Jumping off from last week’s post, about the phrase “I’m supposed to,” there’s another word that I’ve become particularly sensitive to the past few years.
The word “should.”
A friend said it in the context of a decision she is grappling with. There were three of us having brunch, and when it came out of her mouth, it sounded piercing and artificial.
When the friend asked me why I called her out on the “should,” why it’s so important to avoid the word, I realized I’d never quite thought to put into words why that word is so dangerous. It’s been a compendium of many things I’ve read over the years, coupled with my own experiences and other conversations. It’s like saying the sky is blue and having someone ask you to prove it. I mean, just look up, it’s obvious.
But perhaps that someone is blind, or it’s a cloudy day. So, okay, there are ways to prove it.
For me, the proof of “should” starts by comparing it to the alternative. For the sake of argument, to have a specific example, let’s say this friend is grappling with the decision to quit her job. Take a look at these two sentences and see how they land for you:
“I should tell my boss and not let her try to talk me into staying.”
“I want to tell my boss and I won’t let her talk me into staying.”
Which sounds stronger to you? More empowering? Less whiny?
“Should” almost always sounds like things are totally out of your control. That you’re letting the world dictate the course of your life, that you have no agency. That you have no wants or needs or desires that drive you to make your decisions.
Taking it a step further, think about where this “should” is coming from.
My Webster’s dictionary (yes I have a physical dictionary) gives five definitions for “should:”
1 – part of shall (I had hoped I should see you)
2 – used to express obligation, duty, propriety, or desirability (you should ask first)
3 – used to express expectation or probability (he should be here soon)
4 – used to express a future condition (if I should be late…)
5 – used in polite or tentative expression of opinion (I should think they will be pleased)
Take a look at those words! Obligation, duty, expectation, tentative… even #1 and #4, which are grammatical uses and seemingly benign, are dependent on something else happening.
To what do you have an “obligation” when you say the word “should?”
“I should quit my job.”
To what to you have duty or propriety in that statement?
“I shouldn’t have that cake.”

Who are you giving agency here—yourself or some omniscient “they” who are telling you not to eat the cake?
It’s not just about the word, it’s about the intention behind it. Giving yourself the power and not being pushed along by expectation and obligation.
“I could quit my job:” Yes, you could! What would that mean? How would you do it? You have a choice here—many of them, in fact. And then that moves into, “I want to quit my job” or “I will quit my job.” That is firm, clear, and it will be hard for someone to talk you out of that.
“I don’t want any cake.” Great! Don’t eat it! No one cares about your diet or your stomach issues if you eat sugar: no explanation is needed, you simply don’t want any. How freeing it is to just say no and move on!
Or: “I, in fact, do want some cake and I’ll fucking enjoy it without feeling guilty.”
That boss will always be able to talk you out of leaving if you use the word should. You will take that damn cake the second someone says, “But it’s a birthday cake, you have to take at least a bite.” Because you are by definition making yourself dependent on a future condition, open to someone else’s expectations, and motivated by duty and obligation. And you will fill yourself with guilt if you don’t live up to those expectations, needlessly so.
Words matter, again and again, they matter. Both in the way they’re received in the world, and the way they are received in your brain. Some words give us confidence and courage. The word “should” is not one of them.
Try it for yourself. See when you catch yourself saying the word and see how it feels to try on another word.