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This year, most of our episodes are centered around what Buddhism calls the six perfections. These six practices are centuries-old altruistic ways of thinking, speaking, and acting in the world that evolve our minds (and the minds of the people we touch) toward happiness, better relationships, and a better world. 

As the Dalai Lama often says, “If you want to be happy, cherish others.” But what exactly does that mean? Dr. Jan Willis answered this question a couple weeks ago in our first episode of the year by giving us an overview of all the six perfections: generosity, morality, patience, joyful effort, calm abiding, and special insight into the ultimate nature of reality, also known as emptiness.

I’ll be interviewing different Buddhist teachers and authors all year long about these perfections. But for this episode on the first of the perfections, I want to share some of the beautiful lessons about generosity that I’ve learned from a host of people in my life including my Buddhist teachers, my college girlfriend, and, to start off, my mother. I want to focus on just one form of generosity: the generosity we choose to share (or not to share) with homeless people.

My mother’s love for homeless people

My first real experiences with homeless people came as a teenager. My mother had started a costume jewelry business in Boston that operated out of a street cart she parked just outside the Filene’s Basement Department Store where Boston’s Downtown Crossing T-station let out from underground.

All summer, as a 15-year-old boy in the nineteen eighties, I’d take a bus into Boston myself, haul the heavy wood-wheeled cart out of its warehouse, and stand outside all day through hot sun and pouring rain selling costume jewelry to office workers, punk rockers, tourists, and panicked men hunting for a last-minute birthday gift for their wife.

The first time a homeless person approached the cart, my mother was in the process of training me for this job. I was about to shoo the person away, when my mother broke out in a huge smile and gave the scraggly, bearded guy a big hug. Then she introduced us. The guy and I shook hands and, for the first time, I saw a homeless person as a person instead of an unpleasant obstacle on the sidewalk. This continued as others of my mother’s friends who lived on the street came by to say hi, and soon we had a crowd of homeless men and women around us, smiling, making jokes, and posing for pictures with my mom’s camera.

The Homeless Harvard Professor

I tried to copy my mother’s kindness and ease with homeless people, and in the long break between lunch, coffee break, and workers’ commute home, I started learning their stories, which tended to share a few similarities. 

When I asked a surprisingly well-dressed homeless gentleman how he came to live on the city streets, he started off by saying, “Well, I used to be a Harvard professor,” which kind of floored me. Then he went on to explain how his wife had left him, then how he had fallen into depression, then couldn’t manage to do his job (or even show up for it), and eventually how he got fired from the university, burned through his savings, lost his apartment, and ended up on the street. “What about your family, friends?” I asked him, scrolling in my mind through the names of people I’d call if I fell upon hard times. But he told me that he had no family or friends to turn to.

The more homeless people I met, the more I heard this same pattern. They were people that hit a bad patch in life—some facing problems no worse than you or I have faced. But they didn’t have a network of friends and family to fall back on. Whether they were estranged from family, runaways, orphans, or immigrants far from home, for one reason or another, they lacked the network of support that I and many of you take for granted.

Witnessing the arc of a homeless person’s life on the street

Many of the homeless I met also suffered from addictions and mental illnesses. The most striking case of this was a tall, handsome blond guy in his twenties who I knew from the first day he started living on the street right up until the day he died.

The first day I saw this man, he was getting ejected by security from Filene’s: I don’t know why they threw him out, but he landed on his side right by my cart, and I helped him up. His clothes were clean, but his breath was foul with alcohol, and I could do little more for him than help him stumble to the department store wall, where he slumped and fell asleep.

Day after day, week after week, he was there downtown, in the same clothes getting dirtier and dirtier, growing a beard over his formerly clean-shaven face, almost always drunk or on some other substance. I offered him food and small change, and I tried talking to him several times, but when I did, he would just stare open-eyed at me. I grew impatient with what I perceived as his rudeness, his smell, and the fact that he seemed to spend every cent I or anyone else gave him on alcohol or drugs. A year into knowing him, I lost my temper when he stumbled over to my cart and started peeing all over it.

I kept my distance after that, and would shoo him away whenever he came near the cart. Often, he’d be lying asleep on the edge of the department store wall, snoring loudly in the same place he landed his first day on the street. One day, a couple years later, when I was a senior in High School on summer break about to head to college, I noticed him sleeping again, in the same old spot, with a department store guard crouched beside him, shaking his body to wake him up. Other people started to gather, then eventually sirens came from a distance until an ambulance parked right by my cart, and paramedics rushed out to his side. They checked his breathing, his chest. Then, more panicked, they started CPR.

I grimaced as I watched the EMT press his bare lips onto the unresponsive man’s to blow into his lungs, thinking to myself about the smell and disease, and I doubted whether I’d be willing to do that myself. But the EMTs’ efforts had no effect. The man died right there on the street while I was selling jewelry and fantasizing about my Freshman year of college.

Should you give cash to homeless people?

After watching the entire course of this homeless man’s journey, I resolved to remain more miserly with homeless people, giving them food and clothing, but never cash, which they might use to harm or kill themselves with drugs or alcohol. 

But that all changed when I became a Buddhist.

One of the first lectures I attended as a new Buddhist more than two decades years ago was the lively Buddhist nun, Venerable Robina Courtin. She’s been on the podcast a couple times, most recently talking about How to Deal with Despair. During the Q&A, someone in the audience asked what they should do when they passed a homeless person because they didn’t want to give money, fearing the person would spend it on drugs.

Venerable Robina launched into a passionate speech: “How dare you try and dictate what someone does with their money?” I remember her saying. “If someone’s working for you and you pay their salary, do you restrict them from spending it on things you don’t approve of?” She told us that the purpose of giving is to show that we care, and not to control a person’s behavior. The connection and concern you show for that person is what matters most, through your smile and your attention. The cash you give a homeless is also a sign of your care. They might spend it on food or clothes, or, yes, maybe on drugs. But that’s not under your control. She also reflected on how so many aspects of our life are beyond our control, including how rich or poor we are in a society with so many forces of inequality in play from the day we are born.

My first wife, who was a social psychologist, had also taught me about this—how the single most significant predictor of a person’s financial success and life achievements is the zip code they are born into—their socioeconomic status. Following Ven. Robina’s advice, I started giving a dollar or two to homeless people. But, more importantly, stopping to talk with them, as I had learned from my mother in my teens, but forgotten somewhere along the way.

An easy way to make someone’s day

A former college girlfriend, who remains a good friend to this day, taught me one of the most valuable lessons of my life about generosity toward the homeless.  She and I were driving around San Francisco one afternoon, when we pulled up to a red light across Market Street. As she came to a stop, I saw that there was a homeless man standing on the median with a handwritten cardboard sign asking for money. “You wanna see something cool?” She asked me. “Sure,” I said. Then she pulled out her wallet, took out a twenty-dollar bill, and handed it to the guy.

“Woo hoo!” The man yelped, threw down his sign, and said, “You just made my day.” Then he skipped away.

As we drove off, I asked her whether she wasn’t worried that he’d spend it on drugs? She said to me, “If it’s that easy to make someone’s day, why not do it all the time?”

A few days later, I found myself alone in my car, passing by another homeless person on the same median. I pulled out my wallet to give her twenty bucks, but something inside me hesitated. It felt like a lot of money to part with, especially when I had college loans to pay off, debts to manage, and things I was hoping to save for. And so, I ended up putting my wallet away.

Several months later, though, I discovered something fascinating about how I identified with money. Out and about, I was rifling through my car’s glove compartment when I found a twenty dollar bill in a ziplock bag. I had put it in there for an emergency, then forgotten all about it.

My stinginess with the homeless person I’d seen before came back to mind. Now, looking at this money, it no longer seemed mine, but a lucky find I was meant to give away. I drove around for a while, finally heading to an underpass where I knew homeless men and women camped out, and gave the twenty to the first person I saw. They too hooped and hollered, my gift having just the same effect my friend’s had. 

On one level, I felt good about that first twenty-dollar gift to a homeless person in need. But on another level, I couldn’t shake the feeling that I didn’t have much to brag about. The truth was, I’d been born into a better zip code—that’s probably what it all came down to, as my ex-wife had taught me. Now, here I was, finally redistributing a tiny bit of an up-and-coming twenty-something’s growing wealth.

Still, I still found it hard to regularly give away the so-called “hard-earned” money from my wallet. So what I did was replace the twenty I had given away from my glove compartment and let it sit there until I forgot about it again. I started to call this “marinating” my money: letting it rest until my strong attachment to it dissolved. Looking back, I now see this as a valuable lesson in the Buddhist understanding of attachment: how I tend to exaggerate the value of money and possessions, believing that I need them to be happy and that I’d be unhappy if I lost that twenty-dollar bill. But, in reality, I’d be fine with twenty dollars less, and I’d be making someone with far fewer possessions much wealthier in proportion to what they had.

Eventually, this “marinating” process taught me to be less attached to money. As we learn through all the lessons of analytical meditation on this podcast, just about any behavior can be cultivated (or let go of), through habit. So, I cultivated the habit of giving twenty bucks to a homeless person every week or so: something there were plenty of opportunities to do living in San Francisco.

I got to know many fascinating people this way. One guy who I’d see in the Montgomery BART station most weekdays started handing me thick stacks of ripped out note paper on which he’d written touching, explicit stories from his boyhood. I also learned from him the challenges of homeless shelters, which he had access to, but chose to avoid for many reasons. 

One was that he couldn’t bring all his possessions into a shelter, so his things would get stolen while he slept there. Another was the strict curfews of shelters—much like a prison’s—where they lock everyone in from 7pm until the next morning. He also talked about the difficulty of getting along with others, being harassed, and getting into fights in the close quarters of the shelter, especially with people who struggled with mental illness and substance abuse. But, most of all, he said it came down to habit: he was used to sleeping out in the city, and it felt easier to do that every night than to stay in shelters with fancier, warmer accommodations—places he’d inevitably have to leave and adjust back to the roughness of urban outdoors.

Giving away twenty bucks to homeless people wasn’t always as ebullient as those first few times, though. I remember one guy in Atlanta who I handed a twenty to who immediately collapsed onto a bench and started balling. I sat with him for a long time, and he told me how rare it had been for him to experience kindness and generosity in his life, or even the simple acknowledgment of his humanity. That’s happened more than once.

There’s never enough to give away

Another experience that’s happened more than once occurred one day when I ran into a homeless man on my way from seeing a James Bond movie by myself in downtown San Francisco. This was a guilty pleasure I used to indulge in when I didn’t feel like working. When I bumped into this homeless guy afterward, I offered to buy him lunch.

We sat down at a restaurant he chose, and he began telling me a chunk of his life’s story. After lunch, as I was about to leave, he asked me if I’d buy him a sleeping bag. So we went to a nearby department store and picked one out. This took a long time, as he was looking for something quite particular. He chose a couple other items too that we passed by on our way to the register. And then, outside the store, as I tried to say goodbye, he asked for two hundred bucks to rent a room for the night. I told him that I’d hit the limit of what I could afford, and said goodbye a little guiltily after our hours together.

As a Buddhist, I had a name for this, what we call the “suffering of change.” It’s the idea that even pleasant experiences don’t fully satisfy us, because we always want more, and eventually, everything runs out. Lunch was digested. The sleeping bag bought. But this guy still had plenty more problems in life. And I wasn’t satisfied either, feeling disappointed that I couldn’t help him further.

Are homeless people more violent than those with homes?

I’ll tell you, though, one thing that has never happened to me in 35 years of knowing hundreds of homeless people: not once has anyone attacked me, struck me, or shown me any violence whatsoever. I don’t know if my experience aligns with the statistics, but based on what I’ve seen, the incidence of violence among homeless people seems as rare as it is among ordinary people. It’s like the Dalai Lama’s quote that I’ve shared before: “Civilization is kindness.” As much as the daily news might suggest otherwise, it’s our human nature to show one another basic civility.

After writing this paragraph, I went and looked up the statistics. It turns out, I was right: the incidence of violence perpetrated by homeless people is the same as that of the housed population. However, sadly, homeless individuals are far more likely to be the victims of violence than housed people, and the perpetrators of the violence against them are more likely to be people with homes.

Of course, I’m not suggesting that you drop all your boundaries with homeless people. And I fully recognize that women and children have different needs for feeling safe in such situations than I do as a grown man. But I’ve diffused many tense moments with homeless individuals by simply acting open and kind. 

Once, I was standing outside an art opening with friends when a homeless man came up to our group and started yelling at us. My friends were getting scared, tense. Someone pulled out their phone to call the police. But I motioned for him to put the phone away, walked over to the homeless man, put my arm around him, and gently steered us away from the group to ask how he was doing and if he needed any help. That’s all it took—a tiny bit of care and listening. It’s something that many people involved in police reform talk about today: using the smallest, most compassionate action to diffuse tense situations. Because, in general, people just want to be heard and cared for.

The perfection of generosity

I told you about Ven. Robina’s take on generosity and at this point I want to talk in more detail about what Mahayana Buddhism call “the perfection of generosity.” Clearly, my generosity is far from perfect, and yours probably isn’t either. It’s biased, erratic, and tied up with my own ego and sense of self. Still, there is much good to be found in even imperfectly practicing generosity, and it’s inspiring to learn about what it takes to practice Buddhism’s highest ideal of generosity. 

In the framework of the six perfections, the perfection of generosity is the first. It is said to depend not on the action of giving or the size of the gift but most of all on the state of mind in which you give. So, what kind of mind makes for “perfect generosity?” One motivated by what we call bodhicitta, the altruistic wish to benefit everyone, regardless of our relation to them, or even whether they behave rudely or with kindness.

Clearly, though, it is impossible to eliminate the poverty of all beings. So does that mean perfect generosity is impossible? In Buddhism, the answer is, “no.” No one is omnipotent, and the universe’s resources are finite, so it is physically impossible to give everyone what they need.

But the paradox of Buddhism is that the mind wishing to provide everyone with everything they need is what ultimately sets one free from one’s own suffering, loneliness, sadness, and longing. When you develop the attitude of being willing to give everything you possess—both in body and mind—from the depths of your heart to benefit others, that is when you have perfected generosity.

In the same lecture I mentioned earlier, Ven. Robina explained the gradual path toward perfecting generosity. “It’s okay if you’re not ready to give away anything at all,” she told us. “But at least start practicing in your mind. As you walk past a homeless person,” I recall her saying, “First, you can simply smile at them. Acknowledge their humanity, that you’re both in the same boat, that you have at least a little bit of care and concern for them. Then, next step, imagine handing them the keys to your home. Imagine giving them the place you live, freely, without attachment. Imagine them stepping inside the front door to your apartment or home, making themselves comfortable, settling down for the rest of their life.”

Try this right now in your mind. It’s uncomfortable, right? Our discomfort shows us the mental roots of generosity and stinginess. You are not giving your house away to a homeless person and neither am I. Please don’t do this, or tell anyone I said you should. But even with that steadfast warning: You are not giving away your home, isn’t it revealing how hard it is for our minds even to imagine it!

This is where meditation comes in: this is an analytical meditation that you can do actively as you walk down the street. With the next homeless person you see, imagine giving them the keys to your home. Imagine giving your car to the next one you encounter. A month’s salary to the next. And so on. Try this without giving away anything material at all. Try it for a few months, and see what effect it has on your mind.

Four types of generosity

In the form of Tibetan Buddhism I learned, they love numbered lists, so there are four types of generosity listed under its perfection. The first, and they say the weakest, is giving material things. (Though of course we want to do our best to give as much as we are able).

Here are some instructions for altruistic giving that come from a millennium old teaching: First, we are encouraged to give without expectation of result, repayment, or reward. This is a good one to remember. I once had a friend with a shopping addiction who asked to borrow five thousand dollars from me to pay off a credit card. From experience lending money in the past, I remembered how tense even a small loan between friends and family can become. Even though it was a lot of money for me at the time, she was a dear friend, and I told her, “Sure, I’ll give you the money, but consider it a gift. I don’t expect you to pay me back. Our friendship is more important than that.” “No, I’ll pay you back,” she said. I smiled and told her again that it wasn’t necessary. And I also kind of smugly remembered others who had said the same thing, I guess a bit judgmentally.

But in this case, the result was surprising, because a year later, she actually did end up paying me back. I wonder if making the money a gift hadn’t, in fact, made it more possible for to pay me back, because we lacked the tension and guilt that accompanies a loan between friends.

In Buddhist cultures, giving is so ingrained that one of my lamas shared a famous saying that, “There’s no such thing as a poor beggar in Tibet.” When someone is in need, everyone naturally gives. This is also why monastics thrived for centuries in Tibet and other Buddhist cultures, despite the prohibition of monks earning or holding money. The benefits of generosity for oneself were so well understood and ingrained from birth in Tibetan and other Buddhist cultures, that everyone in need was freely supported, without any official welfare programs, taxes, or bureaucracy.

“There’s no such thing as a poor beggar in Tibet.”

Another instruction on perfecting generosity from Buddhism is that it is far better to give through your own hand than through others. Making that personal connection with those you give to is extremely powerful, and in many ways, the greater point of generosity, not the gift itself. This is why it’s also often good to give under your own name rather than anonymously: to put a face on a gift and encourage others to put their face on one too.

In teaching about generosity, there are some extreme stories, the most of famous of which concerns a past life of the Buddha when he was a Prince named Sattva. Walking through the forest, the prince came across a starving mother tiger trying to feed her cubs, yet on the verge of eating them herself due to her extreme hunger. In this barren place, the prince was unable to find anything else to feed her, so, out of extreme compassion, he starts cutting off strips of his own flesh to feed her, but even these she is too weak to eat.

The prince has an epiphany that our own callousness in the face of others’ pain comes from two things: attachment to our own pleasure, and the difficulty of helping. But then, he realized, “I cannot have pleasure while another grieves. And even now, lacking food, I still have the power to help, so why should I be indifferent?” So he climbs a precipice nearby and fling himself from its cliff face so that his dead body breaks up for her to eat.

Even if you don’t believe that the karmic virtue the Buddha accumulated from this act helped him attain enlightenment in a later life, this is still a powerful story of sacrifice. We know of similar stories from non-Buddhists even today, like people who give away one of their kidneys so that a stranger might live instead of die. Of course, just like Robina’s story, please don’t take this one as advice to go off and perform one of these extreme acts yourself. 

Giving protection

As extreme as the gift of one’s material body is seen, it still falls under what Buddhism says is the weakest form of giving: giving material things. The second form of giving in the perfection of generosity is called “giving protection,” or sometimes, “giving fearlessness.” This is when we are able to genuinely protect others from danger. Most parents show this form of protective generosity toward their children every day.

This form of giving also including helping others overcome their fear and anxiety through our friendship and care; and through various practices and therapies like somatic therapy, yoga, massage, acupuncture, and medical and psychological care. Offering healthy ways of living is included in this second form of generosity, like encouraging one another to exercise, eat healthy meals, sleep well, spend time in nature, and live a balanced life. The benefit of this second type of generosity is seen to be greater than giving material things. It’s “helping people help themselves,” as they say.

One striking example of the benefits of what seem like small changes to one’s lifestyle is a story from Eric Schlosser’s Fast Food Nation. In his book and movie, he talks about how how the fast-food industry has infiltrated school cafeterias, often through corporate-sponsored meal programs and vending machines filled with junk food and sugary sodas. These processed diets have been proven to cause student health and behavior issues like hyperactivity, increased aggression, and poor focus. When schools serving junk food switched to fresh, healthy meals, student immediately showed better behavior, academic performance, and overall well-being. These are all examples of this second type of giving: protection.

Giving the dharma

The third form of giving, one seen as more powerful than material things and protection, is giving the dharma. In Buddhism, the dharma refers to the Buddha’s teachings on the causes and suffering and happiness. In my book, How to Train a Happy Mind, I define the dharma in secular terms as, “those teachings that help us to develop our good qualities and understand reality.”

In practice, giving the dharma is tricky, because it’s also considered an ethical downfall in Buddhism to proselytize or impose one’s beliefs on others. Also, as I was sharing with my daughter the other day, a downfall most of us sometimes succumb to is the dreaded “Do as I say, not as I do,” where we encourage people to have greater ethical discipline than we ourselves possess. Yet, when there are opportunities for sharing the genuine causes and happiness and suffering as we best understand them, we shouldn’t be shy about sharing whatever we know, however clumsy or imperfect.

The perspective of this third type of generosity is that fumbling through conversations trying to understand how to treat ourselves and others better, how to live a meaningful life, and how to make the world a better place is far better than complaining about politicians we can’t control, gossiping about others’ faults, and other ways in which we waste our power of speech on negative, harmful, or pointless matters. This third way of perfecting generosity says that, however imperfect, we create a better world when we share our own experience and understanding of the genuine causes of happiness and suffering.

In our culture, sometimes it seems that we celebrate the authentic jerks, while then attacking those who imperfectly try to do good. But “fake it till you make it,” is a common Buddhist adage that encourages us to make an effort to do good, however half-heartedly, and that, through habit, it eventually becomes second nature.

Still, if you want to keep your virtue to yourself, there’s another way of “giving the dharma,” described in this third type of generosity. This is the practice of dedication, the last step of a meditation session, in which you privately aspire that your meditation practice result in benefitting not just yourself, but all other beings. The promise of dedication is that your secret, private practice eventually does make your words and actions genuinely beneficial. Thich Nhat Hanh calls the result “engaged buddhism.” It’s when we each are finally ready to step up off the cushion imaging a better world to go out to actually make it so. 

Giving love

In many Buddhist schools, only those three items are listed under the perfection of generosity: giving material, protection, and dharma. But in some schools there is also a fourth: giving love. The Dalai Lama himself has said that sometimes a smile can be the greatest gift, one that may be more powerful than even money, protection, or meditation. 

The Dalai Lama himself has said that sometimes a smile can be the greatest gift, one that may be more powerful than even money, protection, or meditation. 

It certainly doesn’t sound easy, but the aspiration with this fourth type of giving is to continually view all other beings with love and affection. The result of doing so is to continuously experience happiness yourself, and to make it easier and easier for you to make others happy.

It may sound nonsensical to talk about loving everyone, but this makes more sense with the Buddhist definition of love. In Buddhism, love, or loving kindness, isn’t feeling that someone is particularly admirable or special. It is simply acknowledging that everyone wants to be happy, and sincerely wishing that everyone might enjoy the genuine causes of happiness.

To be clear, cultivating a heartfelt wish for everyone to be happy doesn’t make it so. Perfecting generosity isn’t some form of magical thinking, or “manifestation” as some people call it. Though this attitude is magical, in a way. The effect it has on your personality can be transformative, almost alchemical. Because cultivating the virtuous thought that you might give everyone everything they need ends up transforming at least one person for sure, and that is you. You transform your mind toward one that is loving, happy, and content through the perfection of generosity, the sincere wish to give everyone everything they need, both materially and mentally.

Those are the four type of generosity Mahayana Buddhists cultivate in perfecting generosity, the first of the six perfections: giving purely without expecting anything in return.

Giving is hard 

Whether you’re someone for whom generosity comes easily, or someone for whom generosity doesn’t come at all naturally, you may have discovered something that I too have found, which is that giving can be hard.

This is the last story about a homeless friend that I wanted to tell, and the hardest. Some of you may know that I am an artist who works with technology. There is a whole community of people similar to myself, and we sometimes call ourselves creative coders or software artist and have different forms in which to connect. 

About fifteen years ago, one of my friends from this community fell upon hard times, in a series of challenges that’s hard to tease apart. She had some substance abuse problems, she took on a different gender identity, she had some financial and relationship problems, and she was quite vocal online about all of her challenges, so that our broad community knew about these struggles, and many of us tried to help.

Despite this person’s genius, she was having trouble finding work. So I invited her to my studio, which at the time was thriving, and offered her work on a project. But she turned it down, saying it wasn’t to her liking. Almost a decade passed, and then I saw posts from my friend that she was now living on the streets, in and out of shelters, yet still trying to function as a creative professional. 

This came at a time when I was working at a bigger company with vast resources. I took the opportunity while there to create a whole new class of job for these artistic programmers, and had helped orchestrate the hiring of dozens of them throughout the organization.  So I tried again to hire my friend. But when I hosted her for an interview, she spent most of it complaining about the products and values of the company. Don’t get me wrong, most of her complaints were justified. But there was no way the people making the hiring decision were going to hire her, and like the last time I tried to hire her, she made it clear she didn’t want the job, despite showing up for the interview. 

Fast forward a year and this person’s online pleas were becoming more desperate. I learned in a post that she was now living on the street quite close to our home. She set up a GoFundMe to raise money for her support, and I put in what for me was a generous contribution. Many others did too. Month-after-month, she posted similar pleas. My first instinct when she posted again for financial help was wanting to reach out and ask if she wanted to go for a walk, have the ear of a friend, and see if I could help further.

But after the prior difficult experiences meeting with her, something made me stop. I think I was afraid she might ask for too much, or that my attempts at generosity would simply fail again. I feared that she would be as difficult to deal with and speak with as she had been in our last conversations over the prior decade. So I failed to reach out. Now, I also chose for the first time to make my donation to anonymously, because I also feared she might reach out directly to me, as one of her dwindling supporters.

Her pleas online quieted, and I hoped that maybe she had found some work or a place to live. But six months later, I opened my email one morning to find a long letter from one of her close friends giving notice that she had died. Her death occurred during the early months of Covid, so we had one of those Zoom funerals some of you may have lived through, imperfect gatherings where everyone does their best to honor their friend. But I missed the hugs and side conversations you’d normally have at such an event, and I’m sure others did too.

I like to brag that I have few regrets in life, but the memory of failing to reach out to my friend when I knew she was just a short walk from my house still pains me. Among many other lessons, it shows me that I certainly haven’t yet perfected generosity, which is giving without expecting anything in return.

It’s humbling to look into my mind of that time: one that didn’t want to be rejected once more for my valiant generosity. Her death helped me realize that, if I’m honest with myself, I do want payback from those to whom I’m generous. Maybe  not money, or a returned favor, but at least gratitude. With decades of Buddhist practice, a lot of things that used to anger me in life no longer do. But one that still really irks me is when I’ve done something kind for someone, and in return they act ungrateful, rude, or even spiteful. 

In Buddhism, they say this is the hardest and the very last attachment to get rid of: the attachment to what I like to call “being a good guy.” I like people to thank me when I’ve been generous. And when my wife or a student or colleague or friend fails to thank me for my kindness, I can start to feel grumpy and resentful inside. This attachment to reputation becomes the root of defensiveness, and can lead me (and maybe you too) to lash out, get mopey, or withdraw. It’s a subtle form of miserliness, where you’re only willing to give so long as you get some praise back in return.

Though I’m still embarrassed about my behavior back then, I’ve tried to use the Buddhist antidotes to miserliness to steer ever so slightly toward selflessness. Buddhism teaches three antidotes to miserliness, in its gross and subtle forms. We’ve gone over the first two over the course of this episode.

The first is reflecting on the benefits of generosity: how in its purest form, generosity becomes the cause of endless satisfaction, and even joy. If you doubt this, consider some of the purely generous people you know of in life, and how it reflects in their personalities. The second antidote is reflecting on the drawbacks of selfishness: how, at its core, all suffering comes from the disease of self-centeredness, putting one’s needs and desires above others. And how selfishness in fact has the opposite of its planned effect, because it ends up making you miserable.

A third antidote draws from the earlier stages of the Buddhist path, the powerful topic of impermanence, where we recognize that we’re going to lose everything anyway: by using it up, losing it, wearing it out, or through the ultimate impermanence that comes with losing everything at the end of our life. As they say, you can’t take it with you. True happiness comes not from using up everything you have all by yourself, but giving it all away with the altruistic wish to benefit everyone.

True happiness comes not from using up everything you have all by yourself, but giving it all away with the altruistic wish to benefit everyone.

So, even though I warned you off those more heroic forms of generosity, I do encourage you to try, at least once in your life, to give twenty bucks to a homeless person, then stick around to hear their story, and see what effect it has on both your mind, and theirs. If you have a hard time, stick the twenty bucks in your glove compartment or in a jacket pocket for a few weeks until you forget about it, then discover it later as a nice surprise, and a chance to try and practice “perfect” generosity.

Thanks for joining me for this conversation about the first of the six perfections, generosity. Next week I’ll offer a meditation on generosity to pair with this episode. 

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