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What Does Success Mean to You? 7 Questions to Ask Yourself

By Mary Shippy


The definition of success has been highjacked by our culture’s obsession with fame and fortune.

The original root definition of success from the Latin “successus” is to advance, a good result, a happy outcome, as in to accomplish a purpose or aim. But we now live within the confines of a very narrow definition of what success truly means.

In our culture today, success is defined by the ability to achieve popularity, prosperity and fortune. Don’t get me wrong, we all need resources that allow us to provide the basics in our life, but when did we begin thinking we are somehow owed more than that which sustains us?  When did a B+ become failure, or a well done job become mediocracy because it wasn’t perfect?

Hope For the Flowers

When I was in high school we all had to take a class called “Social & Family Life” in our senior year. We basically sat around a room on beanbag chairs and practiced what today I would call mindfulness. We wrote in journals, reflected on our lives (past present and future), we read books, listened to music and talked about our fears and hopes.

One book I remember reading was a young adult book entitled “Hope For The Flowers”. It was about two caterpillars and their journey toward becoming butterflies.

These two caterpillars, Stripe and Yellow, had a strong yearning to climb. In the process of understanding this yearning, they came across a hill of caterpillars pushing and shoving to get to the top of a high pile. They joined the pile and climbed, pushed and shoved to get to the top.

They learned quickly that the secret to the top was to treat every other caterpillar as an obstacle in their way.  No eye contact was made and no conversations were had.  Everyone was out for themselves.

As they neared the top, Stripe began to realize that there were these winged creatures flying around the pile trying to communicate to all of the caterpillars in the pile. In a moment, he realized there must be another meaning in this yearning that wouldn’t require them to fight to the top.

With this recognition, he felt some regret and uncertainty. He and Yellow decided to curl into a ball and roll down the caterpillar hill back to the bottom where they started… Eventually they discovered that this yearning and motivation inside of them wasn’t to fight to the top of the hill, but it was a yearning to fly—to become a butterfly. This also meant that their present state of being literally had to die in order to be transformed.

Emerging Leaders vs. Senior Leaders

As I work with emerging leaders, one of the questions that often comes up in their development work is the desire to be successful as defined by our cultural definition – to climb to the top of the pile.

When I work with senior leaders who are in transition out of their leadership roles – who are rolling down the pile, they often talk about how money and title did not buy them the happiness or contentment they craved.  They define success as having a happy marriage, being a proud parent, being a good friend, or being a productive citizen in their community. Being a good human being became far more important than climbing to the top of the pile and that is what they yearned for in their leadership journey.

My work with both sets of leaders is to help guide them in creating their own definition of success. The following questions have been helpful for these leaders in defining success in their own terms instead of succumbing to our culture’s fixed definition of success.

  1. What gives you the greatest satisfaction at work and at home?
  2. What are the roles you assume on a daily basis, and how do they impact you?
  3. Looking back on your life, what do you want to be remembered for by your colleagues?  Your family? Your friends?
  4. What provides the greatest satisfaction and meaning for you?
  5. What types of things do you get lost in- where time literally flies by?
  6. The opposite of scarcity is not excess, but enough. – What is “enough” for you?
  7. When you go to bed at night and review your day and the events, what are you grateful for?  What are proud of?  What makes you smile?

Today, I challenge you: what is your definition of success?