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Stop “Shoulding” All Over Yourself (and Everyone Else)

There’s a word we use so casually that we rarely stop to consider its weight. It slips into our

thoughts, our conversations, and our expectations without permission. That word is should.


“I should be further along by now.”“They should know better.”“This should be easier.”


At first glance, it seems harmless—maybe even helpful. But “should” carries a quiet pressure that can shape how we see ourselves and others in ways that are anything but healthy.


The problem with “should” is that it creates a standard without grace. 


“Shoulding” builds an invisible rulebook, often rooted in comparison, assumption, or unrealistic expectations. And then it holds us—and everyone around us—accountable to it.  When we “should” on ourselves, we trade growth for guilt. Instead of asking, What am I learning?, we ask, Why am I not there yet? Instead of recognizing progress, we fixate on perceived shortcomings. “Should” turns our journey into a judgment.


When we “should” on others, we trade connection for control. 


We begin to expect people to think like us, act like us, or grow at the same pace we do. We assume their awareness matches ours. Their capacity matches ours. Their circumstances mirror ours. And when they don’t? Frustration builds. Resentment creeps in. Relationships strain.


“Should” doesn’t just describe expectations—it creates them.

Here’s where this becomes even more important: many expectations are born from a single “should” thought. One moment of internal dialogue—They should have handled that differently—can quietly become a long-term expectation—They always need to handle things the way I would. That’s a heavy burden to place on someone else…especially when they never agreed to carry it.


So what do we do instead?


We start by noticing. Awareness is powerful. When you catch yourself thinking or saying “should,” pause. Ask yourself: Is this rooted in truth or assumption? Is this helpful or harmful?Is this creating clarity or pressure?


Then, shift the language.

Instead of “I should be better at this,” try:“I’m still growing in this area.”

Instead of “They should know better,” try:“I wonder what they know or understand right now.”

Instead of “This should be easier,” try:“This is challenging, and I can learn through it.”

That shift may feel small, but it changes everything. It replaces judgment with curiosity. Pressure with possibility. Expectation with grace.


In leadership, this matters deeply. 


Whether you’re leading a team, a business, a ministry, or your family, or Yourself, the words you use internally shape how you show up externally. Leaders who operate from “should” often create environments where people feel they can’t measure up. Leaders who choose curiosity and clarity create environments where people can grow.

This doesn’t mean we abandon standards or accountability. It means we approach them differently. We communicate expectations clearly instead of assuming them. We coach instead of criticize. We ask questions instead of making judgments.

And maybe most importantly, we extend that same grace to ourselves.

You are not behind.You are not failing because you’re not where you think you “should” be.You are in process.


Growth isn’t linear. Leadership isn’t perfect. And people—yourself included—are wonderfully complex and constantly evolving.


So today, notice where “should” is showing up in your life. 


Notice how it’s shaping your expectations. And then, choose something better. Because the moment you stop “shoulding” all over yourself and others…is the moment you start leading—and living—with greater freedom, clarity, and connection.


I'd love to walk alongside you on the journey. Please reach out.


I look forward to chatting with you soon!

Kris

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