‘The Ragged Bridge of Regret’ - Rev. Adam Slate

‘In Praise of Regret’ by Charlie Smith

Somehow the longing we speak of,
the look on the young woman’s face that reveals
her desperation,
the way my friend gives his sadness away
like a crime he can’t keep from talking about,
somehow this is representative of the best in us,
as lovely
and important as the spiky pink flowers
and the hydrangeas, a condition celebratory in itself,
occasion for gratitude this marvelous
regret, this agony
a father tries to conceal from his children
that is exactly the experience
to be brought up at the famous dinners of family and friends,
this uncontrollable sobbing
interrupting sleep, this anguish
cut on the bias and chronic,
it too, this delightful outcome, should be
given a place at the table, this honored guest
now raving among us, this fabulous sorrow,
enchanting dolor, the night sweats
and feverish cries, the exhaustion
so like repose,
this heartbreak just lifting its head,
the foolish, stupified grin of the totally bereft,
sister and kin, the lost
and now found (the foundered),
twitch and cry, the cock-eyed
consequence of happiness dashed, pale
cousins weeping in shame, let us embrace you.

Introduction

One of the gifts… and responsibilities… that sometimes comes with being human is getting to be present with the people we love at the end of their lives—and sometimes, being the one who has to make decisions for them. These sacred, impossible times arrive in many different ways. Expected and unexpected. After a long illness or a sudden accident. Surrounded by lots of family, or just a few loved ones.

My father became ill unexpectedly five years ago. He was hospitalised, and by the time I got there, he was already on a breathing tube, on painkillers, and only barely present in any way I could reach. For about a week I sat with him—keeping my siblings informed, consulting with doctors, and making decisions about diagnostic tests and courses of action. And then, eventually, about when to remove life support.

Afterwards—for a long time afterwards—I relived that week over and over. Scrutinising my choices. Wondering what he would have wanted. Did we try everything we could? Did I wait… too long? Were there things I should have said to him? Music I should have played by his bedside? Should I have asked more questions, better questions, about what he might have been able to hear or understand through the fog of painkillers and disorientation?

I’m sure there are wiser people than I who can move through that very human kind of experience without second-guessing their choices, but it turns out I am not one of them.

On Regret

Regret is one of the most powerful emotions shaping the contours of our lives. Research tells us it is the second most commonly reported emotion—second only to love. This comes from the author Daniel Pink, who wrote The Power of Regret: How Looking Backward Moves Us Forward, a book based on surveying more than 16,000 people across 105 countries. Most of the research I share in this message comes from Pink’s work.

One of the book’s important findings is that everyone feels regret. From around the age of seven or eight onward—unless we are living with one of several conditions that affect emotional processing—regret is part of the texture of human experience. It is not a sign of weakness or a failure of faith. It is part of what it means to be a creature who can imagine how things might have gone differently.

And Pink points out that regret is evolutionary. It is painful because that is useful to us. Regret wouldn't have endured as a human trait unless it served a critical function. Like physical pain—like the sharp lesson of touching a hot stove—the pain of regret is a signal. It is trying to teach us something.

The Four Core Regrets

Daniel Pink identified four basic categories of regret that show up across cultures, regardless of age, gender, or other background. He calls them the four core regrets, and they map surprisingly well onto what human beings most deeply value.

The first is foundation regret—the sense that we failed to do the work, put in the effort, or prepare for the future. These are the financial choices we wish we had made differently, the health habits we let slide, or the education we didn't finish. They often carry a quiet, grinding quality—less dramatic than other regrets, but persistent. Foundation regret.

The second is boldness regret—the roads not taken. Pink finds that we consistently regret the things we did not do far more than the things we did, and this dynamic becomes more prominent as we age. The business we did not start. The person we never told how we felt. The year we almost moved abroad but talked ourselves out of it. Writer Mark Twain captured this perfectly in this well-worn quote that may be familiar to you: ‘Twenty years from now, you will be more disappointed by the things you didn't do than by the ones you did.’ There is something clarifying about this. Failure stings, but it fades. Wondering ‘what if’ tends to stay with us.

The third core regret is moral regret—times when we took the low road. When we said something cruel. When we stayed silent when we should have spoken up. Or acted out of fear or self-protection rather than integrity. These regrets can cut deepest of all, because they can make us question not just our choices but also our character. And they can arise from both action and inaction—the hasty word and the missed moment of courage belong to the same family.

The fourth, and the largest category of regret, is connection regret—the slow drift away from people who mattered. A friendship that simply faded after a move. Siblings estranged over something that now seems impossibly small. A parent we meant to call more often. These regrets are so common, and so ordinary in how they happen, that they are easy to dismiss—until suddenly they are not.

Notice what these four categories reveal. Together, they point toward what we humans actually value, underneath all the noise of daily life. We want to have built something meaningful. We want to have been brave enough to really live. We want to have acted with integrity. And we want to have loved well and been present to the people who mattered. The regrets we carry are, in a strange way, a map of our deepest values.

The Power of Regret

It is tempting when talking about regret, to focus on its reassuring characteristics—the ways it can teach us, the growth that comes from looking back. And real and all important. But let’s stay here a moment longer with the pain that comes with our regret.

Processing it thoughtfully, and being willing to talk about it, does help us. It can unburden us—there is something about naming what we wish had been different, rather than carrying it in silence, that can bring relief. That can remind us we are sharing something very human.

It prompts us to think about next time, to imagine how we might act differently when a similar moment comes. Sharing our regrets—being honest and vulnerable about them—tends to draw people closer. 

We can sometimes be too proud to admit when we feel we have made the wrong choice, but it has been shown that people like us better when we do. Humans tend to trust people who have failed and reflected more readily than people who are less open about ever having stumbled.

Think of some of the people around you—friends, colleagues, public figures—who have navigated this most gracefully. Particularly people in positions of leadership or visibility who, rather than defending every choice, have been willing to say: ‘I got that wrong. Here is what I learned.’ That kind of honesty is disarming. It is human. And it tends to matter to people far more than a polished image of perfection and strength.

The Ragged Bridge

In my reading this week, I noticed that a lot of writing about regret falls into one of two categories. There is the enthusiastic camp—regret is a gift, lean into it, it will make you better. And then there is the cautionary, don’t-make-the-same-mistakes-I-did camp—accounts of deep regret that people are still struggling with; regret that hollows a person out, that is hard to find one’s way out of.

The truth, I think, is that regret is neither just a gift nor just a trap. Somewhere between these extremes, regret lies like a ragged bridge leading us from sorrow to wisdom—if we are willing to cross it.

The bridge stretches over a deep and menacing chasm. It sways and creaks under our weight, casting doubt on whether it will support us as we make our way across. There are missing planks, and it is hard to see the other side.

Crossing this bridge is not easy, or graceful. It asks something of us. Processing regret can take time, self-reflection, and courage. It is not a straight path, and it does not happen on a predictable schedule.

And it also takes support. Here at New Unity we have spaces—our grief support group, our monthly sharing circle—precisely because this work goes better when we do it in community, when we can witness one another on the bridge.

Conclusion

I was commiserating with my brother this week about how I have been wishing I was reading more, exercising more—the usual kinds of things. He pointed out, with his gentle, direct practicality, that we can start changing these habits as soon as tomorrow. And he is right. There is something I find genuinely surprising and exciting when I return to running after a break—how quickly my body remembers, how quickly I return to loving this part of my life that seemed like such a chore to keep up with just a few weeks earlier.

Many of our regrets, like these, stand as open-door invitations. The conversation we wish we had had can still happen. We can reconnect with that friend we have drifted away from. The thing we were afraid to try is still out there. With open-door regrets, yesterday's hesitation does not have to be tomorrow's constraint.

And even for all those closed doors—the losses that cannot be undone, the words that cannot be unsaid, the people no longer here to hear them—there are, still, other doors. The wisdom we carry from those experiences does not belong only to the past.

The year my father died I was doing a chaplaincy placement at a hospital near where I lived. The week after he died, right after I returned home, I was scheduled to work my monthly overnight shift. These shifts were usually uneventful–maybe one or two alerts for things we did not have to attend to, seemingly just for the experience of having a pager wake us up a couple of times in the night.

But on my first shift back, almost immediately upon arriving at the hospital, I was paged to support someone who was taking a parent off life support. The coincidence was remarkable; it was the only case like this I had during the entire year of my internship. After meeting with the family member, I remember taking some time to centre myself, and think about whether I would need to call the backup chaplain.

Yet even though my dad’s death was still very fresh, I could already see how regret was beginning to serve as a teacher. Giving me insight into when I should offer support and when I should step back; which questions I should try to answer and which should be left as mysteries. Contributing to the insight and experience I could use to function effectively as a chaplain.

We may never arrive at a place of complete peace about every choice we wish we had made, about the words we have left unspoken, the moments we cannot return to. Maybe that kind of peace is not what we are aiming for anyway.

The bridge from regret to wisdom waits for us—ragged and creaky, but fit for purpose. And when we begin our crossing, we may find ourselves more present, more honest, more willing to say the hard things and stay in the difficult moments for those we love.

Henry David Thoreau wrote that to regret deeply is to live afresh. May we have the courage to feel our regrets fully—and the grace to let them lead us.

Amen