Living With Regret: A Midlife Reckoning

The Low Level Ache of a Life Half-Lived

We don't talk much about regret in midlife. We say things like "no regrets" while quietly avoiding certain memories like they’re radioactive. Sometimes we don’t even recognise regret when it shows up. It doesn’t wear a sandwich board and announce itself. It’s just a quiet dissatisfaction. A pause before you answer, "How are things?" The twitch of envy when someone else chooses boldly. The way you scroll past your own dreams like an ad you’ve seen too many times and now seems to lack relevancy.

Midlife has a peculiar knack for revealing the gap between what is and what could have been. The ghost of an unlived life. You start hearing the ticking clock not as pressure, but as punctuation; a question mark at the end of your sentences.

Are you really okay with how this is going?

And if not, will you do anything about it? Or will you just continue to avoid it and pretend that this is your “lot in life”; pretend that you’ve made peace with everything.

Regret is not just a feeling. It's a location. A place in the psyche we retreat to when life didn't pan out how we hoped. And for many, it becomes a place of permanent dwelling.

Midlife regret isn’t just about the past. It's about what the past cost us: time, identity, intimacy, potential. And for high-achieving, emotionally intelligent adults, that cost doesn’t just sting, it gnaws and lingers with parasitical intent.

Regret Is a State of Being

Regret isn’t just a feeling; it becomes a state of being.  The head on collision of hindsight and hope. It’s a potent emotional stew made of self-blame, loss, and the longing to undo what can’t be undone. Unlike guilt, which is moral, regret is existential. It says: I wish I’d been someone else, just for that one moment.

It embeds itself through routine and repetition. The same job, the same argument, the same uneasy Sunday. Over time, it stops being a response and becomes the lens you look through. It becomes your posture, your personality and your postcode. You don’t just feel regret; you start living from it.

It loops through your brain’s decision-making circuits, becoming the undercurrent to every choice, and trying to rewrite the past with the logic of the present. Spoiler: it can’t.

The real danger? Regret thrives in emotional autopilot. In the stories we don’t question. In the dreams we shrink without noticing, and by the time we do, what’s lost isn’t just time, it’s trust in ourselves. It’s the sense of who we were meant to be.

Why Midlife Turns Up the Volume

Midlife is brutal and brilliant in equal measure. You’ve amassed enough experience to know what could have been, and enough self-awareness to realise you didn’t do it. You’re not young enough to be reckless or old enough to be excused. You know better; but knowing better doesn’t mean you did better.

This is the age of reckoning, a life stage where our brains are developmentally primed for life review. It’s also a time of relentless change. The children are grown or not happening now. The career has plateaued or taken over. The relationship is either hanging on, long gone, or under quiet renovation. And what’s left is you, centre stage, butt naked, asking: Is this it?

This is the point where the stories we built our lives on come under the microscope. For those who never stopped on the way to midlife to consciously edit, the edits come for you – suddenly the job feels hollow, the marriage has a limp, the body is not in a forgiving mood and the past dreams we buried under layers of practicality, resurface. Ouch.

Regret spikes in midlife, not just for what you did, but for what you tolerated, because you’re finally still enough to reflect and notice.

The Unseen Cost of Not Reassessing

Some people aren’t living in regret yet. Not actively. Some people will decide that they are going to skip the reflection phase of midlife, head down, and just keep on keeping on. Functioning under the false notion that if they just keep going the same way it will be okay and all work out. It has to, right?

Mark my words, they’re on the conveyor belt, moving steadily toward outcomes they didn’t design, ignoring the nudge, avoiding the hard conversation.

They are postponing joy.

Choosing later. Always later.

The problem is: later becomes never. And one day, when you really have nothing else to do but sit in a chair and think about your life, you don’t just regret what you did and didn’t do, you regret everything you didn’t let yourself want or prioritise.

·           “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

·           “I wish I hadn’t worked so hard.”

·           “I wish I’d had the courage to express my feelings.”

·           “I wish I had stayed in touch with my friends.”

·           “I wish I had let myself be happier.”

If you don't reassess your life now, end of life regret won’t be a distant possibility. It will be a predictable destination. You’ll have arrived by default, not design.

Regret Has Got a Crew

Regret has two dangerous allies: If only and What if. These are the mental distortions that reanimate the past and paralyse the present. If only is about self-blame. If only I hadn’t said that. If only I’d left sooner. It keeps you chained to a single decision. What if is about fantasy. What if I’d taken that job? What if I’d stayed? It keeps you chasing an illusion.

Together, they create a mental landscape where you’re always the villain or the victim, but never the protagonist. This really puts a dampener on your hero’s journey, it’s hard to slay dragons when you're busy narrating your own shame spiral.

What Regret Really Steals

Regret doesn’t just steal your joy. It steals your capacity to imagine. It robs you of trust in yourself, in life, in your own ability to rise. It makes trying again feel like a setup. Left to fester, regret becomes identity. You stop seeing a choice you made and start seeing the flaw that you are.

It can wreck your relationships too. Those stuck in regret often turn inward and away from connection. What I lost. What I didn’t get. How I messed up. It makes intimacy feel unsafe, because it reveals vulnerability. It makes self-forgiveness feel impossible, because it requires softness you think you don’t deserve. You become self-referencing, unable to see beyond your loss.

When you’re living in the loop of regret and its allies, everyone else becomes a character in your cautionary tale. You stop showing up fully. You stop risking love. You stop laughing with your whole body. Which is not only sad, but it is how loneliness wins.

The Flowers Never Arrived

I have been searching my memories for one in which I can put my hand on my heart and say that to this day I live in regret, but the truth is that regret is something I detached from and reframed long ago. I see it as pointless, beyond pointing to the learning that allows us to grow and be better. In my adult life I have not taken up residence in the campsite of regret.

Now, that is not to say that I haven’t done stupid things that have led to the passing emotion of regret. I have hurt people; stayed in jobs or circumstances I should have left sooner; left things unsaid that might have made a difference; not taken the risks that could potentially have led to dream fulfilment; abandoned myself to fit in; eaten my feelings instead of acting on them; and drifted in apathy instead of course correcting. I’ve got the whole uniform, not just the T-shirt.

But there is one memory that follows me. Not daily, but quietly.

I was eighteen, on a summer exchange in Germany and my nan was taken to hospital. I was told, but the severity was played down. At the time I had a kind and attentive boyfriend, (you know the ones that you completely take for granted at that age), and he offered to help me send flowers to the hospital with the note that said, “I love you”.

All I had to do is make the choice between first class and second class postage; and I chose wrong. I went cheap. The flowers and the note arrived after she had died. To this day it makes me cry.

It was a small thing, and it wasn’t.

It was the last thing I would have sent her; it was the last thing I would have said to her. I didn’t do it properly. That’s the part that stays.

That regret became my teacher. It taught me to discern what matters most and to approach those things with best intention and effort. It taught me that there is not always tomorrow with loved ones, so you need to show up while the opportunity is there. It taught me that saving a few quid is not always smart in the long term. It taught me that hesitation can cost more than action ever could. It taught me that gestures matter most when they’re timely.

Grief teaches you what matters. Regret teaches you how.

Since then, nothing that matters gets second-class treatment: not gifts, not family, not love, not words, not friendships. I’m a first class-or-nothing girl, well, except when I travel, obviously. That’s extortionate.

How to Live Without Carrying Regret

Living without regret isn’t about getting it all right. It’s about refusing to let the wrong moments become permanent fixtures.

Regret is a thinking trap. You must notice the pattern, the rumination, and interrupt the loop.

Let me be clear on this next point, I don’t say this lightly. I’ve seen this logic misused to justify appalling behaviour. When it comes to regret, it’s essential to remember that the version of you who made that choice or did that dastardly deed was not today’s version you, even if it was only yesterday.

That version knew less. That version that was doing their possible best with the resources and level of consciousness available to them.

You must show self-compassion in the face of regret and stop making yourself the villain. You didn’t fail. You didn’t know. You were doing the best you could with the tools you had in that given moment.

The next step is to ask better questions instead of just assigning a meaning to the action and consequence. Don’t ask, why did I do that?  unless you enjoy emotionally waterboarding yourself with unanswerable questions.

Instead ask, what did I need then that I didn’t have? or What is this trying to show me now?

Then externalise the lesson, tell someone, write it down, teach it – you need to get regret out of the mind’s echo chamber and transmute it into wisdom by applying the knowledge you have gained from it to your future.

Lastly, channel it. Fix what can be fixed. Now I am not suggesting you drunk dial every ex-partner at this point, self-respect is also important, but create the opportunities you missed now, love like you wish you had, live to feel alive and safe, say “yes” before you feel ready, take the meaningful leap, be far too much.

You have to face the grief, the anger, the sadness, the longing, because it is going to wait for you and as the years tick by it just gets heavier and heavier.

Reframing regret means picking up the pen. Editing with compassion. And choosing to see your past not as a verdict, but as a volume in a longer story.

Final Reckoning

There are few universal truths, but here’s one: nobody on their deathbed ever says, "I’m glad I played it safe."

They say:

I wish I’d tried.
I wish I’d said it.
I wish I’d loved harder, risked more, spoken sooner.

And they would give anything for the time you still have.

Regret doesn’t have to be a life sentence. It can be a pivot point. But only if we’re willing to listen - not to the voice that says you should have known better, but to the one that says: you still can.

You still can choose better.
You still can speak the words.
You still can show up fully.
You still can stop saving your life for later.

Because later isn’t promised. And first-class effort, when it matters, is never wasted.

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