Should I or Shouldn’t I?

Am I ‘shoulding’ all over myself?
On Tuesday, it was a characteristically Un-Vancouver day, it was sunny and warm with an undertone of autumn coolness. The ongoing sunshine my town has been experiencing this summer, and now into fall, has buoyed everyone’s spirits and a sense of happiness and friendliness permeates the air. People are smiling and some are even saying hello, it’s a bit disconcerting, but a welcome change from the normal torrential downpour that I am sure is on its way! However, back to Tuesday.  

Tuesday I had an appointment downtown at 3:30 in the afternoon. Like most large cities, the traffic situation is less than desirable, at any time, but especially at that “rush-hour” time. Knowing this and it being such a beautiful sunny day, I decided to take the Seabus from my home on the North Shore into downtown and walk to my appointment. While in transit, I was texting with a new friend of mine and we decided that perhaps it was a perfect day to rendezvous and partake in some food and drinks. Tacos and margaritas. Perfect. After my appointment, I walked a few short blocks to meet my friend and we walked together in pursuit of Mexican yumminess. Sitting across the table we ordered our food and drinks and continued the conversation that we had started during our walk. Well, in truth, continued the conversation that we had started several weeks ago, upon meeting. After what felt like a few minutes, but was likely a few hours, we decided we should get up and go. I remember saying, “I guess I should go home, I should get ready for work tomorrow and I should do some laundry.” I ‘shoulded’ myself right out of the restaurant and right out of the great time I was currently having. 

As I was on the Seabus and floating toward home, I thought to myself, “are we ‘shoulding’ all over ourselves AND do we ‘should’ on others?” I had this startling thought and realized, my answer was yes! I ‘should’ myself frequently. I pull myself out of the present moment, that I’m enjoying and engaging in and ‘should’ myself right into a sense of obligation and responsibility. I also ‘should’ on others. I was aghast! I do that! I say, “you ‘should’ this” and “you ‘should’ that”. I couldn’t believe it. As someone who has Present as the first word of their mantra, ‘shoulding’ myself or others feels like the complete opposite of that.


[SHo͝od, SHəd]


used to indicate obligation, duty, or correctness, typically when criticizing someone’s actions:”he should have been careful” 


We all have those ‘shoulds’, and for me, it makes me feel the weight of obligation or expectation. It’s about an external sense of what I feel like I should be doing, rather than listening to my internal narrative and desires. Joanna Holsten, in 2011, in her “Stepping out of the Should Trap” said it so well: 

“I ended up being disappointed with myself or fearful of disappointing others. When I would obey the “should” in my mind, I felt far away from the ideas, needs, and values that I authentically desired. When I would choose to do something not on the “should” list, I felt guilt, shame, or fear that other people would disapprove and judge me negatively.”

I remember being in my youth and dreaming of being an adult. In my mind, I couldn’t wait for this milestone of “adulthood” because then I could do whatever I wanted! There would be no more curfews or needing to leave a party or dinner conversation to make it home in time. I had no idea, that my parent’s rules would be replaced by a weightier, more oppressive and more difficult to disobey should-ness of society and societal norms, pressures and expectations.  

Why am I forcing myself to deny who I am or what I want in the moment? Especially when what I want is to spend more quality time with my friend? Being present in the moment, means to live a more authentic life. This is also a loaded statement because living authentically means taking off that mask we show to the world. The mask that we wear when we are complying with all the ‘shoulds’ in our lives.  

What would have happened if I stayed out for another two hours with my friend? Well, I likely would have had to buy my lunch, if I didn’t end up making it. I wouldn’t have had a specific shirt to wear, as it was in the laundry, but I still have a closet full of other options. And I may not have had that hour to watch an episode of my current Netflix binge, but I would have had that extra time with my friend. I’ll never know if something may have been revealed in that extra time that I may never have a chance to experience again, because although I didn’t want to go home, I felt like I should.  

Breaking out of the should trap does not mean not going to work or shirking all responsibility and social goodness, but rather living a life you desire. It means giving back to the community or volunteering or going home early or helping a friend move because you want to not because of obligation or expectation. Someone once told me that she aspires to, “say ‘yes’ without resentment and say ‘no’ without guilt”, a worthy aspiration. I’m not quite there yet!

Breaking out of the should trap also means that I need to stop shoulding others. It means no longer applying these same expectations and obligations, that I am suffocating under, to others in my life. It means creating an environment for my family, friends and partners that is nurturing and safe for them to be themselves and free of the shoulds of the world.  

To my friend, if you read this, I promise to never leave you for a should again. And I promise to create that environment for you. At least I promise to try…I’m working on it, but for now am embracing my perfectly imperfectness and I hope you will too.

5 thoughts on “Should I or Shouldn’t I?

  1. I really enjoy reading your blogs…very interesting….<3


  2. I should have read this yesterday when I was shoulding all over myself in misery. Maybe I would have stopped and done some reading or writing or taken the dogs down to the bridge for a walk and, Tom-willing, a brief swim for them.

    But I didn’t. I did laundry and house chores and ran all over Redding getting things I’m going to need next month.

    On the bright side, I’ll have some free time next month I wouldn’t have had otherwise. I should stop looking backwards. 😉

    Thank you for the gentle reminder. When you tell you there’s a better way to face your day, you tell us all as well. Another fine piece!


    1. Thank you for your thoughtful comment! My friend texted me this morning and said “I think I just stepped in a whole pile of should!”

      I’m finding my favourite part of writing about my experiences is not necessarily the self-processing that gets accomplished, but the support of the community found here in the Blogosphere! Thank you for being a part of that!

      Liked by 2 people

      1. I completely agree, Ms Jane! The connections I’m making are definitely my favorite part of the whole blogging experience … we’re all in this calamity together! 👏👏👏


  3. Oh my gawd I have been living in a HUGE pile of should for a long time! Great piece! 🙂

    Liked by 1 person

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