This week, I’ve had multiple conversations with my friends, and, funny enough, they’ve all been about the same thing: regret. The rise in this theme may be in part the very nature of entering our 27th year; having enough distance from our younger years, with just enough insight into their consequences to hope things had gone differently. 

Of these conversations were four different friends, some working on their education, their families, their aspirations and their interpersonal relationships. They are each unrelated to the other, choosing vastly different lives from one another and from me. How can we all regret our hand in the unfolding of time? 

Regret is a byproduct of self-blame, and I will only refer to it this way. We do not simply wish things happened differently, but we explore our histories and past decisions with the belief that a different choice would’ve or could’ve produced a more desirable outcome. We begin imagining alternatives to reality, and we enter the process of counterfactual reasoning, that is, inventing outcomes that did not happen. Often, we relate to our memories this way, coating our past in the feeling of what could have been.

In my four conversations, the stories, though different, were all the same. They had each pinpointed a decision or series of decisions that sent them on their way. For some, these were smaller decisions but were impactful in their eventualities. These are decisions that snowballed, small acts that became large with time. Others made big life changes, moving cities and changing jobs before they were truly ready. There were regrets about love, there were regrets about self-advocacy; all in all, we could have done better.

Catch-22 is a book by Joseph Heller that took me way too long to get into, though it was great once I did. The phrase Catch-22 has entered the common lexicon to describe the inescapable dilemma of Heller’s protagonist, who wishes to be free of flying for the U.S. Army. His only way out of this fate is through being evaluated as “unfit” to fly, with sanity as the primary thing called into question. The dilemma is simple: to be unfit to fly, you must have degrading sanity, but the very act of asking for an evaluation would demonstrate the wherewithal sufficient for continued service.

See where I’m going with this?

Regret is a Catch-22 because your wishes to change the actions of the past are the result of the exact actions necessary for your wish to have manifested. You only regret because you have changed, learned and earned the rewards of hindsight. 

Regret is a perverse outcome of reflection. The idea that our examination of the past is a tool for becoming better selves is only one side of looking back. When we use this process, it often creates the very suffering needed to form regrets. We hold two versions of ourselves in opposition; we punish our present self for the knowledge we have only gained through the actions of the past, and we hold the past prisoner to the consequences beyond the scope of its time or place. 

So this is the dilemma: you are here, and you have grown. You have changed enough to regret the past; you are now regretful of the only thing that cannot change. Though regret is not rational, it relies on rational reflection to survive, where we have adopted the changes in perspective necessary for us to recognize that things could’ve been handled differently, but they weren’t. This was the way you found that out.

So you wind up with what is the most annoying feature of our existence, and that is that we will never be able to fully understand life. Our propensity to look backwards but live forwards is our only proof of the paradox of living and learning. That is, that we only hold the potential to gain from our lives in the very circumstances that take from it. We only learn to regret through consequences and personal development. Kierkegaard spoke of this extensively, that our inability to stop forward time from becoming backward time leads us to an impossible predicament. Our Catch-22, our regrets, our talks with our friends where we share our wishes that something had been different, that we had been different. 

In between the conversations I’ve been a part of this week, I listened to a podcast. One of the guests had spoken briefly about the need to enter the past from time to time. I’ve wanted to talk about this for a bit now, and now feels like the right time. 

The only way to resolve regret is to recognize that the past has happened and that your regret is merely evidence of said happening, but also of self-progress. We may become avoidant of our histories because of shame (which is different than regret), or delve too deeply into our regrets, to drown in our wishes and ruminate on the past (nostalgia). Though regret and shame make good friends, acceptance doesn’t tend to get along with them. 

Acceptance has an air of compassionate neutrality that both recognizes the depth of our consequences and the nature of our behaviours as context-based, and therefore knowledge-based. To be clear, I am saying that our acceptance comes with our recognition that we behaved with the tools we had, and though our toolkit now has more tools, we didn’t fucking have them back then, so cut yourself some slack. 

We are better able to accept our past actions when we don’t believe that they are proof of our own insufficiencies (shame) or hindrances (regret) that derailed the ideal path of our lives. The only way through regret is by looking at the past, but as the podcast I listened to so casually stated, you can’t go too deep, just enough to say that it happened. 

There is liberation in the process of facing the past with this view, as we no longer feel that there is a dilemma or decision to make. We have no choice but to accept the past as it was, as it brought us here. The feelings and thoughts of your present self are not going to be heard by the past. If it does not help better your life today or tomorrow, it’s probably rumination, not reflection. It’s not helpful to invent outcomes in our imaginations that stand no chance. We are holding ourselves between impossibilities.

Catch-22s tend to come from a lack of control and a set of rules that contradict. As people operating through consciousness with no real role in designing the human condition, I’d say we’re subject to a whole lot of both. We act, we change, we regret. We want better; we look back at when we could be better; we are upset by the opportunities missed. 

Until you develop the capacity to hone in on prophetic visions or master the science of time travel, I would say regret is going to be an annoying little fucker, like all paradoxes seem to be. But I learned young to move on from the unanswerables, opt out of the question of what could have been, and use that fascination to instead ask what could be. If you don’t like how regret feels now, you won’t like it later either. Drop the past into the ‘how it was bucket’ and thank it for getting you here. Things can be as they were when they were; there’s no use for it now.