Rewriting the “Shoulds”: Letting Go of the Life You Thought You’d Be Living
Have you ever caught yourself saying, “By now, I should have…” or “This isn’t how it was supposed to go”? Oh, I know I sure have! 🙋🏼♀️
Those “shoulds” are sneaky. They creep in when we’re looking at the calendar, when we scroll through social media, when we sit in the quiet of our own lives and wonder why it doesn’t look the way we imagined.
For many of us in midlife, those “shoulds” carry heavy stories:
I should still be married.
I should have my parents around.
I should have the grandkids around.
I should feel more settled, more successful, more…something.
But here’s the truth: the life you’re living right now may not match the story you once wrote in your head. Loss, betrayal, unexpected change—none of those were in your original script. Yet here you are, standing in the middle of a life you didn’t see coming.
And here’s the other truth: you’re allowed to rewrite it.
The Cost of Holding On to “Shoulds”
Every time we hold tightly to a “should,” we reinforce the idea that we’ve failed. That somehow, we missed the mark. But those “shoulds” weren’t written with your real, lived experiences in mind. They were old drafts. Outdated storylines.
Releasing them isn’t about lowering the bar—it’s about lifting the burden. It’s about acknowledging that life changed, and with it, your story gets to change too.
Rewriting Your Narrative
Instead of: “I should have it all together by now.”
Try: “I’m learning what ‘together’ looks like for me, in this season.”
Instead of: “I should be over this loss by now.”
Try: “Grief doesn’t follow a timeline, and healing is my own story to write.”
Instead of: “I should know exactly what’s next.”
Try: “I’m giving myself permission to explore what’s possible.”
When we rewrite the “shoulds,” we begin to shift from shame to self-compassion, from pressure to possibility.
Try This Today
Grab a journal and write down the top three “shoulds” that weigh on you most. Then, try rewriting each one into a gentler, truer statement. Notice how your body feels when you read them back. Does it feel lighter? More open? That’s the power of rewriting your narrative.
✨ Want to go deeper?
Inside the Pathfinder membership, this month’s masterclass is You Are the Storyteller Now: The Power of Narrative in Healing. Along with the class, members are walking through a 30-day challenge that helps you practice rewriting, reframing, reclaiming, and living into a new story.
Sometimes all it takes is one small, intentional step to shift your story. The Pathfinder membership offers that step—with new masterclasses each month, practical challenges, and a safe space to keep moving forward. Discover Pathfinder here →
Next week, we’ll explore how storytelling helps us make meaning from loss. Read it here →
