Shoulda, Woulda, Coulda: How to Stop Overthinking Past Choices
- Joanna Baars
- Jul 2
- 10 min read
Updated: Jul 3
The Trap of “Shoulda, Woulda, Coulda” Thinking
Most of us have been there. Sitting with that heavy feeling in the chest, replaying something over and over again in our minds. The thoughts sound like a broken record. I should have done this. I could have done that. Why didn’t I do something different? It feels like standing in front of a door that has already closed but being convinced that if we just think hard enough, we can somehow go back and open it.
This mental loop can be brutal. It is exhausting. It keeps you stuck in a cycle of questioning yourself, doubting your decisions and feeling like you are constantly falling short. It is that awful cocktail of regret, self-criticism and frustration that leaves you wondering why you just cannot seem to get it right. The hardest part is that this thinking usually comes from a place of believing we are not good enough. Somewhere inside, there is that quiet voice whispering that we should have known better. We should have done better. And if we did not, well, that must mean something is wrong with us. It is a really painful place to sit in.
What often goes unnoticed is how sneaky this mindset really is. It convinces us that we are being reasonable. It dresses itself up as reflection or problem-solving. But it is not. It is rumination. It is turning the same question over and over in our mind without ever arriving at peace or resolution. It does not lead to learning. It leads to feeling stuck, small and ashamed.
There is also an assumption hidden inside this pattern that we rarely stop to question. The assumption is that if we do not like the outcome of the choice we made, then the opposite choice would have definitely been better. But how can we possibly know that? How can we measure a real-life outcome against an imaginary one that only exists in our heads? The truth is, we cannot.
The brain does not like uncertainty. It does not like not knowing. So when something feels uncomfortable, painful or disappointing, it tries to reverse-engineer a different version of the past. A version where if only we had done X instead of Y, everything would be fine now. But life does not work like that. There is no proof that the road we did not take would have been easier, smoother or more successful. It is just that the outcome we are living with feels uncomfortable, so the brain assumes the other option must have been better. This is how the trap keeps us stuck. We end up comparing a real situation with all its complexities, imperfections and lessons against a perfect fantasy that lives in our imagination. No real outcome can ever win that comparison. And so we keep spinning in circles of regret, convinced that if we were smarter, stronger, braver or just better, we would not be here feeling this way.
Why the Other Choice Might Not Have Been Better Either
When we get caught in those spirals of shoulda, woulda, coulda, one thing often gets overlooked. We assume that if we do not like the outcome of the choice we made, then the other option would have turned out better. It feels like the one we did not pick was the golden solution that would have spared us from discomfort, regret or pain. The mind paints this picture where the path not taken is flawless, smooth and problem-free.
But truthfully,, we cannot actually know that. We are comparing something real, something we lived and experienced, with a version of events that only exists in imagination. The brain is excellent at filling in the blanks with idealised outcomes when we are hurting. If only I had done that instead, this would not have happened. That sentence feels so true in the moment, but it is built entirely on guesswork. What if that other choice had come with its own challenges, its own disappointments or even entirely different pain? The reality is that every choice carries uncertainty. Every decision leads us down a path we cannot fully predict. Just because one outcome feels painful does not automatically mean the alternative would have felt easier or safer. It is simply that we know the discomfort of the path we walked. We do not have the same emotional data for the one we did not choose.
It is also worth remembering that most of us are making choices with the information, tools, capacity and awareness we have in the moment. You were not standing at that crossroads with the perspective you have now. You were doing the best you could with what you knew, what you felt and what you were able to handle at the time. Of course it is easy to look back with hindsight and wish you had made a different call. But hindsight is a privilege that only exists because you walked the path you did. The mind tends to jump to the assumption that discomfort means failure. That if something hurt, was hard or did not turn out the way we hoped, then it must mean the choice was wrong. But discomfort is not always a sign of a bad choice. Sometimes it is just the natural outcome of growth. Sometimes it is life showing us something important about what we value, what we need or what is no longer working.
There is also this very human tendency to believe that the lessons should come without the struggle. That if we were smarter, stronger or more self-aware, we would have skipped the hard part. But that is not how growth works. Growth often happens because of the hard parts, not in spite of them. When we step back and really think about it, the other choice is just a theory. It is not a fact. There is no version of life where we can run both scenarios and check which one was better. We only get the road we are on. And the fact that you are reflecting now does not mean you failed. It means you are evolving. You are seeing things you could not see before. That is not a mistake. That is progress.
Turning “I Could’ve, I Would’ve” Into Self-Understanding Instead of Shame
It is so easy to fall into the trap of thinking, if I could have, I would have, and then letting that spiral into shame. It sounds like a simple statement, but when you are already carrying the weight of regret, disappointment or self-blame, it can feel like confirmation that you failed. But what if we could shift that? What if that statement was not a judgment, but an invitation to understand ourselves better?
When you say to yourself, if I could have, I would have, the next natural question is, so why didn’t I? This is where a lot of people get stuck. The automatic response tends to be, because I am lazy, because I am weak, because I always mess things up. But none of that is the truth. Those are shame responses. Those are the old narratives that have been wired in from years of thinking your worth is tied to doing everything perfectly.
The real answer to why you did not do something the way you wish you had is usually something much deeper and more compassionate. It could be that you were scared. It could be that you did not have the tools, the support, or the nervous system capacity to make that choice in that moment. It could be that you were stuck in an old pattern that once kept you safe but no longer serves you. These are not character flaws. These are survival strategies. They are protective responses that were developed for a reason, even if you do not consciously remember when or why.
Curiosity is what transforms this entire conversation. Instead of asking the question as a way to punish yourself, you start asking it as a way to learn. What was getting in the way of me doing what I now wish I had done? Was it fear of conflict? Fear of being rejected? Fear of failure? Maybe it was simply that you did not know then what you know now. And how could you? Growth is not linear. It is not something we download overnight. It happens in layers, over time, often through the very experiences that now make us pause and reflect. This shift into curiosity does not erase accountability. You can absolutely hold space for the truth that you want to grow, that you want to handle things differently next time. Accountability means being honest with yourself about what patterns are no longer serving you. It means noticing when avoidance, people pleasing, fear or self-doubt is running the show and gently working on changing that.
But accountability without shame is an entirely different experience. It is not heavy. It does not crush you under the weight of you should have known better. Instead, it feels like clarity. It feels like, I see now what I could not see then. And because I see it, I can choose differently moving forward. There is power in that. There is freedom in that. This is how you start moving from being stuck in a shame spiral to actually making meaningful changes. When you understand what was getting in the way, you can start offering yourself what you needed back then. Maybe that is more self-compassion. Maybe it is learning how to regulate your nervous system. Maybe it is practicing boundaries or letting go of perfectionism. Whatever it is, it becomes part of your healing. Not as a punishment for past mistakes, but as a gift to the version of you who is still growing.
You start realising that the fact you are even reflecting like this means something has shifted already. You are not the same person who made that decision back then. You are someone who is learning, someone who is evolving, someone who is actively choosing to become more aware, more connected and more aligned with your own truth.
Moving Forward: Learning, Healing and Building Self-Trust
Once you begin to move out of the old cycle of shoulda, woulda, coulda thinking, something really important starts to happen. You begin to realise that the goal was never to avoid mistakes forever or to figure out the perfect choice every single time. The real work has always been about learning how to meet yourself with kindness. It is about learning how to trust yourself again, even after moments when you wish you had shown up differently. Building self-trust is not something that magically happens because you made all the right decisions. It grows from knowing that no matter what happens, you will not abandon yourself. It means being someone who can say to yourself, that was hard, or that was not how I wanted it to go, but I am still here. I am still on my own side. I am still willing to understand myself rather than shame myself.
This is what real healing looks like. It is not about becoming someone who never doubts, never struggles or never second-guesses. It is about becoming someone who knows how to navigate those moments with softness instead of self-criticism. It is about knowing that you have the ability to repair, to reflect and to grow from every single experience, whether it felt like success or not. A huge part of this process is recognising that discomfort does not mean failure. The fact that something feels hard or messy does not mean you made the wrong choice. Sometimes it simply means you are stepping out of old patterns and into new ways of being. And growth almost always feels uncomfortable at first. That does not mean it is wrong. It means you are moving.
Healing also comes from learning how to ask better questions. Instead of asking, why am I like this, or what is wrong with me, you start asking, what support do I need right now, or what would help me feel safe enough to choose differently next time. These are not just gentle questions. They are powerful. They are the kind of questions that shift you out of shame and into self-awareness. This is where self-compassion becomes a practice, not just an idea. It is reminding yourself that the version of you who made that choice in the past was doing the best they could with what they knew, with the tools they had and with the emotional resources that were available at the time. You do not have to keep punishing them for not knowing what you know now. You get to offer them understanding. You get to offer them care. And as you do that, something shifts inside. The pressure to be perfect starts to loosen its grip. The old stories about how you always mess things up start to lose their power. Instead, you start creating new stories. Stories where you are someone who learns, someone who grows and someone who gets better at being on their own side every single day.
This does not mean that fear will never show up again. It does not mean that doubt will magically disappear. But it does mean that when those things arise, you will not automatically believe they are proof that you are failing. You will start to see them as familiar visitors that simply show up when you are moving into new territory. And rather than letting them pull you back into old patterns, you will be able to meet them with curiosity and care.
Moving forward with self-trust means allowing yourself to be a work in progress. It means knowing that there will always be more to learn, more to heal and more to understand. But none of that means you are broken. It simply means you are human. A human who is brave enough to look at their patterns, who is gentle enough to let go of shame and who is wise enough to know that healing is not about getting it perfect. It is about getting free.
So the next time your mind drifts back into that old space of shoulda, woulda, coulda, pause. Breathe. Remind yourself that you are learning. You are healing. And you are already doing the real work of becoming someone who trusts themselves enough to keep moving forward.
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Joanna Baars is a psychotherapist and writer based in London. Her work explores how we can learn to understand ourselves, in a complex world. Find out more...
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