The Problem With “Should”

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A woman working on her computer.For most of my life, I’ve lived according to a long list of rules that I created for myself, rooted in what I thought I should be doing.

I told myself I should work harder, parent a certain way, and make decisions based on the invisible “right” path I imagined. I thought following my “shoulds” would keep me on track, but instead, they often left me feeling trapped, frustrated, and disappointed.

The thing about “should” is that it doesn’t just stay within me. I started expecting my family, my coworkers, my kids, and even strangers to live by the same “shoulds.” And when they didn’t (because, of course, they couldn’t possibly see the world exactly as I do), I felt let down. Relationships were strained, work felt harder than it needed to be, and parenting became filled with expectations instead of genuine connection.

I’ve realized I live in extremes. For me, things are either right or wrong, black or white. But life is not that neat. It lives in the messy gray middle area I’ve spent years resisting. And resisting that gray has kept me from flexibility, growth, and peace.

Change has never been easy for me. In fact, I’ve often fought it. But now, as I get older and my children grow more independent, I see more clearly that “should” has been holding me back. It’s kept me stuck in rigid patterns instead of allowing me to grow into new seasons of life.

Here’s the truth I’m learning: what works for me might not work for someone else, and that’s okay. My kids may make choices I wouldn’t make. A friend may parent differently from how I do. A coworker may solve a problem in a way that would never occur to me. And none of that makes my way or their way wrong.

Letting go of “should” doesn’t mean letting go of my values or goals. It means loosening my grip on perfection and control.

It means allowing space for grace, curiosity, and new possibilities. It means accepting that life doesn’t have to fit neatly into black and white boxes—it can be a spectrum of gray, and maybe that’s where the most beautiful living happens.

I don’t have it all figured out, and I still catch myself clinging to “should” more often than I’d like. But I’m practicing. I’m practicing choosing could instead of should. I’m practicing curiosity instead of judgment. And I’m practicing letting people (myself included) live in the gray.

Because life isn’t about what we should do. It’s about learning, growing, and finding the freedom to simply be.

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Michelle
Michelle is the Owner and Editor of Fairfield County Mom and Westchester County Mom. Born and raised in Norwalk, she now lives in Fairfield, CT, with her husband, Chris, whom she married in 2008, back when she thought she was “busy.” Fast forward to life with her son Shane (2011), twins Blake and Brynn (2013), a black Lab named Hank, and a Frenchie named Bruce, and she now laughs at her pre-mom self. By day, Michelle is a second grade team leader at a local public school, which means she’s a chaos-managing, data-collecting superhero in sensible shoes. By night, she’s a list-making, laundry-folding, sideline-cheering multitasker who runs on coffee and Diet Coke (RIP tequila). She believes in storytelling, building community, and finding the humor in this wild ride called motherhood (preferably from the quiet of her parked car).

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