How Counterfactual Thinking Fuels Regret & Keeps the Past Alive
Exploring how imagined alternatives turn past events into present emotions
Anthony1 still remembers the night he gambled everything.
Of course, that was the night when a decision that took just seconds left an aftermath that will last his whole life. He told me that even though he’s learnt to move on, one day at a time, there are days when he can’t help but think that if he’d just chosen differently, things would be so much better now.
In psychology, we call this counterfactual thinking: the mind’s habit of imagining the decisions we didn’t make, the experiences we didn’t live.
A habit that makes regret feel so burdensome and personal.
Beyond sadness or disappointment, regret carries the weight of responsibility, the sense that we could have acted differently and changed the outcome. It’s a punishing emotional state because it makes us both the victim and the culprit.
We’re the one who suffers, but also the one who caused that suffering.
The Engine of Regret
When Anthony first lost everything, he was immediately greeted by disappointment; a dull ache at how the event had turned out.
Disappointment doesn’t necessarily entail accusation. Normally, it’s what we feel when outcomes fall short of what we hoped for.
However, as time went by, Anthony’s disappointment turned into something more oppressive: The thought of “What if he’d bet on the opposite direction”.
Indeed, Coricelli and colleagues identified counterfactual thinking as the cognitive mechanism that transforms disappointment into regret [1].
The difference lies in how we interpret the cause of what happened, they explain. When outcomes feel tied to our own actions, the mind compares reality with the alternative version we could have created, and regret emerges.
But we all know that the boundary between emotional states isn’t always that clear.
When researchers revisited the “standard conditions” of regret, they found that people can also experience it when events are outside their control [2]. That is, when choices are constrained or forced by external circumstances regret can still surface.
For example, someone who takes a job they never wanted, simply because there was no other option at the time, may still look back and think ‘I should have waited’. Even when that choice was never truly there the mind imagines it afterward, and that imagined freedom is enough to make us suffer for it.
This is what makes regret so persistent.
See, oftentimes, rather than to the truth of what happened, regret is tethered to the stories our mind constructs afterward.
It turns out that the same imagination that allows us to learn from mistakes also traps us in hypothetical worlds where we endlessly relive them.
When Regret Turns Against Us
That imagined freedom (the sense that we could have done otherwise) indeed can serve as lessons, but it can also turn against us.
When the mind becomes caught in these imagined alternatives, regret stops being a passing emotion and starts becoming a pattern.
Research by Zheng and colleagues shows this vividly. Their study compared how people with major depressive disorder responded to counterfactual thoughts [2]. They found that those living with depression not only experience regret more intensely, but also struggled to regulate it.
For those experiencing depression the “what if” scenarios are more vivid, more emotionally charged, and far harder to let go of. In depression, the mental replay doesn’t end; it loops.
A more recent study by Huang and colleagues (2024) helps explain why [3].
Using neuroimaging, they found that the looping feature of counterfactual thinking reorganises patterns of activity in the brain’s default mode network (the DMN), an area involved in memory and self-referential thought.
In these instances, it seems, regretful memories are not just recalled, but re-experienced.
When this happens, regret ceases to serve its original purpose. Instead of helping us learn from experience, it keeps the past alive in the present, not simply as memory, but as repetition.
I suspect this is where Anthony lives now, in that unforgiving space where remembering has become reliving.
The Constructive Side of Regret
But Anthony doesn’t have to stay there.
Feelings of regret are not solely negative. In fact, when the mind learns to work with them, rather than against them, they can become a source of insight.
Parikh and colleagues explored how different ways of thinking about the past influence emotional recovery [4]. They found that not all counterfactual thoughts deepen regret.
Some can ease it.
Imagining how things could have been worse, known as downward counterfactual thinking, helps some individuals regulate negative emotion and regain a sense of balance.
For Anthony, admittedly, imagining how things could’ve been worse might even seem impossible. What could be worse than losing his livelihood, his home?
I thought a lot about his situation and came to the conclusion that worse than that would’ve been to lose the will to rebuild, to start again.
When regret is seen through this lens, it starts to resemble reflection rather than rumination.
Living With Regret, Not In It
It’s true that reflection doesn’t erase regret.
But it can develop our capacity to live with it.
This capacity is part of what defines psychological maturity: the ability to tolerate ambiguity, accept responsibility without self-condemnation, and integrate painful experiences without denial or idealisation.
When reflection reaches that point, the past no longer needs to be rewritten. It can be accepted as it is/was.
For Anthony, this would mean the night he lost everything is no longer a story to “undo”, but one he would learn to absorb.
And so, living with regret instead of in it leads us to coherence: the understanding that what once fractured us can still belong to the story of who we are, exactly as it happened.
Reference List
[1] Coricelli, G., & Rustichini, A. (2010). Counterfactual thinking and emotions: Regret and envy learning. Philosophical Transactions of the Royal Society B: Biological Sciences, 365(1538), 241–247. https://doi.org/10.1098/rstb.2009.0159
[2] Zheng, Q., Liao, M., Liu, B., Ou, W., Chen, W., Liu, J., & Zhang, Y. (2021). Counterfactual thinking–related emotional responses in patients with major depressive disorder. Frontiers in Psychiatry, 11, Article 589335. https://doi.org/10.3389/fpsyt.2020.589335
[3] Huang, S., Faul, L., Parikh, N., LaBar, K., & De Brigard, F. (2024). Counterfactual thinking induces different neural patterns of memory modification in anxious individuals. Scientific Reports, 14, Article 10630
[4] Parikh, N., et al. (2022). The efficacy of downward counterfactual thinking for regulating emotional memories in anxious individuals. Frontiers in Psychology. https://doi.org/10.3389/fpsyg.2021.712066
This is not his real name.
I appreciate how you've traced regret's arc from cognitive mechanism to potential prison—and then to something we might actually work with. The distinction between disappointment and regret through counterfactual thinking is crucial, and you've illustrated it beautifully through Anthony's story.
What strikes me most is your point about imagined freedom. We suffer not just for what we did, but for choices we retrospectively believe we had, even when circumstances left us with none. That's the cruel irony: our capacity for mental simulation, which should help us navigate future decisions, becomes the very thing that torments us about the past.
The neuroscience piece about the default mode network is particularly fascinating. It suggests regret isn't just an emotional state but a mode of neural organization patterns that literally reshape how we process self-referential thought. When rumination becomes our brain's default configuration, we're not just remembering differently; we're experiencing reality through a distorted temporal lens where past and present collapse into each other.
Your framing of psychological maturity as the capacity to tolerate ambiguity resonates deeply. It's not about positive thinking or reframing trauma into triumph. It's about integration—allowing painful experiences to exist as part of our narrative without either defining us completely or being denied entirely.
The shift from "living in regret" to "living with regret" isn't semantic. It's the difference between being imprisoned by counterfactuals and acknowledging them as part of a larger, ongoing story. Anthony's journey toward that acceptance—however incomplete is perhaps the most honest thing we can offer about regret: not resolution, but coherence.
Oh, this one really got me thinking. Applying it to losing my son Dom, it is very illuminating, showing why my regrets are so very difficult to shift.
The advice that things could have been worse of course is very difficult to reconcile with. Losing a child does feel like rock bottom for so very long.
I wonder whether this is the place where Gratitude needs to come to the table? I think that’s my most powerful tool atm 🙂Interested in your thoughts, Dom!