Grieving the Life You Didn’t Live: Lets Go There
A reader asks: “Is it normal to grieve a life that never happened?” Let’s talk about midlife regret, missed chances, and what you can still build from here.
Midlife has a way of pulling your old dreams out of storage. The business idea you once scribbled in a notebook. The country you almost moved to. The relationship that flickered but then faded before it ever became real.
Angelie from the U.S. wrote in and said:
“I’m grieving a life that never happened.
I made reasonable decisions at the time, but lately I keep wondering who I would be if I hadn’t. Nothing in my life is objectively bad… but I can’t shake the feeling that I missed something.
Is it normal to feel regret this strongly in midlife?”
Short answer? Yes.
Let’s Go There is a candid, question-led column where we unpack the real stuff behind remote work, solo travel, and midlife reinvention. No filters… just honest answers to the questions you’ve been carrying around.
By this stage, we have enough distance to see our crossroads clearly. We remember the job offer we declined because the kids were small. The move we postponed because our parents needed us. The leap we didn’t take because security felt smarter.
And sometimes, in the quiet, those unlived lives tap us on the shoulder.
What if?
Here’s the turning point I’ve seen again and again — in readers, in friends, in people rebuilding after layoffs, divorce, loss:
Regret isn’t always a verdict. Sometimes it’s just information.
It’s not there to shame you for what you didn’t do. Think of it as pointing you toward what still matters.
If the business idea still stings, maybe you’re not done building.
If the country still calls to you, maybe you don’t need a permanent move… just a three-month test.
If the relationship you didn’t pursue represents passion or depth, maybe that’s the quality you want more of now.
We can’t live every version of our life. That’s the human deal.
But we do get to choose what we do with the ache.
See what you can mine out of the unlived versions for clues.
Take one of the “what if” stories that keeps resurfacing. Write it down. Not the fantasy version, but the emotional core of it.
Maybe it’s: I should have moved to Italy when I had the chance.
Or: I wish I’d started that coaching business ten years ago.
Or: What if I’d chosen him instead?
Write the story down in one paragraph, the way your brain usually tells it.
Now strip it back. What did I believe that version of my life would give me?
Be specific. It wasn’t just “Italy.” Was it freedom? Slower mornings? Excitement and wonder? Distance from family expectations?
It wasn’t just “the business.” Was it autonomy? Recognition? The thrill of building something from scratch?
And it’s never just “that relationship” with that one person you never knew that well to begin with. What did you feel you missed out on? Was it passion? Feeling chosen? Emotional intensity? A sense of being fully seen?
This is where we tend to get stuck; we think they’re grieving the event. But often, we’re grieving the feeling we thought the event would unlock.
Once you name that feeling, the question changes.
Instead of: Did I miss my chance?
It becomes: Where could I create more of that feeling now?
If what you miss is freedom, could you negotiate one remote month a year?
If it’s autonomy, could you carve out a small income stream that’s fully yours?
If it’s passion, could you stop tolerating lukewarm connections?
You’re not trying to recreate the old fantasy. You’re trying to extract the essence of it, and design a new experience for that.
Think on that today. Where could I create a smaller, current version of that feeling, without burning down my entire life?
Could you pilot the business idea on weekends? Take a one-month remote work trial instead of emigrating? Choose relationships now that reflect the depth you once craved?
You’re not too late. You’re just working with better information now, and that’s a great place to be.
✌🏻 Miranda
P.S. Have a burning question about remote work or nomad life, particularly in your 40s and beyond? Submit to hello@midlifenomads.com and I’ll do my best.
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