When 'Should' holds you back

From “Should” to “Could”: A Different Way to Think 

Have you noticed how often the word “should” comes up in leadership? “I should do this,” or “They should know better.” These “shoulds” are everywhere. Sometimes useful, sometimes less so.

“Shoulds” are the rules and expectations we pick up from work, culture, or how we were brought up. They can keep us on track, but they can also box us in. When we lead from a place of “should,” we might end up holding ourselves and others to fixed standards that don’t always fit the real situation. This can lead to guilt, frustration, or even perfectionism if reality doesn’t match the “should.”

There’s another way to approach things: acceptance, flexibility, and paying attention to what’s actually happening. Instead of focusing on what “ought” to be, we can notice what is. This means responding to circumstances as they are, not just as we wish they were. It opens the door to nuance, self-compassion, and adaptability—and often, it reduces stress and inner conflict.

One simple shift is to move from “should” to “could.”

“I should have all the answers” becomes “I could ask the team for their thoughts.”

“We should stick to the plan” turns into “We could adjust if things have changed.”

“They should know what I expect” becomes “I could check in to see if we’re on the same page.”

There are other ways to look at it, too:

Shoulds vs. Wants/Values: “I should work late” vs. “I want to finish this project because it matters to me.”

Shoulds vs. Curiosity/Exploration: “I should have known better” vs. “What can I learn from this?”

Shoulds vs. Self-Compassion: Swapping self-criticism for a bit of understanding and kindness towards yourself.

This isn’t about ignoring standards or letting everything go. It’s about making room for choice and being curious about what might actually work best, right now. Sometimes, just noticing your own “shoulds”, and wondering what happens if you try “could,” or focus on what you value (or simply accept what is) can make a real difference.