I am guilty of chasing shiny objects given I am a serial entrepreneur, constantly creating the next new service or product. And like many entrepreneurs, I find the management of things I generate to be a bit of a challenge. Am I in good company? You bet.

Our coaching colleague, Eileen Brown shared her observations about the distinction between “can” and “should” when she came upon a deceptively simple adage in her daily reading, “Just Because You Can, Doesn’t Mean You Should”. It made her pause to think about how it applies to the coach/client conversation. Here is Coach Brown’s take on this distinction:

“Let me start by comparing the word can versus the word should. I close my eyes and free-associate on the word can.  It is limitless, free and uninhibited. It is jubilant and powerful and is a strong motivator. As the “Little Engine That Could” so aptly demonstrated: “I think I can, I think I can, I think I can” quickly turned into: “I know I can.” This simple three-letter word opens up possibilities and is a great tool for envisioning the future.

When I follow the same process for the word should, I have a different reaction. Should is censoring. It subtly imposes judgment and conveys, to me, negative energy. It is the voice of authority and has the power to bring me back to my childhood and being admonished for being disobedient. It represents rules and order and boundaries.

Can and should, therefore, are at opposite sides in the way we view the world. One is expansive, and the other is closed. How do we reconcile the two?”

Brown’s observations got me thinking and started to notice how often we encounter “can versus should” on a daily basis. Sitting on a packed commuter train, I know I can use my cell phone. But should I? Is it worth it to disrupt the other passengers with my personal business? When driving my car, I know I can pull out into traffic and cut someone off. But should I? I may get to my destination sooner, but I could also cause an accident.

In a work environment it is imperative to know and understand the corporate culture. Is it more important to maintain the status quo or to integrate new ideas? Is it okay to be a truth-speaker? If you do choose to push the boundaries, what are the risks and rewards? How will it impact your career?

On a personal level, what would be the consequences of living your own life completely without restraints? What will you gain? What will you lose? How will you achieve balance?

It really comes down to possibilities versus realities.  When we coach, we want to free the client to paint a future state with the broadest possible brush. To do this, begin by asking a simple question, such as “what can you do about this situation?” Then, when all possibilities have been explored, ask “what should you do?” and use the responses as a filter for success. You can do it, but should you?  This introduces an entirely different conversation, one that brings values into the mix.  Any change is possible; however if it goes against your value system, it has little chance for success.

Coaching is about more than a traditional definition of success or goal attainment.  Coaching is really as much about surrender as it is about gain, and as Eileen points out above, about how you honor and live from your values.

I believe most people who are purveyors of possibility find themselves overcommitted due to the simple word, “yes,” when “no” might give us all more freedom.

For me, this message hit home right now as our company launches some exciting new initiatives.  I want to do it all, yet I know that I have to do what I can manage and give others space to contribute to the success of each endeavor.

Taking these lessons to heart, I have made a top three list for how to hold the concept of “can versus should” for the foreseeable future:

  1. Give yourself permission to creatively delegate anything that doesn’t need your personal attention as a way of saying, “yes, I can” to those things that most need your attention.
  2. Be forgiving when you sign up for more than you have the capacity to manage, and gracefully take something off the “to do list” that you don’t have the time to take care of.
  3. Work with your coach to gain clarity around what you are most passionate about completing and the timeline for completing it.

Perhaps these lessons will inform yours.

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