5 Ways to Stop “Should”-ing All Over Yourself

Over the course of five minutes on a recent phone conversation with my client Abby, I heard “I should go to bed earlier,” “I know I should meditate more,” “I should probably cut out sugar,” and “I shouldn’t drink as much wine.”

Abby was doing something I affectionately call “shoulding” all over herself.

Should Keeps You Stuck | Jessi Kneeland | Empowerment | Free Yourself

As a culture, we are often held captive by the internalized voice of what we think we’re supposed to do and be. We use the word should so frequently that it takes the place of more accurate and powerful phrases like “I want,” “I can,” and “I will.

Shoulding all over yourself sucks. It not only breeds shame and feels awful, it also actually keeps you from making positive changes.

Feeling guilty and overwhelmed breeds inaction and stagnancy, so the more you feel like you “should” do something, the less likely you’ll actually do it.

Not taking action toward your goals makes you feel worse about yourself of course, adding to your feelings of shame and overwhelm. Which naturally brings about more “shoulds.”

Should Keeps You Stuck | Jessi Kneeland | Empowerment | Free Yourself

Can you see why this is such a destructive habit? Good. We should all stop shoulding all over ourselves immediately. (See what I did there?)

Here are 5 ways to break the habit.

1. Answer Who, Why, and Under What Circumstances.

“Should” has no actual definition when used without context, and yet we rarely provide any context when we use it. The word “should” is technically intended to indicate a specific obligation or appropriateness, not some universal blanket truth.

This gets very confusing. Should I wear a bikini to a funeral? Well, no. That would be inappropriate. But does that mean I should not wear bikinis, or I should wear black pantsuits? No, because a black pantsuit at a pool party would be just as inappropriate. What one should and shouldn’t do is entirely based on the specific context of who they, what they want, and what the circumstances are.

The next time you catch yourself saying “I should…” force yourself to get really specific about the context.

Include in your statement who should, why they should, and under what circumstances they should. For example instead of “I should eat healthier,” you could say “I should eat healthier if I want to feel more energized, which I do.”

2. Use specific, actionable details.

Adding who, why, and under what circumstances for context to your should statement is a good start, but often people say they “should” do vague and difficult-to-take-action-on stuff like “get in shape,” or “be nicer.” These statements are incredibly disempowering, because they make it super easy to fail and super difficult to know what to do next in order to succeed.

By creating specific action statements, you make it a lot easier to take action, create change, and avoid the guilt.

Ask yourself: what exactly do I want, and how will I know if I’ve succeeded? Then determine what the next action step required would be to get closer to your desired effect, and use that to replace your should statement.

Should Keeps You Stuck | Jessi Kneeland | Empowerment | Free Yourself

In the example above, instead of saying “I should eat healthier if I want to feel more energized,” you might say “I should eat a protein-rich breakfast if I want to avoid a mid-morning energy crash this week”.

3. Let your “should” be a red flag.

“Should” is a judgement that you learned somewhere and then internalized. Rarely do we say “I should” about stuff we feel totally aligned with, so let the word be a red flag indicating where you’ve internalized something that doesn’t quite feel right to you.

Should Keeps You Stuck | Jessi Kneeland | Empowerment | Free Yourself

Where did you learn this should? To whom does this should really belong? Do you actually agree with, or want this should? What are you afraid will happen if you don’t do this should, and why?

For example, maybe you’re deciding about your future and think “I should be a doctor.” Odds are pretty good that if you really felt passionately about being a doctor, you would say “I want to become a doctor,” or “I’m going to become a doctor.” The use of the word should here indicates that you feel pressure to be a doctor for some reason, but that the decision doesn’t feel quite right.

Get curious! Who really wants you to be a doctor? What are you afraid will happen if you don’t become a doctor?

There is so much you can learn by allowing your shoulds to guide you deeper into nuanced self-awareness.

4. Prioritize.

What happens if you feel like you should wake up early to meditate, but you also feel like you should sleep in to catch up on rest? When the things you feel like you’re supposed to do conflict, you’re condemning yourself to failure one way or another, and brings with it guilt, shame, and paralysis. Learning to prioritize your actions solves that.

Prioritizing is simple, but not easy. The trick is that you need to stop asking yourself which thing you should do, and start asking yourself which is more important to you right now? (Notice I said right now, because specific context is very important.)

Should Keeps You Stuck | Jessi Kneeland | Empowerment | Free Yourself

Which outcome aligns better with your highest values? Which one offers you the biggest benefit right now? Which one do you want most right now?

Getting in touch with “what’s most important to me right now?” is a fantastic way to strip “should” of it’s unwarranted power.

5. JUST STOP.

There are exactly zero circumstances under which “I should…” is the most specific, accurate, powerful, and useful language to express a thought. You could literally stop saying the word should forever, and you wouldn’t be missing anything. There is always a better and more valuable linguistic choice.

So stop. Seriously. I challenge you to stop saying the word “should” completely, for a week. Or even for just 24 hours. Keep a journal for every time you notice yourself saying it or wanting to say it, and edit every single example to be more accurate and powerful, using any of the tips above, or by simply replacing “should” with something more accurate and powerful like “I will,” “I want,” or even “I feel pressure to…”

Note: Be careful here of simply replacing should with “have to,” “ought to,” or “must,” since those have basically the same intention and meaning, and are just as disempowering and conflict-creating as “should.”

The language we use matters. Using more accurate and powerful language has an amazing way of elevating your self-awareness, as well as signaling both to yourself and everyone around you that you are in charge of your own life.

Should Keeps You Stuck | Jessi Kneeland | Empowerment | Free Yourself

Over time, the practice of freeing yourself from the shackles of should will strip away mental fogginess, anxiety, self-judgement, guilt and shame. In their place, you will find clarity about who you are and what you want, along with a feeling of empowered self-acceptance.

Go forth and be powerful, my darlings.


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I am passionate about helping women learn to love their bodies. That includes unlearning what a woman “should” be, feeling empowered and confident in yourself, embracing your authentic power, and creating a life so kick-ass and beautiful that you hardly have any time or energy left over to think about how your body looks. 😉

That’s why I created
The Empowered Women Project

— for women like you, who are sick of being judged for what you look like, and want to focus instead on all the amazing things you can do and be. Click here to know more

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