A listener wrote in with something I hear some version of often. She's turning forty this year, in what looks like an “objectively” good place. Stable job, a marriage that works, two kids she adores. She used to make art, back in college she'd dreamed of having her own show one day, before the safe path took over as the actual plan. Then a friend's first solo art show at her birthday dinner cracked something open, and she found herself crying in the car on the way home, unable to explain why.
My first instinct wasn't to ask what she wants to change. It was to ask what she's never let herself grieve.
This week's episode is about a specific kind of grief, the kind that doesn't come from losing a person, but from realizing that even a life you chose on purpose, and don't regret, can still come with grief for the paths you didn't take. It has no funeral, no clear ending, and it's easy to talk yourself out of, precisely because nothing actually went wrong.
The Science:
There's a researcher, Pauline Boss, who calls this ambiguous loss, grief without the things that normally give grief its shape, no death, no funeral, no clear boundary between before and after. She originally studied it in families with a missing loved one, or a loved one present in body but gone in every other way. I think it applies just as directly to a version of yourself you didn't get to become. Nobody sends a eulogy for her, because nobody else even knew she existed. That doesn't make the loss any less real.
Try This:
A fillable version of this week's exercise, The Letters to Her
LETTER ONE: TO THE LIFE YOU DIDN'T LIVE
Set a timer for about seven minutes. Write to the life you didn't live, or the version of you out there living it. Say what you actually miss, no "but I shouldn't complain."
Dear ___________,
What that path represented to me (e.g., freedom, creativity):
_______________
What I actually miss:
_______________
Closing line, naming it as something that's allowed to matter, not a failure:
_______________
LETTER TWO: TO THE LIFE YOU'RE ACTUALLY LIVING
On a fresh page, about seven minutes. Write to the life you're actually living. Get specific, not general gratitude-journal stuff, and don't frame it as an apology for Letter One.
Dear ___________,
Something specific that only exists because I'm here and not somewhere else:
_______________
Another one:
_______________
INTEGRATION:
Read both letters back to back. Write one line that holds them together.
_______________
Reflection: What might it feel like to let both of those be true at the same time, the grief and the gratitude, without needing one to cancel out the other?
Work with Me: I take on a small number of coaching clients. If you've been reading this newsletter and the same question keeps surfacing, there's a next step available. The first step is a discovery session.
Have a question you want me to dig into? Reply to this email or DM me on Instagram.
I'm in it with you.
Ilana