Reclaiming Choice from the Language of Obligation
There’s a subtle word that weighs heavy on our lives – quietly chaining us to guilt, resentment, and unrealistic expectations. That word is “should.”
You should be farther ahead.
You should call more often.
They should know better.
I shouldn’t feel this way.
Each one might seem harmless, even helpful. But underneath, “should” often signals a tug-of-war between who we are and who we think we’re supposed to be.
Let’s unpack it.
What Is “Shoulding”?
“Shoulding” refers to the habit of using the word “should” to impose obligation, judgment, or pressure – on ourselves or others. It rarely reflects desire or authenticity. Instead, it often arises from inherited rules, fear of disapproval, or the pursuit of worth through compliance.
We “should” ourselves into people-pleasing.
We “should” others into our comfort zones.
We accept “shoulds” from others and call it love.
It becomes the grammar of guilt.
The Three Faces of “Should”
1. Shoulding on Yourself
This is the inner critic’s playground.
- “I should be over this by now.”
- “I should say yes even if I’m tired.”
- “I should be grateful, not overwhelmed.”
These are not acts of empowerment. They’re quiet betrayals of what you really feel, want, or need. Over time, this pattern erodes self-trust and replaces it with performance.
2. Shoulding on Others
This version disguises control as care.
- “They should know how I feel.”
- “They should behave better.”
- “They should want what I want.”
Behind many “shoulds” is an unmet need we haven’t owned, or a boundary we haven’t voiced. “Shoulding” others creates tension, not intimacy. It asks people to read your mind, then resents them for failing.
3. Being Shoulded by Others
This form is often absorbed unconsciously:
- “You should smile more.”
- “You should be like your sister.”
- “You should never quit.”
Whether it’s family, culture, religion, or relationships, being “shoulded” shapes us into roles we didn’t choose. It can feel like love, but it’s really performance in exchange for approval. And eventually, it becomes internalized – so you carry the whip yourself.
The Hidden Cost of Shoulds
“Should” is often a shame signal. It implies a “right” way and suggests you’ve already failed it.
Living in a world of “should”…
- Breeds guilt and resentment
- Distances you from your inner truth
- Replaces desire with duty
- Turns connection into compliance
And perhaps most painfully, it postpones self-acceptance until you’ve earned it.
From “Should” to Sovereignty
To step out of “shoulding,” we don’t need more rebellion – we need realignment. Try this:
Swap the Language
- “I should call her” → “Do I want to connect with her?”
- “They should invite me” → “Do I feel left out, and what do I need right now?”
- “I should go” → “I can go. Do I choose to?”
Ask the Deeper Question
Where is this “should” coming from?
- Fear of disappointing someone?
- A story about what makes me lovable?
- A rule I never agreed to?
Give Yourself Permission
To not go. To not please. To not perform.
And just as powerfully –
To go. To connect. To commit.
But only if it’s chosen, not coerced.
Practice: A 3-Day Should Detox
Day 1: Awareness
Notice every time you say, think, or feel “should.” Write it down. No judgment – just observe.
Day 2: Inquiry
Choose 3 “shoulds” from your list and ask:
- What do I actually want here?
- What belief or fear is driving this “should”?
- Who does this rule belong to?
Day 3: Reframe
Replace those “shoulds” with empowered language:
“I choose to…”
“I could…”
“I’m willing to…”
“I’m not available for…”
Final Thought
You don’t need to “should” yourself into being better.
You’re already worthy.
You get to choose your actions, not as proof of goodness, but as a reflection of it.
So here’s the invitation:
Stop shoulding yourself. Stop shoulding others. And let go of the shoulds placed on you.
Return to choice. That’s where freedom lives.
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