Beyond the Regrets of the Dying

We can move through years without ever stopping to question the shape of our lives. Habit takes the place of intention; what began as accommodation becomes identity, and what once felt temporary gradually hardens into the way things are. Every so often, it’s worth stepping back — not to condemn the choices that brought us here, but to see them clearly enough to decide what comes next.

.   .   .

“One is never afraid of the unknown; one is afraid of the known coming to an end.”

― J. Krishnamurti

We’ve all seen these “top 5 regrets of the dying” lists at one time or another. I’d suggest it’s a worthwhile exercise to check in at least once a year to remind ourselves, and perhaps inspire ourselves anew, to lean into courage, authenticity, and to seek out what is true.

Life rarely operates on a set, predictable schedule. The idea here is to become more aware of who we’re being, what we’re doing, and why, because, for most of us, time is a limited resource.

Bronnie Ware’s top five regrets of the dying, observed during her eight years in palliative care, are:

1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.
2. I wish I hadn’t worked so hard.
3. I wish I’d had the courage to express my feelings.
4. I wish I had stayed in touch with my friends.
5. I wish I had let myself be happier.

In my view, regrets are pointless, depleting, and overly reductive. They’re an aspect of a disempowered victim mentality, rather than the mindset of a potentially prolific, entirely unique, creative being. You can’t make love or art or anything else useful with them in mind. So, let’s explore these top five regrets and see if we can’t make them more useful in our here and now.

“The more you know yourself, the more clarity there is. Self-knowledge has no end — you don’t come to an achievement, you don’t come to a conclusion. It is an endless river.”

― J. Krishnamurti

I wish I’d had the courage to live a life true to myself, not the life others expected of me.

Most of us are captured early on by ideas, ideologies, priorities, and values that were never our own. They’re certainly useful in our formative years. They help us define our personality, our framework for reality, and our identity. The trouble is that we unconsciously take ownership of them, integrating and embodying them, but rarely do we again scrutinize these elemental building blocks of who we are in any meaningful way. Not until much later. As a result, we may remain attached to that same identity, playing the same role for life, though perhaps with minor variations here and there: functional, but not all there. Engaged, but unfulfilled. Alive, but not really living.

We adopt rules, beliefs, and behaviors that contain and constrain the clarity and truth of who and what we may be. For any number of seemingly justifiable reasons, we suppress the courage to pursue that path. We’re not seeking a magic bullet here, nor pretending that every day should be blissful and happy. That’s simply another way of lying to yourself, bypassing the real in favor of the performative and superficial. That’s not courageous. It’s cowardly.

And no, this isn’t more reason to hate on yourself. The world offers plenty of that already. It is a clever, all-encompassing, violent, simultaneously parasitic and predatory framework, designed to break you, dissociate you from your better knowing and your spirit, and remake you in a mechanistic image that serves, works as a slave for, and feeds the machine — the system and its futile, predominantly material pursuits that foster toxicity within ourselves and our relationships and, of course, lead to frequent, if not chronic, illness and disease — and, in all likelihood, premature death.

You’re not wrong for living the way you have chosen to live. But much of what you do is motivated by a desire to avoid pain, suffering, and the general feeling of being hopeless and unhappy. It is this very patterned, repetitive, unconscious practice that keeps you under the synthetic world’s spell, under the thumb of those who thirst for power and control, normalizing dysfunction and despair and leaving you fatigued, apathetic, and perpetually exhausted.

We’re allotted only so many minutes in this one short life. Courage, like truth, is always there, at the ready, awaiting our decision to embrace it again.

“When you once see something as false which you have accepted as true, as natural, as human, then you can never go back to it.”

― J. Krishnamurti

You’ve tried from time to time to live true to yourself. Every few years, or perhaps after another failed relationship or business, or worse, after a relative or friend has died, you feel that soulful fire and renewed passion again. For a while, it gets you springing out of bed in the morning with a Hell yeah! Let’s get to work! Let’s do this!

It might take the form of a “new year’s resolution,” or some such meaningless nonsense. It could be renewed energy for that “must do before I die” project, the decision to start or end a relationship, to go on an adventure, or whatever keeps showing up every few years when you’ve, yet again, had enough of this shit.

You hate your job, so you quit, bringing all kinds of repercussions you weren’t prepared for. This can be a good thing, even a great, life-changing thing — exactly the kick in the ass you need. But do you have the courage to follow through? You’ve never had a real conversation with your partner or your children, so, in a moment of pure exasperation, you finally bring up the truth — your truth — and it blows up the fragile, yet entirely superficial, stability you’ve barely been maintaining.

That’s one way to do it, and it’s going to be messy, if not inevitable. But, as you probably also know, it’s unsustainable. You acted on a rebellious impulse, powered by a momentary spark, but if that’s all it was, it won’t take much to humble you again.

Life takes over before long. Getting out of bed gets harder as the anxiety and worries kick in the moment you open your eyes. The reality of such a dramatic shift in your paradigm reminds you that this courage stuff is hard, stupid, and frustrating. You remember the feelings of futility and unworthiness. Responsibilities you subscribed to long ago start getting in the way again, providing easy excuses to delay and defer. People quit on you (the same people you’ve relied on in the past) or start making the same old excuses (as they always have). Slowly but surely, the flame burns out, and the project, challenge, purpose, or life’s latest invitation for more, for the next-level you, gets pushed aside or goes back on the shelf.

But you can’t really blame “life” and “people and their shit,” can you?

Can you? This brings us to the second regret.

I wish I hadn’t worked so hard.

This regret is prevalent among men. Since the 1960s, though, I have no doubt it has become progressively more common among women as well. In the modern era, the programs of wage slavery and “hard work is virtuous” capture us all, equally and fairly.

Before going forward, we need to distinguish between three different concepts. First, there’s the slog and slavery of working for the sake of working: working for peanuts while making someone else wealthy, paying far too much in taxes, keeping up with the bills that just keep coming, maintaining a semblance of normality, and/or performing our roles as providers. Second, there’s the inspired, passion-driven kind of life’s work that, one presumes, is generally more like playing than endless toil, drudgery, and the mere marking off of repetitive tasks for pay. A day well spent in this pursuit, working harder than most, has the effect of rejuvenation and replenishment. Third, there’s the underlying principle we’ve bought into: the false and fabricated capitalist, corporatist offer, framed as the necessity and meaningfulness of always being on — of perpetual activity, doing more, producing more, and “doing our part” to contribute to the system. Either you’re part of the team, or there’s something fundamentally wrong with you. Everybody needs to earn a living, right?

Something else to consider is the idea of “freedom,” especially when it’s tied to finances. The idea that amassing wealth and material gains equates to being free of the very system from which that freedom was derived is ridiculous on the face of it. There’s a category error in thinking that we can comprehend how the truly wealthy live, what they value, and what their day-to-day lives look like simply because they seem to “have it made,” or to have no worldly concerns because “they were born into it,” and therefore enjoy a freedom we can only ever dream of. The trap of working hard to one day finally be free, or to “retire” (i.e., wait around to die), is an old one, but it still plays out in our society in various ways. It is a lie, plain and simple. I think the kids have figured out that their parents and grandparents were sold a bullshit narrative.

If you suddenly won the lottery, would you keep working? Of course not. You’d escape as quickly as possible, telling off anyone and everyone you’d been quietly resenting for years — and worse, you’d very likely burn through those funds in record time. Why? Because up until that moment, you’d been working for money, and shifting away from that deep-seated paradigm doesn’t happen overnight. You’re not even aware of it yet. You just see the shiny car, beautiful home, and five-star getaways, not the downstream costs and responsibilities. Money is a form of energy, and it amplifies who and what we already are. If we believe we need money to be free, to be empowered, to be resilient, to finally be able to do what we desperately desire to do, we’re at the whims of the system, because value and worth are defined by the machine, not by you.

Don’t kid yourself: “self-employment” and “entrepreneurship” can offer or develop into the very same traps and pitfalls — and possibly far worse, given the inherent risks — as the arguably simpler, cleaner, predictable, autopilot concept of a preconfigured day job. No matter the path, there are compromises and accommodations to be made. Every opportunity and offering requires education and training. There are costly mistakes, and perhaps, if things work out, some generous profits to be made. Where you choose to fit into the model matters. One way to look at it is this: if you’re living a life you need a vacation from, you might not be living your best or most authentic version of life. Nor is it certain that breaking away entirely from the system will satisfy you in the long term. That’s for you to decide and discern.

The ideas of working hard and working for a living are ancient, even a trick of sorts, rife with mechanisms of extraction that keep us forever spinning our wheels. Working hard has, in general, been weaponized against the majority of humanity. This isn’t something that suddenly emerged in the 20th and 21st centuries, though it has continually morphed and adapted to suit our generational and sociocultural “needs” — or, more accurately, our unchallenged, broadly normalized programs and conditioning.

Far too many fall into traps that define a road ending in regrets. This is complex because we need to better scrutinize self-judgment, self-admonishment, and their sources more closely. Life is a living tapestry of choices: decisions made in the moment, paths walked without knowing where they’ll lead. If, in the end, we judge ourselves negatively for those choices, are those judgments based on truth or on sociocultural, spiritual, familial, or other extrinsic conditions? On expectations, unconscious contracts, and passive agreements? Are they truly regrets — your regrets — or adopted perspectives, as in the first regret, based on someone else’s idea of what is meaningful, right, and just? There’s no way to know how our choices might alter our trajectories as we move through life. Second-guessing ourselves at every crossroads, every signpost, is a recipe for psychological and emotional fatigue and existential crisis.

It’s tricky because we cannot benefit from hindsight until well after the fact. We can borrow some foresight, certainly, from the lived experiences of others — usually our parents or guardians — and from what we observed as their “mistakes” along the way. But, more importantly, we learn through our own successes, mistakes, and failures, forming our best guesses and intentions about what we choose to value, prioritize, work toward, and pursue in life.

That’s the courage at the heart of this process: the courage to check in with ourselves regularly, to alter course, or to stay the course, to be brutally open and honest with ourselves and, more often than not, to catch ourselves in a lie. It’s the courage to own up to our failings and momentary weaknesses, to glean wisdom from our many transitory experiences and lean into our inevitable transformations.

And, of course, the courage to accept responsibility for all of it.

Get clear about what it means to “work hard” first, and why.

I wish I’d had the courage to express my feelings.

This one is another multilayered concept, isn’t it? On a physiological level, we know that repressed or suppressed emotions can cause harm, contributing to all kinds of health issues and even chronic disease. We also know that, when we educate ourselves about Recall Healing and Family Constellations, some of those suppressed emotions have deep roots, and physiological issues can often be traced back multiple generations. So, on the one hand, we develop behaviors, patterns, and coping mechanisms during our lifetime, most of which may forever be hiding in plain sight until we start taking apart our stories in earnest, and “doing the work,” as the saying goes.

On the more practical level, holding back feelings and self-censoring manifests in all manner of dysfunction in relationships, but primarily the one we have with ourselves. Childhood experiences, especially emotionally charged ones involving fear or psychological or physical abuse, whether experienced directly or indirectly, may imprint on us deeply, and carry tremendous weight. How and when we process them, if at all, informs our lived story. Becoming passive, pacifistic, overly accommodating, and endlessly compromising (i.e., people-pleasing) can all be downstream effects of emotional suppression. But doing these things to avoid conflict, argument, or upsetting the delicate balance, only does us harm.

And then there’s the truly terrible aspect to this regret. A well-practiced, well-performed emotional suppression paradigm inevitably spills over into other areas of our lives, to the point where everything is average, acceptable, tolerable, but mostly mediocre. This form of self-torture is essentially a mode of self-hatred that serves nobody. In the end, we’re better off treating it as a reminder that we’re not living courageously. Whatever the issue might be, wherever its roots may lie, it should be examined, exhumed, and excommunicated posthaste.

I wish I had stayed in touch with my friends.

People come in and out of our lives all the time. At least, I believe they should. Sometimes, they may be friends for life. Sometimes “found family” serve us in ways we didn’t have previously or otherwise. Sometimes, our actual family members become distant, disconnected, and never associate with us again. The latter is likely rarer, partly because many of us hold cultural expectations and assumptions about family and the blood ties that bind us. Usually it boils down to faith or religion, but it doesn’t have to. Abusive relationships with those who raised us can break things early on and they may never recover, or reconnect, nor should they, if the abusers choose to remain broken, even criminal, of mind and behavior.

Maintaining friendships or relationships that are lasting and transformative requires effort and a willingness to check in from time to time. When living at a distance, this can certainly become more difficult. And it’s usually quite different for men and women. It’s also quite different before and after, or during, marriage. That’s only natural. But if the friendship really matters, make the effort. If it’s eternally one-sided, perhaps it’s better to find new friends — and they may be much closer than you think.

I wish that I had let myself be happier.

“Happiness is strange; it comes when you are not seeking it. When you are not making an effort to be happy, then unexpectedly, mysteriously, happiness is there, born of purity, of a loveliness of being.”

― J. Krishnamurti

The idea of happiness is a fairly loaded one, isn’t it? Similarly, a “wish” is essentially a hope without taking any action, or, at the very least, the willingness to change. We cannot change unless we begin to know ourselves. We cannot begin to know ourselves until we stop seeking and simply know.

The feeling of happiness is purely subjective. It’s fleeting, transient, unpredictable, and comes in varying degrees of expression. What it means to be happy changes throughout our lives as well. We’re marketed the idea of happiness, usually alongside other loaded terms such as joy and pleasure, conflating or diluting them even though they’re very different experiences. But marketing is about selling something to someone, and usually from the standpoint of fear — the fear of missing out in particular. It’s all fiction, of course. Happiness isn’t simply achieved through novelty, the acquisition of material things, or competition with others. Happiness cannot be sold, and it cannot be bought. It cannot be won or lost. It exists in the absence of terms and conditions, similar to love in many respects.

But in this context, it’s more about the disappointment one may feel at not being more courageous, expressive, emotionally open, daring, and brave when it came to breaking patterns and routines, allowing ourselves to be truly seen, and, most importantly, evolving, healing, adapting, and thriving in ways we’d probably only imagined to be remotely possible.

We’re given every opportunity to look, listen, and feel the message — the quiet voice from within, that increasingly distant beckoning. All of these regrets are interrelated in this manner, for none of them would exist if any of the others were meaningfully addressed along the way.

I’ll leave you with one more quote from the inimitable Jiddu Krishnamurti, which sums up all of these so-called regrets rather well:

“We carry about us the burden of what thousands of people have said and the memories of all our misfortunes. To abandon all that is to be alone, and the mind that is alone is not only innocent but young — not in time or age, but young, innocent, alive at whatever age — and only such a mind can see that which is truth and that which is not measurable by words.”

― J. Krishnamurti

Solvitur ambulando