Shed The Shoulds

Jan 31, 2024

I should get to that project. I should call my mom. I should get up earlier. I should exercise more. I should go to her birthday party this weekend.

I shouldn’t have left that work event so early. I shouldn’t have said “yes” to that project. I shouldn’t have said “no” to that incredible opportunity that felt a tiny bit too far out of my comfort zone.

Just reading these sentences feels heavy. Should is a disempowering word. It implies a lack of trust.

The Oxford Dictionary's definition of the word should is that it's: “used to indicate obligation, duty, or correctness, typically when criticizing someone's actions.”

“Shoulds” are crappy. That’s why there’s a popular phrase, “Don’t should on yourself.”

Words have power. This one carries a sense of pressure, internal or external, which can lead to feelings of guilt, anxiety, shame or regret. These feelings may be subtle and escape conscious recognition, but they still have an effect. Slowly over time, they can erode self-esteem and joy.

We all live with programming from family, culture and our personal experience. Many of us who are highly sensitive have been programmed with messages about this trait being a liability instead of an asset and so we mask and attempt to fit in for much of life. This involves a lot of shoulds.

Becoming aware of them and choosing different words is a way to rewrite this program. It’s a path to freedom, first in the mind and then in the world because there’s a renewed sense of confidence and conviction. Should is on the other side of the scale from freedom.

Should is a symptom of fear. It’s the bubbles coming up to the surface from the mouth of some deep lurking fear. This is a benefit of using the word “should.” It’s a pointer to something that when understood and released can create more freedom. Now you know where to go fishing. Pull it up from the depths of the unconscious program that’s running beneath the surface.

Let’s go fishing, shall we? Through each of these steps, feel it in your body. Where does this live inside you? You can journal, dance, drum or walk through this process. Whatever feels true for you.

Step 1: When you catch yourself saying, “I should…”, ask yourself why. “Why should I?” See what comes up. You may discover that the should comes from a need for validation from others, which may come from not feeling confident in yourself. Or, just being so used to not fitting in. Then, ask yourself, “What happens if I don’t?”

Step 2: Evaluate whether these shoulds align with your true desires and values or if they are influenced by societal expectations or external judgments. Or, are they internal judgments that don’t suit you any longer? Ask this North Star question: “Is this going to bring me more (core value – freedom, joy, etc)?” You get to have what you want.

Step 3: Begin to recognize this word and its effect and then choose a more empowering word. Replace and restate. How does that feel?

Words to use instead of should:



Would like




Let’s try them on.

I desire to get to that project. I want to call my mom. I will get up earlier. I want to exercise more. I could go to her birthday party this weekend.

I can be gracious with myself when I feel the need to leave a work event early. I would like to practice healthy boundaries instead of saying “yes” to that project that’s more than I can handle right now. I desire to say “yes” to the next incredible opportunity that feels a tiny bit too far out of my comfort zone.

Step 4: Be kind to yourself. You’ll probably miss more than you catch, and you’ll likely find yourself using the word again down the line. But you’ve made a choice, you’ve made an effort, you’ve set an intention and all of this contributes toward a more positive mindset.

Should may also be a symptom of people-pleasing which is associated with fawning – a stress response. These shoulds are part of the guard rails that keep us in line with the dominant culture. But now as culture transforms, the opposite is true. Your inner knowing is what’s needed. There are no guard rails for what’s next. The more you can sense into the moment, the more you’ll be aligned with right action and your truth.

Should is masculine. It’s like a strict sergeant making sure you toe the line.

Could or would is feminine. It’s more suggestive. There’s more room to play. 

Journal Prompt: What are you doing just because you think you should or out of a sense of obligation to others? What do you truly desire?

To cultivate more trust in yourself, more connection to your truth and more freedom, shed the shoulds.

There’s much to shed. Re-align with the cycles of nature with a seasonal reset for body, mind & business. Join us for Spring Revive. We begin February 28.

“Should” is a great word to watch out for when it comes to business advice as well. It’s like a code word that reveals the dominator culture. It indicates “power over” versus “power with."

Each one of us has inner guidance. This is the advice to follow whether deciding to go to the birthday party or to launch a new program for your customers.

By reprogramming thinking to reduce the word "should" and cultivating a more positive and growth-oriented mindset, highly sensitive entrepreneurs can better navigate the challenges of work, reduce stress, and increase the chance of success while maintaining a deep sense of well-being.

I opened up the Insight Timer app this morning to time my meditation and was greeted by a quote from Sri Ramana Maharshi. It said, “Your true nature is that of infinite spirit. The feeling of limitation is the work of the mind.” Dismantling destructive thoughts by discontinuing the use of words that link to them is one of many ways to experience true nature.

Highly sensitive person (HSP) is a personality trait that 20% of the world's population has. Do you? Take this quiz to find out.

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