Have you done something you really regret? If so, how did you recover from it?

A student asked:

Have you done something you really regret? If so, how did you recover from it?

I started thinking seriously about issues pertaining to regret when in the early stages of dating with my girlfriend (now wife). She had a lot of apprehensions about commitment, and she asked: “What if this relationship doesn’t work sometime in the future. Wouldn’t you regret your decision to be with me?”

I didn’t have an answer then, but the question forced me to think deeply about the issue. There is a famous phrase that you often find in self-help books and articles: “make decisions you won’t regret.” I found those articles rather fluff and unhelpful. But I did think to myself what would it mean to make a decision that I won’t regret? What would that mean to me?

After much thought, it occurred to me that there are two distinct types of regret: (1) regret over the decision; and (2) regret over the outcome. This was a very helpful conceptual distinction because it made me realise that there are some things in life where the outcome might have been regrettable, but I would not have regretted the decision. In which case, I may feel upset about what happened, but I wouldn’t live a life of regret over the decision I made.

Here’s a trivial example to illustrate the distinction between the two: I may have made the decision to spend time with a good friend all the way till late in the night. The outcome is that I am so sleepy I cannot focus and work throughout the day. I may regret the outcome, but I do not regret the decision to spend time with that friend.

Furthermore, there are situations where the outcomes are beyond our control. The success of some decisions is dependent on external factors like people and the current situation, and sometimes even luck! We may say that we regret doing something because we could have known, or should have known better. Yet, the reality is that there are many things that we could-have or should-have known but we just could not have known because those things lie in the realm of the unknown unknowns (I don’t know that I don’t know). When I’m personally involved in a situation where the outcome turns out really bad (very regretable), I do ask myself: is this something I could have known from the beginning? If, from my own reflection and assessment, I realised I could not have done anything to mitigate it there and then, despite my best efforts, then I would class this regret as a regret about the outcome. I would not regret the decision I made then (doesn’t mean I don’t feel upset over what has happened – those are two separate things).

Then the question now is: what ARE the sorts of decisions that I would or would not regret? I am aware that I, as an individual, change and grow over time. So my perspectives, my maturity over certain issues, and sometimes even my values change (or evolve) with every experience I acquire over the years. I reflected on situations where I look back to the past in regret, and realised that I regret the decision because I am using present-day-me to evaluate past-me. But past-me would not have had the maturity or insight or even the same values to have made the same judgement as present-day-me, nor would past-me have the same knowledge and awareness as present-day-me would have about the wide array of options available to handle specific situations (these were learnt over time through experience). So, just as how we can’t fault people for ignorance over certain issues, I too can’t and shouldn’t fault my past self for that lack of awareness or knowledge.

If I do want to validly and fairly fault my past self for a bad decision, it would have to be in a situation where past-me was aware of the range of available options and possible outcomes and making a poor decision fuelled either by fear or insecurity. Because those were moments where I could have – there and then – rationally made the right decision, but I chose otherwise. Those would be decisions that I would regret.

To put it another way, for me, to make a decision that I would not regret means that if I could go back in time and undergo the same decision-making process, the same past-me with that same level of finite knowledge and bounded rationality – would still want to make the same decision again and again. I don’t even consider my present-knowledge of the outcome, because who I was at that time could not have known what the outcome would be.

Were I driven by fear, anxiety, or insecurity, I might have made a poor choice then. But if I could repeat that moment in time where I could have handled my fears and weaknesses better, I would have chosen otherwise. And this would be how I can conclude that I made a decision I regret.

To answer your question, I use this way of thinking to evaluate my regrets. I have since stopped regretting a lot of things that I used to regret and emo heavily about because either (1) they are regrettable outcomes beyond my control or knowledge; or (2) the same past-me would have chosen the same decision again and again no matter how many times I replayed the scenario. So all these fall under the rubric of decisions that I do not regret – these were decisions made to the best of my ability. And I can only learn the painful lessons that may have arose from them, or indulge in the happy memories that they create.

And for the decisions that I truly regret, they become very valuable lessons on how to manage myself better: how not to cave in to fear, how not to cave in to insecurity, etc. They are very vivid memories of pain, and they serve to remind me not to repeat them again.