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Five “Whys”

One of the most important questions you can ask yourself is one you are likely to be most reluctant to ask.


Until you address that question you can be pretty dense about your work and your life; just keeping your head down, turning the crank every day and getting by.  When you stop to ask yourself “why?” everything starts to change.

Why are you working your job? To pay the bills? To get ahead?  You don’t have any other options?  You love what you do?  You are making a difference?  You don’t know?  There are an almost endless number of answers.  When you ask yourself why you are doing what you are doing you begin to gain some clarity about what is important to you.

But, to simply ask the question one time is not enough.  In order to improve your career and life, a deeper dive into what is truly important requires you ask the “why” question multiple times. Five is the ideal number. Once you have asked yourself “why” five times you will be close to the bedrock of what is important to you.


Let’s practice:

Why do I go to work?

                  To make a living.

Why is making a living important to me?

Because I want a certain lifestyle.

Why do you want that lifestyle?

Because it is like the one I had when I grew up.

Why do you want to have what you had when you grew up?

Because it makes me feel successful.

Why is it important to feel successful?

Because I want to feel good about myself.


Ok. Now I understand what drives me to go to work. I want to feel good about myself. Once I realize that is my driver, I can be open to many new opportunities that had not appeared before.


  1. Is my work success the best way to feel good about myself?  Perhaps there is a better way.
  2. Are there other lifestyles that might actually be better suited to me and my circumstances?  Perhaps I want a more simple life.  Or, perhaps I want to create wealth far in excess of what my parents had.  I can begin to consider new options.
  3. Is this really the work I want to do? Many other opportunities may equally meet my financial expectations and might actually fit my interests more.

You can ask yourself the 5 “Whys” about any issue in your life.  Stick with it. Drive your awareness to the very foundation.  It will open up new vistas of choice for you.

Build a career roadmap to put yourself on the path to a better “why.”


About Jack Skeen

Jack Skeen
Jack Skeen, founder of Skeen Leadership, has been coaching bright and successful leaders for close to two decades, spending thousands of hours addressing every imaginable leadership, business and life issue with wisdom and professionalism.

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