During the Holiday season, it’s common to hear “You should be thankful! ‘Tis the season to be grateful and joyful!” 

        Do you ever feel this way? 


When I get it all done or, when I get to a good stopping point, then I should put gratitude on my TO DO list…”

If you’re like some of my clients, there is a list that most of us accumulate of spoken (or often unspoken) things  that “should” be a certain way. All around us, we see confirmations that underscore this high bar, and most people report feeling they are less than, not as good as, or not up to par with others around them, at work and at home.

The Cost of Should

The culprit beneath these insurmountable mountains are the “shoulds” that lie beneath them. Looking at this definition  of should:

  • obligation, duty, or correctness, typically when criticizing someone’s actions
  • desirable or expected state
  • used to give or ask advice or suggestions

is it any wonder you feel some version of resentment, overwhelm, exhaustion, guilt, frustration, or unhappiness when those “shoulds” are present? These are but a few of the costs women described they feel in my research study on Challenges Women Leaders Face. (And by the way, this is universal – male clients have resonated with this as well!)

Where Do “Shoulds” Come From?

At first pass, most people will immediately think “should” indicates an unreachable, ideal “have to” created by “them” – culture, family, religion, company, boss, spouse, kids, etc. Yet when I ask – where are you getting these messages? the majority say “from myself” (often in the form of our Itty Bitty Shitty Committee that live in our heads – read about them here). 

“Should” tells us to be, do or have something different from where we are today.  I should have volunteered at school…I should have spoken up more in the meeting, I should have reacted differently with my peer…I should have not missed the exit sign…I should have given direct feedback when my boss asked…etc.

Stop should-ing all over yourself!

When you are being run by your shoulds, you are not present in the “as-is reality” of right now. You are in a reactive state feeling more like a hamster on a wheel than in charge of your own life.

To shift behavior, we need to focus on our mindset, toolset and skillset in order to create new habits.

How Do We Stop Should-ing?

  1. GET TO KNOW YOUR SHOULDs: This is one of the hardest parts – to have the self-awareness to notice them in the first place. Most of us run on autopilot and rarely listen to the chatter in our minds. Becoming aware of our thoughts and feelings sounds easier than it is. It’s easy to beat ourselves up, so notice if you’re taking this on as one more should! Instead, be a neutral observer as you might with a best friend. Gather data, hold the judgement.
  2. DROP SHOULD FROM YOUR VOCABULARY: One of the most powerful and immediate actions starts with our language.  Most people gasp when I suggest they drop “should” and replace it with “I choose” or “I want”.  The reality is, if you cannot make it a “choose,  want, or get to” then it definitely means you are should-ing all over yourself. Other sneaky words that operate in the same vein:  supposed to, need to, always, and never. They are data points into your mindset that become obvious through your words. Many of us can’t hear our ingrained habit. If you want the bonus assignment: tell your kids or someone you trust – call me out when you hear me say should. (Kids LOVE helping with this assignment). That’s a way to hear yourself and pivot in the moment.
  3. CHOOSE POWERFULLY: Choose what works for you that can also work for them. Insanity is doing the same thing, wanting a different outcome. Last year we tested a new tradition at extended family Christmas that turned out to be a hit. Instead of setting a formal table, we had an “Open House”, built a fire, and people could choose where to sit, which made it casual, fun and connecting. At recent family gatherings, everyone now requests “Open House.” 

This year, I was asked to host again. I’m traveling before the holiday, and it would have been easy to get stressed and slightly resentful. So this year, we are bumping “Open House” up a notch and ordering from a favorite catering place with fabulous food. They win, and I win, too.

When we are clear about the “as is reality”, we can make choices that align with what what works for us, and what works for others. 

The faster we let go of what it could or should have looked / been like, the quicker we will get to what brings us joy and allows us to operate as our best selves.

Here is to a holiday where you take care of yourself, connect with others and focus on what matters most. Consider saying no or renegotiating a “should”, and/or creating one thing 10% different than you would otherwise do. Please let me know how it goes! 

Yours in practice,


If you are interested in exploring whether we are a good fit to help you and your organization, contact us for a complimentary discovery conversation.

Want to Build More Trust on Your Team?

Download The Leader’s Roadmap Trust Tool