There’s a particular kind of sadness that hits you at unexpected moments.
You’re doing fine, maybe even content, when suddenly you remember the person you thought you’d become or the life you assumed you’d be living by now.
That alternate version of yourself, the one who made different choices or caught different breaks, feels oddly real.
Almost like someone you knew who moved away and never kept in touch.
At 64, I’ve watched enough people wrestle with this feeling to know it’s not just nostalgia or regret.
Psychologists call it “ambiguous loss,” and it’s a legitimate form of grief.
You’re mourning something that never existed but somehow still feels like it should have.
The research is clear: this grief affects our mental health, decision-making, and even our physical wellbeing.
Yet most of us dismiss it as self-pity or tell ourselves to “get over it.”
The truth is more complex.
This grief for unlived lives is both universal and deeply personal.
After years of observing how people navigate major life transitions, including my own retirement, I’ve identified nine signs that you’re experiencing this particular form of mourning.
Understanding these signs won’t make the grief disappear, but it will help you recognize what’s happening and why it matters.
1) You feel jealous of younger people making choices you can’t make anymore
When I see young professionals starting their careers, something tightens in my chest.
Not because I want to be 25 again, but because they still have all their chips to play.
They can still become the version of themselves I thought I’d be when I was their age.
This isn’t ordinary envy.
It’s grief for expired possibilities.
At 35, when I finally got married after years of prioritizing work, I realized certain paths had closed.
The marriage with college sweethearts growing together through their twenties.
The kids in my thirties with energy to spare.
Those versions of my life were gone, not through any single bad decision, but through the accumulation of reasonable choices that led elsewhere.
Psychology research shows this is actually a form of disenfranchised grief.
Society doesn’t give us permission to mourn these losses because nothing “real” was lost.
But your brain doesn’t distinguish between grieving an actual loss and grieving a possibility that felt real to you.
2) You catch yourself saying “I should have” more than “I will”
Listen to yourself talk for a day.
How often do you use past-tense language about opportunities?
“I should have taken that job overseas.”
“I should have started that business.”
“I should have left earlier.”
This backward-looking language is a clear marker of unprocessed grief.
You’re not planning or problem-solving; you’re mourning.
The psychologist Pauline Boss, who pioneered research on ambiguous loss, notes that we get stuck when we can’t achieve closure on something that was never fully there to begin with.
3) Major milestones leave you feeling empty instead of accomplished
Retirement hit me differently than expected.
After decades in high-stakes negotiations where competence and usefulness defined my worth, I achieved the thing everyone works toward: financial security and freedom from the daily grind.
But instead of satisfaction, I felt hollow.
I keep a notebook where I return to the same question: “What am I optimizing for now?”
The answer keeps changing because I’m grieving the version of myself who had clear metrics for success.
That person knew exactly what winning looked like.
This new person has to create meaning from scratch.
4) You avoid certain places or people that remind you of who you “should” have been
There’s a neighborhood in my city where startups cluster.
Young entrepreneurs work from coffee shops, having the kinds of conversations I once imagined for myself.
I avoid that area.
Not consciously at first, but I noticed myself taking longer routes to avoid driving through.
This avoidance is classic grief behavior.
We stay away from triggers that remind us of our loss.
Except in this case, we’re avoiding reminders of lives we never lived.
The psychology is the same: our brains are protecting us from pain, even if that pain comes from comparing reality to imagination.
5) You feel anger at people who “wasted” opportunities you wanted
A former colleague left a prestigious position to travel for a year.
Another turned down a promotion to spend more time with family.
These choices shouldn’t affect me, yet I feel genuine anger watching people squander what I would have treasured.
This misdirected anger is grief in disguise.
We’re not really angry at them; we’re angry that life’s timing means we can’t swap places.
They have what we’ve lost: the luxury of those choices.
The anger feels more acceptable than admitting we’re mourning our own closed doors.
6) You create elaborate fantasies about parallel versions of your life
Sometimes I construct detailed alternate histories.
What if I’d taken that international assignment?
What if I’d had kids earlier?
These aren’t quick daydreams but elaborate narratives with plot points, challenges overcome, different relationships formed.
Psychologists recognize this as a form of “counterfactual thinking,” and it serves a purpose.
We’re trying to process our grief by imagining the lost object more clearly.
The danger comes when we spend more time in these parallel worlds than in our actual life.
7) You struggle to answer “what do you want?” without referencing the past
Ask yourself what you want from life now.
Not what you wanted, not what you should want based on your age or situation, but what you actually want today.
If you can’t answer without referencing past dreams or explaining why certain things are no longer possible, you’re stuck in grief.
This paralysis happens because we haven’t separated who we are from who we thought we’d be.
Until we properly mourn that other person, we can’t fully inhabit our actual life.
8) You feel like you’re running out of time even for things that aren’t time-sensitive
Reading a new book feels urgent.
Starting a hobby carries weight.
Every choice feels like it’s stealing time from other potential choices.
This artificial scarcity mindset is another grief symptom.
We’re mourning all the time we “wasted” not becoming that other version of ourselves, which makes every current moment feel impossibly precious and pressured.
9) You dismiss your actual accomplishments as “not what I planned”
My career was successful by most measures.
I negotiated deals, built reputation, achieved financial stability.
Yet I often minimize these accomplishments because they weren’t part of my original vision.
This isn’t humility; it’s grief interfering with reality.
When we can’t celebrate what we’ve actually done because we’re mourning what we didn’t do, we’re stuck in a grief loop that psychology says can contribute to depression and anxiety.
Closing thoughts
Recognizing this grief doesn’t mean wallowing in it.
The research on ambiguous loss suggests that acknowledging this type of grief is the first step toward integrating it.
You can mourn the life that didn’t happen while still engaging with the life you have.
Here’s what helps: Write a letter to that other version of yourself.
Thank them for keeping you company all these years.
Acknowledge what they meant to you.
Then, consciously choose one small action in your actual life that honors what that imagined self valued.
If they were creative, create something small today.
If they were adventurous, take a different route home.
The grief may never fully disappear, and that’s normal.
Those unlived lives were real to us in important ways.
But we can hold that grief while still moving forward, making peace with the gap between imagination and reality.
After all, the life you’re living now was once just one possibility among many.
The fact that it became real?
That’s worth something too.
