When you live in, work in, or frequently visit the intown neighborhoods of a big city, it’s a foregone conclusion that you will encounter people begging: asking for money, asking for food, sitting on the sidewalk with a cup. You’ll probably also encounter people who aren’t asking but whose demeanor indicates that they’re not in the best shape. You could write a whole book on this topic, and in fact plenty of people have, but as I work in emergency assistance and live in the city, it’s a problem that I ponder a lot. I’m not going to lie, people often make me uncomfortable. I want to be a model of “Christian charity” and be friendly and generous, but I’m also a young, reasonably attractive woman, and fear tends to jump to mind before generosity. Also, working at a nonprofit where I encounter people in need most days, I think I’ve become even more skeptical of the stories people weave to try and sway me on the street. I don’t like this about myself, but it’s a fact. Watching the news makes me feel justified in being afraid, but reading the Bible makes me feel convicted that I’m falling short.

So what to do? I don’t know all the answers. Here are two situations I’ve encountered recently.

One Sunday afternoon, a teenager in a baseball uniform came up to me with a grungy laminated paper and a bucket with a story about collecting money to try and get his team to some tournament. I smiled politely and said, “Not today.” (That’s my canned response…it sounds polite, but I also know in the back of my mind that it won’t be tomorrow either…) He very well may have been collecting money for his baseball team, and a lot of people would say it’s not my place to judge: I should just give if I feel led to give and move on, not worrying about what he did with the money. But I think sometimes our charity can hurt more than it helps and so I am wary of generosity in the form of cash.

Another night, I was driving home late after a work event. Andy was out of town, so no one was expecting me. I had multiple takeout containers of leftover catered food in my backseat. As I exited the interstate to a mostly deserted intersection, I saw a man standing by the red light with a sign that said something about being hungry. I glanced at the food in my rearview mirror. I didn’t need it. But I was afraid to roll my window down; afraid to be a woman alone in a car opening the window to a man, even just enough to reach out and hand him some food. I sat awkwardly avoiding his glance until the light turned green, and I went home. I felt ashamed, but I also felt like I had made the right decision for my safety. I hate that dichotomy, and I’m in awe of stories where people go above and beyond to help a stranger, especially this one I read recently where a mom and her kids did things I would have been terrified to do.

I’m pretty buttoned up with my cash. Andy and I keep a budget, as you know if you’ve been reading this blog for any amount of time, and it’s a zero-based budget: we give every dollar a job, and some of those dollars’ jobs are to go to charities of our choosing. So for me to hand someone a 20 on the street would be outside of my budget. That’s a lame excuse, but it crosses my mind. Should I budget some 20s for those situations? I don’t know. I’m also a rule-follower and trust in our systems, probably because the system has never let me down. I can’t imagine what it must be like when you fall through the cracks, or even when you follow all the “rules” and things still don’t turn out right. I would hope that people on the streets could find other avenues for help than my wallet, but perhaps my trust in those avenues is a little too strong given the number of people that still need help.

I love the idea of keeping “blessing bags” (though the name is pretty patronizing) or even just granola bars in your car to give to people. Food is tangible, and I’m not skeptical of giving it like I am of cash. I don’t know exactly what I think is going to happen if I engage with someone enough to give them help in the form of food. Andy and I were semi-approached by a guy one night when we were walking home with a to-go box, and Andy happily turned it over to him. He said thanks and kept walking, and we went home. It was fine. But whenever I see someone who looks they might be going to approach me, my heart starts to race a little bit. When I see someone hanging out by the sidewalk asking everyone who passes by for help, I put my eyes to the ground and pick up my pace. I usually try to at least give a quick glance and a smile, not that that helps them at all.

I’m not proud of these stories, but they’re the truth, and I think this is a conversation we all need to be having. It’s not okay to turn a blind eye to folks in need, but I think you also have to be true to yourself. I just wish my true self were a little more open to fearless generosity.

How do you handle situations when you are approached for money or assistance? What philosophy colors your interactions with people who need help?

Laura Lindeman

Laura Lindeman