image by Digital Explorer, some rights reserved

I remember my first encounter with beggars. It was, oddly enough, while I was accompanying my parents on a trip to England when I was ten years old. We passed a few on the stairs into the Tube, brown women sitting on blankets with cups out, obviously miserable. I remember expecting my parents to throw them some change as we approached them. It was so little money, and they obviously needed it so much, I thought. I knew we weren’t rich, not by a long shot, but come on, we wouldn’t miss a ten pence or two. But my parents just walked on by, like everyone else, carefully calculated aloofness in their faces. It was kind of shocking and disappointing to my 10-year-old heart. My parents are good, honest, compassionate people. They had always taught me that people deserved a fair shake in life. This seemed to be against everything I had learned in school, at camp, etc. What happened to the Golden Rule? Wouldn’t you want somebody to give you some money, if you were down on your luck like that? The whole thing just seemed so Wrong on so many levels.

Of course, as adults, we learn that things are a bit more complicated. Mostly, that there are perverse incentives to consider; if it becomes lucrative for people to solicit money on the subway, for example, then a lot more people will do it, making subway rides a lot less pleasant for everyone. And then of course there’s the whole question of what happens to the money after you give it. If you want to help the homeless, sensible voices intone, direct your money to an outstanding organization that helps alleviate the problem at its root and doesn’t just reward the squeakiest wheels.

But is it enough to listen to the sensible voices? What if they’re just a way of giving yourself an excuse not to do anything? A license to avert your eyes for now, and something to procrastinate endlessly on or forget about later?


For those of us in the business of generosity, as it were (i.e., the nonprofit sector), our expectations of others can sometimes make turning the mirror on ourselves an uncomfortable proposition. That was the position Brigid Slipka found herself in earlier this year, when she realized that despite spending her days cajoling other people to give money, she was parting with precious little of her own.

Everyday in my news feed I see folks in the philanthropy world debating the best nonprofits to support and fellow fundraisers offering strategies on how to garner more support.  I take all these suggestions to heart, affirming to myself that yes, giving is so critical right now.

This is what I’ve actually done about it:  Nuthin’.

Here’s a fun fact! I just calculated the Percent of Income Given (which henceforth shall be known as PIG!) by me last year.  Disturbingly, the relevant numbers were to the RIGHT of the decimal point.


This revelation was the impetus for 40 Days of Giving, a “generosity experiment” of sorts during which Brigid (a) gives some money to a charitable cause every day and (b) blogs about the experience in funny, self-deprecating style. The website is called Actually Giving.

It’s now getting towards the end of the 40 Days, and Brigid is feeling a little burned out. More about that in a bit.


As sensible as ignoring beggars on the street may be, it still takes a special kind of callousness to ignore (and worse, rationalize ignoring) the obvious suffering of people right in front of you. It’s that sense of collective negligence that leads to horrific human behavior like the bystander effect. Moreover, it offends the parts of our brains that apparently are upset by inequality.

A while back, I came across an interesting post by the Acumen Fund’s Sasha Dichter describing a “generosity experiment” he conducted:

The idea, sparked by a homeless man to whom I did not give, was to spend a period of time saying ‘yes’ to all requests to give – whether a person on the street, a donation request from a nonprofit, whatever.

Like Brigid, Sasha raises money for a living. He acknowledges that his experiment is at odds with an analytical approach to philanthropy, but says that misses the point:

The people who didn’t like my experiment all said something like, “If I pass a person on the street asking for money, I don’t give because I know it makes more sense to give to a homeless shelter.”  Put another way, one could better purchase social change for a homeless person by giving to a shelter or a food bank.   Objectively, that’s probably true (though one doesn’t know for sure).  However, it also misses something: first, because whether or not you give a dollar or two to a person on the street really doesn’t affect the larger donation you’ll hopefully make to the homeless shelter or the food bank; second, because the act of saying ‘no’ over and over again is reinforcing something in you and in me.

Sasha’s right. However true the argument may be that street charity is not an efficient use of funds, even for altruistic purposes, the habit of consistently refusing help when directly asked has the unfortunate side effect of codifying, even for the generous, the basic power imbalance between those of us with means and those of us without. It presumes that we, the rich, know what’s best for you, the poor, and what’s best for you is that you continue to suffer. I am not saying that this, on its own, is reason to follow Sasha’s lead and never say no; just that the issue is complicated.

For his part, Sasha believes we could do more:

I’m not saying give every time, I’m asking us to be honest about why we do and don’t give, and to recognize the effect it has on us.

Let’s take an extreme example: suppose that over the course of the year I’m asked to give 200 times – maybe 100 times directly and 100 times by various nonprofits in various ways.  And let’s say I have a limited amount of money to give, which I do.  Isn’t the practice of saying ‘no’ 195 times and ‘yes’ 5 times reinforcing a mindset and habit that I’m the kind of person who says no when people ask for help?  And couldn’t there be a way to say “yes” 15 or 50 or 100 times that would reinforce something else entirely?


Maybe a request for a gift isn’t always chance to analyze what is or isn’t the “best” use of my money.  Instead, maybe a request for a gift is an opportunity to practice being the person that I want to be – someone whose first response is to be open and generous.

Sasha conducted his experiment for a month, and reports a positive experience overall. He will continue to give more often when people ask than he did before, and will think of it as practice for self-improvement.


I had a different result when I conducted my own generosity experiment, five years before Sasha’s and Brigid’s. I was living in New York, making a pittance of a salary and losing most of my meager expendable income on my band. Still, I was doing better than the homeless people I kept passing on the subway, so I decided I would try saying yes for a change. My terms were similar to Sasha’s: I would always give something, no matter what. I’d give change if I had it, but if I didn’t and the smallest bill I had was a 10, they would get the 10. The differences were that I only gave in person, not to fundraising appeals, and I didn’t have a particular time frame in mind – I would simply keep giving until it actually started to hurt me in the pocketbook.

Like Sasha, I also had people warning me what a bad idea this was. They seemed genuinely freaked out that I was actually serious about doing this. And when I say “freaked out,” I mean that I don’t think their opposition was entirely on rational grounds. At some level they seemed to find it very threatening to the way they thought about the world. To be honest, I think that only egged me on more. (I do have a bit of a subversive streak.)

For the first week or so, I felt absolutely vindicated. I said yes to whoever asked me for money, and it felt great. I mean, seriously, so, so good. Not just because I was helping these people, but because it felt so liberating. I had broken free of the stern voice inside my head warning me that what I wanted to do was helping to reward bad behavior and upset the social order. I was just treating people as I would want to be treated were I in their shoes. It was Right.

But it didn’t last. I ultimately had to cut my experiment short after a few weeks. Not because my generosity was a problem for me financially; even with my limited means, the pocket change I was giving out was insignificant in the context of my overall budget. No, it was because the pleasure I was getting from helping people soon dissipated. It dissipated because, given my regular route to and from work at similar times of the day, after a week I was no longer helping random people on the street and subway. I was helping the same people day after day. And our relationship was changing. They were beginning to recognize me as someone who gave them money, which led them to expect it when they saw me. I was becoming part of their revenue stream. This is not what I signed up for, I thought. It felt like too much responsibility, too much for me to do on my own. I wasn’t really going to change this person’s life, was I? A buck here or there was hardly going to do that. But there was an irrational element too. I began to feel disgust at seeing the same people ask me for money again and again. As soon as they were not anonymous, the image of the poor unfortunate soul was stripped away and all I saw was this person who was always bothering me on my way home from work. I grew impatient; I didn’t actually want to give them my money anymore.

And so I stopped. I can’t say that I’ve given to beggars that much more often than I did before since then. Maybe a little. I kept the wallet pretty closed when I was in school and unemployed after that; now that I have a job, I’m a little looser with my change. But most of the time, I say “sorry” and move on. Just like my parents did twenty years ago. And it doesn’t feel any better than it did then.

Maybe I could have done it differently. Maybe if I’d gotten to know them, it would feel more natural to help. But how do you get to know someone with whom you have so little in common?


My aunt Pam is a semi-retired financial advisor and consultant. She and her late husband started a business that made them both quite wealthy, to the point where she was inspired to write a book called How Much Is Enough? Before all that, though, she was a Peace Corps volunteer in Panama for two years in the late 1960s. During that time, she happened to rent a house from a local woman named Minga, who despite her third-grade education became a strategic partner of sorts for my young aunt during her stay.

Despite the close bond between Pam and Minga, they didn’t stay in touch after the Peace Corps gig was up. Pam wanted to return, but circumstances always got in the way. Then, four years ago, she found herself traveling to Panama City for work, and decided to pay a visit to the old village to look up Minga. Sure enough, her old friend was still there 40+ years later, and thus began a series of extended annual trips to Panama to spend time in a completely different environment than Rochester, NY, where Pam spends the rest of her year. And so was born the blog Pam Klainer’s Day, which is a beautifully-written travelogue and fascinating cultural study all in one. Pam Klainer’s Day began last year, during the third post-Peace Corps visit, and continues now as she prepares to wrap up her fourth.

One of the things that makes Pam’s blog so compelling is that she does not shy away in the least from the looming class issues that pervade her experience in Panama. In fact, I would go so far as to say that class is one of the central themes of her writing. (Not surprising for someone who has made a living talking and writing about the meaning of money in one’s life.)

Though Pam will sometimes assume the role of Lady Bountiful for the family, buying them computers and helping with one of the grandsons’ medical issues, for example, she is honest with us about the limits of her generosity and sacrifice. When she visits Panama, she does not stay with the family, but rather in a fancy villa with tourists and wedding parties. She has written about the barriers of class even when she is trying to help. Yet story after story demonstrates that in such a context, the simplest gifts can have the profoundest of impacts. Pam writes of two tear-jerking notes she received this year from two of Minga’s daughters that lay bare a sad reality: that simply by taking them seriously and showing concern, Pam sets herself apart from the other people in their lives.

Gloria’s note tells us that she was born into a poor and humble family. By the age of 14 she was working in Panama City as a servant, and suffering great humiliation – such as the employer who counted the slices of bread, and docked Gloria’s pay if she ate more than one piece for breakfast. From then until now, the blows have come often and hard. Moments of even slightly better fortune have been few.  People such as Gloria learn to keep their heads bowed, their eyes downcast, their shoulders bent, the better to escape the enmity of the world around them. One of her employers told Gloria that the problems between rich and poor are the fault of the poor, who envy all the blessings God has rightly bestowed on the upper class who know what to do with them.

Gloria asked me if I remembered 2008, when she and I first met. As I was leaving the villa, I gave her some money so that she would have a financial cushion of sorts. I told her that it pained me greatly to hear of her being treated badly by employers. I said that if people were unkind to her, she needed to be able to leave and find other work and not have to worry about whether her family would eat that night. And I told her that when she talks to people, she needs to keep her head up, her eyes looking straight ahead, and her shoulders back. The renters who followed me were, in fact, people she describes as “ogres”. Instead of crumbling, she called her supervisor in the rental management company and told her she wouldn’t work for these people if they continued to treat her badly. This was a first for Gloria, and the outcome was good. The supervisor spoke to the renters, and their demeanor improved.

The crux of Gloria’s letter today is that we have given back her dignity in small but enormously significant ways. I invite her not just to prepare the food, but to sit at the table with us and eat. I and my guests visit her home. We take her on outings with us: to the casino, the zip line, on shopping trips to Penonome. If she stays here late and misses the inexpensive transport I give her money for a taxi, instead of expecting her to walk the four miles to the village. Here, in her words, is the essence of the gift:

“Although I am born poor and humble, you and your friends have shown me that we are equal in the eyes of God. It doesn’t matter to you that I am dark, that I never got to study, that I wear inexpensive and poorly made clothing and shoes because that is what I can afford. It matters to you that I am a person, a wife and mother, a good worker, a person of faith. You care whether I have had breakfast, if I look tired, if I am preoccupied about something. When you can, you help. You care about me, and you have helped me care more about myself. Now I am a woman of boldness and courage, and not just an ungrateful servant.”


As compelling as my aunt’s own adventures in Panama are to read about, the latest plot twist has me thinking even more about beggars, misfortune, and generosity. About a month ago, Pam mentioned on her blog a “lost boy” who sometimes hangs around the neighborhood where Minga’s family lives. His father had abused and abandoned him (though he still would force him on occasion to scavenge for cans and bottles on his behalf so he could trade them for drugs), and no one else wanted anything to do with him. Gloria’s (the same Gloria quoted above) son Luis suggests that the family take the boy in, but Gloria demurs: “they have all they can do to keep themselves afloat.” But what do you know, two days later, the boy “who not only has no last name but has been called at various times by three different first names” found himself with a new home and a new family. Gloria spoke with his biological father and got him to agree to give her something akin to legal guardianship, which allows her to access his official records and assume care of him. As he is twelve years old but cannot read and write, Arturo (as he is now called) already been enrolled in a school for kids with special needs, been baptized, and generally welcomed into his new family.

Arturo’s story is inspiring to watch from afar. And it is humbling when I think about my discomfort with facing beggars on the street. I stopped my generosity experiment because I found myself resenting having to give a quarter or a dollar to the same strangers in the subway day after day. Gloria gave a stranger off the street not just a dollar, but her home, family, and unconditional love. Her generosity experiment will last a lifetime.

I suspect that economists of the traditional sort would have difficulty rationalizing Gloria’s decision. Gloria just made a huge sacrifice. She is not a woman of means. Just a few days before she took Arturo into her family, she declined because she said she couldn’t afford it. (Her own son, Luis, has suffered from a foot deformity since birth and is only now, at age fifteen and with Pam’s financial assistance, receiving proper treatment for it. Luis, you might recall, is the one who suggested taking Arturo in in the first place.) The economist’s first resort would be surmise that Gloria derives some large measure of utility from raising a child that had been abandoned by society, enough to outweigh the sacrifice involved. Fair enough, but if that’s the case, why didn’t she make the conscious decision to seek out and raise foster children before? Why did she wait until one fell in her lap? Were the transaction costs really that much of a factor? Does the high cost of adopting abandoned boys off the street make it a luxury good? And if so, why don’t more rich people do it?

My intuition is that Gloria made this decision, a decision that will irrevocably change her life as well as those of Arturo and everyone in her family forever, on the basis of her gut and her devotion to God. “Rational” is not really the framework to use here, nor, in a way, is “choice.” I wouldn’t be surprised, based on Pam’s writings, if Gloria felt almost compelled to do this by her religion and her moral compass.

Ironically, someone like Pam or I would be in a far better position to adopt a strange, abandoned child, but I suspect neither of us would ever consider doing so. I’m reluctant enough as it is to give a quarter to guys on the subway – not because I’d miss the quarter, but because facing up to how much luckier I am than they, even for a moment, would be too much of a bummer for my day. Does having more to lose make one less generous to one’s fellow human beings? And if so, what are the implications for philanthropy within a capitalist system that rewards the accumulation of wealth with more power, access, and wealth?

  • What a remarkable post. I am stunned and moved and my response is lengthy.

    Thank you for questioning if “…having more to lose make[s] one less generous to one’s fellow human beings”. And thank you for your brutal acknowledgment that “…facing up to how much luckier I am than they, even for a moment, would be too much of a bummer for my day.” I do the same thing, and I’m not proud of it. I tell myself that I contribute to the cause in more meaningful ways, and automatically tune out and walk on. Thank you for questioning the implications of my behavior on the future of philanthropy. You make a profound connection that could wield powerful influence if enough of us are moved to spread the word.

    Your post reminds me of an experience with my young son during the Michael Dukakis presidential campaign, and I am compelled to share it:

    Walking by the hungry and homeless people on the streets of Manhattan in the 80’s bothered 6-yr-old Sam. Repeated conversations about it made no sense to him and worried me that he was over-identifying with the needy. I needn’t have worried. One day he decided to write a letter to Governor Dukakis after I told him I had a friend who would deliver it to the Governor personally. Writing was a painstaking endeavor, and I sat with him as he struggled to describe the dilemma in his 6-yr-old, left-handed-scrawl. He concluded “…so please take care of them, because I don’t have enough allowance to do it all by myself.” (To his credit, the Governor wrote Sam an encouraging letter validating his concern.)

    We all see that the beggars are still on the street. And I see my grown son – now a professional photographer – as he says yes. It matters to him as he gets through his day that he doesn’t tune out and turn away. He doesn’t make a big deal of it, he just gives something: spare change, hot tea, a slice of pizza. I believe that Sam and his like-minded Gen-Y friends are a model for the rest of us; YOU are going to make the difference.

    Because of your post, Ian, and the vivid memory it stirred about Sam, I am NOT going to tune out and turn away. I am going to tune in, say yes, and turn towards everyone I know to spread the word that having more to lose does not give us the right to turn away. It is up to all of us to impact the future of philanthropy. For that, I extend a final thank you.

  • I’m humbled by your heartfelt response, Ann. Sam sounds like a wonderful son. For my own part, I struggle with doubt that my generation has the answers, at least to this particular problem. You’ll notice that I speak about my hesitation and discomfort on these issues in the present tense, not the past. It takes courage to confront suffering, and too often I find myself playing the coward. But at least talking about it is probably better than pushing it under the rug.

  • Yes, having the conversation is what matters now, Ian, and it is very much in the present! That’s what gives me hope – that you are presenting the dilemma in a context that makes the conversation possible. I told Sam about your post (you and he must be about the same age) and he has the same doubts as you. To me, seeing you two extraordinary young men, both making your living in the arts, struggling with this seemingly insurmountable issue, means that you will be part of the solution. No matter what happens – in moments of courage and cowardice – just keep the conversation going.