When Should I Give?

Settling In To the Discomfort of Saying No

Biking home on a recent afternoon, approaching a stop-light, a middle-aged guy straddling a bike by the curb waved at me, “My son just went into the emergency room. I’ve got most of the money for a taxi to get there, but need a few more bucks. Can you help?”

He’s on a bike. Why doesn’t he just ride to the hospital? It’s only a 30 minute ride. But what if he really needs it and I don’t give it to him? What if I was in his shoes and I needed help? Aren’t I supposed to give whenever anyone asks? It’s not just thoughts, but my insides are oozing, burning and pulsing uncomfortably and I want it to stop.

In theory, the easiest way to stop it is to say yes. But then I wonder, Am I really helping him or am I just teaching him he can get money for making up a guilt provoking story?

Perhaps no question has plagued me more throughout my life than how to handle requests for money on the street. I’ve had times of saying yes to everyone and times of saying no to everyone. At the moment, I’m on a no kick because I’m troubled by giving out of guilt rather than from my heart.

I forced myself to look him in the eyes, smile, and say, “I’m sorry. I can’t,” in a tone of voice that tried to convey love and genuine remorse. I think he’d rather have the money.

The light changed and as I rode off, under his breath he said, “I help everyone else’s kids, but no one helps me.”

He hasn’t helped my kids so what does that have to do with me? Maybe he really is a giving person and now he needs help and I’m not giving it to him. But he’s on a bike! Why doesn’t he just ride over? Or, if he can’t, why doesn’t he take the bus? He’ll probably spend more time sitting on that corner asking people for money than the bus would take. But what if he really needed help? What if it was me? I’d ride my bike. My thoughts like a record with a skip in it repeating the same lines over and over my entire ride home.

The Guilt and Resentment When Asked for Money on the Street

Most often, though, there’s no story. Just a person outside my grocery store or while walking my dog asking, “Spare some change?” Mostly I look at them kindly and say no. Occasionally, though, the uncomfortable ooze gets the better of me and I’ll ask if they want a sandwich. The responses are mixed between those who add “and could you also get me . . .” and those who say “could you just give me the money? I’d rather get Wendy’s,” which is next door. So much for trying to do a good deed.

A few weeks ago I bought a man long underwear at a nearby shop because it was freezing cold out. As the storekeeper rang up the purchase, I asked if the guy was going to return them. He said, “no, but he usually sells the stuff to someone else.” It was too late to change my mind, but the guy I was buying them for assured me, “not these. I need them.” Yeah. Right.

They don’t all respond this way, but it’s frequent. That said, it’s humbling when I tell a man asking for money I’m broke, and he offers me a few dollars. Or when I’m crouched on the sidewalk suffering sciatica and the only one who asks if I’m okay is a homeless man who knows my excruciating pain.

These heartining moments aside, the barrage of requests and struggling with guilt leads to resentment. As if it is their fault that I feel so uncomfortable. I genuinely want to help, but why should I give to this person when I’m already giving to numerous charities that provide food, housing, and services to the homeless and people with addictions and other mental health issues?

When to Say Yes. When to Say No. I Don’t Know. But Sometimes I do.

I’ve read articles advocating saying no to these requests because it keeps homeless people from seeking the food incentive that will also provide them with additional beneficial services. Other articles encourage saying yes because there are a myriad of reasons why people can’t or don’t access those opportunities or still ask for money. These same articles contend that being homeless is miserable and they should have the autonomy to decide whether they want to access services or if they want to drink or do drugs rather than eat. I agree with all of these perspectives leaving me with no right answer. It’s physically uncomfortable not knowing the “right” thing to do.

Sometimes I do though. I once biked past a woman j-walking across a busy street with no pants or underwear on. I got off my bike to talk to her and she let me help her off the street. When she told me she was lost, I called an ambulance and waited with her. The EMT’s discovered that she had recently been released from a mental health unit at the hospital, and had snuck out of her mother’s apartment while she was in the shower. Her mother had been worried, not knowing where she had gone. When her mother arrived, they sorted out what needed to be done for the woman and I left.

I have helped others like her. Rarely do I find these people because they asked me for money. Usually it’s because I noticed them acting in a way that suggested to me they were lost, confused, or needing help and I’ve never struggled with my decision.

The Gratitude for My Blessings Leads To My Shame in “Having”

Much of my difficulty in saying no when asked for money comes from the gratitude and shame I experience for having been born with plenty and for continuing to always have my needs met and more. I took to heart the saying “to whom much is given, much will be expected” and “give until it hurts.” I heard as a child in church that I was to give to everyone who asked. Adding fear to the shame was the parable of the rich man sent to hell because he didn’t help the poor man, Lazarus.

Yet that was a child’s understanding. As an adult, I know that unhindered giving can be harmful. We wouldn’t give a child everything they asked for, for example. But when it comes to people I perceive as “poor” I find it difficult to escape these powerful, but unhelpful, motivators.

The Fear of Judgment: Do You Care About Children?

My conflicted feelings around being asked for money on the street, though, isn’t focused only on the seemingly homeless who ask, but to those raising money for non-profits who question as I pass, “do you care about the environment?” or “do you care about children?” I hear in their question – if you care about these issues, then you will use your precious time to talk to me and give my organization money right now. If you don’t, then you’re a monster.

The proliferation of birthday fundraisers on facebook and crowd funding has engendered a similar reaction from me. I already give to numerous charities and try to support friends when they launch new projects. Each request is worthy, but giving to all of them would have a significant impact on giving to the charities and projects that I personally care about.  I suspect that if I were still running a non-profit, I would love to have someone raise funds for me this way, yet I still find these seemingly endless requests frustrating.

As with the homeless, I want to help, but perhaps the bigger dilemma for me is my worry that I will be judged, not based on the entirety of my heart and who I am, but solely on the basis of my saying no in these moments. I resent that I’ve been put in that situation because regardless of my financial situation, in my mind, I always have enough to say yes and I should always be “giving until it hurts.”

As a wise friend pointed out, however, no one is forcing me to say yes. Just as I’ve supported music bands, friend’s documentary projects and theater companies, and other charities, I’ve done it because I want to. And just because I can’t support every other project or non-profit, doesn’t mean that someone else might not want to. They are free to ask and I am free to say yes or no.

In her wise words, I realized the crux of the issue. That ooze of shame and fear of judgement flowing through my body does not leave room for me to feel free to say yes or no. It’s in that lack of freedom that I end up in the land of resentment, even though the restriction on my freedom is due solely to my own beliefs; it’s easier to blame the person doing the asking.

Learning When to Say No

As a spiritual person and in the hopes of maturing my understanding about giving, I was curious what various faith and spiritual traditions say about when to say no. Because the teachings of Jesus are the most accessible to me and perhaps speak most profoundly to my childhood shame and fears, that is where I turned. Jesus was incontrovertibly a holy man who powerfully advocated for the poor, and he’s respected by people of many faiths. What I found about him refusing requests was helpful. I tried searching for other teachings, but in my short research time, I came up short. I’d love to learn more from other traditions though and I hope others might share their insights in the comments.

In one story, Jesus, while on the shores of a lake, miraculously feeds a crowd of over five thousand with five loaves of bread and two small fish. Following the feeding, Jesus crossed the lake and some members of the crowd went in search of him. When they found him, they asked “Rabbi, when did you get here?” To which he responded, “I tell you the truth, you are looking for me, not because you saw miraculous signs, but because you ate the loaves and had your fill. Do not work for food that spoils, but for food that endures to eternal life, which the Son of Man will give you.” John 6:25-27. In yet another passage, Jesus refuses to keep healing the masses clamoring for him because his mission is not only to heal, but to preach God’s message, which he sets off to do. Mark 1:35-38. Even someone who advocated so strongly for the poor said no sometimes, recognizing his mission to preach would be compromised if he spent all his time on feeding and healing.

Yesterday, I took a break from writing to walk my dog and passed a woman asking for money from cars stopped at a traffic light. She turned to me with a smile and asked if I had any change. I warmly said no. Her smile didn’t waiver, “okay,” and she turned back to the cars.

While I walked, I realized that much of what is so uncomfortable and even painful to me about seeing homeless people, or people asking for money for whatever reason, is that it is right in front of me, unlike many of the world’s distant or less visible problems. I have the sense that I should be able to fix this person’s problem.

I acknowledge that I am making an assumption about why this woman is on the street asking for money in the first place. Without the time to sit and talk to her, I can’t know. And while I regularly stop to talk to people who ask for money, which has often led to fascinating conversations, I don’t always have the time so I am left with my assumptions and my discomfort and wanting to repair the problem.

But it isn’t easy to solve. Yes, we should have more and better housing, food, and services. Those measures would help. I vote for politicians, give to charities and volunteer to try to provide them. But even these actions will not end the alcoholism, the drug addiction, the mental health issues, and even just the personal decisions that lead some people to asking for money on the street. Because while we can offer people the opportunity to change, they can only do it when they’re ready. Giving that person some change or even a sandwich may momentarily remove the discomfort I feel in the face of that reality, but it won’t end the root causes.

Reading how a holy person like Jesus, who cared about the poor, said no, reminds me that if he couldn’t meet every person’s physical needs, neither can I. For that matter, neither Bhudda, Muhammad, nor any other exceptional holy person ended poverty. I can be more effective when I stay focused on the part I feel moved to do, whether that is volunteering, donating, my legal work, or writing this blog.  I do not need to, and cannot do everything.

Loving Myself In the Discomfort of Saying No

Often to find the right balance, we need to go to extremes. So for the moment, I will keep saying no to find the freedom of giving from my heart and not from the discomfort of misplaced shame and fear. I will still try to treat each person who asks with kindness and love, but I need to settle into my oozy discomfort while I learn to trust that the solutions are not dependent solely on my efforts. I can be far more effective in whatever I am choosing to give if I am not saying yes to everything and everyone. And perhaps as importantly, when I go to the place of discomfort, I can be compassionate to myself and still love myself trusting that I am trying to find the place of love even if I don’t always get it “right.”

Also published on Medium.

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  1. Judson Richardson says:


    1. nosaintjennifer says:

      Thanks Judson. I’ve been a little nervous about this one (Okay, I’ve been nervous about all of them.).

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