Write like your life depends on it.

I'm conflicted about what I'm going to say here. I feel uncomfortable using people's tragic circumstances as a lens through which to contemplate copywriting. But I'm also intrigued, and I want to dig into this. So please understand that I mean no disrespect to anyone.

Now. I experienced a weird coincidence this morning.

I was listening to the Copyblogger podcast in my car—an episode about writing effective headlines. I stopped at a red light in Boulder, and next to the road I saw a man holding a cardboard sign on which he'd written, "Love is the answer." And it made me wonder how effective that sign is at getting people to roll down their windows and give him money. Then I started to wonder which signs work best in such circumstances, and why.

Every form of advertising is fighting an uphill battle. Your audience recognizes that you want from something from them, and they are inclined to either avoid your message altogether or to take it in with suspicion and resistance. If you are a homeless person, that battle must be increased a thousandfold. People regard you and your sign with discomfort, guilt, disgust, pity, disdain, or some mixture thereof. What could you possibly do with a cardboard sign that would make people look, read, make a quick decision, and immediately give you money?

I racked my brain, trying to think of what drives me to give cash to people directly. Of course, it's difficult to parse our own motivations, as so many of them are buried deep in our subconscious. But I think I'm propelled more by my mood and current financial circumstances than anything else. I think some of the decision must be based on the sign-holder, too. In a matter of milliseconds, we surely judge that person on their age, gender, physical condition, dress, and demeanor.

But back to the sign. What works?

I remember a sign I saw in Florida that was shockingly honest. It announced that the man holding it needed money for beer. He was unlikely the originator of that candid approach—a quick online search pulls up many photos of people taking a similar tack. I imagine it's pretty effective. It might elicit a smile and a sense of humanity and connection. Readers might also feel willing to pay for the jolt of amusement.

The humor approach has also produced this: "Father attacked by ninjas. Need money for karate lessons." I suspect that may veer too far into silly territory. The advertiser in me wants to conduct A/B testing with the "beer" and "ninja" headlines.

Most often, the signs describe the circumstances the signholder is facing—being a veteran or disabled, or having a family to feed. Often the signs say, "Anything helps," a two-word version of "What feels like pocket change to you can have a significant impact on my life. I won't judge you, no matter what you deign to share with me." As with much copywriting, brevity is key here.

Many signs include a "God bless," which may be a straightforward thank-you, and may be a reminder of our moral obligation to help one another. Probably both.

Possibly the most clever approach I've seen is the one pictured above. It's interactive and amusing, and it harnesses a sense of pride and competition in passersby. These are strong motivators that are more pleasant to experience than guilt or pity. And as with all copywriting, it's how you make your reader feel that matters.

I'd love to hear how these quick cardboard pleas affect you personally. There is a larger lesson to learn for philanthropies needing to drive donations. What makes you give? What makes you turn away?

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Postscript: As I searched for photos of "homeless signs" online, I discovered the "We Are All Homeless" project (weareallhomeless.org), in which artist Willie Baronet has purchased more than 1,300 signs from homeless people over more than two decades. He uses them in installations to "explore the humanity of the signs, and questions regarding the nature of home, compassion and what it means to truly see each other."