Stop ‘Should-ing’ Yourself: Transforming Your Mind from ‘Should’ to Authentic Living

“Don’t should all over yourself.”

I learned that expression from a therapist. When he repeatedly heard me use the word “should” in our conversation, he said, “This self-talk is not serving you well.”

I found myself repeating this expression to a friend. At thirty-eight, he is struggling with his next stage in life.

He kept telling me about other people he knew and how impressed he was with them. He went on and on about all they were doing, becoming, and building.

My friend is a successful large account sales rep in the software business. Over the last five years, he has turned down multiple promotions. He doesn’t want to manage people. He wants to sell. But when he admits this, people make him feel like he is not living up to his potential.

He enjoys managing his client base and owning his book of business. He develops deep relationships with his clients. He is a great advisor to them in his area of expertise. This is rewarded with loyalty. He is a consistent, above-quota performer year in and year out.

But at thirty-eight, he has people whispering in his ear. They think he should want to be more than a salesman. He should aspire to management. He should want to hire, train, mentor, and manage a salesforce. This is his next step…according to them…according to the world he lives in.

These whispers are causing my friend to compare himself to his peers of the same age. These people include entrepreneurs creating businesses and self-employed business people. To him, they appear to be building a more significant life than he is. After all, they are creating something. He is simply building an income.

These comparisons result in my friend getting down on himself.

He said, “Maybe they are right. I should aspire to more responsibility.”

And there it was in plain sight for everyone to see. The “should.”

That’s when I shared my story and what I learned from the therapist.

The therapist told me there was a running joke in his profession. They hear the “should” word from patients all the time. And therapists, being people, find themselves saying the “should” word too. He told me when they get together, they sometimes fall into the trap of saying “should” to each other. And that is when one of them blurts out,

“Stop should-ing all over yourself.”

And the reason is simple.

When I say “should” to myself, it breeds feelings of shame or, worse yet, guilt. It is the essence of negative self-talk. I FAILED when I talk about what I should have done in a situation but didn’t. And the failure which comes from something I should have done is crushing. I am a victim of my own choice. It screams, “What is wrong with you? You know better.” The blame is placed squarely on me by me. It is my “should,” and I didn’t do it.

So if it is not healthy for me to say “should,” what word should I use instead? (There’s that should again)

Use “want” instead. “Should” is lazy. “Want” is thoughtful.

Our conversation moved from what others thought my friend should do with his career to what he wanted for his life. Thinking about “wants” and not “shoulds” changed the conversation to an upbeat track.

He said without hesitation, “I want to continue to make a great income. I want to live. I want to continue to invest in entrepreneurs building businesses I am interested in. I want to help them and build wealth doing it.” He just said this, just like that. His want came out straight away.

When I heard this, I said, “That’s it. Listen to how settled you are when you say this. You are confused and struggling emotionally when you speak of what others say you should do. When you tell me what you want, you are at peace, settled.”

But to stay in this zone, he had to consciously stop comparing himself to others. He realized the people he admired were doing what they wanted to be doing. This is what my friend was missing. He thought he should be building something just like they were because it was the next right step for him. At least, that was what people were telling him.

But because he didn’t want to do this, he concluded something must be wrong with him. Then he admitted he didn’t want to build something. He wants to help others build what they want. When he does this, he is doing what he wants. And there he finds peace and fulfillment for him. This was his secret to discover.

Maybe it is time to:

1. Stop saying “should.”

2. Stop comparing yourself to others.

3. Start using the word “want.”

4. Start doing what you want.

5. Stop caring about what others think.