Four about 8 months, I was a homeless dude about this guy's age.

I wanted to work as much as I possibly could, and I worked 60 hours a week at a call center. My hours there were so irregular that it was impossible for me to get a job anywhere else, so I was stuck with what I could make in that extended work week.

Some nights slept a few nights a month in roach motels, and spent the rest in my car in a rest stop on the side of the highway. I showered at the gym (such an amazing resource for the price) and ate shitty fast food because it was all I could afford, especially without a place to cook.

Things were pretty desperate for me at times. I remember a few times where I had less than $5 in my back pocket, my car was out of gas, and there was still a week until payday.

I never did become a sign holder, mostly because of how awkward it would have been. No matter how bad things got, I couldn't bring myself to ask for help. Maybe it's just the kind of person I am. My pride just wouldn't let me do it.

So I parked my car on a side street near my work where I was unlikely to be disturbed (a car cover was another great investment that helped greatly in this). I took saltines and condiment packets from fast food restaurants. I drank as much coffee with sugar and cream as I could at work, because it was free and calories were calories.

Whenever I see these guys now, yes, I know that they could be doing something more productive with their time, like working or studying a new skill. For most people, though, if you've ever found yourself in the position of holding a sign on the side of the road, you're more desperate than even the rest of the world understands at this point.

That's not to say that you should give these people money. If you see people like this and you want to help, find out what it is that they need, and then fill that need. Spending a few minutes with someone to find out they need clean socks, or their first real meal in a week, or their clothes washed, or a warm place to sleep tonight, and then working to fill that need for them, is usually infinitely more helpful than throwing money at the situation. It won't work for everyone, but for those that want to help themselves out of the desperation that is poverty, even the little needs we can fill make the biggest difference.

TL:DR Was homeless and about this guy's age. It sucked, but I couldn't bring myself to hold a sign. Help these people out by filling a need, not necessarily by giving them money.