“Do not judge, or you too will be judged.”
–Matthew 7:1

Therefore let us stop passing judgment on one another. Instead, make up your mind not to put any stumbling block or obstacle in the way of a brother or sister.
–Romans 14:13

Shoulds’ come only from leftover thinking. If we are truly in this moment (the only one there really is), we don’t should on ourselves. It’s a great freedom.
–Kelly Corbet

Should is my all-time least favorite word. It’s this sort of guilt inducing, finger wagging word that we use to beat up others and ourselves.
–Frank Beddor


Dear Munchkins,
This chapter is my most self-indulgent, because I actually wrote a book on this particular topic, Stop Shoulding All Over Yourself.

No one read it, but I did write it. So, if you will permit me, I’d like to pontificate for a couple of pages about the evils of shoulding all over yourself and others as you go through life. Also, please read my book as a way to honor Pop’s effort, okay?

First, there are very few words in the English language that are more toxic than “should” and “shouldn’t.” Any time these words are banging around in your mind or coming out of your mouth, you have just left reality and are going to bring a lot of shame and self-condemnation on yourself and others.

As Margaret Atwood put it, “Should is a futile word. It’s about what didn’t happen. It belongs in a parallel universe. It belongs in another dimension of space.”

Second, the reason should and shouldn’t are such toxic words is that they lead you to stiff-arm reality just because it’s not how you want it to be. When you say, “I shouldn’t have missed my exit,” you are refusing to accept the painful reality that you missed your exit, something you didn’t want to happen.

When we refuse to accept things as they are, your mental health goes flying out the window and you’re not going to deal with failures and miscues in an emotionally healthy manner.

Third, when you should all over yourself, you’re talking to yourself in a way that is condemning and shaming. You’re putting yourself down for being a fallen human being who proves their fallenness each and every day by doing the misguided things you do.

Fourth, shoulding all over yourself causes you to miss out on one of the most important truths of all, “What should have happened did.” For example, when you’re four lanes over and texting on your cell phone, you should have missed your exit and did. What would have been more surprising in a situation like that is you actually making your exit, not missing it. “I should have . . .” or “I shouldn’t have . . .” forces you to completely deny and ignore that all the internal and external stars were aligned for you to do exactly what you did.

Fifth, shoulding all over yourself leads to shoulding all over others. Anytime you get on your own case for being human, you’re so much more likely to get on the case of others for being human as well. You’re going to should all over every person you know if you don’t stop doing it to yourself all the time.

Just like we have to offer ourselves compassion and acceptance first in order to offer them more fully to others, you have to stop shoulding all over yourself first in order to stop shoulding all over the folks who occupy the planet with you.

Sixth, shoulding all over yourself is especially likely when you experience a major moral failure. It’s one thing to miss an exit, but it’s a whole different matter when you get drunk and kill another human being while driving under the influence, embezzle money from the company you work for, or lie to others to advance your career.

If you should all over yourself about the small stuff, you’re going to should all over yourself ten times worse about the big stuff.

Let me quickly walk you into one of the deadliest shoulds of all, “People should always give me what I want when I want it.”

Why is this such a toxic way to think about things? A few reasons come to mind.

  • First, just because we want something doesn’t mean the rest of the world is going to stop doing what it’s doing and deliver the goods. Everyone has their own life to attend to, and no one should be expected to instantaneously meet our every wish and whim.
  • Second, some of the things we want are selfish, unhealthy, and immoral, and no one in their right mind would give those to us. Let’s say you want someone to worship the ground you walk on or agree with everything you say. Neither are legitimate wants, and people are only demeaning and denigrating themselves to give you these things.
  • Third, thinking people should give you what you want when you want it keeps you from being grateful when others deliver the goods. Why? Because “should” implies you believe you’re entitled to others meeting your needs, and you’re not. When you feel entitled to your wants and needs being met, all you can say in your own head when they deliver the goods is, “That’s what they should have done.” That’s not gratitude.



I could go on (and on and on) about just how emotionally and relationally toxic it is to should all over yourself and others, but, hopefully, you get the point.

I hope and pray you will eliminate the words should and shouldn’t from your vocabulary. If you do, you’ll find a great deal of psychological and interpersonal health waiting for you on the other side.

Oh, and don’t forget, read Pop’s book, Stop Shoulding All Over Yourself.

I’d like to know at least you guys read it.