What Should We Learn From Our Shoulds?

Have you checked in lately with your should voice? Who is that speaking to anyway? Kinda bossy eh?

Can’t a brother have a guilt-free donut once in awhile? Or what should you really be doing right now instead of surfing the internet and reading this here blog post?

I bet you have an answer (probably several).

Shoulds, and their equally bossy cousin, Shouldn’t, are always ready to lend us their wisdom (or opinion at least).

I find we can learn a lot from exploring the source of our should voice. We first need to become aware of it. Then we can investigate a bit more about its origin and whether we want to welcome it or not. As we get underneath the source and motivation of our shoulds, we can find out where they come from and their true intention.

Let’s do a quick example: Breakfast

  • What should you eat for Breakfast tomorrow to have a great start to the day?

  • Or should you skip breakfast because you are intermittent fasting?


What was your answer?


Where Do Our Shoulds Come From?

Now, let’s learn a bit more about your should: Where does this “should" come from?

  • Source: Was your should born from your own idea or from someone you trust?

  • Timing: Was the should recently acquired or rather old?

  • Legitimacy: Was the source reputable? Or from a caffeine-fueled Twitter tirade?

  • Considered: Did you blindly adopt this new should into your life? Or did you weigh if this should is helping you in the way it was sold to you?

If we aren’t careful, we pick up new shoulds like stray piles of animal droppings in the yard.

We all need to be careful about where we pick up a should.


Even more challenging are deeply seeded shoulds that have gone unexamined for decades.

Let’s try a spicier example situation: How to bring up a conflict (aka the Conflict Resolution Dragon)

How should you (or should you not!) approach an important conflict?


To deepen the learning, I recommend you answer these three questions on a scrap of paper.

  1. How should you bring up a conflict?

  2. What’s your style or an acceptable approach?

  3. What should you avoid? What’s taboo?


Again, let’s go to the source to learn about your conscious approach to conflict:

What is the source, legitimacy and wisdom of your best approach?

You might have to do some digging to think back on how you acquired your shoulds and should nots for conflict resolution.

Most of us learned about how to give feedback from early bosses or teachers.

We also picked up on modeling from Parents.

If you are lucky, you worked with a good mentor or colleague that taught you how to broach conflict.

How about society’s expectations or your own past experience?


To deepen the learning, re-read over your answers from the section above and answer the following:

Which of these shoulds are serving you well?

Which ones might need to be re-examined?

In case it’s helpful, I’ll share my answers to the above:

Breakfast is easy: I should have something healthy because I’ve read in many journals and heard from my doctor that it’s important to start the day with energy. Lately, though, I’ve heard a lot about the power of fasting early in the day to improve focus, clarity, and mental concentration. I should not eat before noon.

By knowing the sources of my breakfast shoulds, I feel more free to make the choice I want for any given day. Am I looking for energy, clarity, or a fattening, feel-good, and gooey cinnamon roll?

Now, on dealing with the more sticky issue of bringing up a conflict. Combing my memory banks for “shoulds”, I realize that I learned a lot about conflict from my parents.

Controversial vs. Non-Controversial Shoulds

  • I should treat others with respect, but I should also bring up what’s bothering me as things that don’t get addressed tend to have their own psychic weight, or fester in undesirable ways

  • I should mind my own energetic levels (stay reasonably calm, cool and collected). I know that if am not present and aware, I might vent or get overly emotional which can be counterproductive

  • If overly emotional, I should take a break to get more clear on what’s important to communicate

I also discovered these two questionable shoulds that I’m now reconsidering:

First Questionable Should: I should wait for “the perfect time” to bring up the conflict.

This seems to be something I read or heard from an old adage, “timing is everything."

Waiting for the perfect time may mean it never comes, or that I’m carrying around something unresolved for too long. Upon reflection, I think it is good to wait for a better time if one is in sight, but if not, I can lean into the old adage: there is no time like the present.

Second Questionable Should: Be careful bringing up conflicts that might hurt someone else’s feelings. My should says Never hurt someone else’s feelings!

This one is sticky and hard to argue against. Who wants to hurt anyone’s feelings? I traced this back to some spiritual principles (Golden Rule, Do No Harm, and so forth), as well as early lessons learned when making friends. All sage advice.

However, upon reconsidering this should, I remember that sometimes, hurt feelings are part of the deal. By dealing with this hurt and repairing, we might even be closer in the end.


I also notice the fallacy: at what cost am I avoiding something?

Also, am I really responsible for other people’s feelings?

Because hurtful behavior or action is not my intention, I can do my best to make it safe and let the other person know that I am aware of potential hurt. Said another way, isn’t it perfectly reasonable to bring up conflict in a respectful way with the healthy intention of seeking a resolution?

My actions may upset the other person, but if I’m deterred simply by that, resentment will build up and/or I may never find a resolution.

So how was your should analysis?

Did you learn something from looking at your shoulds?
Please let me know. Until next time, wishing you much health and wisdom.

BTW, You may know I wrote an entire ebook dedicated to the voice of doubt called Doubt Riding Shotgun. Here’s the original blog post on that book.

Addendum:

As an example of a should I just discovered in writing this post, I used to think I should ALWAYS have a photo with every blog post. As I traced the lineage of this should I realized that it’s an old prejudice I have about how marketing content should be created and experienced. I’ve been in many marketing roles in my career and thus carry around a large bag of shoulds over my shoulder. Well, there is no photo for this post; sorry, I just don’t think it needs one and would rather post it than wait to find the right image.

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