Homelessness Part 2 – Conversations with the Homeless

Last week I took it upon myself to offend everyone by saying why it is I don’t usually give money to homeless folks. Well, I thought it would be offensive, but was surprised to find a fairly unanimous chorus of similar-minded people. Read the comments from last week and you’ll see what I mean.

And today, we’re going forward with part 2 because I think it’s an eye-opener.

It’s pretty easy to categorize and stigmatize the homeless. I’ve done it myself in the past. However, that’s a prejudice, and I’m not happy with those in my personal life or my attitude. But it’s also sort of hard to be objective with it at the same time. You can’t really know what it’s like to be homeless without becoming homeless yourself, and frankly I’m not willing to research the subject that closely.

Next best thing? Ignore the prejudice and get to know some homeless people. And that’s what this post is about.

If you’ve ever thought of homeless people as just grimy folks, people with bad luck, idiots, ne’er-do-wells, subhuman…all those wonderful sentiments we humans are capable of, I think you might like what you’re about to read.

What follows are real conversations I’ve had with real homeless people. Enjoy…

The Unicycle Guy

If you’ve spent any time downtown Portland, you may know this particular homeless guy. You can’t miss him, as he’s a jazzy fellow who wears checkered pants and rides a unicycle around. And he does this Jackie Chan thing where he’ll run at a wall, run up it a couple steps and then do a back flip off it.

I spoke to him a few times in the years I lived in Portland, and in one of the most profound conversations I’ve ever had with anyone, he told me why he does what he does. He said that panhandling is dishonest and makes you worse. That’s right…a homeless guy said that to me.

I asked him how that could be. He said it doesn’t feel good to be on the receiving end of unending altruism, knowing you can’t pay it back. He said he’d tried it for a long while and hated how it made him feel. He started to dislike himself and the people who gave him money for the simple reason that the equation was broken. Begging, he said, is in itself very demeaning whether you’re making money at it or not. He also mentioned that the people who gave him money for panhandling never looked too happy about it and wanted to just get the hell away. He was, ultimately, being paid to stay away and not bother people.

Begging, he said, is in itself very demeaning whether you’re making money at it or not.

Way to go, us. Our handouts just made him feel like a leper.

Instead of panhandling, he turned to what he knew from his school years: gymnastics. He started performing on the sidewalks. Not amazing Cirque du Soleil stuff either. By performing I mean he’d ride his unicycle back and forth and not break his head open. He’d end off each performance by doing his trademark back flips off a wall. Not the greatest show on Earth, but the kids loved it. And because the kids loved it, so did their parents. He’d get quite a throng of people around him from time to time and make a big chunk of change.

I once asked him if was ever going to get a real job (shame on me, I know) and he looked like he was going to punch me. Which I would have fully deserved, along with a kick to the groin.

He said, “I do have a real job. I just performed for you. I do shows for kids, parents, anyone. I get paid for it. That’s my job. I just don’t work in a cubicle.”

*Game, set and match to Unicycle Guy. Crowd goes wild.*

The last time I saw him he had a shiny new unicycle with pneumatic shocks and some bitchin’ checkered pants. He was doing just fine and had the smile to prove it.

Now, Unicycle Guy was fairly enlightened and the viewpoint he had is certainly not shared by all homeless people. In fact, I’m sure most of the gainfully employed folks I know don’t say shit that bright. But look what he did with his life. He didn’t like panhandling. He didn’t want people feeling sorry for him and he didn’t want handouts. So he got a “job”, had “clients”, discovered self-worth and was a productive and additive member of society. Awesome in every way.

The Joke Guy

“Not everybody can ride a unicycle and do backflips.”

A bum said that to me. I had just gotten done telling him about the Unicycle Guy and how he at least did something in exchange for money.

I said, “Well, what can you do then?”

Long conversation ensued and it turned out he used to be a sailor. Being a sailor and hanging around other men all the time, he was an endless fountain of jokes so godawful they’d curl your toenails and strip the paint off your house.

I said, “Dude! I love jokes! Tell me some jokes!”

And he did. And I laughed my ass off. And I gave him money. As will happen, my laughing attracted a few more people, who attracted a few more. I stood nearby as he continued to tell people these absolutely horrendous jokes. He got a quite a payday. I gave him a wave, he smiled and said, “Dude thanks, bro!” and that was that.

The thing I didn’t mention is that when he started talking about jokes and his old shipmates, his eyes lit up. And when he started telling his jokes, he looked alive. He commanded the space like a pro who’d been doing it for years. And just ten minutes before that, he’d just been a depressed guy who could barely mutter, “Spare change?” under his breath.

So tell me honestly, what do you think would have helped him more? A five dollar bill we gave him because we felt sorry for him? Or a real conversation that added to his self-worth and increased his income?

Paul Bunyan Guy

There was another homeless fella I met in Portland. I remember him vividly because he had a big red beard and a HUGE disaster of bright red hair on his head. This dude was like Paul Bunyan, but ultra skinny and without the axe. He also didn’t have a big blue ox, but that should be obvious.

I spoke to him a couple times and told him why I didn’t want to give him money. And every time I spoke to him I’d leave thinking, “Something is wrong with this picture.”

One day I realized what it was. Paul Bunyan was amazingly “there” and present. Every time he and I talked he’d look me square in the eyes, not blinking, not looking away. He was fantastic at communicating, immersive even.

So one day I saw him again and told him straight out, “Dude, I can tell you’re fucking brilliant. What are you doing out here?”

He said, “I don’t want to go back to work.”

He told me a story of being a executive bigwig at his old place of employment, getting fired for no reason and how it destroyed his confidence. He was basically too afraid to go back to work because he never wanted to feel that shitty about himself again. At least on the streets, he knew how shitty he was going to feel from day to day, and no surprises were coming.

I asked, “Do you think ‘I don’t want to work’ is a good enough reason to not work and just keep panhandling? Hell,” I said, “I don’t really want to work either. Do you want to pay me for that?”

Without pause he said, “Nope.”

I said, “That’s why I never give you my money.”

He said, “Cool. Now what?”

I asked him what he wanted to do. He wanted to make t-shirts with his art on them. In fact, he was wearing one and it was awesome. I asked him why he didn’t get some printed up and sell them at street fairs. He laughed and looked away uncomfortably, which I’d never seen him do before. Finally he said, “I don’t know why I didn’t think of that.”

I’d be lying if I said I know what happened to him, or if he started his own t-shirt business. I have no idea, but that’s not the point.

The point is that somewhere beneath the facade, here was another homeless guy who actually had a personality, had interests and was a somebody.

Now what?

I don’t know now what. I’ll carry on doing what I do and you’ll carrying on with what you do. I doubt a blog post is going to change anyone’s mind about such subject matter.

I think the only thing I want to leave you with is the idea of help. Real help. Continue to donate to homeless folk if you wish. I probably will too when I feel the time is right.

But you can also donate time instead. You can donate conversation. You can donate money to a group like Citizen’s Commission on Human Rights (CCHRInt.org). CCHR International’s sole purpose is to clean up the mental health industry which itself wreaks devastation on veterans and the homeless.

Thanks for reading, gang. It’s a touchy subject, I know, and I appreciate your time.

Keep rockin’!

Profit From Your Passions

Create and market infoproducts and courses your fans will happily pay you for!

Powered by ConvertKit

Thank you very much for reading! Follow me:

Want to get in touch? Would love to hear from you!

  1. Oh, the tomes that could be written about Portland-area bums.

    For me, my favorite was The Recorder Guy: This long-bearded fellow used to sit splayed-legged on the ground, and all day would be blowing into his recorder, moving his fingers on the holes totally randomly. I approached him and asked him what he was playing. He, very learnedly, went on to explain to me that he was “Improvising on Improvisation”, and asked if I would like to see his latest composition on such. I agreed, and he went on to blow into the recorder, randomly. Amazing.

    • The Recorder Guy! That is too funny, I remember that fella. I love that you talked to him. And his answer is priceless.

      Thanks for the comment, dude.

  2. I like this post a lot. It really communicates. I feel exactly the same way. I had 2 homeless guys walk up to me at the test center while washing windows and they ask if they could help. Because I have the same viewpoint as you, I of course handed them the squeegees. They did a very bad job but felt good about helping and said so. The next day both of them returned for more of the same, and talked about their new job prospects.

    Keep rocking the internet 🙂


  3. I have seen a bunch of the guys you mentioned in the Portland area. I had always wanted to talk to them. I really appreciate the fact that you did this and got so much from them. What a cool thing to do. Thanks, Chuck.

  4. Dude, I can tell you’re f***ing brilliant. Thanks for being out there!

  5. Love these posts on the homeless situation. Last week I was walking to a bus stop from an appointment and it was pouring rain. This guy was crouched against a wall and boldly asked, “Hey lady, wanna buy me a burger?” looking right at me. He was confident and really kind. We went into the burger joint, he ordered what he wanted and didn’t want to order too much – he got the cheapest thing on the menu and didn’t want fries or a drink (I told him to get a drink and he did). He was humble and unselfish. He asked my name, I told him, and he told me his. He talked the whole time – just wanted the connection I think. We shook hands, and he held mine with both hands, smiling brightly and holding my eyes with his. I left after making the purchase, and regret not sitting down with him. I’m sure he would have had a lot to say. And, no one likes eating alone. I still look for him whenever I’m out. Would love to do this with others in his situation. They all deserve connection and a good meal.

    • Hey, Laura!

      That is the coolest story, and I’ll admit it got me a little misty-eyed. It means a lot to me that there are people out there who would take the time to do what you did. And that you’d stop by to tell us about it.

      Keep up the good work, you 🙂


      – Charlie

Leave a Reply

Your email address will not be published. Required fields are marked *


Friends, Clients & Appearances