A Checkbook Can't Make You A Hero

In November 2019, I was sitting in the majestic lobby of the Breakers Hotel in Palm Beach, sinking into a plush sofa and reading a random newspaper article that was making my blood boil.

I was reading about an injustice done to teachers who had given ten years of themselves to teach at public schools on the false federal promise that their student debt would be forgiven.

A NYC middle school teacher named “Erin” was featured. Her debt burden was $500 a month. That made the difference for her between a stressed life and a non-stressed life. No relief was coming, so her life would continue to be stressed.

I had just paid the hotel bill for our family vacation. Each of our hotel rooms had cost more than $500 a night.

The disparity between the scale of our hotel bill and the scale of the injustice done to Erin seemed obscene. The contrast between what I was reading and where I was sitting seemed incongruous and inappropriate. In that moment, I felt that my life lacked a sense of proportion and decency.

The article reported that although teachers like Erin had done everything they were supposed to do to earn debt relief, the bureaucratic system of actually granting the relief was so supremely screwed up that only one per cent of those eligible had received the promised relief.

I put the newspaper aside. It was time for us to leave. I lifted myself from the sofa. What would I do about the article?

I could say to myself that we were already sufficiently and respectably philanthropic. The Talmud would back me up.

“It is not your responsibility to finish the work of perfecting the world, but you are not free to desist from it either.”

Or I could use the moment to reassess our entire lifestyle, e.g., to translate the cost of an extravagant hotel room into an alternative, charitable use for that money.

I thought about the question that the philosopher Peter Singer asks: would you jump into a pond in your best clothes and ruin them to save a drowning child. And if you would, why would you squander your money on frivolous, unnecessary luxuries while people drown in poverty?

Neither of the two choices appealed to me.

I didn’t want to give up our lifestyle, even if I knew it contained an inherent aspect of selfishness.

But if I failed to act on my anger over the article, I’d feel weak and guilty. Having read the article at that specific moment in that specific place, I knew I wouldn’t forget it. It would come back to haunt me, like Pandora sprung from her box.  

There was a third choice. I didn’t have the resources to help all the teachers screwed over by the Department of Education, but I could help one teacher, ¹ Erin. That would do something to propitiate whatever gods of guilt were rumbling inside me.

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I was resourceful and lucky. I found a way to get to the reporter who then connected me to Erin. I was filled with the self-satisfaction of someone about to deliver surprising good news. I wrote to Erin that I wanted to take over her $500 a month in loan payments. I waited for her grateful response.

Erin was indeed grateful for my offer but she turned me down. She had pride. Of course she did. Everyone has pride. Especially her. After all, she’d stepped forward to be the featured teacher in the article. 

She wrote to me that she’d always been self-reliant and had never accepted assistance from anyone. Left unsaid, but etched upon my mind was that, to her, I was a complete stranger who knew nothing about her or her life.

Still, I was determined for Erin to accept my offer. It had become a matter of my own pride. Erin and I had a rapid-fire, vigorous, and respectful email debate. I couldn’t break her resolve.

Then I found a new tactic. Erin was one of those generous teachers who will help their students out of their own pocket as much as possible. And in the middle school where Erin taught, there was endless need.

So, I leveraged Erin’s own generosity. If I took over the $500 monthly payments, that would free up more resources for Erin to help her students. That was manipulative of me, almost a transference of guilt. I think it was that and her family convincing her that there was nothing wrong with accepting help that finally let me “win.”

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The victory of convincing Erin to let me help her made me feel good for a while. But then Covid struck. Erin and I had kept in touch, and I learned from her that the population of her middle school, mostly recent immigrant families from the Dominican Republic, many undocumented, had been hit especially hard.

As soon as Erin told my wife and me a few of the specific stories I knew we were going to help.

Pandora’s Box again.

Per Erin, these families lived under extraordinary precarity. Many of them lived in a single room, sublet from the official tenant on the lease. If they fell behind on the rent, they’d be kicked out. Given their unofficial sublet status, they had no protection from the pandemic’s eviction moratorium, so their next stop would be a homeless shelter, a disintegrating blow in so many ways but especially to the family’s dignity.  

Erin gave us other examples. A family’s sole source of income might be from a taxi, sidelined because they didn’t have the money for repairs. Or a family might lack the expense for a funeral so they could properly mourn.

I could not imagine living under that type of stress.  

Erin introduced us to the administrators at her school who had earned the trust of their families. The families came to them when they were in peril, because the administrators listened without judgment and had grown up in the same neighborhood.

Discovering that we could help directly but anonymously felt to me like finding an undiscovered gem of an investment. There was no red tape. The money flowed from us to Erin to the administrators who knew which families needed it the most.  

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Briefly, we felt like we were really making a difference. But the reality was that our emergency fund was the mother of all band-aids. We were forestalling a handful of immediate tragedies, but we were not changing lives. We wanted and needed to do more.

That’s what giving can be like. Perhaps it’s the only model of an hedonic treadmill ² that is not corrosive to the soul.

My favorite line from Hamlet:

“As if increase of appetite had grown by what it fed on.”

We were told that one pervasive problem faced by most of the school’s families was food insecurity. I had learned from the Robin Hood Foundation (which many of you generously support through your paid subscriptions) that in some of the most impoverished neighborhoods, utilization of pantries was exceedingly low.

The reasons seemed obvious in hindsight, but I had never really thought them through for myself. Another indication of how far removed I was from what was happening on the ground.

Here are the barriers to using food pantries we learned from Robin Hood.

• Time: For the working poor paid in hourly wages, time is money. And so the travel time to and from a pantry and waiting on line is a significant cost.

• Stigma: Families don’t want to be seen waiting on line for food handouts or inside a pantry. It’s a blow to their dignity.

• Undocumented: Some food pantries ask for basic information, such as a recipient’s name. The undocumented live in fear of giving any information to any institution, because the consequences of getting deported are so devastating.

• Type/Quality of Food: Often the food at a pantry is unappetizing and not geared toward the tastes of the recipient’s demographic.

We decided to dig in to the next level. Robin Hood introduced us to a local food pantry who knew the middle school well. We provided the pantry with the means to deliver substantial weekly bags of demographically appropriate and reasonably nutritious food to the school for every family to pick up. That system addressed the barriers above, if not completely, at least part of the way.

The director of the pantry is a visionary. But he’s like any other entrepreneur of a small and rapidly growing business. His vans break down, food costs shoot up, he needs to find bigger space. He’s helping the migrants in the community, which has added to his pantry’s burdens. I’m helping him, as an investor would, with advice and connections.

We may be at a different level of helping, but we’re still very near to the surface. There’s so much further to go, and there’ll never be an end in sight.

I’ve become realistic. I’m not the solution to any problem. Instead, I’m a small cog in a vast and fragile machinery that alleviates some of the poverty that unnecessarily immiserates so many in current day America. The bigger cogs, the heroes, are the people like Erin and the school administrators and the leader of the food pantry.

But for my own sake of propriety, better to be a small cog than no cog at all. And I know that until we as a society commit to a far stronger safety net, people like me must continue to play a role in the necessary evil of philanthropy.

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1. I’ve heard this story many times.

“A man spotted a girl throwing beached starfish back into the ocean. He said, “Do you not realize that there are miles of beach and starfish all along it? You cannot possibly make a difference." The girl listened, then bent down to pick up another starfish, and threw it into the ocean. She said, ‘It made a difference for that one’.”

2. In this context, the hedonic treadmill is the concept that we are always stuck at a baseline of happiness no matter what we achieve.