Emotions explored: The Regret Paradox

The Regret Paradox: A Masterclass in Turning Heartache to Hope

I love talking about regrets. 

NOTHING gives you more insight about a person than their regrets. And nothing gets you closer faster to people than when there’s a conversation on regrets – it’s just so easy to bond over because it is so deeply human. And I’ve had so many conversations about regret that it has blown my mind how vast, deep and impactful this feeling can be. 

Because feeling regret is feeling heartache, probably quite literal heart-pain. And that’s just the physical aspect, but more than that: regrets are the painful knowing of how you broke your own heart. And ugly does not get more beautiful than this.

If regret is something you’re struggling with then this is THE episode for you. And if you think that regret is a non-issue in your life, but there is one area in your life where you feel stuck, or certain patterns keep repeating itself in your life, then let me tell you: it’s most likely because you have unaddressed regret. And in that case: This is THE episode for you.

And I admit it is a bit freakish of me to be laughing when talking about regret let me tell you this: dealing with your own regrets is tough and painful work, but if you talk with other people about regret you will see their vulnerable, and beautifully human side and it is hard NOT to empathize with others, even love them for their regrets. And once you get to this point, of loving them for being imperfect, love them for knowing what it’s like to have a broken heart… and getting to the point of seeing how it is making them a fuller, more flavorful and complete person… once you’re there, it’ll be easier for you to extend the same compassion and admiration to yourself. Listening to this episode will make you think more deeply about regret, will empower you to talk more about regret and will help you deal with your regrets… and I’m not just talking about the shmoosy interrelational stuff, but the research and psychology behind regret. I’m going to nerd out completely, I promise there is so much here: you will want to listen to it 3x to get every single bit of it.

Lets get started.

Dear fellow Wisdom Enthusiast, this episode is all about regrets and I’d like to invite you to try a little experiment with me. bring one regret of yours top of mind for just a split second – got one? Got a good one? Good. Now tuck it away. Becaus enow We’ll dive into the research and science of regrets and at the end of it we’ll come back to your regret. We’ll back to check if your relationship to your regret has changed. 3-2-1

Allez – on commence.

Hi. welcome – regrets. Let’s not beat around the bush because all soft transitions I recorded earlier sound really shmoosy. The opposite of what regrets actually are.

What do you know about regrets? Not yours in particular – but regrets in general? 

Here’s what I know: 

Most people talk about regret in hindsight – meaning regret has already happened and now we have to live with the consequences of it. Because this how regret came to be:

First life was one way for you, then you screwed up, and now life is worse than before.

A regret is a feeling, but a particularly powerful one, because it’s also the painful awareness that you’re the cause for a bad situation. 

So regret is full of guilt, and if it involves the wellbeing, or unwellbeing of another person, sometimes even full of shame.

Regret is so freaking personal. 

Even though most mistakes can be rectified it is those associations to guilt and shame that keep us from doing so.

It is a regret, because trying to repair a broken heart is hard, hard work and often causing even more pain along the way – or at least more exposure to those feelings of guilt and shame… and so rather than keeping, what feels like a dark stain, top of mind, being forced to look at it all the time, from a behavioral standpoint, the most common and obvious reaction to regret is: trying to avoid it. 

Even though we know it’s unavoidable, we analyze and take mental note of everything touching our sore point that lies in the past and we then avoid any and all situations that resemble that past happening in the present and future. So even though our regret lies in the past, it regularly comes to visit us in the now and, not just that, but we know it will come back in the future as well.

And the metaphor that I can give you for living with regret is: regret is like your nose.

Just like your nose is smack in the middle of your face, so is regret smack in the middle of your being and your memories of the past. But because of it’s location it is really hard to see. If you make a real effort and try to squint your eyes then you can see the tip of your own nose, but only vaguely and extremely blurry and your eyes will feel very strained after just very few seconds of trying.

But since we know that everyone we encounter will look straight into our face, we use mirrors and look into themevery day to make sure our face looks presentable – and that’s when we can’t avoid our nose: right there smack in the middle. Same goes for our personality and character (a differentiation I should and will explore in some other episode), we all reflect about our own life and how we handle it, who is in it and how we interact with and impact each other. Thinking of our own behavior, what we want to achieve and how we want to get there is our mirror and that’s when we get confronted with our regrets – smack in the middle of our past, present and future.

So what do we do with that?

How about we rationalize it?

I don’t know you, dear listener.

And I do not know if you’re anything like me, but I am someone who is much more comfortable feeling emotions, once I’ve thought them through. The information that emotions carry scare me sometimes – feeling all those feelings and understanding what they’re trying to tell me and what they want me to do and how they impact my own behavior and where my life is heading if I act on them or not… and what makes ‘negative’ feelings such a ‘bad’ experience is the fact in a given, particular situation they are such a trigger and I’m not sure if I will be able to keep my calm and able to keep my composure. Or at the very least: it will be hard work to do so. And understandably, I am then very hesitant to dive in deep into something where I feel at a loss of control. 

So, as nerdy as I am, I like to read up and look at the research first.

Taking a step back from my particular emotion, looking at it from a distance and maybe even a bit more abstract helps me get comfortable. It helps me to be courageous. I have an entire episode on courage from last season and it helps me to remind myself that courage is easier to come up with when it’s scripted. All professions that require courage practice being in a staged scenario before putting their people in the actual situation. Because having to have courage is by definition uncomfortable, confrontational, extremly energy draining and sometimes even life threatening. So They take the theory and practice apart, bit by bit, they explain and then they train, increasing the intensity step by step. Let’s do the same here:

Let’s look at regret from the distance to classify what it is . And we’ll start with what it is not.

A regret is not a disappointment. 

Because in contrast to regrets, disappointments are only unmet expectations. And whatever led to the disappointment was outside of our control. So disappointments are missing the blame, shame, guilt cocktail. Of cause, if we keep getting disappointed over and over again, it’s time to look at the fault a little closer to home: what is our contribution to this repetition? So yeah, accumulating disappointments can lead to regret. 

On the other, more severe, right side of regrets, we have a deep life crisis. We could simplify that one as an accumulation of regrets, undermining our personal purpose and meaningfulness of life. Burnout could be such an accumulation of regrets.

So, Tadaa,  we’ve cataloged regret between disappointments to the left and life crisis to the right.

What about regret-timing? 

We all know that there is something called ‘instant regret’ and that is usually happening whilst we’re still in action, still talking and already regretting our reactions or big mouth. These instant regrets are usually less severe, une betise, and sooner or later we can laugh about it, because they’re rooted in an overestimation of our own capabilities or ego. Instant regrets are what I like to call face-palm-moments. 

Their counterpart is therefore the ‘delayed regrets’. Those are much more long-term and heavily persistent – those are the ones we fear because they are rooted in an under-estimation of the impact that our behavior has.

We can laugh instant regrets off because they can serve as a lesson learned – we seriously did not know what we did not know. Delayed regrets however, those are the ones where we did not show up at all, or not at the level we could have. With delayed regrets we know that we knew better. Ouch!

And, since 3 times is a charm, here is one more category:

The 4 types of regrets.

The author and marketing expert Daniel Pink used his fame and popularity to ask his fans and readers about their regrets and after some 80000+ answers he came up with 4 types of regrets .

  1. Fundamental regrets, the kind of regrets everyone will tell ‘I told you so!’. It’s the health we didn’t take care of, the money we didn’t save, the repairs we procrastinated taking care of. The serious adulting kind of tasks.
  2. Boldness regrets, we set out to do something, but then got bored, or scared and just half-assed the whole thing leaving us with unsatisfying results and annoyance for having used energy and resources but not daring to be better than mediocre, if that at all.
  3. Moral regrets. Pretty clear what those are. There was a clear right or wrong way to do it and we’ve chosen to be an arse.
  4. Connection regrets. Those are the heart breaking ones. The connection we did not show up for, that we let slip, that we messed up because our ego had to be right.

Those sound all familiar right? And sometimes one regrettable event – our regrettable behavior falls into more than one category.

So we classified regrets on different scales here. On a scale of severity, on a time scale and then lastly put them into categories.

How does this sit with you? Sounds all pretty logic and conclusive, right?

And how do you feel NOW about regrets?

Does this topic more like something that you can face and handle?

It is one thing to say: everyone has regrets. It is another to hear the research about it. It makes that pollyanna sentence more true – Everyone has in fact regrets and so there is research on it – that’s how big the topic is. Again, I do not know about you, but zooming out like that makes me feel less threatened, or personally attacked by my very own regrets. Some emotions are hard to feel and just like facing hard situations is easier with a friend at your side I want to invite you to continue using your mind to help your heart start feeling into your regrets. Keep on thinking and use it as a lifeline for tipping slowly into feeling.

And here’s my next question to you:

What is the function of regret? Why do we keep regretting?

If this sounds like a weird question, Let me give you context: Have you ever wondered why we feel in the first place? What is the function of feeling emotions?

I will not beat around the bush and make this episode an endless loop, so let me cut straight to the answer: We need to feel in order to remember. And we need to remember in order to learn and survive. Our brain is a beautiful organ with the most amazing capacities, but we can’t remember everything that happened to us in our lives. Our brain has limited storage capacities and needs to select which information is valuable and worth giving up storage space for. It uses emotions to do so. The stronger our emotional reaction the deeper the memory will be stored and harder to kill the lesson we learned. THAT is why we call it emotional intelligence – emotions carry information. 

So if I asked you what is the function of regret is, I mean: which information which lesson does your regret want you to remember?

Maybe you have a specific regret memory in mind that comes up. Maybe you have enough distance at this point to go into that, but stay with me for a second longer and let’s look at regret with our analytical, abstract thinking mind first.

We said regrets never feel great – they make us cringe. We said most often they’re paired and mixed with guilt, or even shame. Most of the time we do not have the courage to face, or fix our regrettable situations and avoid confrontation with our past behavior. 

We said regret is the painful awareness that we’re the cause for a situation or other person to be worse off than before. So what is the function of feeling regret, if we’re unwilling, or unable to do something about that past event?

Shout the answer out now, please!

Argh. I wish I could hear you. That is… IF you actually have an answer to this. If not, let me give you another hint, another question to get to the answer: 

What is the opposite of regret?

If the definition was: Regret is the painful awareness that you’re the reason/cause for life to be worse than before., then let’s swap some words out and flip the whole thing: ___ is the joyful awareness that your behavior is the reason for life to be better than it used to be.

How do we feel, when we get mirrored from the external world that we did well, that this current result (that is of our making) is appreciated – that WE are appreciated?

The answer is proud. We feel proud when we did well. PRIDE is the joyful awareness that your behavior is the reason for life to be better than it used to be.

Now don’t confuse feeling proud with acting prideful – that’s not the same and that is not what I’m talking about.

Doing good. Making life better, for ourselves and or for others, makes us feel good. Doing ‘bad’, causing life to be worse, makes us feel bad.

I claim that the opposite of feeling internal regret is feeling internal pride. 

Now, our upbringing, our life in society our life living with other people taught us to feel guilt and shame, and so we get scared to reap even more rejection. Because others lost trust and faith in us, we lose trust and faith in us, because we use society’s reactions to us as a mirror of how we see ourselves. My nose is ugly. I have this thing in the middle of my face, in the middle of my being and others do not like it. My regret is ugly. 

But remember what I said earlier?

Science has come to the conclusion that emotions serve memory formation, serve learning and finally serve survival. Now here’s the beautiful piece: as humans we’re gifted with the ability of self-, internal-reflection so that we can make better choices in the future.  And just as a fox can use his feelings to remember and decide to run faster, or hide longer so that he can survive better, with less effort spent – so we do the same. In the case of feeling regret we usually choose to avoid future situations that remind us of our past regret.

Or, we can choose to think one bit further.

What if our emotional intelligence is not there to support our cognitive intelligence?

What if feeling is not supposed to impact thinking and acting, but what if it’s the other way round? What if we got it all wrong?

What if us feeling ‘bad’ about the past is supposed to remind us that we now know better, and so therefore we should do better so that we can then feel good, feel proud about ourselves? We were never meant to self-shame, blame, guilt more. Isn’t that the purpose of leaning and memory: be better than before? isn’t the real end goal not only are we meant to survive, but even go past that and evolve to actually thriving? What if the purpose of having stored this memory was not remember who we used to be in the past, but who we want to be in the future? So we’re remembering and feeling so that we use our thinking and doing in order to feel better – feel more proud of ourselves.

And in that sense then, let me repeat the question: what IS the function of regret? 

I would say: Our regret is the guardian of our integrity.

It is our inner knowing, our inner authenticity – the way we want and long to be – speaking up to remind us that we know better. It’s the internal knowing that we can do better – we can show everyone better – especially ourselves. And so our inner self – subconscious, soul…. Whatever vocabulary speaks to you… wanting to be part of our external self the part everyone can see.

And if THAT is true, then it means – we keep regretting – remembering that regret for as long as we have not shown that better behavior. We WANT to be able to look into the mirror and say: I did well. We want to look into the mirror and say: Yeah, I screwed up one time, but I learned my lesson and I did better after that.

So our usual behavior of avoiding situations that resemble our regretful past only cements that uncomfortable feeling that we did badly and we have not moved on from this.


Maybe that heaviness that comes with feeling regret is not because we can’t change the past – maybe it comes from: I’m not doing anything to do and be better from here on onwards. Because clearly we care!

Think about your own situation of regret: Can you see it under that light? Can You look inwards and have that conversation with your inner knowing, asking it: How do you see me be and do better? How can you help me have my own back in the future?

Argh, again – I wish this was a conversation because this is the point where getting specific really helps. We zoomed out, now it is time to zoom in.

But since we can’t talk at this very instance:

I can give you example:

Remember those delayed regrets and their 4 categories?

It was a bit simplified when I said that with some regrets we did not know what we did not know and with others we do. Sometimes we have an inkling that what we’re currently doing might not add up to the result we hope for in the future.

I’m an expat – I have a lot of expat friends and A LOT of expat clients. And many of us go abroad and get at some point confronted with the question: Should I stay or should I go? The specific circumstances are really not important for our discussion here. It does not matter if we like the new place or not – there is that point where we question whether we will regret our choices. What might the future be like if we act and leave, and what if we don’t?

‘What if….’ Is a very haunting question.

You can imagine a million scenarios and there is sooo much that you have no control over – but it all starts with a decision of yours and that decision will require you to make a million more decisions in order to make that first one work. And that can be paralyzing because we’ve been there already – in fact, we’re are there already now. As expats, We made that really big choice of moving abroad and played the gamble between: moving abroad and living with daily uncertainty of not knowing how this culture functions and if we can function in this culture, that could be ending up in hopefully feeling like an exciting adventure, but might just as well end up in feeling like a daily uphill battle.

Now, I read Ester Perels book ‘The state of affairs’ that deals with one of the biggest regrets people have: having cheated on their partner and what it takes to move on from it. And in one passage she writes about the experience that the betrayed partner has – let me read it out to you, because Ester says it best:

We’re willing to concede that the future is unpredictable, but we expect the past to be dependable. Betrayed by our beloved we suffer the loss of a coherent narrative (of the past) that helps us create a stable sense of self (in the present).

So whilst usually we think of regret as a thing of the past that haunts the present – in that case, when we ask ourselves ‘what if’ questions, regret becomes the thing we’re afraid of in the future. What if I will come to regret the life I chose to live? – the life I’m living right now. Am I the person that is currently cheating myself out of a good future? Am I betraying myself and what really matters to me right now?

This sounds like a mindfuck – and it is.

As expats we know what it feels like to grieve the life we consciously chose not to live – am I willing to do this again?

And so, whilst we’re absorbed with and by our ‘What if’ worries, we’re also not really living a good life now. This is how not exploring the our past regrets and consequently wanting to avoid future regrets leads us to living a second-best life. One little trade-off, one little downgrade at the time.

Or we can flip it around and ask: what do my regrets want me to remember? What is actually important to me? How can I show up better and live outwardly what I inwardly value?

Now you: what is your regretful situation about?

What are the actions I keep shame-blame-guilt-tripping about? Is it instant, or delayed regrets and in which categories does my regret fall?

And most of all: Can I imagine – just for a moment that my regret does not want me to be afraid, but wants to remind me that there is potential? What if there is a way that I can show up and have my own back in the future?

Alors mes cheres amis, my fellow wisdom seekers and emotion explorers: You can choose. Does anything I said in this episode feel true?

The truth is, afterall, what you believe it is.

Regrets usually emotionally document a negative change in facts. The situation was one way, then you did something and the situation is now worse. So they’re about the transition from past to present and keep us from looking forward into the future with hope. And if you want to know what hope is… go and listen to that episode on website – that too is a really good episode.

We’re at the end friend, and as usual I want to leave you with some last words – and this time I have 3 points to sum this all up.

  1. This is the Worth Having podcast – my topic is belonging. So remember that you DO belong – your regrets belong to you and you can decide what happens to you and them. Treat your regrets with respect, because they’re like Kale, or spinach: bitter, but full of nutritionous emotional intelligence. All you need to do is figure out how to extract exactly what you and your life need from it.
  2. Speaking of extracting the good stuff: If you are a private person and feel your life could use some more moments of internal pride, but you do not know where to start: I can help you extract that info in a half day session of coaching: which I call The Next Right Step. Together we audit, measure and emotionally evaluate what is currently happening in your life – and then we extract that emotional intelligence of yurs and you decide where you feel good and best and confident in yourself and your competence and capabilities. And with all that: we come up with a hands-on action plan for what you should focus on doing so that you feel better, create the kind of change that create moments of pride for yourself. We don’t do this for others to give you recognition, but for you to really make yourself feel seen, feel recognized and feel strengthened and acknowledged.
    Btw. I can do that also for teams in companies workshop format if you like
  3. Thirdly: If you liked this episode, if you found value in this: please share it with your people. or show some love over on LinkedIn and support me there

In anycase; I’m looking forward to hearing back from you.

Au revoir et a bientot, cest Nic.

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About Nic

Nic is a Designer, turned Cultural Adaptation Coach, turned Positive Psychology Practitioner and Workshop Facilitator.

She lived in 7 different countries, on three different continents, speaks 6 languages, and an avid advocate for the Inner Development Goals and on a mission to help design belonging and raise hope for all.

Meet with Nic via zoom