Seth Godin asks:

Is this:

• someone in real need of help
• someone you should give money to
• someone who will take whatever money you give and go buy a substance that makes his problem worse
• someone you should cross the street to avoid

Although Seth tries to help with a hint, “there is no right answer,” I have the nagging feeling there is. Maybe there’s more than one right answer, that all of these could be true.

This exact question has been bothering me for more than a week. On our drive home from Sacramento at the conclusion of spring break, my family stopped at my favorite rest stop, just north of Yreka. As we were leaving the stop, a man standing near the back of his parked pick-up held a cardboard sign asking for food, gas, or money. The tailgate was down and the camper shell door was up. A couple of kids were lying in sleeping bags in the back, their heads to the opening. A puppy sat attentively next to the man.

I pointed out the cute puppy to my family as I turned left onto the road that would take us to the northbound freeway onramp. In response, one of my daughters said we should stop and give our traveling food to the man. As I continued on, silently preparing a response explaining why we wouldn’t, she said, “You’re so mean!”

In the next few miles, I was unable to convince my kids that we shouldn’t help this family so we took the second exit, turned around, and headed back to the rest stop. We gave the man some apples, chips, raisin-oatmeal cookies, and a little cash. We turned around again and headed back toward home.

I’d like to say that I felt better helping this man, but I didn’t. I felt like a sucker. And I felt guilty for feeling like a sucker. The car was silent for miles. As I drove, I replayed all the arguments I’ve heard why we shouldn’t have given anything.

• The man didn’t need money. He’s just lazy and he probably makes more money than I do at no cost other than his dignity.
• The man would squander the money on drugs or alcohol and throw away the food.
• I already support homeless people with my taxes.
• I already support homeless people with my offerings at church, some of which go to our local community service programs and our church’s international relief organization
• Organizations do a better job helping homeless people; if I want to help, I should donate to an organization.
• I had other places to spend my money, such as on my family.

Weeks later, I still don’t have a good answer for my kids. Do you?