Breaking Free From the Tyranny Of “Should”


Every next level of life will demand a different you.

Leonardo DiCaprio


Maybe it’s because the world keeps tumbling upside-down that in the last month I’ve encountered several people who spent a lot of time telling me how life is not fair and, in particular, how each of their lives shouldbe different – and not just because of Covid.


As I emphasize in my workshops, we’re prone to telling ourselves “lies” – statements of belief and attitude that are untrue and unrealistic. One of these self-deluding lies is that life should play out the way I think it should play out. And if it doesn’t, then something is critically wrong.


Ray (all names changed) is the Assistant Director Of Finance for a mid-sized business. He came to me upset with his performance review that landed him on a PIP.


He speaks to colleagues abruptly and takes the rejection of his ideas personally, usually by raising his voice, storming off from a conversation, and shutting down. While he later apologizes, the drama is taking a toll on his performance record and on the climate in his department.


In our first session, he became heated as he explained to me how “they” SHOULD see the truth of his opinions.


Clinging to should makes him a martyr for his convictions.


Without intending to be, he is a harsh, demanding and unforgiving task master especially to himself.


He reminds me that people obsessing about how things should be are seldom happy people.


Oh, and in addition to all that, he asked me, “Why should I smile in the morning at my colleagues if I’m not happy?”


Alana, who works at an IT start-up, quickly explained to me that she has a high work standard – if she sees a need, she does it without being asked, she’s willing to go the extra mile AND she proudly told me that she doesn’t need to be complimented on any of her work.


This is what she expects from her team and she thinks she should not have to spell it out for them. They should follow her lead.


As she said (in an annoyed tone of voice), “I’m not here to hold their hands and I shouldn’t have to give them compliments for work they’re being paid to do.”


Say should in the tone of a mantra and you will charge up feelings of frustration and anger that will result in you either shutting down or blowing-up.

And then, when the other(s) reacts in kind to these energy-draining out-burts, the should folks label them “difficult.”


And so, the circle is formed!


BUT – here are some questions to reflect on –

  • Why should your team share a work ethic with you?
  • Do they know the benefits of doing things your way?
  • Why are you certain that if others do things your way, they will succeed and be happy?
  • What needs to be done so they know the benefits?
  • Why should they believe you? Trust you?
  • How did you develop your should beliefs?
  • Would you have developed them without the influences you had?
  • Is your should really THE best way?


And THE most important question –

If you truly believe that something should be done a certain way then

what is your responsibility in bringing that SHOULD to life?


YOU have the responsibility to help people see – understand – relate – to the benefits your SHOULD will bring them.


To manage means you agree to be willing to have hard conversations. Helping people understand your should is one of those hard conversations.


There’s more (of course!)

I’m reminded of David, a UCLA Extension student, who wrote about his struggle with “should.”

I had a boatload of expectations for how my life was supposed to work out. I kept wondering, though, why things always fell apart. 

I was convinced that if you act a certain way, dress a certain part and do what you’re supposed to do then life would fall into place as it ‘should.’ 

I resented that my life hadn’t worked out the way I was told it would and was always waiting for things to happen as I expected they should.

I’m now at a phase in my life where everything is uncertain. If you asked me three months ago what my plan was, I’d have given you a road map, foolishly thinking I could walk it through without failing.

Now I see that expectations of how life SHOULD be can be the demise to almost anything.

I’ve recognized the many ways in which I’m hard on myself, the areas of opportunity where I can grow and most importantly I’ve discovered the ability to be surprised again – something I thought was long gone.


David believed life “should” be the way he envisioned and when he encountered disappointments he became disillusioned and discouraged. He couldn’t envision alternatives and couldn’t see the opportunities smack in front of him.


He hasn’t given up on his dreams; he has, though, given up on insisting how those dreams “should” become reality.


And so, his life has expanded.


Do you want to loosen your grip on SHOULD and so expand your possibilities – for your own self and for those you impact?


Practice these steps:

  1. Be aware of what you’re feeling, especially chronic irritation.
  2. Explore how your feelings affect your attitude. Do you believe you’re a victim? Hopeless? Helpless?
  3. Gauge the certainty of your commitment to “should.” How do you know it “should” go your way? There is a difference between needed technical procedures vs. mere preferences.
  4. What are you afraid will happen if life is not as it “should” be?
  5. What is your willingness to explore reasonable alternatives?
  6. Remember – experiment is not a permanent commitment!
  7. If your experiment fails, can you commit to learning from it?


Practicing these steps is what Emotional Courage is all about.

All emotionally courageous people are confident because they live free of the “tyranny of should.”

How about you –

Is there a “should” you need to let go of?


Do you want to break through the negative thinking that is preventing you from being influential and heard?

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