The Tyranny of "Should"-ing On Yourself

leadership life skills mindset
The Tyranny of

If you’re reading this article, you are a grower — a person who wants to live better, more skillfully and with more ease.

I want to make your goal of growing and expanding easier by sharing a single transformative and life changing practice.

If you commit to ONLY this one practice and no other, you will find that one year from today, you are a noticeably more relaxed, joyful and (surprisingly!) productive version of yourself.

If you’re ready to test my offer, begin by asking yourself this question:

In the course of a day, week and month, how often do I use the word “should”?

I put it to you that it's hundreds of times a week and perhaps more than you can count if you keep track long term!

“Should” is a dictator dressed as The Buddha. It presents itself as a word, thought and belief that feels right — one that appears to be useful and helpful. We think it wants the best for us. We think that telling ourselves and others that we should do, think or be something will lead to necessary and positive action.

So we go through life using this word generously, throwing it around like confetti.

“Should” is not Gandhi — it’s Mussolini.

“Should” is a tyrant who wants what it wants without any true understanding or compassion for its subjects (me and you). “Should” is tremendously practiced at giving speeches and getting us riled up, but ultimately it’s all talk and no action.

Do you remember that last time you were able to sustainably change a habit or create a new positive one by telling yourself that you “should”? 

Me neither.

We confuse “should”-ing with inspiration, motivation, willpower and discipline.

This is a profound misunderstanding and if you take an honest look at your life, it has never worked as a long term and sustainable practice.

We “should” our kids, partners and friends. We “should” our employees and the world at large. But most often and destructively, we “should” ourselves.

It doesn’t work for two reasons.

First, behavioral and social sciences have proven beyond a shadow of a doubt that we cannot create positive actions from negative emotions. To believe that we can force ourselves to any desired action by a relentless barrage of “shoulds” is to believe in shame and guilt as motivators.

It’s true that as a tactic we may motivate ourselves and others through shame and guilt in the short term, but it simply doesn’t work as a long term strategy.

Shame and guilt don’t have the power to transform. Only desire does.



Which takes us to the next reason “should” doesn’t work.

Human beings are designed to want — to desire.

Desire is the ultimate creator. Every single thing in the world came about because someone or a group of people wanted it.

“Want” is filled with the energy of action, creativity, and resourcefulness.

“Should”, on the other hand, makes me want to grab a jumbo size popcorn and binge on the latest Kardashian show.

But I hear you!

“What if I don’t want to do something, but I know I should?”

Here are the five steps I use and teach my clients to get out from under the tyranny of Should:


1. Question your “Should”

When the thought surfaces that you should be doing, saying or being something other than your natural desire dictates, actually question the validity of the should.

I have a brilliant client who is fortunate to have the freedom to travel often. But the moment she touches down in one place, she starts questioning whether she should be somewhere else. She wonders if her time and energy “should” be better spent elsewhere.

The annoying person who while talking to us is always looking over our shoulder (yeah, you know who you are) is thinking, “I should be talking to someone else…”


2. Slow down to the present moment

Once we question our “should”, more often than not, we realize that we are exactly where we want, even need, to be, doing exactly what is best for us at that moment.

We can then mine the experience that’s in front of us rather than tyrannize ourselves with a future focused demand. By the way, this is where “ease” begins to gently move into our moments, days and life.


3. Know your “Why”

If after an honest attempt at steps one and two, your “Should” is still alive and well, it’s time to get back to your “Why”.

Your “Why” is related to your Life Values and your Life Values is what I call Human Being 101. Knowing your top Life Values, helps you understand the reasons you are drawn to or conversely, have resistance to certain goals.


4. Turn Your “Should” into a “Want”

If you believe like I do that desire is the clean and long burning fuel for action, then your job is to take a “Should” that is clearly and deeply connected to your values and transform it into a “Want”. Like everything else in life, this transformation begins with our language.

Slowing down to questioning your “Should” and when appropriate turning it into a “Want”. And I don’t mean, fake it till you make it.

I want you to make it till you make it.



5. Delete, Delegate or Do

Even after you’ve transformed your “Should” into a “Want”, you may find that now is not the time to devote resources to this particular desire. In that case, it’s time to delete (for now) and take the activity entirely out of your list of things you want to create.

Take note that this step of deleting is the hardest, but most crucially impactful, decision for most of us.

Sometimes, the work can be done by another — perhaps even more skillfully.  In that case, get over whatever beliefs are holding you back (hello perfectionism and control) and delegate the work.

Leaders delegate!

After all the steps, if you still find a deep abiding reason why you want to do the thing yourself, it’s time to turn pro, use your calendar powerfully and shift from intention to commitment.

And on those days that you “don’t want to” — because they will arrive but only 100% of the time — remind yourself that you “do want to” and nobody is forcing you.

We have the privilege of making the choice between Want and Should every day anew.


Photo Credit: The New Yorker

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