The Double-Edged Sword of “Should”

I should have issued my newsletter last month. I certainly intended to finish it (or was that an expectation?). My self-imposed deadline came and passed while I met work deadlines set by others. I kept postponing my newsletter. “I should get up earlier – then I could write.” “I should work longer – then I could write.” “I should manage my time better – then I could write.” I was plagued by a thousand shoulds. Did it successfully guilt me into finishing? No. But it started me musing about the nature of “should.”

One of my favorite Dad sayings is, “Just because you can doesn’t mean you should.” “Should” seems gentler here, perhaps because it appears to be more appropriately within its helpful context. It invites you to pause – step back – contemplate whether an action is required or warranted by you.

Many people equate ability with action. If you have the ability to do something, then you should (there is that sneaky word again) do it. But let’s take a moment to unpack that. Are you merely reacting to a situation (programmed behavior) or are you responding to it (thoughtful behavior)? As someone who carries around an outsized sense of responsibility (to everyone! for everything!), I like to use Dad’s phrase when I need to remind myself about boundaries. Is my help needed? Should I intervene? Is this my problem to solve? Oftentimes the answer is no. In this case, I can use “should” to my benefit: Should translates to “I need to”, and upon closer examination, no, I really don’t.

“Should” also provides guardrails. It keeps me on track. “I should drink more water.” This “should” prompts me to make good choices. Now, I don’t have to make the best choices all the time. That kind of perfectionism is another prison of my own making. However, I know that my body needs to be hydrated to function properly. Drinking water instead of an energy drink helps my body help me. The “should” in this case is a gentle reminder that I always have a choice. I may not make the best one, but it’s mine to make.

“Should” is more insidious when it begins to level guilt, shame, or others’ expectations at you. The guilt/shame/expectation can be trivial: “You shouldn’t wear white after Labor Day.” Who says? Why is/was that ever a thing? Or it can be extensive: “I guess I should marry so-and-so since everyone thinks s/he’s such a great catch.” “Should” in this context is externally-oriented; it is the expectations imposed upon you by others, whether family, work, society, culture. In this case, it does not matter if it lines up with your inner truth or knowing. You must do it because it is expected. If you don’t, there will be fall-out.

“Should” is even more grievous when paired with “have.” “I should have just agreed.” “I shouldn’t have called in sick.” I “should/n’t have” keeps you in a replay loop of lamenting or ruing prior behavior or circumstances. It cruelly traps you in the past when the only action that can address or rectify the situation lies in the present.

So what I’ve come to is this:

“Positive Should”


Thoughtful behavior

Internal orientation (true for you)



“Negative Should”


Programmed behavior

External orientation (determined by others)



“Should” is an indicator that I have a choice to make. And it is a cue that I do have a choice. “Should” is helpful as a gentle reminder, but not helpful when it becomes a haranguer. It is to my benefit when it nudges me about my boundaries, not so much when it is packing my suitcase for a guilt trip. When deciding which is which, I can ask, “Is ‘should’ lighting my way to the choice that’s best for me?” Or is the heaviness of others’ expectations threatening to outweigh my own inner compass?

When “should” shows up, whose voice do you hear in your head? yours? or someone else’s? Welcome “should’s” reminders, but when it hangs around a little too often, pay closer attention. It should be working for you, not against you.