Bronnie Ware spent years as a companion to the dying. Her memoir, The Top Five Regrets of the Dying, recounts her observations from this experience.
First, there is some elided or accepted-without-analysis context around Ware’s work. Ware is in Australia, and she was working as an end-of-life companion for people who could afford to hire and house her around the clock. Based on her reports, her clientele did not generally spend their last days in a house bursting with friends and relations.
In short, Ware’s experience has a sampling bias skewing toward affluent people who spent their life working to accumulate financial wealth. The experiences and regrets she outlines may not be universal, but rather culturally determined.
With that caveat, the culture she describes is a heck of a lot like the one I live in here in North America, and her observations reflect the regrets of the “winners” of this culture.
Their regrets are telling.
“I wish I'd had the courage to live a life true to myself, not the life others expected of me.”
This was the #1 regret Ware observed.
To some extent, we all conform to the expectations of others; it is an adaptive behavior.
Consider a child responding to a parent's raised eyebrow as they are considering throwing a tantrum and thinking better of it. That is conforming with another's expectations. Functioning in any society requires some amount of acquiescing to external expectations to one degree or another every day of our lives.
Most of the time it is harmless; other times it is life-ruining.
While I have met some attorneys who love their job and live a life they truly enjoy, I have met more who have done eight or more years of schooling to come out the other end hating their career field, the amount that it impinges on their life, and feeling trapped because that is the “only thing they can do,” and likely came with significant student debt financially trapping them in a high-earning career.
These paths are so insidious because many of these decisions are made before one's own sense of identity is fully formed. Depending on when one realizes they are on the wrong path, it can be damned hard to course correct.
I don't think there is any foolproof way to avoid this trap, especially given how much of our early circumstances (and opinions) are shaped by our environments. If you have beloved youngsters in your life, do your best to see them for who they are, not who you think they should be. We all project our own inner life onto the world around us, but do your best.
Furthermore, to serve others well, we must first serve ourselves well. To quote Brené Brown, “When we don't give ourselves permission to be free, we rarely tolerate that freedom in others. We put them down, make fun of them, ridicule their behaviors, and sometimes shame them.”
Give yourself permission to be free. If not for yourself, do it so that you may give that gift to your beloved young people. Now, permission alone does not grant one the means to follow that path, but it must be granted before one can begin.
We all have a mishmash of values, some of which are our own and some of which we inherit or adopt from the cultures in which we live. These values are essentially never all in perfect accord; there will always be dilemmas, and there will always be tradeoffs. It can be incredibly tricky to tease these apart, but it is worth coming back to time and time again, getting a little more clarity with each attempt to understand. The closer you can get to living in alignment with your own true values, the happier and more contented you will be, and the better you can support others who wish to live their own life.
“I wish I hadn't worked so hard.”
This one screams “status game” to me.
The people Ware is reflecting on are those who sacrificed their personal life and/or relationships to accumulate more points in the money/status game long after they had acquired more than enough to take care of themselves and their family. No matter how high your “score,” there is always someone ahead of you, and the time spent racking up an arbitrary score beyond need or actual want, is time not spent tending to (or even recognizing!) the things you do value.
In short, even when you win a status game, you lose.
Anne Helen Petersen touched on this in an article1 in which she discussed remodeling culture. This is the trend in which we constantly compare our home to professionally-produced imagery and assume that we must meet some ever-shifting, content marketing-driven standard to demonstrate that we “belong” (to what?) or are “good enough” rather than designing around our actual needs and preferences, which might involve leaving dated or un-trendy options that are functional because we genuinely like them — or just don’t care!
I think of this trend as the status game of our living space. From Petersen: “remodeling culture makes you look at every place in your living space and see it as broken — which strips it of its capacity to comfort you.” Your home stops being your home once it becomes an object to show you can meet or exceed externally-imposed standards.
The status game writ large applies this same logic of infinite comparison to every facet of your life — even the kids aren't “good enough” if they don't jump through the correct hoops on the correct timetable. The game is rigged to be both unwinnable and deeply inhumane to its players.
Spoiler: You don't have to play.
As a counterpoint, I am not convinced that a person coming from poverty working those same hours to give their family financial security and their children a shot at a better life would necessarily have that same regret.
Regret requires agency; there is a fundamental difference between wishing the constraints of your reality were different and understanding that you had a choice — and whiffed it.
“I wish I'd had the courage to express my feelings.”
The only thing I can come up with for this one is allowing one's fear of rejection to drive. Every scenario I can think of with boils down to a fear of being uncool or not fitting in (being rejected by a group) or not having feelings reciprocated (being rejected by an individual).
Rejection is not a pleasant feeling. In its mildest forms, it stings. Its more potent forms can be devastating.
Yet it, too, is a part of life. As deeply unpleasant as it feels to be rejected, optimizing your actions to please people and groups that wouldn't actually want your whole self is how you set trap #1 for yourself.
Cliché as it is, the people who like you for the whole of you are the ones you should be focusing on, not the ones who only like the most curated, polished, or prospective version of you.
As painful as rejection is, it can also be interpreted as dodging a metaphorical bullet; those who would reject you for who you are are not who you need in your life. And those who accept you warts-and-all are the same ones who will give you the space to live your own life, not the one defined by others.
“I wish I had stayed in touch with my friends.”
It seems nearly everyone in the society this work describes is swimming upstream on this one. Our society is designed around work and the nuclear family; this is insufficient for our needs. We need a mix of people and relationships far broader than a nuclear family can provide and much deeper than coworkers can — and heaven help you if you move in adulthood and have to start from scratch.
Call your old friends. Call your parents and siblings. Arrange to meet people who you like when you are doing things you would do anyway (such as going to the farmers' market or a local event), and make an effort to meet up with friends to do things you both enjoy. Take the time to sit and have a beverage with someone whose company you enjoy. And keep making time for friends. Easier said than done, I know, but crucial nevertheless.
At risk of being morbid, while your besties from the beginning of time are worth their weight in rubies, keep making new friends as you go. All relationships are ephemeral through either drift or death, so we can never have too many. A gentle reminder: you can't do this if you are working every hour of the day.
“I wish that I had let myself be happier.”
This one just makes me sad. Excluding things like the anhedonia that comes with depression, we really do have a say in how we experience our life.
An anecdote: Ages ago my friend an I joined a photowalk in the Phoenix, AZ, warehouse district to photograph anything that caught our interest before urban decay succumbed to the wrecking ball and gentrification. Being photographers, quality of light was considered a higher priority than quality of living, so we were meeting the group just before dawn.
I picked up my friend in the dark, and we took I-10, which is a 6-lane freeway, to the meetup site. We got stuck in totally [redacted] stopped traffic before the [redacted] sun came up.
Grace in traffic snarls is not my strong suit. Someone had rolled an SUV across all 6 lanes and everyone who had somewhere to be at that wretched hour was channeled to the far-left shoulder. Needless to say, I was fit to be tied by the time we finally (FINALLY) parked the [redacted] car.
And then we started our photowalk through the grimy, dilapidated warehouse district at dawn.
With that, I was looking for beauty. And I found it.
I found artful graffiti, the grace of natural decay, collaborations between man and nature. At one point, I recall inching (very carefully) on my stomach across an alley filled with broken glass because the juxtaposition of faded teal paint and vivid orange rust on a Dumpster wheel was an object of transcendent beauty.
Needless to say, by the time we had shot a few rolls of film (I am old), met up with the group to discuss our favorite things, and decamped to the Village Inn for breakfast pie, I was a different person.
That is the day I learned that I will generally find what I am looking for, so I might as well look for something good.
There is nearly always a valid reason to feel upset. There is nearly always a valid reason to feel wonder. Look for the wonder. Don't worry, you'll still have plenty of frustration and disappointment, but this way you will also get transcendence and joy.