Chet Childress has no home. He’s not homeless, he’s just a man of the world – constantly learning, constantly traveling, constantly moving. Different cities are his drug, his sponsors are his dealers. And at 40 years old, after two decades of traipising around Europe and professional skateboarding, he shows no signs of slowing down. Fresh off of the Cliche “Gypsy Life” tour we wrangled a few minutes with the North Carolina native and asked him about the vagabond life, hangover cures, and jerking off with a crooked arm.

When you go around do people ever think you are a hobo?

Probably. If they do, they don’t say anything to me. It’s kinda rad, it’s a defense system to keep assholes away from me. Its always rad when you see that one dude from your old school that you don’t wanna see and they don’t recognize you. You are psyched. Like yes, I didn’t have to have that fucking conversation with this asshole. “So, do you still skateboard man?!”… Suck a dick.

I heard you have a slightly crooked arm. Is there anything weird or cool you can do with it?

Uhm… Nah. I can’t lift heavy furniture, that’s what I can’t do.

Does this affect you jerking off?

[laughs] No, not at all. I know you are Jenkem, but… no, it doesn’t. It works great.

Where are you right now?

Wilmington, North Carolina. I’m just kinda visiting… In June I went to Europe for the Cliche Gypsy Tour then I stayed an extra month taking trains all around Europe and skating. I’ve just been couch surfing and staying with people. I haven’t paid rent for the last couple of months. I’ve just been flying out of here, I’m in for a week, out for a week, out for a month, in for a month.

You seem to lead quite a nomadic lifestyle. How long do you stay in one place until you start itching to travel?

It just depends what’s going on. The sleeping situation, people you are skating with, the city, the biking… I don’t know dude, it’s a disease. After a week anywhere I start losing it again. It’s something I have to work on because it’s kinda turned into a problem. I like change, and traveling is the thing that keeps everything exciting for me. I never thought at 40 I would still want this much change. I know I’ll have to settle down one day, but, right now, I could just keep going. A couple weeks here, couple there, that’s the way it is I guess.

At some point your gonna have to have a sit down with yourself and face it right?

Oh yeah, it’s gonna suck. I mean, I’m already preparing for that. But that’s why I think I’m staying so busy right now and staying on the road. I’m hoping to find that comfort zone… where I can live somewhere, find a job, figure out where I fit in in this fucking world.

Any items or things you bring on every single trip?

Socks, some drawing pens… Same shit as everyone else. I’m learning everyday how to bring less, not bringing “the asshole bag.” Bring just what you need because half the time you go on a trip and you think you need all this shit, but then you wear the same clothes every single day. With age I’m not trying to look fresh or hip. I never really did, but I think with age, you just remember all those dumb trips where you brought that extra pair of pants, or those 3 t-shirts, or that one longsleeve you never really needed and had to lug all that stuff around.

What’s the worst thing about constantly traveling?

Nothing.

Do you have any type of retirement plan? Is your art something to fall back on?

Nah, I mean art isn’t anything to fall back on. I have an apartment and some old man money sitting in some bank account somewhere, but I don’t have a retirement, art isn’t going to take care of my retirement. Plus, I don’t want art to be part of that shit. I’ve been a pro skater almost 15, 20 years, it’s just something I like to do, and luckily because of skateboarding I can put it out there a bit. If you think you can pull that bullshit off, you are brave. There are only a couple of dudes that can succeed in that world, and I definitely can’t. I like drawing pictures, but I’m just burnt on that right now. I know I can’t do it for a profession because I cannot produce what people want me to produce. I can only produce what comes out of my dumb head. But that’s really it. I’m not trying to go down that art dude road. I don’t even like that title, “art.”

What do you spend your money on?

Living… I don’t make a lot of money, so I just put money on gas, camping, eating good food. I’m lucky I own an apartment in Portland, but I’ve never been that pro that has made a lot of money. I made decent money for the way I skate, but I’m not rich… I never expected to make it this far, so anything skateboarding has handed me, I’m just stoked. I’m 40 years old, I haven’t had a job since I was like 21. I will tell you that Nike skateboarding did save my ass in a lot of ways. They have been so good to me. If I wouldn’t have started riding for Nike 10 years ago, my life would be completely different. They still continue to have my back.

”I’m 40 years old, I haven’t had a job since I was like 21.”

What are some of the most valuable things you own?

My damn Volvo that just blew up. I will have to bury it in the ground. That, my bicycle, and my skateboard.

How many miles did you put on your car? What about bike?

I probably do 100 miles a week on the bike. My Volvo just blew up at 230,000 miles though dude. I bought it with 14,000 miles, that car has been across the United States 20 or 30 times. It would have been to Europe if that motherfucker would have floated. Now I gotta deal with these asshole car dealers, which are like the shittiest people on the planet. It sucks, it has been such a heartbreak hotel over the last two weeks. I was on the plane and I heard that my car blew up and I almost shed a tear. That car has been with me so long. I’ve had it since 2001, and it’s 2014 or ’15… It did me right.

Do you think that you are crazy?

I don’t know… No, I don’t think I’m crazy, I just think we’re all different. I feel insane at times, I feel lost, but that’s what keeps you moving. That’s all it is. It’s like how can I get through this ADD day, what can I do to make myself sleep well at night. Everyday it’s like that for me. I need to ride a bike. I need a hike. I need to skateboard. I’m not a sit on the couch dude, ever. I don’t know how to nap. You always sleep so good when it’s like, “I biked 15 miles or hiked 10 miles or skated”… Anything to get through the day, to feel that, yes, I’m alive.

You don’t have days where you sit in front of the TV and smoke weed?

Aw nah, that never happens. I get jealous of people who can do that, take naps and sit on the couch all day. That’s not the cup of tea I want. It’s boring, it doesn’t do it for me. If I’m inside I just get anxious and walk in circles.

I quit the stoner thing a while ago. I drink wine and beer and that definitively helps, but I’m trying to chill out on boozing. I love going to bars with my friends when I’m on the road, but I’m over wasting my time when I’m home at a bar. It’s way better to just get up early, 6 or 7 am, and by like 12 you’ve done so much stuff already in your day, your day is pretty cool..

I made so many mistakes when I was younger, like I’d go to Europe and sit there and wait for people to get up and get moving by the afternoon. All I cared about was just filming my dumb trick or getting my photo and I didn’t take advantage of where I got to go travel, how much I could see. It was just get a trick, film a clip. Now I Just take advantage of as much of it as I can. I get up in the morning and walk around the city, explore until other people are ready and awake instead of sitting inside the hotel.

What’s the best thing about camping?

It’s rad to always be on the move. Camping out, you have a different perspective and you get to enjoy way more. The bonding with your friends: you gotta find a place to sleep, you gotta set up camp, you gotta cook food together, it’s rad. When you are camping no one can get too comfortable, so in the morning everyone has to get up and get back on the road, instead of a hotel where people get a little comfortable and start taking a long time to get going. Out in the woods there’s not too many places to go, so you’re kinda forced to rest and drink by the fire instead of going out and chasing chicks and shit. That happens too though of course. Your hangover is 10 times less when you sleep under the stars too. Try it. Do the test. If you are under the stars, it’s a hangover cure, I swear to god. I think it’s just like so much oxygen and shit…

”I got a hangover cure for everyone, don’t fucking sit at home and whine”

You got any other secret hangover cures?

No… Wake up, drink another beer. Actually, I got a hangover cure for everyone, don’t fucking sit at home and whine. I don’t care what condition you’re in, get outside and get after it. Wake up, clean your house or do anything so you don’t sit there and be a little bitch about your hangover. I watch a lot of people just suck at hangovers. Number one cure for a hangover is get up and do shit. It’s way less rough on you. It could be just going up and going on a walk, even if you can barely walk. As rough as it is, you will be stoked in the long run.

You seem to have found your own voice in your skating and in your art… How does someone find that, or does it just come with age?

I think it just comes with age. Age and time. Who you hang out with, what you do, the things that make you tick. You find what’s right for you. It’s pretty rad when you a see a 20 year old already find themselves because if they find out by 20, by 40 or 50, they are fucking doing it. I kinda just found this shit like 10 years ago, you know? I was lucky enough to go on so many rad skate trips with so many different individuals. It was crazy. My first tour, when I was 16, it was Wade Speyer , Karma Tsocheff and Cardiel . I got to go on all these unreal missions, I’m fucking lucky, dude.

”I wanna do more, but if it did happen – if I died trying to get somewhere, I won.”

You ever thought you were gonna die on any of these trips?

Nah, not yet. A couple of flights I thought it was on, and I was just like, “alright, here we go!” Heavy turbulence, the plane kept dropping in feet. There was an Indian woman in front of me screaming and praying out loud. It was like, “oh shit, here it is.”

But then I was like, “I lived a good life, I’d rather die on this plane then die doing something dumb. If the plane went down right now, I could deal with it.” I wanna do more, but if it did happen, if I died trying to get somewhere, I won. You know what I mean? People are scared to get on planes or travel, fuck that. I’d rather die trying to get somewhere to see something radical than sitting around gathering dust.