Meaning of Life
How to Live a Life Without Regrets
This is a topic worthy of further thinking and debate

We must have read this subject header multiple times on covers of best-selling self-help books and magazines. I will go on the record to say most of what they have written leaves us scratching our heads.
For one, this question is too broad. It will require more than a book or thesis paper to answer this question with depth. Secondly, life experience is required to answer this question convincingly.
I came across this question multiple times in my life, though unrelated events separated by a huge block of time. The first event is more recent and has to do with an imminent mid-life crisis. The other was a parting message from a beloved Aunt who passed on a decade back.
Let me share these stories, my reflections on these stories, and then come back to tackle this question. By doing so, I will be able to provide context to this story.
The first event that gave rise to this topic was a recent ex-colleague catch-up over evening beer. It was a Friday, and it was after work. It started with the standard how are you, and it progressed rather uninterestingly towards our sentiment against bosses we do not appreciate.
After a few rounds of cheers and badmouthing, Kevin, an ex-colleague turned long-time confidante went on a sentimental mode. He let out a heavy sigh before muttering a sentence that closely resembles the very topic of this story.
“It is difficult to lead a life with no regrets, especially when we are fast approaching 40 years old.”
I was shocked. So was the other guy. I asked what happened, and Kevin recounted a story when he discussed the flow of a client presentation with his boss one evening before the Big Dance.
It was an unhappy occasion for Kevin. All his proposal points got rejected by his boss, despite explaining again and again that these points are direct requirements from the client.
His boss did not buy that, refuted all points, included all his points, and sent Kevin to re-do the entire presentation deck overnight.
The both of them got crushed the next morning. Kevin got it hard from the client because they told him explicitly what they wanted. The client was really pissed.
His boss noticed that the situation took a nosedive and tried to salvage it by pacifying the client. He mentioned that Kevin would pay more attention the next time.
The client team stormed out of the meeting room, and Kevin was battling an internal Hurricane Sandy. When the Managing Partner asked what happened, his boss said that Kevin screwed it up and that he will pay more attention to scrutinize his work the next time.
The Managing Partner left the meeting room unimpressed, and Kevin kicked the wall of the meeting room when no one was around.
He blamed himself for keeping quiet each time when he should fight for the best professional outcome. He got frustrated for allowing his boss to take control of the client presentation.
I regret keeping quiet. It was a choice to make, and I chose to focus on my promotion prospects. Yet, by doing exactly that, I lost the customer revenue to support my promotion.
I listened to his story. It spiraled into a different one. It was one where my beloved Aunt said something remotely similar.
When Kevin was recounting his story, it brought me to the second one deep in my memory lane. It was what my Aunt said to the pastor in the hospital ward before she passed on.
“I did not live a life of regrets. I did what I wanted, and I have done my best in everything I have ever done.”
I was in the ward when the pastor was around. My Aunt, who has been weakened tremendously battling liver cancer, showed visible signs that she was losing the fight.
My emotions swelled to the nose when I heard her final words. It was a complicated web of emotions containing grief (she was close to passing) and admiration (for what she said).
I have been serving duty at an Old Aged Home for 3 years by that time. I have witnessed many nonagenarians and octogenarians mentioning that they regret doing this or not doing that over multiple occasions.
My Aunt, who passed away at 55 years old, was clearly on a different life path. And I got curious. What did she do differently?
My mum had nothing good to say when I asked her. In her accounts, my beloved Aunt has been a selfish individual who never helped out in household chores when she was younger (because my Aunt was pursuing a scholarship).
She would rather attend client meetings than bringing her daughter to the clinic for a Hepatitis B injection (my Aunt is an entrepreneur).
My mum believed that my Aunt must be filled with regrets and remorse during her final hour because she never played her role as a sister and a mother.
1 family, 2 sisters, 2 lines of thoughts, 2 divergent philosophies of life.
Both Incidents Got Me Thinking Harder About Life.
Specifically, thinking about minimizing regrets in my life. It turned out to be tougher than I have initially imagined.
This is not some motivational, productivity, or finding the North Star issue. It is neither strategic nor tactical in nature. It is about a way of living.
But how do we minimize a sentiment that cannot be easily understood and is highly contextual?
Kevin concluded that he would not have to bear that element of regret if he had my level of openness to voice candid opinions. And, opinions from my Mum clearly did not jive with the way my Aunt had assessed herself.
To prevent throwing darts in the fog any further (which I already have for many evenings), I decided to do what good students always do. I looked up the definition of regret in the online dictionary.
This definition is from dictionary.cambridge.org.
A feeling of sadness about something sad or wrong or about a mistake that you have made, and a wish that it could have been different and better.
And this definition is extracted from collinsdictionary.com.
VERB TRANSITIVE
1. to feel sorry about or mourn for (a person or thing gone, lost, etc.)
2. to feel troubled or remorseful over (something that has happened, one’s acts, etc.)
NOUN
3. a troubled feeling of remorse over something that has happened, esp. over something that one has done or left undone.
4. sorrow over a person or thing gone, lost, etc.
While the definitions did not give me any form of clarity, they bring out the elements that have to be present for a regretful instance to be invoked.
- First, there is an action or inaction.
- Next, there is an emotional response triggered by the action or inaction and is negative in nature.
Given that such parallels exist within different definitions, we need to take these anchor pillar elements and examine how they constitute regret and how they apply to various individuals with different experiences and perspectives in life.
We start with action or inaction.
Action Or Inaction Is A Response, Not A Trigger.
Our response determines whether we act or we do not. In the face of fear, we either flee or fight.
That means our response is a result of our decision-making process. And our neocortex is preoccupied with making decisions for today and the long term all the time.
Decision-making is about making a choice. That choice determines our response in a direct fashion. Should I head for a run today? Should I go for a beer?
At the core of decision-making is a binary consideration. In its simplest and purest form, decision-making is about Yes or No. And it is either-or. We cannot drink beer and not drink beer at the same time. It defies the Laws of Natural Science.
And that sets the stage for regrets to manifest. More on that later. For now, let us focus on the binary options that are presented to us.
It is true that Yes or No is a form of binary option. However, it is not the only form of choice we make daily. Consider the following: -
- Should I go for a beer this evening?
- Should I eat the apple or the orange?
There is a subtle and critical difference between the above options. Option 1 is a manifestation of Yes or No. To drink or not to drink. This comes in the form of choosing A or non-A. If we choose A, we cannot choose non-A. They are mutually exclusive.
Option 2 is an extension of the comparison between 2 different choices. Should I eat the apple or the orange? That comes in the form of choosing A or B. There are zero elements of mutual exclusivity. And orange is not a non-apple, so to speak.
Understanding the nature of options provided in our decision-making process will allow us to understand the depth of regrets as they arise.
From Decision-Making To A Swell Of Regrets.
The scarcity of time and resources dictates our decision-making process. I learned this in Economics 101 class. The easiest way to explain this human phenomenon is through the use of money.
The value of money is derived through its utility. A dollar of Zimbabwean currency does not spend the same way a dollar of United States Dollar or Singapore Dollar. Utility governs consumption and acceptance for commercial transactions.
When we operate on a budget, our brains start to freeze. We start to transit from spending without a care in the world to thoughtful expenditure. Thoughtful expenditure is about decision-making.
- The same dollar spent on an ice-cream waffle is gone. It cannot be deployed for a can of coke.
- That $10-dollar note used to pay for Starbucks coffee is gone. It cannot be deployed to pay for a family dinner by the beach.
- We cannot save that $50-bill that we have spent away.
Because we have limited financial prowess, we need to make choices that affect our daily life. It goes from ice cream to dinners to savings. We have to maximize the value of what we have.
Now, the science of decision-making intertwines with value-judgment. Economic value is not hard science. It embodies a strong element of psychology and circumstance. That means what matters to you may not matter to me at all.
And that plays out around us daily. Let us use the example of having lunch.
There are 2 types of people I encounter when it comes to food. Some eat to live, and others live to eat. I belong to the former. My spouse is the latter.
Our orientation towards food influences our value-judgment in terms of lunch. For me, a $2 simple fried rice is as good as a $10 set meal because I eat to live. I do not see the point of paying an additional $8 from an economic standpoint to derive equivalent utility levels.
My spouse is the opposite. She derives $100 worth of perceived value from a $10 set meal because she gets to enjoy her food at a leisurely pace and get to converse in between bites, knowing full well that she paid for that premium for a quality ambience.
So, $10 is as good as $2 to me and is worth $100 to my spouse.
Interesting, right?
Now we can start exploring regrets with choice and value judgment out in the open.
Regret is an emotion we experience as a result of not choosing the other option. We can experience it immediately, or we can experience it later. It does not matter in terms of the time continuum.
From a logical standpoint, we regret our decision because new variables have entered the consideration headspace, and we can no longer rescind our decision. We know that happens when we shout shit!
Let me use the previous example of apple or orange to explain.
In that example, the real estate in our stomach dictates the consumption of the final serving of food. So, we have to choose between an apple or an orange. We cannot eat any more than that.
Let us assume that we chose an apple for our post-lunch snack. Now, what happens when we take a bite into the apple, and it exposes a worm in it?
The first thing that will happen is a natural reptilian response. We will spit that bite of apple out from our mouth, throw that apple away, and rinse our mouth. That is perfectly human.
And we will start talking to ourselves almost immediately after that.
“Damn it. I should have chosen that orange instead. I regret choosing that stupid apple!”
This is what I mean by the appearance of a new variable. Without the worm, we chose that apple. With the worm, we choose the orange. This is based purely on logic, I mean, unless you love to eat worms.
Some regrets are invoked and magnified by emotions, which is different from logic. Money and time take centre stage.
This utility of money and time is most vulnerable to that element of regret because they represent what we cannot get back. We can never regain lost time, and we can never recover the family fortune that is lost to Las Vegas.
As such, we tend to revisit our previous decisions when we are not doing very well. I could have passed my examinations if I have not gone out for soccer. I need not have to borrow from the bank at a higher interest if I have adequate savings.
Sounds familiar?
The nature of time and money does not invoke regret through our historical decision-making process. The reason sub-optimal decisions are regretful and painful is that they involve our future.
Having to repeat our examinations means we have to study the same thing for one more year. Having to borrow from the bank means I have to repay the principal plus the interest. I get to buy less stuff until I am done with the loan repayment.
And because our future is held hostage by our historical decisions, we regret it big time.
That element of regret is magnified as we go through time. When we accumulate a string of regrets, we start living our lives staring at the rear-view mirror, and we will be stuck in our past forever.
That is not the best place to be at.
The Million Dollar Question — Living A Life Without Regrets.
I doubt we can live a life without regrets. However, I do think that we can live a fulfilling life when we actively minimize regrets.
Eradicating regrets from our lives is impossible. The issue is with control. You can do that if you are the decision-maker. If you are not, then we have to live with the consequences of decisions made by others.
When we are in the position to make decisions, every decision can be considered carefully before committing. That is about minimizing regrets, in my opinion.
How can we decide on thoughtful considerations? I say go with my Aunt and not Kevin.
My Aunt listens to her inner voice. She routinely journals her thoughts even when she was in her forties. I know because I occasionally stole a peek.
She would write down her previous-day experience and reflect upon it. Did I do well? How could I do better? Is there something that I miss? Would I make the same decision I did yesterday, today?
She marches forward, embracing continuous improvement.
And she is quick to detach herself from the work that has no meaning or presents zero value to her. Remember, any form of value judgment is deeply personal.
My Aunt values excellence and is a high achiever in the games that she chose. She excelled as a student overall, winning scholarships. She won book prizes for Mathematics and Sciences because she focused her attention on subjects that come naturally to her.
According to Mum, my Aunt skipped Art & Craft lessons and was never bothered with sub-par grades from English Literature. Oh, she does not do any household chores either. My Aunt either plays or not and excels when she does.
She accepted the lack of results when she did not invest the necessary effort. In a world of binary options, Yes is an All-in, and No is No, nothing more. Her expectations are pegged to the perceived value of the choice that she exercised.
In other words, she is always playing her own game.
While she has been regarded as a pain in the ass to other family members because she refused to play a part in maintaining the household, she wins by living a life that she wants to live.
Every point of consideration is about self-actualization. She seldom does anything because someone told her it is the right thing to do. She does the right thing for her.
She never understood why my cousins choose to be highly paid salary workers when they are highly educated. Her opinion is rather simple.
“That $5,000 per month you earn by working for other people is not comparable to the $5,000 you make growing your own business.”
She is a strong believer in minding her own business.
I am not in a position to tell if she is right or wrong. Time will tell. However, this is what I know.
My Aunt stood out among others because she lived her life the way she wanted it to be. She listened to herself.
She never doubted the conversations she has within herself. In fact, strangely, she seemed to have found her North Star before that concept was invented. She looked at her North Star all the time when finding her way through the jungle in life.
And this is how I believe we can live a life with minimal regrets. That is when our Quality of Life starts improving drastically.
Living A Life Of No Regrets Is A Life-Long Journey.
Aldric
About the Author:
As a content contributor, I write my observations from daily life and my business exposure.
Because our life experience is the bedrock of our unique perspectives.
