A Tale of Two Umbrellas
by Bruce DeBoskey

It had been raining hard for days. Reports of 100-year floods were coming out of Boulder and Lyons to the north. A colleague and I were walking a few blocks to a nearby restaurant for a breakfast meeting. As we walked, a man who appeared to be homeless stepped out from the side of a building. He was standing in the downpour, drenched from head to toe. Looking at both of us, he asked, “May I have your umbrella?”

Our reactions were startlingly different. I grabbed the handle of my umbrella more tightly and tried to frame my response. In the very same instant, my colleague handed her umbrella to the stranger – who thanked her politely. We walked on, sharing one umbrella, and entered the restaurant for our meeting.

As we looked out the window, dry and cozy, we saw the man making his way slowly down the street in a wheelchair. My colleague’s umbrella was providing him with shelter from the deluge – at least for the time being.

Should philanthropy be instinctive or strategic?

I was stunned by my colleague’s instinctive generosity – her willingness to expose herself to the elements in order to provide protection for a complete stranger. I thought that I had witnessed true philanthropy, a term that derives from the Greek philos anthropos, or love of humanity.

At the same time, I was disappointed with my own instinctive response. After all, philanthropy is my profession. I regularly donate money, food and clothing to homeless shelters and food banks but, in that moment – where the stranger asked for precisely what he needed, and I had the capacity to help – should I have said yes to his direct request?

In sharing this experience, I’ve received a wide range of responses. Some say my colleague’s generosity reflects true philanthropy. Others say that my instinct to keep myself dry and to provide for the disadvantaged in more thoughtful, strategic ways is the better approach and ultimately helps more people.

Upon reflection, I’ve concluded that both approaches are equally correct. One provides a short-term solution to an immediate problem for one person. The other provides broader solutions for a community of people in need. Aspects of each approach may well produce the best outcomes.

This thought-provoking experience reminded me of another story, where two men arrive at a riverbank to discover a number of people drowning. One man jumps into the water to rescue as many people as possible. The other runs upstream along the shore to discover how they fell into the water in order to prevent additional victims. Good philanthropy requires both types of responses: instinctive and strategic.

Soon, many of us will gather around the Thanksgiving table with family and friends to indulge in an abundance of delicious food and to give thanks for our many blessings and freedoms. This setting presents a perfect opportunity to tell the “tale of two umbrellas” – and discuss your reaction to these questions.

• How would you have reacted to the man in the rain?
• Is one approach better than the other?
• Would you have reacted differently if he asked for money?
• What is our responsibility to help others in need?
• How can we be more kind in our day-to-day interactions with people less-fortunate than us?
• As the holidays approach, should we set aside a portion of our “gift purchase” money for each other to be contributed to a common “family and friends” cause that will improve the lives of others?
• What philanthropic behaviors do we aspire to? How can we serve as models for our children and grandchildren?

As we approach the Thanksgiving table, let us be grateful. But let us also recall that 50 million people in the United States regularly go hungry, including one of five children. What can we do to share our abundance with others? How can we do it most meaningfully and effectively?

Bruce DeBoskey is a Colorado-based philanthropic strategist working with The DeBoskey Group to help businesses, foundations and families design and implement their philanthropic initiatives.