Stop “Shoulding” Yourself: A Personal Reflection for Women

How many times a day do you tell yourself what you should be doing? 

- I should work out more. 

- I should spend more time with my kids.

- I should have said yes to that work project. 

- I should be further along in my career.

- I should be more organized.

- I should/shouldn’t have said that.

As women, we’ve been conditioned to carry the weight of expectations—some from society, some from family, and some self-imposed. The word “should” is like a quiet, persistent critic sitting on our shoulders, telling us we’re never quite enough. 

I know this struggle all too well. For years, I measured my worth by a mental checklist of “shoulds” I was failing to meet. I should’ve been a better friend. I should’ve cooked a healthier dinner. I should’ve asked for that raise sooner (or at all). Every day, it felt like I was juggling a dozen invisible balls and dropping them all.  And I felt like everyone noticed.

But here’s the thing: “Shoulding” ourselves keeps us stuck. It keeps us living by rules we didn’t create and prioritizing things that might not even align with our values and dreams. 

Why Do We Do This? 

For many of us, the habit of “shoulding” starts early. We’re taught to prioritize others’ needs over our own, to be accommodating, and to strive for perfection in everything we do. Add the pressures of career, family, and societal expectations, and it’s no wonder so many of us end up chasing impossible standards caught in the overwhelm of it all.

And then there’s guilt—the ever-present companion of the “should.” When we don’t meet those expectations, we feel like we’ve failed. We carry the weight of “not enough” with us, which only fuels the cycle further. 

The Turning Point 

For me, breaking free from the “should” cycle started when I asked myself one simple question: Whose rules am I living by?

I realized that many of my “shoulds” weren’t even mine. They were based on what I thought others expected of me or outdated ideas of success and happiness. 

I started replacing “should” with “want” or “need.” Instead of saying, “I should go to that event”, I’d ask, “Do I want to go?” or “Do I need to go?” And how does this align with my current top two values. This shift was liberating. It gave me permission to focus on what truly mattered to me rather than what I thought was expected of me. 

Moving Forward Without the “Shoulds” 

Letting go of “shoulding” yourself isn’t about shirking responsibility. It’s about redefining success and fulfillment on your own terms and based on your own values. It’s about trusting yourself to know what’s best for you. 

Here are a few steps I’ve found helpful: 

1. Identify your top two values to have as a handy filter tool.

2. Pause and Reflect: When you catch yourself saying “I should,” stop and ask why. Is this something you truly value, or are you trying to meet someone else’s expectations? 

3. Practice Self-Compassion: Remind yourself that you’re human. You can’t do it all, and that’s okay.  Practice giving yourself grace.

4. Set Your Own Rules: Decide what’s truly important to you and let go of the rest. Create a life aligned with your values, not a checklist of obligations. 

5. Celebrate Small Wins: Instead of focusing on what you didn’t do, acknowledge what you did accomplish, no matter how small. 

Embracing Freedom 

It’s not easy to stop “shoulding” ourselves. It takes intention, self-awareness, and practice. But when we let go of the “shoulds,” we open ourselves up to living more authentically. 

So, here’s my invitation to you: What’s one “should” you can let go of today? Give yourself permission to rewrite the rules. Your journey, your choices, your life—it’s all yours to design. 

With love and grace, 

Diane