The Psychology of your 20s - 374. The psychology of regret
Episode Date: January 12, 2026In our 20s especially, the fear of regret can seem like every choice has the potential to ‘ruin’ our future - the degree we picked (or didn’t), the person we stayed with, the move we... were too scared to make. And then there are the things we didn’t do at all, the opportunities we let pass, the words we never said, that still weigh on us years later. In this episode, we’re unpacking the psychology of regret – what it actually is, why it’s so tied to self-blame, and how it can either keep us frozen or push us forward. We explore:• The role of upward and downward counterfactual thinking• How regret can both motivate and stagnate us • The four BIGGEST regrets people have• The paradox of the ‘perfect’ decision• Why we fear regret more than we feel it• How to grow through regret with acceptance and compassion If you want to quieten the ‘what if’ thoughts, this episode is for you. ORDER MY BOOK Follow Jemma on Instagram: @jemmasbeg Follow the podcast on Instagram: @thatpsychologypodcast For business: psychologyofyour20s@gmail.com The Psychology of your 20s is not a substitute for professional mental health help. If you are struggling, distressed or require personalised advice, please reach out to your doctor or a licensed psychologist.See omnystudio.com/listener for privacy information.
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Hello everybody. I'm Jemma Spike and welcome back to the psychology of your 20s, the podcast where we talk through the biggest changes, moments and transitions of our 20s and what they mean for our psychology.
Hello everybody. Welcome back to the show. Welcome back to the podcast. It is so great to have you here back for another episode as we break down.
the psychology of our 20s.
Today's episode is cutting right to the heart of so much of our fear and our doubt in our 20s.
What if I regret the decisions I'm making right now?
Or what if I regret the decisions I'm not making?
At the heart of I think every DM I get, every discussion I have with you guys, the listeners,
but with my friends, on dating, on jobs, on money, moving.
health, whatever it is, at the center of all that is a deep fear of regret.
There is like this vision we sometimes have in our mind of us looking back in 30 years,
looking back at this moment and thinking, here it is.
Like, this is the moment.
This is the decision I can pinpoint for me for when it all went wrong.
No doubt about it, this fear of like, is this the moment that I realized like I messed up
in the future?
That fear is so amplified in our 20s almost counterintuitively because we actually often have so many opportunities and so many doors open and so little room for regret at this point and so much future ahead of ourselves.
But it's ironic, but it creates this constant pressure to not mess it all up despite just being at the start.
So in this episode, I want to do a psychological deep dive into what actually drags.
regret, what people regret the most, how to manage it when it does show up. And why I actually
think regret is one of the most motivating emotions we can actually access as we plan for our
futures. So without further ado, let's get into the psychology of regret. When we talk about
regret, what are we actually talking about? That's really important for us to understand.
regret is sadness, it's disappointment, embarrassment, it's a sad mix of all those things.
But I think it's mostly rooted in grief, to be honest.
Grief over a life path we could have lived and the stories we could have made and the stories
that we do make up about that life path, that it's better, that it's happier, that we didn't get to,
that we didn't get to have.
This what if that is attached to every single regret,
what if I'd done this, what if I hadn't,
is probably the most important part of it.
When we look at regret under like an emotional microscope,
there are essentially two key ingredients.
One of them is exactly what we're talking about.
It's referred to as counterfactual thinking.
Counterfactual thinking is basically the brain's game of what if,
you mentally go over an event, you imagine it a million different ways.
One of them is obviously going to be better.
There's the life that's actually happened and then there's the alternative reality that you play
in your head.
The versions where you said yes instead of no, you stayed instead of left, you spoke instead of
staying quiet.
Researchers call these counterfactuals, literally alternatives to the facts.
They can go in two directions.
In a downward counterfactual, you imagine how it could have been worse.
Like, honestly, that could have gone horribly if I hadn't left when I did.
That could have really been a disaster for me.
In upward counterfactuals, though, you imagine a better outcome than the one you got.
If only I'd revised properly, I could have passed that exam,
and then I would have a better job than I do now,
and I'd be making more money, and I'd be happier.
Or if I'd only reached out to my friends more, maybe I'd be less lonely.
Maybe my life would feel like it had more meaning.
It's the upward ones that hurt.
But counterfactuals aren't the only element here.
You might think, you know, if the weather had been better, that holiday would have been amazing.
And you feel a little bit annoyed and disappointed.
That isn't regret.
The missing piece here that we're seeing in these examples is self-blame.
You can have counterfactuals, but if you don't blame yourself, you don't have regret.
Regret is what happens when you look at that better imagined outcome, that upward counterfactual, and you think, okay, that was on me.
Like, that was my fault.
Studies on this show, exactly that.
Imagining a better outcome is one thing.
When you tie that better outcome directly to your own actions, those evaluations become really bitter.
and they become really painful.
For example, a study from 2018 from researchers at the University of New England,
they looked at a sample of over 140 individuals,
and they asked them to complete a survey about symptoms of depression,
symptoms of anxiety.
And then they also had them rank and rate past regret and regret intensity
and how much they had to say,
they had the opportunity to correct that situation.
What the researchers found was that having greater regret did not correlate to being more depressed
or unhappy.
Having greater regret that you blamed yourself for and that you felt like you could have
done something about, that was where mental health went bad or depression really began
to crop up more frequently in the participants.
So what exactly do people regret the most?
You may remember I did a full episode on this a while back titled The 20 Regrets People Have About Their 20s.
I asked 5,000 people, what is the thing you regret the most about your 20s?
And the biggest answers were, number one, focusing too much on romantic love or staying in an
unsuitable relationship for too long.
number two worrying too much about what others thought of me number three not fighting more for
friendships number four not investing sooner and then another big theme not going to college but equally
going to college we heard a similar number for both go and listen to that full episode if you want
the entire list of the full 20 because it's honestly so fascinating what we found but
That was just for our 20s. That was just for this decade. If you were to ask a room full of people of all ages what they regret about life in general, some clear patterns do actually appear and become pretty consistent.
Researchers from the University of Illinois published a meta-analysis of this very thing. They looked at 11 studies where people talked about regret and they analyzed it to figure out what the biggest themes were.
they then ranked them in terms of most regret to least regret.
Across all samples, all of these studies, the top six regrets were education number one,
career, romance, parenting, identity, and then leisure.
So above all else, education was interestingly, the thing that people regretted the most,
mainly for not pursuing more of it.
Daniel Pink, the author actually went further into this with his world regret survey.
He turned this into a book, The Power of Regret, it was released in 2022.
When he sorted through, and I think it was like 16,000 people's regrets from more than 100 countries,
what he found was that it wasn't a specific thing.
We might say education is the biggest, but actually what he found is there's categories,
So four big categories of regrets.
Foundation regrets, number one.
That is where education comes down, comes to.
So not building stability, not pursuing an education, not taking care of finances, your health.
Foundation regrets, number one.
Boldness regrets, number two, so not being brave enough, not taking chances.
Moral regrets were number three, not acting in line with your values, doing something that you felt hurt other people.
And number four was connection regrets.
so letting relationships wither or break down or not pursuing the person you really cared about.
There's a phrase he says in the book that I love.
Most people actually ended up regretting what they felt they had the greatest opportunity to change.
They didn't regret the stuff that was totally out of their control.
You know, the person who didn't love them back, the friend who just was never going to be on their team.
But the moments where, you know, if they were honest, they had some power and they didn't use it,
that was where a lot of the pain lay.
They could have chased after that person.
They could have bet on themselves.
They could have started the business.
They could have gone and gotten that education.
That is the stuff that left the greatest impact.
And I think that for people in their 20s, that's both the sobering and strangely empowering thought.
It means that our regrets cluster around our sense of agency.
And knowing that is actually really essential, and it's a vital takeaway, if one of your goals is to avoid regret in the future, I want to explain exactly why, after this short break.
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I think in our 20s we definitely may have regrets.
We may have a few regrets.
Like, you know, I regret how I treated that friend.
I regret not taking that job.
But most of how we experience regret is our future fear of it
and wanting to ensure we have as little of it as possible.
That is why I think personally.
like people love those lists like the lists I was just talking about of like the greatest regrets we
love them so much because they're like this guide right the irony is though the more you think about
what you may or may not regret the more you analyze it the more you actually let that influence
your decision making and the more likely you are actually going to make decisions that you regret
more or not make a decision that you regret why is this why
because it's artificially increasing the stakes for any and all decisions you make if you have
this lingering fear that it's going to be the wrong one. And so that fear and that assessment of
regret and whether this has potential for regret or not constantly interrupts your ability to trust
your instincts. A lot of us live in what we call pre-regret. You haven't made the decision yet,
but you're already imagining that it's the wrong one or how you might feel
if you chose the wrong thing, you are lying in bed thinking already, you know, you haven't taken
the job, but if I take the job and I hate it, I'm never going to forgive myself.
But if I don't take the job and it actually ends up being great, I'm never going to forgive
myself either. So which one am I going to do? This one, that one, this one, that one.
And then you basically do nothing. What's actually happening there with this scenario is that
you haven't chosen the job yet.
Nothing in your actual life has changed.
You have no knowledge of whether it's going to be good or bad.
You have made this pre-assessment or this pre-judgment
that has influenced the decision before you've even given yourself a chance.
You haven't taken the job or, you know, you haven't moved,
you haven't quit, you haven't said the thing you want to say.
But emotionally, you're already, and have already lived through
all of these worst-case scenarios.
The more you let yourself ruminate on these scenarios, on the worst case scenario, the more you believe that it's going to come true.
This is a cognitive bias we call the availability heuristic.
Essentially, we inaccurately judge how likely something is to happen simply based on how easy it is for us to recall.
and of course the emotionally salient disaster regret scenarios your brain is cooking up for you.
They are going to be the easiest ones to recall.
They are going to be the most prominent because they are the most emotional.
The danger here is that you spend so long thinking again or trying to outthink regret,
you do not move, you do not act.
This is the paradox of the perfect decision.
the more you chase a perfect decision, one that is, I guess,
that guarantees like permanent emotional comfort, the harder it becomes to do or to choose anything
at all because the worst case scenario, the regret-based scenarios, all those things your brain
creates, like you cannot release them.
I've been there so many times.
You tell yourself you're just being careful.
You tell yourself like, hey, I'm just waiting, I'm just waiting till I'm 93% sure when you could have made the decision when you were 51% sure.
And you would have still felt as conflicted as you do now.
And I'm sorry to be the bearer of bad news, but that the perfect decision doesn't exist anyways.
100% certainty only exists in hindsight.
Every real choice comes with tradeoffs.
It comes with losses.
It comes with gains as well.
Trying to find the perfect option that is never going to hurt you.
there's never going to give you regret, means you are going to stay in situations that you have outgrown.
What I can say, though, is that even if the worst case scenario happens,
it is often never as bad as we emotionally predict it to be.
This is where effective forecasting comes in.
It is the human habit of trying to predict how we feel in the future and getting it very, very wrong.
When it comes to regret, our forecasts are usually wildly pessimistic.
So we end up organizing our whole lives around an emotion we're probably not actually going to feel.
We don't necessarily even fear regret.
We fear an exaggerated imagined version of regret that is a projection of our deep fears and insecurities
and everything going wrong when actually that very rarely happens.
What we also know from the research is that the easiest way, again, to avoid regret,
is to actually take any kind of action in any direction, even if you don't know for sure it's
going to be the right one. Take, for example, the 1997 paper on regret and self-discrepancy theory.
What researchers found in their research assessing the regrets of thousands of people is that
24% of regrets were about things people did do, 76% of regrets were about the things they didn't do.
What they realized is that there are two types regrets, action regrets and inaction regrets.
Inaction regrets, they are far more common.
So if you want to avoid regret overthinking it is not going to do anything, making a decision will.
Make any decision, any decision at all, the only way out of the paradox isn't to lower your standards so much as to tell yourself the truth.
There is no decision that will absolutely protect me from regret.
at some point I will wish I had known what I do know now, but if I make a choice, my chances
of that are going to be a lot less. So if you are currently in a state of regret, you regret something
you did or didn't choose in the past, I also want you to recognize that the option you're
currently living in is the real one, and it is full colour and it is complicated and it has good
days and bad days and awkward conversations and admin and loneliness and traffic. That is the real
thing that is happening to you. The option you didn't choose that you are torturing yourself with
believing that it was the better one, that only lives in your head. And what it is in your
head is not real. As much as what hasn't happened yet can be convincingly very, very terrifying,
what we expected to happen that didn't can be convincingly flawless.
You see yourself in that other city with instant friends in a cool flat and you're not struggling with paperwork or a visa and you're not missing home or you're not missing your dog.
You see yourself in the other relationship and the relationship you tried one more time to make work and you're laughing now and you're not arguing about money anymore.
Blah, blah, blah, blah, blah.
You're comparing reality, your messy real life to something that is just completely like,
like, just buffed of all badness.
And you think that those things are equally probable
and you think that the one that you're imagining could have happened.
That is not true.
No one's life is perfect the way that we are imagining it.
I think another useful reframe to stop fearing regret
is to also understand when in our lives regret has maybe actually saved us.
We've mostly talked about how regret hurts.
I don't hear people talk about how it can protect.
you. You regret missing that travel opportunity with your friends. You know what that means? You're not
going to miss out again. You regret how you treated that friend when you were 21, that you ghosted them,
that you didn't come through with your promises. That self-blame and pain is going to make you a better
friend in the future. You regret not spending more time with your grandparents. As your parents get
older, you're not going to make the same mistake. In that way, regret functions a bit like a bruise on your
moral skin. You bump up against a line you didn't know was there and it hurts and afterwards,
you remember that, you move a little bit more carefully. Don't keep walking into the same
sharp corner in quite the same way. It's not that you never make mistakes again, obviously you do,
but you rarely make the exact same one at the same level because regret has taught you an important
lesson. When you are tempted to see your regrets as proof that you're a disaster or that something has
failed, it's worth zooming out. Some of the qualities you like most about yourself now, the care
you take with people, the risks, the risk mindset you have are probably shaped by very old
painful moments where you didn't know. Regret hurts, it's also been steering you away from
becoming a version of yourself. You probably wouldn't be able to live with either.
Now, there are some regrets for which this is simply not.
not going to make us feel better. Nothing came from it. You didn't learn anything. It's made your
life worse. Sadly, that is the case sometimes. Then it might be simply worth looking at how we can
live with the facts of what happened. One of the hardest but most important cognitive skills
I think we can master, and I'm yet to master it. I'm being optimistic. I wish I could. But it's
acceptance. Accepting that this happened. Regret will happen.
such as the flow and intricacies of life and not having, not being able to predict the future.
You don't have to put a positive spin on it.
You don't have to turn it into an opportunity.
But you have to be willing to acknowledge that, yeah, it happened and there's nothing, you can change it.
And you can go forward anyways.
I'm not going to ignore the fact that I don't like it.
I wish it were different.
But this is the reality that I'm facing.
As long as you are mentally replaying the past trying to get a different outcome, you stay
locked in a kind of mental argument with yourself that you're never going to win and you will
never be able to move forward from. Regret in that moment just paralyzes you further. It reduces
any ability you have to change. It's also important to note that what's happening there in that
moment where you just ruminate on everything you could have done differently is its own kind of
cognitive bias. It's called hindsight bias. The tendency to believe
that past actions should have been obvious or avoidable, given what you know now.
We all know that's not true.
For every scenario your brain may have cooked up for you of how this could have gone good or bad,
and for all that predictive value you think your brain has,
there's always going to be an option that you didn't think of,
and it's probably the option that happened.
Because, again, you can't predict the future.
And that is why radical self-compassion is so important.
You've made a mistake, you have a deep regret about something,
you're not sure if you can move past it.
Having radical self-compassion in that moment is not an attempt to excuse the behavior or to change it.
It's just the tone you take with yourself when you think back on it.
When I think about regrets I have, I always go back to the Professor Kristen Neff's model of self-compassion.
She defines it as comprising of three components.
Self-kindness, responding to personal failure with care rather than harsh judgment.
common humanity, recognizing that anybody else could have made the same mistake or have a similar
regret to you and what you're experiencing, and also mindfulness, just holding painful
thoughts and emotions in balanced awareness with other more positive thoughts, not over-identifying
with them, not saying that because I made this mistake, because I didn't make this choice,
this is who I am for the rest of my life,
just acknowledging that they are part of your life
the way many more magical parts are as well.
Importantly, this research consistently shows
having that kind of respect and relationship to regret
doesn't reduce accountability,
it doesn't reduce moral standards.
It actually means you're more likely to take responsibility,
you're more likely to apologize, to want to change.
And again, it actually reduces future likelihood
of encountering a similar situation, acting in the same way, and doubling your regret.
As we wrap up this episode on the psychology of regret, I want to say, it is impossible to live
without regret. It is one of those emotional scars we all get as humans. The same as heartbreak,
the same as grief. It also reflects the fact that we get choices and that we have agency
and that we have things that we care about. I've been trying to
do this thing lately for every emotional thing or event I fear or that I think is bad or that I don't
enjoy like regret. I imagine what life would be like without it. Like if regret was an emotion,
we just couldn't feel or we could opt out of or we didn't have access to, would that be better? And
honestly, I actually think the world would be way worse. People would be terrible to each other
because they wouldn't have regrets about it. And again, I think we wouldn't
have the agency we have over our lives now is a worthy price to me, you know, that I am able to
regret because I have choices. If I didn't regret, I wouldn't have choices and I wouldn't have
the freedom to choose and that in itself is a blessing. So that is my final takeaway message
from this episode, not to be, you know, not to be too toxicly positive, but yeah, how can we
see regret as maybe an asset rather than a weakness at times.
If you enjoyed this episode, I would really recommend you go and listen to our episode on the 20 biggest regrets people have in their 20s.
That full list is incredible and so much effort went into that episode and there's so much to learn.
Especially if you like knowing what kind of themes regret clusters around in order to avoid it yourself.
If you have made it this far as well, thank you for listening.
you have made it to our secret question of the episode.
What's something you actually thought you would regret, but didn't?
Leave a comment down below.
And as always, thanks for tuning in.
Thank you to our researcher Libby Colbert for her contributions to this episode.
Make sure you are following us on Instagram at That Psychology Podcast and subscribe wherever you are listening right now.
Until next time, be safe, be kind.
Be gentle with yourself. Thank you for tuning in. We will talk very, very soon.
2%. That is the number of people who take the stairs when there is also an escalator available.
I'm Michael Easter, and on my podcast, 2%. I break down the science of mental toughness,
fitness, and building resilience in our strange modern world. I'll be speaking with writers,
researchers, and other health and fitness experts, and more to look past the impractical
and way too complex pseudoscience that dominates the wellness industry.
We really believe that seed oils were inherently inflammatory.
We got it wrong.
Many of the problems that we are freaked out about in the world are the result of stress.
Put yourself through some hardships,
and you will come out on the other side a happier, more fulfilled, healthier person.
Listen to 2%.
That's T-W-O-Persent on the I-Hart Radio app, Apple Podcasts,
or wherever you get your podcasts.
There's two golden rules that any man should live by.
Rule one, never mess with a country girl.
You play stupid games, you get stupid prizes.
And rule two, never mess with her friends either.
We always say that trust your girlfriends.
I'm Anna Sinfield, and in this new season of the girlfriends...
Oh my God, this is the same man.
A group of women discover they've all dated the same prolific.
con artist. I felt like I got hit by a truck. I thought, how could this happen to me?
The cops didn't seem to care. So they take matters into their own hands.
I said, oh, hell no. I vowed. I will be his last target. He's going to get what he deserves.
Listen to the girlfriends. Trust me, babe. On the Iheart radio app, Apple Podcasts, or wherever you get your podcast.
Do you remember when Diana Ross double-tap Little Kim's boobs at the VMAs? Or when Kanye said that
George Bush didn't like black people.
I know what you're thinking.
What the hell does George Bush got to do a little kill?
Well, you can find out on the Look Back at it podcast.
I'm Sam J.
And I'm Alex English.
Each episode, we pick it here, unpack what went down, and try to make sense of how we survived it.
Including a recent episode with Mark Lamont Hill, waxing all about crack in the 80s.
To be clear, 84 is big to me, not just because of crack.
I'm down to talk about crack on day, but just so you all know.
I mean, at this point, Mark, this is the second episode where we've discussed correct.
So I'm starting to see that there's a through line.
We also have AIDS on the table right now.
Thank you finishing that sentence.
Yes.
I don't think there's a more important year for black people.
Really?
Yeah.
For me, it's one of the most important years for black people in American history.
Listen to look back at it on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.
Welcome to my new podcast, Learn the Hardaway with me, your host, and your favorite things.
Careers, Care Games.
And in recognition of mental health awareness month,
I'm bringing over a decade of my own experience
in the mental health field and conversations
with so many incredible guests.
I'm talking, Tripp Fontaine, Ryan Clark.
Sometimes when we're in the pursuit of the thing,
we get so wrapped up in the chase
that we don't realize that we are in possession of the thing
and we're still chasing it.
And we don't know when we've done enough.
Because people scoreboard watch.
Life becomes about wins and losses.
Steve Burns, Dustin Ross
because you find it important to be a good person
while you hear on earth
or are you a good person
because you're afraid
because that's two different intentions, bro.
Absolutely.
And that's two different levels of trust.
I want you to just really be a good person.
Join me, Kear Gaines,
is we have real conversations
about healing, growth,
fatherhood, pressure, and purpose
on my new podcast,
learn the hard way.
Open your free,
our heart radio app,
search Learn the Hardway and listen now.
Hey, what's good, y'all?
you're listening to Learn the Hardway
with your favorite therapist and host, Kear Games.
This space is about black men's experiences,
having honest conversations that it's really not safe to have anywhere,
but you're having them with a licensed professional
who knows what he's doing.
How many men carry a suit or armor?
It signals to the world that you're not to be played with.
And just because you have the capability
that does not mean that you need to.
Listen to learn the hard way on the AHA radio app,
Apple Podcast, or wherever you get your podcast.
2%. That's the number of people who take the stairs when there is also an escalator available.
I'm Michael Easter. And on my podcast, 2%. I break down the science of mental toughness,
fitness, and building resilience in our strange modern world.
Put yourself through some hardships, and you will come out on the other side a happier,
more fulfilled, healthier person.
Listen to 2%. That's TWO.% on the IHeart Radio app, Apple Podcasts, or wherever you
get your podcasts.
When a group of women discover they've all dated the same prolific con artist, they take matters
into their own hands.
I vowed.
I will be his last target.
He is not going to get away with this.
He's going to get what he deserves.
We always say that trust your girlfriends.
Listen to the girlfriends.
Trust me, babe.
On the Iheart radio app, Apple Podcasts, or wherever you get your podcasts.
On the Look Back at it podcast
For 1979, that was a big moment for me
84 was big to me
I'm Sam J and I'm Alex English
Each episode we pick a year
unpack what went down
And try to make sense of how we survived it
With our friends, fellow comedians and favorite authors
Like Mark Lamont Hill on the 80s
84 was a wild year
I don't think there's a more important year for black people
Listen to look back at it on the IHeart Radio app
Apple Podcasts or wherever
you get your podcasts.
This is an IHeart podcast.
Guaranteed human.
