Four and a half years ago, I was in a mental hospital. A combination of a tumor forming in my pituitary gland altering my brain chemistry and an abusive relationship situation proved to be my breaking point. I needed help. Thankfully, I asked for it. 

The three days and three nights I spent in that hospital were some of the worst of my life. I won’t go into details here, but it wasn’t a place for my healing. When I finally escaped (which is what it felt like) I went to an intensive outpatient group therapy program where, for 10 hours a week, I learned to manage my illness, change my thought processes, and how to understand what was going on in my mind (neurotransmitters and synapses and uptake — oh my!). 

In recovery, you learn not to beat yourself up (in my case, literally) for what you “should” have done because, quite frankly, if you were capable of making a better choice at that point in time, you would have done so. My therapist would stop us mid-sentence if we used the s-word, “No should-ing!” she’d say. 

This lesson, more than others, stuck with me. And as an entrepreneur, I find myself caught into the should-ing trap more than I’d like to admit. I try to stop using the s-word. 

It’s harder than you think.

Start counting the times during a day where you put this conditional word into conversations. In the majority of cases, it’s not a healthy word, and it’s also relatively powerless as a language tool. 

“I should’ve picked a different website theme.” 

“I should think about alternative sources of income.” 

“I shouldn’t have rushed that report.” 

We’re should-ing all over ourselves!

If you knew that the theme you chose wouldn’t satisfy your business or aesthetic needs when you made the decision, you would have chosen differently. Should-ing this is nothing more than a veiled complaint at best, and an excuse for further lacks in productivity at worse. 

Instead, say:

“A website theme with X functionality would better suit my needs.” 

“I will brainstorm additional sources of income.” 

“I need to manage time better, so I don’t rush reports.” 

And then, of course, take action on these statements. Or, even worse — we should all over others! 

“You should’ve ended that relationship a long time ago.” 

“You should change your business model.” 

“You shouldn’t have hired that consultant.”

There’s little to no benefit that can come from this powerless, conditional word. At the absolute best, you get someone to realize that you think he made a poor decision and therefore he evaluates his actions in hindsight (but only after realizing that he has lost standing in your eyes). At worst, you’re belittling someone’s decision, placing blame, and giving no direction whatsoever. 

The words we use speak volumes. When you’re working with clients, you want to communicate confidence. When you’re talking to a friend, you want to communicate empathy. “Should” does not fit into either of these scenarios. 

In the words of Yoda “Do or do not. There is no try.” 

Similarly, you did, or you didn’t — there is no should.

Be proactive with your language. Give direction, not condition. Use powerful words that give advice, not powerless words that place blame. Stop should-ing. Start doing. 


Jill Schiefelbein, Impromptu Guru, is a communication expert who doesn’t like should being thrown at her. She helps others communicate with confidence and be prepared to speak well any time and every time. 

Learn more at or watch her in action on YouTube.