I have a rule: I'll give anyone who asks me for money on the street one dollar per day.
There's a reason for it: working in downtown areas for years, I'd see the same folks multiple days a week, sometimes on the weekends too. By putting a cap on the amount I gave at any one time, I could avoid being frustrated with the frequency of all the times.
It's also not really about the money, I get something out of it too. Let me tell you about the best dollar I've given.
I was walking down Grant Street. I was in San Francisco teaching JavaScript to programmers at Macy's, and it was intense. On top of the technical challenge, the class had the same demands any teacher faces: assessing students, keeping everyone productive and engaged.
I did well at the job, I held a "preferred instructor" status for consistenly good feedback. But the way I did well at it was by beating myself ragged about the tiniest mistakes.
So at first, lost in my head, I walked past this old guy asking for money. Almost got to the cross street before I stopped and turned back.
He stood there holding a soda cup. He wasn't shaking the coins or talking to passerby. His body language sure seemed like he was accepting donations. But in San Francisco, the people who get their clothes secondhand wear last year's styles of trail running shoes and dark-wash jeans, so it can be awful hard to tell. Just to make sure, I looked into the cup before I dropped in a dollar.
"Thanks," he said affably. "How are you doing today?"
I was stunned for a beat. I'd given out money dozens, maybe hundreds of times at this point. No one had asked me how I was doing.
"I'm pretty alright, thanks for asking. How are you?"
"Well, I'm doing better than these people" – he waved his hand dismissively at the whole city – "they don't know how good they got it." He switched to a whiny-kid voice. "Ohh, my iPhone's not new enough. Ohh, my BMW's not new enough. I deserve to live in a fancier part of town."
He looked me straight in the eyes. "I was on a fishing boat that sank 30 miles off the coast of Alaska, 35 degree water. These people don't know what trouble is."
He told me the whole story: the bilge pump failed, the ship started taking on water. The Coast Guard tried to helicopter a replacement pump but the seas were too choppy to safely land the massive machine.
Without the pump the ship took on water terrifingly fast. The crew barely had time to put on their survival suits before hitting the icy water, and wait for the rescue helicopters to arrive.
As he was tossed by the waves, he started to smell liquids floating to the surface. Diesel fuel mixed with sailors' cologne. "I'll never forget that smell 'til the day I die."
We talked a little while longer about life experiences until there was a pause. I realized that I had Big Important Things to go do, and he had other people to share his wisdom with. I left with a wallet a dollar lighter, shoulders immeasurably more.
It's not about the money. It's about the chance to make a brief connection with another human being. Every interaction is different, but I always learn something about my fellow people, gain some perspective on my problems.
That wisdom doesn’t need a home.