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Nice Guys Finish Last

Throughout my life I’ve looked at the world through a positive lens.

While most believe this mentality is optimal, experiences have proven otherwise.

I've often been questioned - even ridiculed - because of this mindset.

For example:

As a high school student I was regularly reminded, “Nice guys finish last.”

As a college student peers would mock me for being too friendly.

As a high school teacher I was told, “You are too easygoing.”

As a middle school administrator a parent told me I smile too much.

As a high school administrator I was told my emails were "too happy.”

As a superintendent other school leaders suggest I'm "too optimistic."

This constant discouragement has caused me to question my rosy view of the world:

Maybe I'm too positive?


Several years ago I was shopping with my wife at an outlet mall. Realizing we were going to be there a while, I told my wife "I'm gonna do my own thing - text me if you need anything" and wandered into a nearby bookstore.

As I browsed the shelves I stumbled upon The 5 Levels of Leadership by John Maxwell.

I picked up a copy and skimmed through several pages. Towards the middle of the book an excerpt caught my attention that reads as follows: "I have sometimes been criticized for being too positive. But it’s a weakness I’m willing to live with because the usual benefits are so high."

"Wait - did I read that correctly?!" I thought to myself.

Fascinated, I continued reading: "Besides, I’d rather live as a positive person and occasionally get burned than be constantly skeptical and negative."

"I knew I was right!" I rejoiced while reading the excerpt a few more times.

Discovering this paragraph changed my life. Desperately needing a reminder that positivity always wins, this passage provided the confidence to ignore society and to live life with an optimistic mindset.


As leaders, our daily mindset has a profound impact on our organization. Cheerful to cynical and everything in between - we must realize our mentality eventually trickles down to employees at every level.

One distinguishing feature of positive leadership is to assume positive intent.

When employees make decisions leaders have two options: assume the best and trust the employee or assume the worst and scrutinize the decision. Leaders who assume positive intent always assume employees are working to the best of their ability with the resources and information they have.

But don't forget Maxwell's warning: Positive people occasionally get burned.

Similar to how kids test parents, employees may see how far they can push a trusting boss. When this happens, leaders must immediately address the situation. Not only will the defiant employee realize this behavior is not tolerated, employees skeptical of an optimistic boss are less likely to question the philosophy.


We all have the power to decide how we come to work each morning. We can choose to be grumpy and bitter or we can choose to have a smile on our face. While the latter seems like the natural choice, realize there will always be pessimists who question this approach.

Do you share these experiences? Similar to what Maxwell's book did for me, let these words give you the confidence to lead with a hopeful mindset.

Living a positive life pays off in the long run.



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