What I learned about leadership from the homeless

I awoke at 4 a.m., my mind full. I never went back to sleep. I have learned on other early morning adventures through my mind, to relax and allow what is there to emerge. Part of the first hour was reflecting on what I am reading in Michelle Alexander’s book, The New Jim Crow. This is a continuation of being ‘uncomfortable,’ by educating myself about the story I find myself in as a privileged white person.

What emerged during the second hour was connecting several dots about my leadership and the work I did with the homeless almost 14 years ago, and its applicability today. That is our topic for this month. Let us see what shows up.

Several of you, who I have the privilege of calling ‘friend,’ responded to “How Uncomfortable Are We Willing To Be?” I always appreciate the encouragement and sharing of your thoughts/feelings that stirred for you. Thank you.

In many ways this posting is Part 2 of being ‘uncomfortable.’ My sense is there will be others, including those that come early in the morning.

Do your best and be well…


What I learned about leadership from the homeless

As near as I can remember it was the winter of 2004 when I accepted the invitation of a friend and outreach pastor to join the group in their weekly visit to a downtown homeless shelter. This began an 18-month physical, intellectual, emotional, spiritual, and social journey. I was transformed by this journey. It touched me in several ways and influenced how I led others and lived my life. Those meetings continue to impact me. Here are some of the things I learned.

  • We don’t come here for them, we come here for us. It is here that we find our humanity and see the face of Jesus.” This was part of the orientation the first day. My previous preconception was that I was coming to the shelter for ‘them.’ I was wrong. In the act of serving, the conversations, and the interactions my ‘humanity’ was challenged, expanded, and I did see the face of Jesus in many of the people that I encountered.
    • I was humbled. The experience reminded me of something my mother and father taught me. “Jim, you are special, a child of God, but you aren’t better than anyone.” As a leader I was able to ‘see’ others through that lens. It made me a better listener, a more empathetic responder, able to respond with greater compassion.
  • The average time a person is homeless was six months. That was the statistic in 2004. That debunked another ‘myth’ I held about homeless people – that they were homeless for months and years. (Those that are part of the cycle of generational poverty, and chronic homelessness, could fall into being homeless longer and more frequently.) I came to see that there was very little difference between many of them and me. Many/most shared the same desire as I did – a steady job paying enough to provide shelter, clothing, food and education for my family. For my kids to grow up healthy and happy.
  • Their sense of ‘community’ was incredible. They shared with one another and looked out for one another. Although not universal, their love for one another was very apparent.
    • I recognized that I was surrounded by accumulating ‘stuff.’ It wasn’t that the accumulation of things was a ‘driving’ force, but I recognized that I had significant energy invested in maintaining my stuff. The homeless people taught me what generosity looked like. It gave me a renewed perspective of what was meant by “It’s all God’s anyway.” It is a lesson that I continue to learn. It helped influence me to give more freely of what I know (from knowledge and experience) to help those around me have a better chance at success. It helped me be more of a servant when I led.
  • We are all in this together.” I came away having a much larger view of “humanity” and our collective and interconnected experience. This view helped me to ‘respond’ to more things rather than ‘react.’ I learned that we were enriched by our collective diversity of race, background, culture, experience, and ideas. I learned to listen to understand.
  • The simple act of washing a homeless person’s feet and presenting them with a pair of new socks was an act of love that reduced many of them and us to tears. In those moments, the served and the being served experienced their shared humanity.
    • If you have ever experienced the act of giving something to someone who has no ability to give you anything in return, you understand the power of giving. If you have ever received something from someone without the ability to give anything in return, you understand the power of receiving. It is my experience that those are the moments that carry the power to transform us.
    • This experience furthered my education in ‘serving,’ including when I was in a position of leadership.
  • As reflect on the events of the last several months and years, and the story we have grown into (political chaos, divisiveness, anger, injustice and increased racism) in the context of this experience I recognize the common opportunities to create a different story.
    • A story born out of more love
    • A story of mutual respect
    • A willingness to listen to understand
    • A willingness to accept you more than I need to change you
    • A desire to find the common ground; a world where individually we have less need to be right in order to find our self-worth
    • Solutions where we can both win
    • A world of greater collaboration and less I win, you lose
    • A world of shared abundance
    • That the acts of mutual caring be applied to our world

While the culmination of thoughts may have emerged at 4 am, I have been incubating them among the feelings of greater disenfranchisement with my own country. I would like to think that there are a number of us, if not the majority of us, who would like to live into and out of a different story. What does your story look like? What will be your contribution to this story? What will I need to change about me? “How uncomfortable will I need to be?”

Toward a better you…


Of Interest: If you have an interest in learning/understanding more about homelessness, I recommend two books to your reading by Greg Paul. I met Greg in Toronto as part of my journey.  His first book was God in The Alley. His second book was The Twenty-Piece Shuffle, where Greg does an excellent job of illustrating why the poor and rich need each other.