How Random Giving Changed My Life

There are moments in one's life that are so profound, we never forget them. I was in Boston, 2015 - The night was cold, 33 degrees and drizzling - typical Bean Town weather. I walked to the Long Wharf hotel from a dinner meeting in Seaport, what used to be Southie. I walked by a 7-11 store and a homeless man.

“Can you help me?” I heard as I passed the dirty man. He sat on wet cardboard and loosely held a sign explaining his plight.

I shook my head ‘no’ and kept walking. Then I remembered the agreement I made with myself. If I had cash and someone asks me directly for help, I’d stop, ask them what they need, and give them the amount of money they requested, up to what I had in my pocket. No strings attached – give what I have and release the judgment of how they spend the money or their reasons for asking.

I stopped, disappointed in myself for not holding to my commitment. I turned around, walked back to the 7-11, and asked the hopeful soul, “What do you need?”

Stunned, lost for words. His hot breath formed a puff of stream as he sat dumbfounded, staring at me. 

“I need $40 to get off the streets,” he blurted.

I reached into my pocket, pulled out a small wad of cash and handed him two $20s. 

The man broke out in tears and shook my hand. “Thank you, thank you,” was all he could muster. He picked up his cardboard bed, ratty backpack and escaped into the mist of the Boston night.

I watched him walk away, grateful for my health and fortune, and committed myself, once again, to stop when randomly directly asked for help.

This is random giving.

My wife and I are active in this form of giving. Some days, it’s the elderly man at a busy street corner, holding a sign asking for money to buy medicine, or the woman walking through a crowded parking lot trying to get enough money for food. More frequently, it’s a drug addict or alcoholic looking for their next blackout.

Sounds like we're getting scammed, doesn’t it? For those who've hit rock bottom the truth of their situation is certainly not written on their signs or the predictable broken story they tell us while standing in a parking lot. The truth is much more painful and rarely makes its way to the surface. The truth of the needy is as hard as the ground they sleep upon.

With so many false-truths and con artists, why would my family practice this form of giving?

Let’s Go Back to the Beginning

We started our practice at the lowest point in our financial history. A friend recommended tithing as a life-long practice, and gave a small book, he said, changed his life. It was The Richest Man in Babylon by George S. Clauson (I like the Audible version, narrated by Grover Gardner). I read the book and committed to the simple plan and, as it turns out, tithing is a critical part of the book’s recommendations. 

We began giving when times were at their worst. We had no money to give, at least that’s what we believed at the time. As it turns out, we all have something to give – even a dollar.

I remember the awkward conversation I had with my wife - how do we start the practice of giving in the face of huge financial fear? The discipline of reserving and then giving dollars to a cause we supported was not easy. We were struggling; our dream house was gone, I sold my car and bought a 20-year-old truck from a buddy and we were maxed out on every corner of debt you could imagine. Bleak times indeed. But she agreed, and we began giving 2% of all cash we received.

Like magic, we found we could afford it, and, over a short period of time, we started to turn our money problems around. Soon, we increased the practice to 5%. As our income grew, so did the opportunities to give. Within three years we were up to 10% of all cash we received in the tithing account.

Enter My Ego

As our giving expanded, I noticed a new and unpleasant pang of resentment when I donated money to a clean water organization. I felt a pull within me to know what they were doing with the money. The more I wanted to know how they spent the money, the more I lost the good feeling of the practice of giving. With each untrusting Google search, I felt my anger rise until all the emotional benefits of the gift were lost.

The benefits of giving were obvious - the more we gave, the more we had to give. Plus, we felt good doing it. Something had to change, otherwise, we’d tumble down the slippery slope of financial insecurity again.  Resentment and judgment had entered my world like a winter fog, blocking my vision of what was really important.

Freedom from Judgment

The first benefit of random giving is the release of judgment. Giving to the homeless, drug addicts, and beggars will activate a judgmental voice of superiority and separation. The voice in my head will sound like this:

“Why are you giving them money,” the internal voice thunders. “They’ll spend it on drugs and probably commit a crime too. Such a waste!”. The judgmental voice ticks off every rational reason why not to give to the lowest of low. It wants to separate me from the great joy I receive when I give freely. If you believe the prevailing narrative of those who would take a harder line on the poor and addicted, giving money to society’s trouble population only adds to their problems, and worsens our homeless situation.

Maybe. Who really knows when an act of kindness is the one thing that snaps their mental gridlock, and they are able to pick themselves up? You? Me? The government?

No one can say for sure.

I have no idea who needs my money or how they ended up in a difficult situation. All I know is I feel great when I give to those willing to asks for help, and I know they are better having asked for my help.

The best way I know to shut down the judgmental voice is to give freely. It’s none of my business what they do with the money. My part is to give and let go. What another does with the money is their business, not mine. Once I hand over the money, it's no longer mine. My wife and I have found great joy in the practice of random giving, so much so we practice it whenever we see the opportunity.

Rules of the Road

Over the years, we developed a few rules for intentional giving. They are flexible and intended as guidelines to keep us safe while at the same time, open to the benefits. Here are our rules of random giving.

Rule #1 - Keep It Safe

Not everyone on the street is sane or safe. You can get into a lot of trouble flashing a wad of cash to a desperate soul. My wife senses the situation before she decides to give, and if she feels safe, she typically gives $20. She does not get into a conversation nor linger around. She gives a relatively large amount and quickly moves on.

For me, I am a larger man. Safety is not the first thing on my mind but always important. If I feel safe, I’ll engage and talk. My goal is to bring a lesson with the giving - to encourage them to ask for what they need, not what they believe someone will give. As a result, you'll find me having longer conversations with the less fortunate, listening to their stories and encouraging them to get off the streets.

For both of us, safety is a priority and it comes before the act.

Rule #2 - They Must Ask for What They Want

This is my rule; my wife does not wait to be approached. I, however, walk the streets purposefully, cash in hand, looking for those who need help.

First, the person in need must approach me. If someone is on the sideway, sign in hand, holding a cup, saying nothing, I do not stop. There’s a strange bug in my brain relating to this requirement – I believe someone should ask or make an effort. It shows they are willing to try - even the smallest of effort works. Say something, get my attention, stand up, yell at me, do anything to gets me to turn and look. 

Otherwise, I keep walking until someone gets my attention.

Rule #3 - Teach the Lesson

I recall a man who approached me in San Francisco on Market Street. It was a sunny spring day, crowds filled the sideways as a cool Pacific wind blew trash up and down the streets. While standing at the corner waiting for a green light, a man approach and said, “Would you buy one of my newspapers?”

The light turned green and we both stepped off the curb. “Tell me about the paper,” I asked.

“I live in that homeless shelter,” he said pointing to a broken building, “and they make us sell these papers to stay.” He waved the stack in the air, dismissing them as useless.

“How much do you need?” I asked.

“$10 would be really great,” he snapped.

As we stepped up on the sidewalk, I took out my cash and peeled off a $10 bill. “Here you go,” I smiled.

He looked at me with wide eyes and said, “If I’d asked for $100, would you have given it to me?”

With hesitation, I said, “Yes!”

The man laughed, jumped up and down, slapping his knee, and yelled, “Damn!”

“Always ask for what you want,” I said shaking his hand. “I’m Robert and you are?”

He told me his name, and we parted ways.

I believe in the power of self-worth. The less fortunate have the lowest self-worth, and the purpose of this lesson is to teach them they are worthy of my attention and to ask for what they need. Without fail, the energy within them rises when we talk. There's hope, and hope is a good thing.

This story is like many others and is not uncommon for me and my family. We believe in the power of random giving. Here’s the importance of this philosophy – there is a need, expressed as an intention, and our purpose is to meet that intention with a giving response. I consider it a blessing to be asked to help and have the ability to fulfill the request. To me, it is the spirit of life.

There’s another benefit of random giving – I believe the creator will continue to provide me with the money to flow to those in need as long as I continue the flow it. As it turns out, the more I give, the more I seem to have to give. This belief system is so critical to my wife and me, that we set up a separate tithing account at our bank. When we receive a paycheck or other income, we immediately move 10% of all the cash into the account. Once the money is in the account, it is fair game for her or me to donate as we wish. I never question her donations, nor does she question mine.

Random giving is not random. When I put $100 in my pocket with the intention of giving it to those who ask for help, I broadcast a signal that I am willing to fulfill a need. I believe we are all connected and my connection to you is communicated through the energy bonds between us. The receiver may not know I am being drawn to them, and they to me, but I’m here to fulfill my role and be part of the ever-creative flow of life.

It is my part and I love fulfilling it.

Random giving set me free. The old and rotten judgmental narrative is gone, replaced with a deep sense of belonging and connectedness. I never feel alone because I am connected to you, and you to me. I see the world through the lens of a soul who learned a hard lesson, and now cherishes the wisdom earned from its pain. 

What more could anyone hope to gain of life?