Stop Regretting the Present

Don’t let an imagined present be the enemy of enjoying reality

Case Western Reserve University, my alma mater, is known by its students primarily for being everyone’s second choice. Case is slightly less prestigious than the Ivies or MIT, and almost all the students were there because they had not got into their first selection. The effects of this were noticeable: claiming we had no school spirit was an understatement. There was no pride in the university and the only unifying force was a desire to be somewhere else.

The effects went beyond meager attendance at sporting events: it meant students spent four years — supposedly the best in their lives — wishing they were at a different school and regretting the choices that led them to Case. This phenomenon — wanting to have made different decisions in the past, and, as a consequence, not enjoying where you currently are — I call regretting the present.

We hear people express a regret for the present constantly in statements such as “if only I had taken that other job”, “if only I had not married my spouse”, or “I always think of how happy I would be in another city.” These capture the same basic idea: somewhere along the line these individuals made a decision they wish they could correct and they know they would be better off if only they had chosen differently.

The Detrimental Effects of Regretting the Present

Regretting the present is one of the most insidious mental exercises we can subject ourselves to. Not only do we criticize our past selves, we also disregard our current selves, and even project into the future by claiming that we will only keep making the same mistakes. The end effect is rather than concentrating on reality in front of us, we lose ourselves in self-deprecating fantasy lives we would have if only we had made different choices.

Even at the age of 22, I have a long series of decisions I replay over and over in my head, imagining alternative scenarios. These range from conversations I was too nervous to start, activities I turned down because I had to work on homework, and of course, where I went to college.

Recently, I’ve decided this has to stop; if I already have this many regrets, how will I be able to live with myself at 40 with another two decades of decisions behind me? There are no possible benefits to this constant criticism of my past decisions (this is decidedly different than objective reflection) and it means I am not fully invested in the present.

What is my plan of attack? I’ve adopted a two-part mindset I remember whenever I start to replay past decisions:

  1. Don’t let imagined presents stop you from enjoying reality
  2. Any sentence that begins: “If only I had done…” must end with “I would have been hit by a bus.”

These are a little ephemeral, so let me explain my reasoning.


There Are No Bad or Good Choices

From an evolutionary standpoint, I struggle to understand why we have a tendency to play out these fantasies of past decisions. It seems like in terms of survival, by definition, we wouldn’t have made it past the decisions we messed up, and, if we survived, then we made the right choice. Perhaps the problem is that now our bad choices don’t kill us (at least not immediately) leaving us plenty of time to mull over what we could have done differently. Although a bad choice doesn’t mean death (which is decidedly a good thing), it means we are stuck replaying and regretting our choices.

Confounding the problem is the proliferation of choices in western society. As Barry Schwartz describes in his book The Paradox of Choice, we have created a society with a nearly unlimited number of options in all situations from the small — which shampoo to purchase — to the life-defining — where to go to college and what to study. However, rather than leading to a utopia, the limitless choices have led to increased rates of depression and anxiety as well as decreased rates of life satisfaction.

Schwartz provides copious evidence indicating that the more choices we have, the longer we take to make a decision and the greater the regret when we finally choose. This is particularly pronounced for us maximizers, those who want to get the absolute best in every situation. Compared to satisficers, who can do with the merely good, maximizers will spend an inordinate amount of time making and regretting decisions.

While those who maximize may make an objectively better choice, subjectively they are much worse off because of the regret they experience.

Having identified my natural tendency to maximize, I have been trying to change into (somewhat of) a satisficer. I’ve been relatively successful in adopting the concept of “don’t let the perfect be the enemy of the good.” This is evidenced by my ability to release articles with only two edits instead of four, and accepting work that is at 95% instead of spending double the time to get it to 100%.

The next step is to take the same concept and apply it to making decisions. There will always be better choices leading to objectively superior situations, but the effort required to evaluate all the options means I am better off accepting a slightly less-optimal option and then not rethinking my decision. This is a satisficer’s way of looking at the world: there could be better choices out there, but once a decision has been made, they don’t matter anymore.


Moreover, I have been trying to strike the very idea of good or bad choices from my mindset. Classifying a past choice as negative only serves to reinforce the idea that you could be in a better place and gives your brain the opening it needs to start constructing harmful imagined presents. Instead, every decision is simply a decision and we need to stop and appreciate where we are rather than thinking of where we could be.

(There is something to be said for reflecting on what one might have done differently or drawing lessons from your past, but this becomes detrimental when we start passing judgment on our past selves. It’s one thing to say “maybe if I went back I would have studied history instead of engineering,” but it has a different connotation when phrased as “I would be so much better off if I hadn’t been so naive and pursued a history degree instead.” The first is relatively neutral, while the second can only be harmful to your current self. )

Just as striving for perfection on an assignment can prevent it from ever being completed, striving to make 100% optimal decisions and rethinking those that you’ve already made means you will never appreciate the present.

The Alternatives are Not Always Better

The second strategy initially may seem morbid: end any sentence that begins: “If only I had done…” with “I would have been hit by a bus.” Nonetheless, the point is not about the exact outcome, but rather that you don’t really know how things would have turned out had you made different decisions. While we like to think of events as a straightforward narrative, the real world is random, and a different past decision would just as likely lead to disaster as to success.

There is a common fallacy, perpetrated by traditional history books, that certain outcomes are destined to happen and successful people were shaped just right by their lives to come out on top. The mistake is that these books are always looking backwards, and in hindsight, it’s very easy to draw a straight line through what was actually a random series of occurrences.

This tendency to think in linear stories is known as the narrative fallacy and affects our thinking by convincing us outcomes are destined and cannot be changed. Reality laughs at this viewpoint: nearly everything in life, from who we marry to where we end up living, is ultimately random (see The Drunkard’s Walk: How Randomness Rules Our Lives). There is no coherent thread of events in the objective world until we look back and construct one.

Why this matters is that the narrative fallacy leads us to imagine different paths for our lives that are straightforward, with us ending up exactly where we wanted (as if we know where that is). In spite of our strong beliefs, it is ridiculous to think things would play out anything like what we imagine.


Any potential fantasy of a different series of life choices you dream up will be better than your current situation; that’s the definition of a fantasy. You’ll imagine a linear path from one good decision to the next, culminating in a dream existence with no worries. In reality, even if you had made all the right choices, there is still the chance you could start your dream job by walking out the door and into the maw of an errant mass transportation vehicle. That is just the randomness of life at work. Telling yourself that you would have been better off had you made different decisions is assuming that reality is linear and proceeds smoothly along a predestined path.

The strategy here is simple: combat those tempting fantasies by ending them in disaster. When your mind starts revisiting past decisions and creates a rosier future, put a stop to it with a random event.

Going Forward

I’m well aware that it’s easier to act yourself into a new way of thinking than to think yourself into a new way of acting. There is only so much (pretty much nothing) that mindlessly repeating a mantra can accomplish. To create lasting change, you need to put the ideas into practice. Part of my solution is right here: writing about my problem (thanks for listening). Writing forces you to think critically, and when I objectively examine my practice of regretting the present, I see that there are no benefits and that I am being irrational by constructing these straightforward stories of imagined success.

(I’ve also started ending other people’s “I should have” sentences with “but then I would have been hit with a bus.” This strategy is not advisable in all situations, but if anyone objects, tell them it’s for their own benefit.)

What’s more, human memories are — for better and for worse — extremely malleable. Although I use to view my college experience — both where I went to school and what I studied — in a negative light there’s nothing stopping me from flipping the script. If I had gone to U Chicago (my first choice), I would have been a small fish in a very large pond and would not have had the chance to grow to love Cleveland. My degree, while not directly applicable to my current job, taught me how to solve challenges and gave me a background in mechanical properties, a useful skill in my data science role at Cortex Building Intelligence. While you should consider your decisions to be set in stone (the ability to reverse choices actually makes us regret them more), your memories don’t have to be. Instead of weaving a narrative about what you could have done, try taking what you did do and putting it in a positive light.

Ultimately, there are always going to be many options, but you can only choose one, and those choices have led to a single present. There’s no use spending effort imaging a better present, and instead, appreciate your reality.


I welcome feedback and constructive criticism. I can be reached on Twitter @koehrsen_will or through my personal website willk.online.