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Developing Decisiveness & Breaking Up With “Should”

July 28, 2022 by Amanda Reill

Developing Decisiveness & Breaking Up With “Should”

“Should” is a word that doesn’t usually occur in a vacuum. One “should” leads to another “should,” which can lead to the feeling that you’re sitting in a pile of everything you “should” be doing. On some days, this word seems so powerful that it doesn’t matter what you choose to do. You may be folding laundry feeling that you should spend more time with your kids, or you are relaxing and feeling that you should be doing more housework, or the real kicker — feeling that you should be relaxing more.

The endless “should cycle” makes self-confidence and satisfaction feel just out of reach, like a carrot hanging in front of a mule. Why is this word so dangerous, and should we consider breaking up with it?

Developing Decisiveness & Breaking Up With “Should”

Why “should” is a four-letter word

You’re sitting on the couch with your feet up for what seems like the first time this week and your mind is spinning with all the remaining items on your to-do list. Sure, you believe rest is important in theory, but isn’t it selfish to choose relaxation when so much is left to do?

We don’t even realize it, but we’re initiating a conversation between our inner parent and our inner child. The child’s natural tendency, when faced with this authority, is to rebel. All of the sudden, the word “should” becomes an authority figure that makes us want to internally run the other way. It’s overwhelming! The “should” asks us to do far more than we have hours for in the day. Deep down, we know “should” isn’t qualified to be in charge. So rather than carefully weighing its suggestions, we plug our ears.

We come by this dynamic naturally, though. Just like how it’s en vogue to say “We’ve just been crazy busy!” it also feels almost heroic to confess that we “should” be doing more of whatever it is our neighbor is doing. It’s a cultural expectation for many of the communities we live in to maintain aspirations and a schedule that exceeds the number of hours in the day.

One of the many problems with this mentality is that it focuses on doing instead of being. We’re constantly asking what we can accomplish and how well we can “keep up” instead of who we are trying to become, and whether our daily activities reflect the future self we’re striving toward.

Getting curious

When we start or stop a new habit, we often gravitate toward sheer willpower to get the job done. But getting curious about why we have the habit in the first place can get to the heart of it, like pulling a weed out by the roots. Consider asking yourself some of the following questions to discover where your tendency to “should” comes from:

  • Where do the expectations I have for my life come from? Which are internal and which are external?
  • What are my real vs. perceived obligations? Are there things in my life I treat like obligations that truly aren’t?
  • What are my highest-held values in life? Do my current time commitments reflect those values?
  • Do I believe that what I do is more valuable than who I am?
  • Is there anything I can let go of today to more intentionally care for something else?

How to stop “shoulding” yourself

When trying to break a “should” habit, doing the interior work is the first priority. Consider setting aside some time to examine your relationship with this word by taking a walk, doing some journaling, or having an intentional conversation with another person where you explore the above questions. Try to take the “shoulds” from broad to granular: rather than “I should exercise,” phrase it as “I should exercise today” and then consider how you can exchange the word “should” for something else.

  • I should call my mom this week
  • I should get up earlier
  • I should keep my house cleaner


  • I should call my mom today
  • I should get up early tomorrow
  • I should clean my bathroom today


  • I’d like to call my mom today
  • I will get so much done if I get up early tomorrow
  • It will feel so nice to have a clean bathroom

If the third version of any of those seems like too much of a stretch, it may be time to re-consider whether that item is truly a priority for you, and why or why not.

Start listening for the word “should” coming into your mind and out of your mouth. It may be helpful to enlist trusted family members or friends to alert you when they hear the word. Leaning on what you “should” be doing could be an indication that you’ve slipped out of the driver’s seat in your life and are feeling dragged around by an external force. 

It’s healthy to recognize things you could use more of in your life. But trading in the mysterious and questionable authority of the word “should” for “I will, I want to, I’m going to” can make you feel empowered to act intentionally — and that’s a beautiful thing.

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