Regret: Facing, Feeling and Healing the Heartache of Lost Possibilities

A friend and colleague, recently turned 40, shared the following sentiment, “I have now reached the age when I experience regret. And it sucks.”

There, he said it. Just like that. I remember the relief I felt, hearing someone speak this out loud. Not whitewashing the experience with something like, “But it’s all good!” or negating the uncomfortable recognition by focusing one-sidedly on all the benefits of choices made and all the good intentions held. Just the raw and honest expression of regret, which, I find, gets spoken rarely these days.

Instead we often focus on forging ahead, ignoring the regrets we may feel (“No regrets!” being a familiar phrase and ideal), pretending them “away,” making do and moving on, even while we may be tripping up over unacknowledged regrets and all the feelings piled on top of or buried under them.

His utterance hit home directly, expressing what I, and I’m sure many others, feel as we reach an age when we have lived enough years that many things may have gone beautifully — just as we wished, hoped and strived for — and others likely didn’t, by a bit or by a lot.

It is a stage in life (for some of us this may come earlier or later) when we can look back and see the consequences of choices we made or that were made for us. We see paths trodden and untrodden, junctures, decisions, and circumstances leading us to where we now stand. While we may still have years ahead of us to take different routes, there are certain things we just wish so very much had gone differently.

I’m talking about the real regrets, the ones that don’t just go away, but keep niggling at us. The ones that really do suck. That keep popping up, when you’re trying to move on. That surprise you in unexpected moments; you thought you had dealt with them. These regrets are frequently tied with dreams and hopes, which are deeply meaningful, essential to you. They may carry heart-aching hurts and disappointments, or deep-seated shame, guilt, grief or anger.

Even when we seek to live in alignment with our values, some things are just beyond our control. Even when we try our best, we may hurt others. Even when we do everything we can possibly conceive of, things don’t always work out the way we hope. And sometimes we miss the mark. Fact is, we humans are fallible, we make mistakes, we are not always kind with one another, we effect each other for better and for worse, life is not perfect, and it is all a much bigger mystery than we could ever fully fathom with our minds and desires.

So what shall we do with our regrets? What does a healthy relationship with regret actually look like?

Here are some reflections & guidelines I use with my clients and, to this day, in my own life.

1. Neither indulge nor repress them.

Imagine you are swimming along a river and then, at one point, you find yourself unable to continue because your feet have become entangled in a riverbed weed. The weed in this case is “Regret” (you can apply this metaphor to any kind of stuckness). You tug and swim harder and harder, to no avail. You can’t swim on, your feet are knotted with this weed.

When we indulge a regret, we swim down to the weed, and then go over it again and again, we analyze it in every detail, and get even more tangled in the endless litany of “should have” and “could have”. We hold on to it and sometimes even become identified with it. We get so caught up in the regret that we feel paralyzed and victimized. We forget to just look at it, feel it, accept it, learn from it, and when ready, untie it and swim on.

When, on the other hand, we repress a regret, we avoid swimming back down and dealing with the “knot”. While paddling furiously forward, we end up making little if any headway, remaining stuck while thinking we are swimming on. By “getting on with life” and ignoring the feelings that need to be felt, we tend to harden, our hearts shut down.

Instead of these two approaches, I suggest you dive down, have a good look at what is going on, and untangle your feet from the weed. Acknowledge the regrets, face them, feel them, learn from them, make good wherever possible, forgive yourself and others, and in doing so, find new footing in the present and the future, rather than being held hostage to your past while thinking you are forging ahead.

Then you can truly swim onward.

2. Be brave and inquisitive.

Stepping into a healthy relationship with our regrets requires courage, curiosity and patience.

Let regret inform and transform you. Allow regret to soften you, to humble you. Let it change you and prepare you for a freer future.

Facing a regret involves figuring out what feelings are buried under or covering up the regret. Is there grief there? Or anger? Disappointment? Or disillusionment? Or a whole mix? Find out, and be present and honest with these feelings. You don’t need to do anything. You just need to be present with them, neither indulging nor repressing. Just feeling them sincerely. And that takes courage. They’re not usually what we think of as fun to hang out with, right?

3. Be honest. Remain curious. Make new choices.

Once you have discovered what you actually feel, you can make a fresh choice, a real one.

An example from my own life: Over the past few years I noticed that whenever one particular and persistent regret bubbled up it would come out as anger (sometimes just a disgruntled remark, other times a distancing and closing off of my heart, or outright blaming). This happened enough times to help me realize I was going around in circles with this particular regret instead of truly moving onward and up. Even if this regret would stay with me for the rest of my life, I didn’t have to stay hostage to the anger it housed. Even as I still wish things had gone differently, dragging bitterness along my future path was not worth it.

It took a while to gain this clarity. And then I curiously followed the anger to its root, where I found sadness. A deep well of: “That really sucks and I’m so very sad about it.” From then on, when the anger would arise, I took the time to soften and feel the grief. I shared it with my husband and spoke about it with a few close friends. I journaled and danced it. I gave it up in prayer and asked for overwhelming peace. I accepted it. And, bit-by-bit, it is easing. The regret is still there, perhaps it will be there as long as I live, but it is not dragging me down anymore as much. I am untying the knot. I am swimming on.

Following curiosity to find the source and making a new choice — taking the space and time to feel the grief whenever the anger has flared up, and trusting that when the true feeling runs its course, new Life becomes possible — has been the doorway through.

4. Just do the work. Don’t worry about the timing.

We like to have timelines attached to transformation. If you’re like me, you would love to know when you will finally be done with a particular regret and freely swimming on. But what if there is no predictable timeline? What if all you have to do is focus on the work, and let go of expectations around outcome and timing? What if releasing your feet from the weed takes longer that you wished, or less time? So what? As long as you are not indulging and not repressing, but simply facing it and allowing it to move through you, you really don’t need to worry about the timing.

Our work is to shed layers that get in the way of living and showing up fully. You may think you are all done and good with a particular regret, only to have it bubble up in an unexpected moment, months or years later, inviting you to shed yet another layer of the past, and refresh the future in doing so. The regret itself may linger for the remainder of our lives. And that’s OK. It’s not something we have to make go away. Every time it arises, we can simply notice it, allow it to deepen our experience of vulnerability and humility, and grow in integrity.

When regret has changed from something that drags you down, overwhelms you, closes down your heart and keeps you stuck into something that makes you more human, more caring and kind, you are swimming on and up. It may linger, but it has lost its sting.

5. You don’t have to do it alone.

Speak your regret out loud — to yourself, to a friend, to a piece of paper, to God, to your partner, to your therapist or coach, to your grandmother, to whomever you trust can simply listen and be present. There is something inherently restorative in this act. You don’t have to carry it alone. An ‘other’ can hold it with you.

One evening, a few weeks ago, my husband and I were sitting on the couch chatting about this and that, and our conversation ended up with both of us sharing our deepest regrets. Speaking them out loud, acknowledging them to one another, especially those that touched the other in some way, offered unexpected healing and intimacy.

I think we could do this more: two (or more) people, reflecting on the respective journeys taken thus far, the choices made, the dashed hopes, voicing apologies and insights gained. No frills, no drama. Not getting swamped in the regrets, neither accusing nor ignoring, but with a calm and gentle courage, facing and voicing, acknowledging, feeling and learning. Knowing that there is a place beyond regret, which can only be reached by feeling it, living through it and moving onward, rather than side-stepping it. Sitting together, heartfully matter-of-fact.

6. Don’t assume you know for another.

We can be so wrapped up and familiar with our own stories that we forget: regret is a very subjective thing, it is a deeply intimate reflection of a particular person’s life, hopes, dreams and choices. This became poignantly apparent to me in a recent gathering with a few women sharing openly what they regretted most at that point in their lives.

One woman’s greatest regret was that she was not able to get pregnant. She had tried for over a decade. She was heartbroken. Still longing so much.

Another regretted not having begun her career before having children. She was struggling with finding her professional footing now that her children had left home. She wished she had held onto herself more.

Yet another, almost shy to speak it out loud, but this was her honest regret: she had 4 sons and, while loving them to bits, silently wished so much she could have also have had a daughter.

One regretted choosing safety over adventure in her life.

Another spoke of the deep regret she felt every time she yelled at her kids.

One regretted marrying for the wrong reasons.

Another regretted divorcing.

There is no right or wrong when it comes to regrets. Let’s give one another the spaciousness and support to honestly face, feel and move through our respective regrets. Let’s be present to one another in this journey.

And let’s remember: We can’t always choose what happens to us. We don’t always make the right choices. But we do have a choice in this present moment about how we respond to our past and make way for our future.