of society, to do things that are not unexpected and which do not ruffle feathers. But oftentimes, the “riskier” option is less risky than it appears, except in the minds of those around us. And we are swayed into a decision that always leads us wondering, what if I had taken that path less travelled? In these times, it is helpful to take a long-term view and ask yourself, what’s the worst that can happen if I take this option, and am I willing to bear that consequence if it comes down to that? This is not an endorsement of any and all risk-taking ventures, since the risks for some decisions are indeed too great. But it is helpful to make an objective decision, casting aside social norms and conventions that may sometimes compel us to fall in line.

Compromise on values.  Some decisions are between doing the “easy” thing versus doing the “right” thing (it’s up to your conscience and values to decide what “right” means), and we may choose easy over right and come to regret it. This sounds like a simple-enough choice but it really isn’t, because things tend not to be black and white and what’s easy or right is never quite so clear-cut. I’d advice sleeping on the decision and listening to your heart. Because your brain can tell you what’s the better decision, but your heart will feel out the right decision.

All that I’ve mentioned is easier said than done, but whatever well thought through decision you make, commit fully. You’ve made your choice, now go and realise the potential of that decision. The action that comes after the decision is oftentimes more important than the decision itself. And anyway, if you’ve made the choice “slowly”, having considered all the information you have and casting aside any fear and doubt you might possess, I have faith you’ll make decisions you won’t soon regret.

I write this letter with great apprehension, knowing that what I wrote may be used against me in future “debates” on what you should do. But so be it, we shall have fun in those conversations.

Love, Dad