Permission Granted: Conquering the Tyranny of Shoulds


Can is about ability

Could is about choice

Should is about obligation

Of course, we learned all of this in grammar school. But the significance of these everyday words is enormous: a can quickly morphs into a could, and often from there makes a small leap over to a should. But hello? Just because you can doesn’t mean you should!

Can is cool because it empowers us with agency.

Could is super cool because it’s about possibility that we either choose or decline.

But should is dangerous because it can mess with us if we are not cautious.

Case in point: In ways large and small, we “should” ourselves to exhaustion:

I should see grandma more often

I should sign up for that online course

I should lose 10 pounds…make that 20

I should exercise for God’s sake!

I should just say no to chocolate

I should, should should.

Substitute a few words here and there and you are looking at my list, and probably yours.

A Well-Worn Path

“Shoulding” is a habit we pick up early by way of example. Parents, teachers, strangers, and even friends model it often and, just as often, without thinking.

I’ll tell you straight out, whenever I hear a should escape my lips, I almost always go for a rephrasing:

“What I meant was that you might want to think about…”

“I’m sorry, I don’t mean to come off like a know it all”

“I hate it when people “should” on me, so I don’t want to be “shoulding on you.”


And that is equally true: when someone wields a should in my direction, I duck. Then I remind myself that:

They probably mean well

They don’t know any other way to be helpful

They may think they know more about me than they really do

Letting Go is Hard to Do

But the bigger issue with our shoulds is how they keep us weighed down and sometimes downright stuck. It’s hard to believe, but some of my shoulds have their origins in my 10-year-old self. To say that they have gathered a lot of dust would be a significant understatement. And here’s the thing: it’s ON ME to dust them off, take another look and then decide if they get the heave-ho.

But letting go isn’t so easy. It means releasing ourselves from an idea or an obligation we’ve placed on ourselves or one we’ve accepted from someone, perhaps a parent, or from our culture. That’s why letting go is loaded. It means releasing ourselves from guilt, a sense of failure, or maybe even a sense of who we are or think we should be.

Let me be clear: I am working on my self-inflicted shoulds, sifting the worthy from those that need a refresh, and yes, tossing the obsolete. The process is painful but oh-so liberating.

Grant Thyself Permission 

Here are a few tips for your “shoulding” refresh:

  • Remind yourself that you are always changing – and that’s a good thing. You are both constant and fluid.
  • Consider what you want and what you value right now – prioritize and then decide which of your shoulds stay, go, or need a revision. Shoulds work for youwhen they support your vision and values and become your chosen “I will’s.”
  • Ask yourself: “How does this matter in the scheme of things? Keep your eye on the big picture and stay flexible.



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