This week has been filled with coaching engagements and in nearly every session there were three common words I heard clients use over and over: “I should have…”

If you are like many of my clients, perhaps you can relate to the common “should have” self-talk.

You know, the narrative in our heads that begins with “I should have…”, I shouldn’t have…”, “I should do this, I should do that,” and on and on it goes.

Here were the classics I heard this week:

  • I should be more appreciative.
  • Should I have said that?
  • I’m told I should be grateful to even have a job.
  • Should I have handled that situation differently?
  • I should spend more time with the kids.
  • I should be more of a team player.
  • I should lose weight.
  • I should exercise more.
  • Should I confront him about this or should I keep it to myself?
  • I should be happier.

However you are “shoulding” on yourself, it all boils down to one thing: You should be better.

Wow, that sounds harsh doesn’t it?

As humans, we are much too hard on ourselves. Our “should-haves” are a learned behaviour. They are stories and narratives we have picked up over the years, stories and narratives that have been imposed on us by others.

Two things happen when we continue to “should” on ourselves:

  1. Our drive for perfectionism or wanting to feel worthy keeps us pushing ourselves harder and harder, leaving us feeling anxious and inadequate,
  2. We eventually crash and burn because we can’t keep up with our never-ending self-imposed high expectations.

And throughout the week, all too often I heard clients using their should-haves as an initial default strategy for motivation to get themselves on track. I, of course, wasn’t going to let them get away that easy In each of these conversations, I challenged the closed-ended “shoulding” by considering the identification of who they want to be, identifying their intimate wants. This shifted the stories from ones of shame, to ones of self-love followed by the creation of motivated action plans for the upcoming weeks.

Here are some ways you can shake the negative “should-haves”:

1. Start listening to when and where the “should-haves” appear.

Is it when you are being pushed out of your comfort zone? Is it when you are comparing yourself to others? When you take the time to notice the “should-haves,” you can use this as an opportunity to pause, think about the situation and determine what you want your next steps to be.

2. Turn the “should-have” statements into “how do I want to” questions.

This opens the door for exploration, possibility and deeper awareness. For example, “how do I want to show up as a team leader?”, “how do I want to confront this person in a way that enhances our relationship?”, “how do I want to make time for the things that are important to me?”

3. Set aside a daily “should-free” zone (preferably for one hour a day!).

This is a time when you think about or do only the things you want. With practice and over time these “should free” zones will stretch out longer and longer, ultimately giving us more peace and the freedom to be who we want to be.


We all should all over ourselves at one point or another, but learning to shift our mindsets will help us be more effective leaders, ones who are more confident, self-aware, and able to lead by demonstration.


Categories: Blog

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