Sometimes when someone asks this question, they may be thinking of something traumatic that occurred, and I want to acknowledge the reality of trauma and be as clear as I can be that at no point am I saying that something “should” have happened in the sense of condoning it, justifying it, or encouraging anyone to accept it. This site and the way we use “should” here is not about any of those things.

At the same time, if someone who has experienced trauma, adversity, or even just everyday stress keeps thinking the same way they always have, tomorrow will be as painful as today. Something needs to change in the way we think about the past. If we avoid using the word “should” because it’s potentially loaded, we also avoid the possibility of deeper change.

So there may be value — only when someone feels ready — in being coached to think in a new way.

Saying “In reality, it should have happened at that time” does not mean that it’s good that it happened or that it’s okay for it to keep happening. That’s the PREscriptive use of “should,” and it has nothing to do with what we are exploring here. Instead, we are learning to move “should” back to its DEscriptive state, which helps reconnect our mind to the world.

The example I gave in the video on “The Power of Should” is that you drop a wine glass and it shatters. In reality, it should have shattered at this time because it’s fragile; there’s gravity; it hit the hard floor.

Notice that if you say to yourself, “The glass should have shattered,” you’re not saying you wanted it to break. You’re not advocating glasses shattering everywhere. You’re just recognizing that you understand how cause and effect work. Things made of thin glass tend to break when they are dropped. People can do hard things — but fragile drinkware can’t. That’s not Prescriptive. It’s DEscriptive.

But what if someone were to say “Well, yes, the glass did shatter, but don’t use the word ‘should’ because then we are ‘shoulding’ all over ourselves. Let’s never again say it should have shattered.” Well, that person is avoiding reality. It did shatter AND it should have shattered at that time, because that’s how reality works. The more fully and completely I see that as true, the more my mind is free of delusion. I clean up the broken glass. Maybe I buy polycarbonate drinkware. But I no longer spend energy stuck in the confused belief that the glass shouldn’t have shattered.

My mind moves from: “‘The glass shouldn’t have shattered’ is true” to “‘The glass shouldn’t have shattered’ is false.” That is the arc of insight. In this trivial example, it may seem silly. But let’s take it up a notch.

Suppose I think, “I should weigh less.” I negate it to, “In reality, I should not weigh less at this time.” And, if I’m willing to be honest, I may see that I joined a gym and don’t go; I eat more calories than I burn; I haven’t studied nutrition or asked people who’ve lost weight and kept it off for a long time what worked for them. I really, really love good bread.

All of this is Descriptive, not Prescriptive. I’m seeing the causes behind reality. I might like to weigh less tomorrow, but seeing why I should not weigh less at this time frees my mind right now. I weigh whatever I weigh, but I’m not carrying the additional emotional weight of my own confusion. And so I move forward lighter, with more energy for exploring change.

That may make sense to you with a broken glass or even weight loss, but as stress moves to adversity and into trauma, the mental mobility required to see “should” descriptively gets greater. This is why I like to compare Active Insight to sports, where you build strength over time. An elite gymnast has tremendous strength and flexibility in how they use their body. An elite practitioner of Active Insight would need real mental strength and flexibility in how they use their mind, in seeing why their beliefs may not be true, and in recovering the missing insights without slipping into passive acceptance or condoning harm.

This kind of mental mobility is still rare, and you don’t want to push yourself too far too soon. The Resilience Academy is divided into levels because our ability to use “should” descriptively starts off small, and gets stronger as we gain more experience.

As you continue doing worksheets, you may find that “should” feels different, and that some of the things that made no sense to you previously now become clearer. Don’t push yourself though. Go slow, stay away from topics that feel “wrong,” and continue doing ones that feel just a little bit challenging. That way you stay within your mind’s current range of motion and increase your resilience gradually.