Are We Mourning the Life We Wanted, or the Life We Were Told to Want?
Here's a question that's been sitting heavy on my heart lately: What if the life we're grieving isn't actually the one we wanted—but the one we were taught to want?
I came across a letter in Slate's Dear Prudence column that stopped me mid-scroll. A 50-year-old mother wrote about her ongoing grief over having only one child when she'd dreamed of "a house full of children." Nineteen years later, she's still having panic attacks over the future she thought she'd have. And here's what hit me: she's not just mourning what didn't happen. She's mourning while her present life—her actual son, thriving and well—is happening right in front of her.
It made me think about my own story. In my late twenties, with 30 breathing down my neck, I felt this crushing weight of being "behind." I wanted the kids, the house, the marriage, my own family—especially during a time when I wasn't close to my family of origin. But I was single. Three years single. And even when I imagined meeting someone, the math didn't add up to my timeline. I'd need time to know him. Time to get married. Time to enjoy being newlyweds before becoming parents. Years would pass, and I'd be even more "behind."
Now I'm 34. Still single. No children. And you know what? I'm grateful I waited. Because of that waiting period? That wasn't wasted time. That was the time I needed to build a strong relationship with myself, one that would enable me to know the difference between my dreams and society's script.
The Dreams We Carry vs. The Dreams We're Given
As little girls, we rehearsed our futures like lines in a play. The dream wedding. The number of kids. The "Prince Charming" who would make it all happen. And we held onto that vision like a lifeline, never considering that the world we'd grow up in—the economy, the shifting cultural landscape, our own evolving selves—might rewrite the script entirely.
Here's what no one tells you: as we get older, pieces of those dreams change. Some get left behind. The woman you were before you became a mother. The career path you abandoned. The version of yourself who thought she'd be married by 25. We never expected to leave those versions behind because they are us—but everything changes when life does.
Sometimes we find ourselves grieving futures that were never really ours. We think we're mourning the lives we wanted, but it's often the lives we felt we should want.
The Self-Relationship Question That Changes Everything
Building a relationship with yourself gives you something revolutionary: the ability to quiet the noise and figure out what your life should actually look like. Not what looks good on Instagram. Not what your mother expected. Not what that childhood vision board promised.
Because here's the thing—we love to say we want "a life we don't need a vacation from." But will that be the same life you don't regret having? Just because you have more time or more money doesn't automatically mean marriage is for you. Or kids. Or both. Or neither.
The question isn't just "What do I want?" It's "What do I want that's actually mine?"
Three Practices for Building a Life You Won't Regret
1. Journal through the "supposed to" narratives. Write down every "I'm supposed to..." that comes up when you think about your life. Then ask: "Says who?" Watch how many of those beliefs aren't actually yours.
2. Create a "present-moment inventory." What's actually good in your life right now that you're missing because you're mourning what isn't here? Like that mother who couldn't see her son's actual thriving because she was grieving the siblings he never had. What are you not seeing?
3. Design your "no regrets" list—not your bucket list. Ask yourself: "If I'm 80 and looking back, what would I regret not doing, being, or experiencing?" Notice the difference between societal milestones and soul milestones. One comes from outside pressure. The other comes from your actual values.
The Permission You've Been Waiting For
You're allowed to want something different than what you thought you wanted at 16. Or 25. Or last year.
You're allowed to grieve the future you imagined while also building one that actually fits who you're becoming.
And you're allowed to take your time figuring out which dreams are yours to keep and which ones you inherited from a world that never asked what you needed.
The life you create through deep self-relationship might be unexpected. But it is a conscious choice—yours. That is what truly matters.
With love and intentionality,
Shay
P.S Want to know where you are in your relationship with yourself? Take my free assessment here.
