Stop ‘Shoulding’ On Yourself

Mike Robbins
4 min readMay 7, 2024


A while back a mentor of mine said to me, “Mike, it sounds like you’re ‘shoulding’ all over yourself.’

And while this sounds funny, of course, this feedback was important for me to hear at the time and is something many of us do to ourselves, whether we’re conscious of it or not.

If I’m not mindful, it is easy for me to relate to even the most important parts of my life — my marriage, my family, my friends, my health, my work, my spiritual practice, my finances, and more — from the perspective of what I think I should do, say, or feel, and not from a place of what’s true for me.

As I look more deeply at this within myself, I realize that my obsession with doing, saying, or feeling the way I think I should, is actually less about a desire to do the right thing, and more about fear, shame, and a lack of self trust.

When we’re shoulding, it often comes from an insecure place within us where we’re not confident in our own desires and beliefs.

This lack of trust and confidence often leads us to look outside of ourselves for guidance, validation, and the insatiable right way something should be done; which can be quite stressful, anxiety-inducing, and damaging.

Instead of shoulding on yourself, you can ask yourself different questions that come from a place of truth and curiosity.

What if instead of asking ourselves, “What should I do?” we ask ourselves more empowering questions like, “What’s true for me?” or “What am I committed to?” or “What do I truly want?” These questions, and others like them, come from a much deeper place of authenticity.

This is not to say that everything we think we should do is inherently bad. That is clearly not the case. Thinking that we should do things like communicate with kindness, exercise, follow up with people in a timely manner, spend time with our families, eat healthy, take breaks, save money, have fun, work hard, be mindful of the feelings of others, push past our limits, try new things, organize our lives, focus on what we’re grateful for, and so much more — all can be very important aspects of our success and well being (as well as those around us).

However, when we come from a place of should, our motivation and underlying intention for doing whatever it is we’re doing is compromised — even if it’s something we consider to be positive or healthy. In other words, we often feel stressed, resentful, worried, or annoyed when we’re motivated by should. This mentality is based on an erroneous notion that there is some big book of rules we must follow in order to be happy and successful.

The distinction here is one of obligation versus choice, or have to versus get to. When we stop shoulding on ourselves, we’re less motivated by guilt, fear, and shame and can choose to be inspired by authentic desire, commitment, and choice.

How to Stop Shoulding on Yourself

Here are a few things you can do to stop shoulding on yourself:

1. Pay attention to how much should runs your life

Take some inventory of your life and observe the extent to which your drive is influenced by shoulding. You may even notice how often the word should comes out of your mouth in relation to your own actions, as well as your thoughts or conversations about others. The more you’re able to notice this, without judgment, the easier it will be to alter it.

2. Play around with different words, thoughts, and motivations other than should

If it’s not about what you (or others) should do, what are other words, thoughts, or motivations you could have? How can you relate to the most important areas and people in your life differently? Think about this and see what comes up. It’s not simply about word choice (although words do have a great deal of power), it’s about altering where you’re coming from in a fundamental way.

3. Ask yourself empowering questions

As I mentioned above, instead of asking yourself the question “What should I do?” see if you can ask yourself more empowering questions — ones that lead you to an authentic and inspired place of motivation. Consider questions like, “How can I make this fun or enjoyable?” or “What sparks inspiration within me?” or “What aligns with my purpose?” or “How can I serve?” or “What choices would nurture my self-esteem?”

There are so many possibilities, once we stop shoulding on ourselves.



Mike Robbins

Mike Robbins is the author of five books including his latest, We’re All in This Together, which released April 2020. He’s an expert in teamwork and leadership.