Unexpected Leader


Leadership is tough. Even if your head and your heart are in the right place, it can be hard to truly connect to those around you.

We’ve all heard the expression “You can’t read the label from inside the bottle,” right?

It can be hard to see your strengths.

So what do we do? How do we gain the perspective and insights to become the leader we want to be? It starts with one simple thing: struggle.


The First Step: Understanding Your Struggle


For years I made the mistake of not sharing how growing up on the other side of the opportunity divide impacted me, and how one true act of kindness gave me something we all want – purpose.

In The Bus Story, the opening chapter of The Gift of Struggle, I share a story from when I was 17 – a time in my life that struggle was a way of life. Like all of us, I wanted my story to matter. But at that point, all I saw was what others had and I didn’t. And that I paled in comparison to the self-doubt I carried.

One kind act helped me see that I, too, could make a difference in the lives of others. That moment was the first time I felt seen (read more here). Looking back and acknowledging the struggles I went through helped me; letting go of the urge to hide this from others helped even more.


The Next Step: Finding The Gift


Identity is important to us. We intuitively want to be a part of something bigger than ourselves and help others. We want our story to be one worth reading.

It wasn’t until I joined the army that I started reflecting on the struggles that shaped me. I came to understand that each of my struggles was a gift that empowered em.

It was then that I realized that before we can lead others, we must lead ourselves. That starts with defining the lessons we’ve learned.


The Key to Leadership: Connecting Struggle with Strength


When my lens shifted – from outward to inward – everything began to change. To this day, I believe looking inward is the best retreat for aspiring leaders.

It has also been my experience that the great majority of leaders pay little, if any, attention to their personal histories or life stories. “What does that have to do with work?” – this has been dogma in business for far too long.

Students of struggle understand that our challenges and failures have shaped our beliefs. These will show up in future behavior.


Putting It All Together


You must understand your defining “marker moments” as my dear friend Dr. Joe teaches (more from him here). They are the points on a map that define the important stops along the timeline of your life journey.

When I finally mustered up the courage to share that defining moment – The Bus Story – with the great people I was leading, it changed everything for me. I was terrified to share it then. But now I’m energized and proud.

It began the transformation of our journey from company to community. Above all, it created a connection between kindness among us that is hard to describe.

It all started with a story. So if you want to become the leader you desire, practice self-reflection. Define your marker-moments. And then tell your story.


How to Define Your Story:


Become a Student of Struggle:

  1. Write down 3 struggles that shaped who you are today.
  2. What was the gift and how did it make you stronger?
  3. Pick one person that you can share that gift with to help them with their story.

Hail the Underdogs!

How have your struggles shaped you? Let us know in the comments or drop me an email at


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