F16 Jets

Fly With Waldo

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Leadership Lessons from a Homeless Wingman

This weekend I gave $5 to a homeless man that looked genuinely down in the dumps. I rarely give money to the homeless as you never know what the money will be used for. But this guy seemed different. He looked around 30 years old and was frail, in dirty, worn out clothes, and was walking slowly with his head down. As I sat in my car, feeling the breeze through the open window while waiting for the light to turn green, I couldn’t help but stare at him. The contrast between his haggard body, the green grass on which he walked and the cool breeze got to me.

I watched as he reached into his pocket, pulled out a square piece of white paper and unfolded it very slowly – as if he was performing some kind of ritual. I looked at the words in black marker, “Homeless and hungry. Please help me.”

I would have given him a dollar (my “personal homeless donation limit”) but the smallest bill I had was $5. I almost started to drive off. But then I stopped myself. “Give it to him.” My conscience barked at me. “Just do it!”

“Here you go, Sir” I said as I extended my arm out the window. His dry, dirty, and calloused hand eagerly took the bill. When he saw it was $5, his eyes lit up. He looked me square on, smiled and said, “God Bless you.”

I felt good for a split second, and then suddenly I had the urge to “preach” to him….to perhaps share a lesson on success or question him on how he got himself into his predicament. Maybe he could clean up the garbage that was lying in the grass as a thank you for my gift. I also wanted to ask what he would do with the money. Would he buy drugs, a can of beer, or maybe a cheeseburger?

Instead, I (reluctantly) kept quiet, gave him the money, and returned his smile. I think I genuinely made his day. And then I thought about how fortunate I was to have my health. To be able to drive my beautiful car, not feel hunger pangs, and have clean clothes on my body. I thought about the four $20 bills that were still tucked inside my wallet next to the $5 bill that was no longer mine.

And then I realized that if I am going to give, I need to give unconditionally, and just let it go. And I need to practice this more in my life. Sure, this guy very well may have used my money for drugs, alcohol, etc. But once I decided to give him the money, I had to release my judgment on this person.

As I drove off feeling rather inspired, I also learned that I need to be a better receiver. I need to give others the opportunity to feel the gratitude and appreciation that comes when we give. This is the essence of Wing-Giving. For when we lend others our wings to fly, we too fly to greater heights.

Never Fly Solo,

Waldo…Your Wingman