The Day a Complete Stranger Handed Me $100

It was around 4pm on a warm spring afternoon in NYC. I had arrived at the Amazon AWS coworking loft and sat down in a shady spot on the outdoor patio. Within a few minutes, a man in his mid-50s emerged onto the patio, scanned the area for seating, and opted to sit in the empty space next to me.

After settling himself in, he turned to me and asked, “What brings you here?” I had just begun a sabbatical from work, so I was doing quite a bit of soul searching and reflecting on the 5 years it had been since college graduation. Our conversation evolved into a discussion of my work, my goals, the events I host, my nomadic living situation, and my efforts to live on under $5k/year in New York city.

At one point, he asked me what I would do if he were to hand me $100 in cash.

I said that I wouldn’t quite understand what the gesture was intended to mean. He replied, “Son, I’m in a good place and there isn’t much you can do for me right now, but it seems that I have an opportunity to help you along.”

He asked again, “So, what would you do?”

At that moment, I was forced to look within myself and inquire about what felt so strange about one-sided giving, and transactions in general. I’ve always been a giver, but as someone who lives on close to $5k/year, money’s never been the unit of my giving; instead, I give time, advice, care, affection, attention, introductions, and whatever else makes sense in the moment.

Ultimately, his question led me to a rather profound revelation. I discovered that I am fundamentally uncomfortable with transactionalizing my desire to connect people. Cash prices can make it easier to exchange goods and services, but putting a price on my connective capacity totally devastates my ability to help people in a genuine and unobstructed way. For me, the language of connectivity is my own personal fluency — it’s how I communicate with the world. To put a paywall on my ability to connect people is to steal my inner voice and render me totally incapable of speaking.

In my professional life, I can connect a jobseeker to their future coworker or manager in less than a minute. Knowing which introduction to make and when to make it is an instantaneous impulse that I feel quite intuitively. But if I need to make money by transactionalizing that interaction, it can take several months of stress, trying to ensure that both parties are properly contracted, signed, paying out, etc..

Worse, that process strains the steady and trusting friendships that allowed it to become so efficient in the first place. The result is that it depletes all the energy and enthusiasm that originally motivated me to make the connection. Like I said, connection is my fluency. It’s how I communicate with the world. Nothing should stand in the way of that.

“I get it,” he said. “But this isn’t a transaction. You owe me nothing in return. I just want to know if you’ll take it.”

I stared at the table, at a loss for words.

He took out his wallet, pulled out five 20-dollar bills, placed them in my hand.

I looked at the money for a moment, then looked back at him and said the only thing that came to mind: “Thank you.”

Then he stood up and walked away.