top of page

Sometimes Winning is a Poor Measure of Success

There are a lot of lonely “winners” out there.

Narcissistic people can win. Even stupid people can win sometimes! Sometimes winning is just about getting lucky. Often, there is no rhyme or reason to who wins. If success is measured by winning, that is a poor measure of success.

When our measure of success is winning, we will often choose the path of least resistance in order to earn a promotion, achieve a business metric, or hit a personal financial goal. Those are not bad goals in and of themselves. However, when those goals cause us to ignore who we are becoming as we strive to attain them, winning turns us into someone less than who we are called to be.

There are a lot of lonely “winners” out there. We may see their successes in the headlines or on company websites while they are winning. They attained the success they wanted, but when it is over, who is there celebrating with them?

Sometimes the desire to win in the short term causes us to:

  • Make it all about us and drive others away.

  • Be too insecure to let ourselves or others fail and therefore learn.

  • Cut corners or fudge information in order to avoid looking bad.

  • Ignore the needs of others and only do what makes our lives easier.

  • Avoid projects or people who can’t help us reach our own goals.

  • Belittle someone else’s weaknesses instead of encouraging their growth.

This is why we like to ask people a simple question: “Would you follow you?” Answering that question is rarely easy, because we must stop and evaluate who we are. The people who work towards being their best selves and maintain lasting relationships are the true winners - that is real success in life.

If winning is all we care about, we may look back and see the awards and promotions we strove to achieve, but who will be there with us to celebrate? At the end of our careers or at the end of our lives, what will people remember?

Someone who exercised Courage, Humility, Integrity, Selflessness, Duty and Positivity? Or someone who decided to ignore who they were being as they strived to win. But, many people can’t handle the discomfort that comes with looking in the mirror and examining themselves. Pride and fear causes them to stagnate. It prevents them from seeing the need to be different and truly growing into the person they are all called to be. Some may look in the mirror and see that things need to change, but fear prevents them from taking action because changing things requires breaking old habits by making new choices. Those new choices mean paddling against the current of the way we have always done things.

You can win and be a person you would want to follow. In his book, Return on Character, Fred Kiel from Harvard found that the high character leaders had five times the financial success of their counterparts of lower character. High character sports figures like Peyton Manning or Drew Brees are now retired and are still surrounded by people who love them and honor them for who they were while they were winning and who they still are. Meanwhile, there are some of their counterparts, who put winning first and have not maintained that same level of loyalty from others.

Don’t fall into the trap thinking that winning is the only measure of success that matters. In fact, real success, at least the success that matters is being our best selves - Leaders of Character.


● What will you consider real success at the end of your life?

● Will success be defined by your relationships and the people around you or something else?


Here is a quick assessment that will take you 5 minutes to figure it out. Nobody will ever see your results but you.

Warning: If you are not going to be honest with yourself this is a worthless assessment.

To take the assessment use the QR code above or go to

98 views0 comments

Recent Posts

See All


bottom of page