What is your Lollipop Moment?

by jon on May 20, 2012

One of my all time favorite TED videos is Drew Dudley’s speech on “Everyday Leadership.” The title doesn’t really tell the full story about the video, and you may be wondering about the meaning of a lollipop moment…


Sometimes we think it takes an important title or some huge world changing act to be a leader. However, I believe real leadership is understanding how we can impact every person we meet moment by moment. And how we can be an example for others in our everyday lives. Drew tells the story of a young girl who was on her first day of college but was certain she wasn’t right for school and ready to leave. She was in line for college registration when she ran into Drew. He made her laugh just by having some fun and then made a young man give her a lollipop for a cause he was supporting. This was a tipping point in the girl’s life as she decided to stick with college after this small interaction. She had been waiting for a “sign” that morning to stay or leave and this put her over the edge. Four years later when she heard Drew was graduating, she told him how important that moment was to her life. And it inspired Drew so much that he travels around telling this story about his “lollipop moment.” Or a special moment you created and may not have any idea about. But when someone tells you about that moment… it means the world. I wonder what would happen if we started sharing these stories more with others.

I recently decided to tell my first boss out of college about when he created a lollipop moment for me. When I worked for Dan, the commercial real estate market was booming and many of his bank clients would do almost anything to stay ahead of the competition. At one point, one bank started asking him to do things that would have been unethical. However, Dan stood his ground and turned away this type of business. It was a very hard decision, because he lost a significant amount of work from this client.

I told Dan that I learned that no matter what happens, it is so important to stick to your values and take the ethical route in all facets of life. The best part about Dan’s story is when the market recovered these past few years, Dan’s law practice was one of the first to start booming again. What an impactful lesson for me at such a young age. You will always win in the long run by staying ethical and acting with integrity. And when I told Dan, he didn’t even realize the impact it had on me. But it meant a lot to him when I shared this story. Sometimes we forget that people are always watching our actions. Thank you Dan for being such an amazing mentor to me.

I also showed this video to our Myers Park High School Leadership Academy students that I work with at the Center for Intentional Leadership. They shared some amazing stories about people who have created lollipop moments for them. Sometimes it was just how a teacher reacted to a test score with words of encouragement and empowerment. Or the lessons learned by watching an older brother always hold true to the honor code at his college.

The students even committed to expressing gratitude to three people in their lives that have created lollipop moments for them. They also committed to creating three lollipop moments for others. We talked about how it could just be connecting with a cashier at the grocery store or making a meal for a family member who has had a long week. Or encouraging someone with a difficult task ahead of them that they will do great! Maybe it is picking up a coffee for the person in line behind you just for the fun of it. Or by acting with integrity and being an example for someone. These students sure created a lollipop moment for me just by making these commitments in their lives. I just love working with them.

So Mr. Dudley, thank you for giving me and many others such an amazing perspective with this video. You created a lollipop moment for our world by being yourself and sharing your story with us.

So my challenge today is who in your life has created a lollipop moment for you? And could you take the time to tell them in person the next time you see them. And how about committing to creating one lollipop moment for someone else this week? Tell me about them in the comments section! This may create a ripple effect of “everyday leadership”, and it could just change someone’s life in the process. That sure makes one plus one more than two for me. Have a great week.

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