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Stop "Shoulding" on Yourself & Others


Stop "Shoulding" Yourself & Others
Stop "Shoulding" on Yourself & Others

What happens when things do not go according to your plan?


You set expectations. Sometimes they are explicit but often, they are unspoken.


When reality doesn't align, you may beat yourself and others up with "I should" and "you shouldn’t have.” I refer to this as “shoulding.” Not only is it a waste of energy, but it is also flawed thinking that can hold you hostage.


We have been conditioned to believe in the concept of "should.” But what if I told you that "should" only exists in our imagination? What if this simple word, and the habitual thinking behind it, is keeping you stuck and disconnected from reality?

When you say "I should" or "you should," you believe that there's only one right way to do something or that a certain outcome is the only acceptable one. And when it doesn't play out exactly the way you have envisioned it, you can feel confused, disappointed, frustrated, and resentful. You start blaming yourself or others for not meeting these imaginary standards.


Here's the thing. Your standards and expectations reflect deep, internalized beliefs. You grew up with particular values, standards, rules, and societal norms to define success and failure, right and wrong, and good and bad. These have been refined daily in your life experiences and many were handed down to you. In reality, you have outgrown small dreams and the rules and beliefs of the past, just as you outgrew your clothes or the hairstyle you had 25 years ago. Like many people, you may be clinging to the old stuff because this contemporary world feels hard to navigate. But why allow old thinking and your younger brain to govern life today?

Historically, ways of interacting and controlling life and work were linear, “black and white,” and tightly time-bound. This created the collective tendency to believe in “should” — the one right way and specific outcomes. This was efficient, organized, and predictable. This thinking and behavior drove progress for centuries.

Today, our world is dynamic, collaborative, distributed, diverse, and often, chaotic. The technology that continues to propel us forward is challenging the stability and effectiveness of hierarchical systems and structures and requires new thinking and behavior. This includes the need to evolve our internal belief systems to allow for a faster pace, more fluidity, and openness to infinite outcomes and possibilities.


In today's environment, an intense need to control and impose your thinking on a situation may lead others to perceive you as closed off to new ideas or new information. This leads to misunderstandings, miscommunications, and missed opportunities.


Another concerning disconnect of being committed to a “should” is the possibility that you are operating with a disregard for reality. For this discussion, I’m referring to “reality” as what is happening in the present moment. When you are imposing a specific way of thinking, you are in your head, where your beliefs and past experiences are stored. Do you remember how you experienced “old people” when you were young? You probably thought they were “out of touch” with that current reality. They could have been “right” in the context of their beliefs and experiences, but for you, their truth and desired outcomes most likely didn’t feel right. When “should” shows up and is anchored to what we believe is truth, there is an immediate disconnect from the opportunities and potential that are presented in the NOW. For partnership, collaboration, innovation, and agility to exist in your relationships, “should” has to go.

So, what can you do instead?

  • Be curious. Open up to possible alternative ways of thinking that you haven’t learned or heard yet.

  • Practice staying present instead of getting hijacked by your “should-based" thoughts.

  • Notice which of your beliefs come up often as “should” thoughts.

  • Retire some of the rules, standards, thoughts, and beliefs that you may have outgrown.

  • Be willing to consider ideas that feel threatening to you. If needed, discuss this with a coach or objective friend or colleague who can help you see what old beliefs or values this new idea is “pushing on.”

  • Replace “should” with:

    • I have strong beliefs about how this is going to play out. Can we discuss all the potential ways it could work or not work so that we are on the same page?

    • I don’t want to make a mistake and all my experience is telling me it needs to play out like ____________. I’m sure other people here might be having the same thoughts with different ideas for execution. Can we efficiently collect all the ideas for consideration?

    • I’m feeling frustrated because I wanted ___________.

    • Help me understand why _________ was a better choice/solution/decision than _______________.

    • I wish ______ instead of ______. I’m trying to reconcile this.

    • I thought _____ and now I’m trying to understand how we/I/you got __________.

    • I’m curious about what I may not be seeing or understanding. My thought was ________, and now I see that wasn’t aligned with reality. Can you explain this to me?


Next time you catch yourself "shoulding" or hear it from others, recognize it as an invitation for dialogue, not a call for blame, shame, and guilt. When you let go of the judgment of "should," you open yourself up to a world of possibility that you might not have even realized was there. You also may notice that your partner, children, or employees seek your advice, experience, and recommendations when it is delivered without the need to control or be right. This is an opportunity to immediately shift your experience of others, stop the build-up of resentfulness and anger, and change how people view you.

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