Leadership Lessons from Picking up Hitchhikers

I pick up hitchhikers. Not all of them, but several over the years. Many tell me that I probably shouldn’t. They may be right, but I have yet to give someone a ride that I wish I hadn’t. This blog article is going to be more personal than professional. However, I have a very relevant leadership lesson to share that I’m certain you can apply to your work. Before I get into that, I’m going to tell you a few stories.

Hitchhiker Joe

I walked out of my chiropractor’s office and encountered smiley young man walking down the street. He approached me and asked me which way I was headed. I told him where, and he asked if he could ride with me for a few miles. I said, “hop in.”

I asked him where is was coming from and where he was going. Joe was very excited to share with me. He said, “I live in a halfway house back there, and I am heading to an AA meeting.” I said, “Great! How’s your day going?” Joe replied, “I’m having the best day. I just got to see my daughter, whom I hadn’t seen in a long while. That was fantastic.”

Soon enough, we arrived where he was heading. He thanked me and went on his way. It didn’t take much for me to figure out how much pain he had in his life, but in this brief encounter, all I saw was pure joy.

Hitchhiker Sue

I drove to my neighborhood grocery store to pick up a few items. Before I got a chance to even open my car door, a middle-aged woman approached my car window. I rolled it down and could see fear and panic in her eyes.

She quickly explained that she walked out of the grocery store and saw her ex-boyfriend’s car, whom she had a restraining order against. She feared that if she went to her car, he would be waiting for her there. She asked for a ride to the police station. I said, “hop in.”

I remember having a hard time making small talk. I didn’t really know what to say, but I felt her fear and my heart ached for her. We arrived at the police station after a few minutes. She offered to pay me for the ride, but I just sent her on her way, glad she was safe.

Hitchhiker Jane

I drove toward home at night through my neighborhood. I saw a young woman meandering on the street. She didn’t seem to be walking anywhere in particular. I rolled down my window and asked her if she was lost. She was obviously confused and didn’t know where she was. She claimed she had been robbed and didn’t have a phone or wallet.

I asked how I could help. She wanted a ride to the bus station so she could go home. I asked where home was, and she said, “North Minneapolis.” I said, “hop in.”

I drove her to the bus station, only a mile away. Since I knew she had been robbed, I asked her if she had any money for a bus fare. She didn’t. I gave her some cash for the fare and dropped her off. On my way home, I called the police, reported the alleged crime, and told them where I picked her up and dropped her off.

What does all of this mean?

Writing down these stories is an interesting exercise. In hindsight, I wonder if I should have done things differently. In the moment, these events just unfolded as they happened. As I reflect on these stories, this is how I think about them:

Fear vs. Compassion

Within each of us, we have two opposing forces: fear and compassion. I’m not overly foolhardy. My spidey-senses go on high alert in these situations. I don’t want to get victimized, tricked, or taken advantage of in any way. There’s a strong inner voice that tells me: “Don’t make eye-contact. Don’t engage. Just keep moving along. This is none of my business.”

There’s another strong force inside of me, and that’s compassion. In a small way, I allow my heart to feel what this complete stranger feels, and I let that influence my actions.

Faith

I don’t consider myself to be a quick judge of character. I don’t know if I am being conned or not. It’s a step of faith that allows me to do this. It’s that simple.

Without a doubt, my faith makes this response possible for me. I’m not using my own logic or reasoning, but instead, I try to look at people the way God sees them, rather than the way I do, or the way the world does.

I don’t do this nearly enough, but when I do, I’m glad I did.

Comfort vs. Perspective

I’ve learned that I am quite comfortable to never interact with poverty. However, that comfort isn’t a good thing. I choose to live in Brooklyn Park, Minnesota, which has a diverse mix of income levels. It’s not fun to interact with hitchhikers, panhandlers, and the homeless, but doing so changes me a little. It creates a connection. It expands my perspective. And, it is always guaranteed to give me one thing in return: gratitude.

What about work?

I promised you a professional application, so here it is. If you are an individual contributor, then perhaps you can afford just to do your job and go home. If you call yourself a leader at work (whether formally or informally), then you have a larger responsibility. Just like a mayor of a city, you need to care for your community at work. Not everyone is just like you. Your community at work is filled with different incomes, backgrounds, hurts, and dreams.

In my city, I’m just a guy with a car and little extra time. There are hitchhikers around me that desperately need someone like me. At work, I’m a leader. I don’t often pick up actual hitchhikers at work, but there are plenty around that need a more figurative “lift.” I can make room in my busy schedule to engage with those around me that have a need.

“Hop in”

Everyone has a story. Sometimes, you should get yourself involved a little. Sometimes, you might not have anything to say. As a leader, you have the ability to help someone who desperately needs a ride from point-A to point-B. They may need career advice. They just may need someone to listen.

Whether literally in the city streets, or figuratively in your work community, take the time to pick up a hitchhiker every once in a while. All you have to do is pause, look them in the eye, feel what they feel, then say, “hop in.” You’ll be glad you did.

Read this article on my blog site or listen to it on my podcast.