The Case of the “Shoulds”

“...don’t worry too much about what someone else says you “should” do. Know what you want to do and why it’s important to you.”

― Melissa Steginus, American author

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“I should have studied harder.”

“I should have been promoted to senior manager by now.”

“I should have recovered from this relationship.”

“I should have invested more time with my family.”

“I should have been smarter and wiser.”

“I should be happier".”

What are the “shoulds” in your life? What situations give you the case of the “shoulds”?

My “shoulds” tend to show up in situations which matter a lot to me. For example, in my coaching business, I feel I should do more marketing. I should find ways to reach out to more people. I should start doing videos and podcasts. I should spend more time and energy on my business. It also shows up when I parent my children. I should be more caring towards them. I should spend more time with them. I should allow them to make mistakes. I should give them all the opportunity to explore their interests.

At first glance, these “shoulds” appear to mean well and have the intention to propel me to succeed as an entrepreneur and a parent. However, upon closer scrutiny, these “shoulds” are judgmental and create doubts and insecurity. They tell me that I am not good enough and that I need to do more. They come with a sense of heaviness and if not properly dealt with, will lead to more stress and anxiety. They also make us feel that we are lacking in something or not doing the right thing.

German psychoanalyst Karen Horney (1885-1952) had a phrase for this: “the tyranny of the should.” She viewed shoulds as dividing our personalities into two selves: an ideal self and a real self. When we don’t live up to the ideal self, we are split and our inner critic comes out. The “shoulds” make up the rules of how we are to live our lives and also how we view the world. The inner critic constantly evaluates what the person says, what s/he does and even what s/he feels by comparing him/her to an ideal of perfection defined by the rules - the “shoulds”.


“Stop asking “What should I do now?” That question only brings up what others expect of you. Free people don’t have shoulds. They have choices.”

— Steve Pavlina, American author

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Is there a cure for the “shoulds”?

I like the quote by Melissa Steginus. “Know what you want to do and why it’s important to you.” The other quote by Steve Pavlina reminds us that we have choices. We cannot dictate people’s expectations of us but we can choose how we want to acknowledge and validate ourselves. We do so by knowing our purpose in life. We also need to accept where we are in the present moment. Accept that we are all work in progress and none of us are “completed” yet.

What can we do the next time we are hit by the case of the “shoulds”?

  • Check its truth

    The next time you find yourself saying, “I should be doing this”, “I should have said that” or “I should be more …”, ask yourself if the statement is true. Is it true that you should have done or said what your inner critic wanted you to do or say? For example, if you think you should have been promoted by now, what is the basis for that statement? Is it because you have worked in the organisation for many years and ought to be promoted simply because you have paid your dues in terms of your years of service with them? Check this truth against the way your organisation typically promotes their employees. Check this truth against your own performance and achievements in the organisation. If after taking an objective, factual view on the situation and you still feel that you should have been promoted, plan the next course of action. This may involve speaking to your manager, fine-tuning your skill-set and increasing your visibility by networking. It may also entail exploring other opportunities within or outside your organisation. By resisting the urge to listen to your inner critic blindly, you are now able to evaluate the situation in a calmer and more rational way.

  • Check its source

    Where did that particular “should” come from? E.g. “I should lose more weight, otherwise, I’ll never be in a meaningful relationship with my ideal partner”. Where did this rule come from? Was it from your upbringing - what your parents and family members used to say to you about your weight? Was it from societal norms and conformity? Was it also due to your own comparison to your friends’ relationships? In the beginning, this “should” may sound like a well-meaning rule that will help you succeed and be happy in your life. However, remind yourself to check its truth and also check its source before abiding by this rule. Is thinking this way really good for me?

  • Reframe

    If you have evaluated the truth and source of your “should” and find that it is a lie and isn’t coming from a place that is helping you, how do you reframe your perspective? In the example of “I should have been promoted by now”, how about saying “I want to be promoted”? What feelings does the latter bring up for you? By choosing another way to look at the situation, you are likely to feel empowered. I want to be promoted therefore, I will do “X”, “Y” and “Z”. You proactively make choices to reach your end goal. You’re not beaten into a corner by your inner critic. I should lose weight then I will be able to find my ideal partner. Ask yourself, what’s my purpose in this intention? Is it to lose the weight or find the ideal partner? What does losing the weight mean for you in the long term? You can start to shift your thinking to look at being fit and healthy and start accepting yourself as you are at your current state. Love yourself, practise kindness and empathy towards yourself. As a result, you will end up happier irrespective of whether or not you are in a romantic relationship with your ideal partner. Ask yourself, “What is it that I want in this “should”?” Question it, dig deep until you find out what you really want and why it is important to you. Use the answer as your compass as you plan your next steps.

You don’t have to journey alone. I will be happy to support you as your coach as you work on checking the truth and the source of your “shoulds”. Together, we will reframe your “shoulds” to bring you closer to your life’s purpose and to live it meaningfully.

“The only impossible journey is the one you never begin.” - Tony Robbins, renowned author, coach and speaker

Begin your journey with me today


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Not Good Enough