Eliminate “Insidious Shoulds” for More Mental Clarity

Gus Vieweg
4 min readJul 20, 2022
Photo by Tonik on Unsplash

We are destroying ourselves with the word “Should”.

It is an insidious word. When we use it, we often refer to ourselves and our choices in a unhealthy way — without even realizing it!

All because Insidious Shoulds fail to acknowledge specific Authorities and specific Effects.

What do I mean? Let’s break down specific Authorities first.

Specific Authorities

“I should save more money.”
“I should start waking up early.”
“I should write my next blog.”

These sentences all appeal to some Authority greater than the speaker. Some nebulous omnipotent Authority. An Authority who has seen the future and determined your fate. You should act in accordance with the Authority’s principles to realize what the Authority has seen for you.

Doesn’t that sound crazy? Yet, we do it all the time.

Insidious Shoulds fester in an unexamined course of action (or inaction).

Has something been nagging you for weeks, months, years? Perhaps something you’ve heard over and over again from parents, influencers, the news?

Has repeated messaging gotten to you and made you think you Should be doing something?

Long periods of low-dose exposure to Authority-based norms can leave you with an Insidious Should. You may not even know the original source of it. You may attribute your “I should exercise more.” to a new research study as opposed to the constant exposure to your fit post-happy Instagram friend, an athletic family, or swaths of healthy people on television.

To combat this, I challenge myself to ask according to whom when I stumble upon an Insidious Should.

Instead of “I should work out.”:

“According to Jocko Willink, whom I admire and wish to be like, I should work out.”

Once you determine an Authority of the Insidious Should, you will be better equipped to evaluate the Should itself.

  • Do you trust this person for advice?
  • How are their situations different from yours?
  • Free advice is worth what you pay for, but what happens if you’ve actually been paying for it with taxing mental loops or gymnastic relationship management?

Specific Effects

I learned how to craft arguments in my high school American Studies class. According to them, the most common missing element from a piece of supporting evidence is:

To what effect does this evidence serve my argument?

In the case of the Insidious Should, we lack the Effect it would have.

Without a clear Authority and clear Effect, these Shoulds can pile up into nebulous, depressive prescriptions. What’s worse, they all have some sort of benefit, morality, or impetus to act… any of which you can’t quite articulate.

If I catch myself mulling over an Insidious Should, I ask myself: on whom’s authority and to what effect?

“I should save more money” becomes

“According to Mr Money Mustache, an early retiree whose values and logic make sense to me, I should save more money to live a happier, freer, and more fulfilling life.”

The Insidious Should becomes a lot clearer. The Authority is now someone you can validate your thoughts against. Do you agree with this person on this issue? Do you admire them? Are they a valid source of judgement or advice?

But the Should’s Effect may be where more of the Insidiousness is shed.

The Effect of Shoulds highlight your values. In the example above, is a happier, freer, and more fulfilled version of you something you want to strive for? Are those values important to you? If so, then yes, you Should save more money.

And the cherry on top? Confirming these values can guide you towards other habits or changes in behavior you Should be making.

I will say one good thing about Insidious Shoulds. They are a step above Supposed Tos.

A Supposed To is a fatalistic tragedy in which the Supposed To-er is unhappy with how the Past led up to the Present. Even if they think they made all the right choices. Those right choices may have been rooted in faulty assumptions about the world. These faulty assumptions then lead them to a place where they are Supposed To-ing. They cannot change the past. And lo, look where it’s gotten them.

But if you’re thinking in Shoulds (even Insidious ones!), you are one step ahead.

Shoulds are the inkling of a plan.

Should is a word pointing to action.

To take the present and carve it into the future.

What Should you be doing right now?

This article was originally published on gusvieweg.com.

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Gus Vieweg

Improviser, teacher, writer. Fascinated by improv and its practical applications such as soft skills + personal development. 🎭