The Strangeness of Regret

an essay

It is purposeful in who is selected. Those who can really sell the experience, the lifestyle. They lead you through the maze of buildings as they speak about all of what is available. To those who never got the chance to (or perhaps chose not to) take that path, a strange pang of unrealized nostalgia can creep up, the idea of a youth wasted. A strange regret of the past. I certainly felt this way as we toured a university campus with my son. The tour guide, a quirky, energetic engineering student in tall punk boots, regaled us with the endless fun and opportunities that could be had. For my son, it is an opportunity; for my wife and me, it tells of one missed.

I am an Ivy League dropout who tried desperately to attend classes while working a full-time engineering-level job, and my wife never attended university. The support for either of us to attend college was limited at best, and we took the opportunities we had and made the choices we made. Yet, as we spoke about this to each other afterward, we both wished we had taken the chance when we were younger to live on a campus and attend school.

One could say we regret our choices. Sure, I attended classes and did college coursework, but I never lived the culture. I was a working professional, never really a college student in the purest sense.

Regret lives in the spaces of the choices we wish we made. Sometimes it is the understanding, a lesson learned too late, of the consequence of a path taken.

One lesson I tried to teach my son, mostly as it sits with me many days, is in how we often have to own the good and the bad of the decisions we make. Sacrifices often occur where life simply cannot fit all of what opportunities exist around us. A saying I hear related to this is how one can only choose to do well in two of three things: family, friends, or career. At best, we can only get two of them right, no matter how hard we may try. While I don’t necessarily think this is wholly factual, I think it is truthful regardless, and at worst, directionally accurate. It touches on how we can only do so much as people, as we are limited by what resources are available to us, time being the most finite and precious among them. If one were to spend all their time at work, what time remains is then left to either friends or family.

One can only slice a pie so many ways.

Thinking back to those days, I remember a similar desire to attend classes. I wanted to be able to be involved in all those things others speak so passionately about. Yet, sadly, I am an introvert with some anti-social tendencies. In other words, I cherish my time alone. Granted, put a few beers in me or a glass or two of a half-decent whiskey, and I can transform into the extrovert of extroverts.

One cannot (and should not) consume alcohol regularly, meaning my extroverted nature remains intact behind a solid wall. Even still, the extroverted nature isn’t guaranteed to show, even with sufficient inebriation. Introversion thus reigns, with a more anti-social nature pushing forward. This renders the question: if I were given the opportunity to attend college, would I have done anything of the sort I believe I wanted? Likely not.

So what is of this regret? Why do I feel like I missed out on something?

Youth truly is wasted on the young. Back in the days I attended university, my mind was nowhere on friends and fun. It was on career. Remember, I said I was working as an engineer? A degree-less engineer, think of that! How common is that these days? Even to this day, I work as a director-level engineer without holding a 4-year degree. What should I regret here?

Life. Choices. The consequences of choice.

My dream is not to be a successful employee. Never was. This, forming thoughts and telling stories by stringing words together, has been my desire since I was still in grade school, though the ideas of becoming a writer full-time, without the need to be employed, always appeared out of reach, as it does to this day.

During my time at school, though my dream was to write, I was focused on furthering my career, making more money, and advancing in position. All my energy was to achieve more in my job. Writing was (as it is today) only a hobby. I daydream about self-employment. If I try to recall whether I had feelings beyond that, perhaps some latent longing for life at college, I cannot tell whether it was there at the time or a reflection of thoughts closer to today.

I would argue much of the problem with regret isn’t anything more than an inaccurate reflection of the past. In other words, our memories of the reasons for our choices, the resistance we experienced, the fear, the joy, the incentives and disincentives in all the decisions presented to us, those memories are tainted by the results and our distance from them. New experiences begin to add details to the past, coloring memories anew, hiding that which was there before. While we might believe our memory is infallible, it is anything but.

Even within seconds of an event, a fog can begin to settle over every facet, clouding our vision of what actually happened. This is only coupled with how our memories are already burdened by the limits of observation itself. At any given time, what we see is limited by the very condition of our 5 senses. Take vision alone; the entire shape of an object can appear distorted from one’s vantage point, further contorting this idea of accurate memory.

It is hard to tell the future, and given the equally poor quality of reflection, regret strikes me as a misreading rather than any accurate measure of how I would behave were circumstances repeated. Or it is an inability to accept the consequences of a decision, the sacrifices required to follow one path or another.

So, is this latent regret, per se, really an admission of feeling wrong for the choice, the sacrifice I made in pursuing a career first and education second? Most likely. Even with that, when I try to reflect back to the time, I conclude that I likely would repeat the exact patterns to bring me to the same point I am today, even while knowing what I know now, mostly because I know the person I am. These things were nice things to dream about, but they were never realistic for me. Not then, and not now.

That’s another thing I have needed to come to terms with regarding my reflection of the past: who I am and who I was. The core nature of what makes me and how that fits into the world. Nearing 50, I continue to struggle with the idea of interpersonal interactions. Given the chance to have a life at college, would I have dared to participate in the ways told to us by the quirky guide?

The path I took was different. And in many ways, the multitude of mistakes I made and continue to make build upon who I am. Can I truly regret something I learn from? Can I regret something in the past I would still choose today? No. I am not certain I can. Then why do I feel like it would be any different? How strange this thing of regret is.


Photo and words copyright © 2026 by Jeremy C Kester – all rights reserved.
Note: this is also cross-posted to Poetically Unlicensed on Substack.

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