Every Time I Open an Envelope, My World Gets Smaller (Chicago)

追加: 2026-06-04

[00:00:00]I'll admit it, my life's being controlled by a briefcase.

[00:00:03]This was my idea because right now my world is shrinking around me. And by the end of the day, I'll be stuck in a room the size of a shoe box. A few weeks ago, this briefcase made my world shrink in New York City. And after surviving that, I genuinely thought I was free. You got to be kidding me. But the briefcase has [music] mysterious plans.

[00:00:22]>> Chicago.

[00:00:23]>> So, I said goodbye to my sweetheart and got on a plane to answer one question: How small can your space get before you lose it? And I'm already here.

[00:00:33]Apparently, the briefcase doesn't travel, it just brings the rules. Every hour my world gets smaller, and every time the world shrinks, I have to open one of these, which for some reason always contains a new problem. Based on what happened in the last challenge, I don't really trust these things anymore.

[00:00:47]But now it's time to open envelope one.

[00:00:51]Become a Chicago local. I've been in Chicago for T-minus 6 minutes, and I've never even been here. This is already crazy. If I'm going to become a Chicago local, I probably need to dress like one. So, step one, look the part.

[00:01:08]You know, I don't think this is it.

[00:01:10]Clearly, I don't know what I'm doing.

[00:01:12]Time for local merch. This is perfect.

[00:01:15]I've reached maximum Chicago dad mode.

[00:01:17]At this [music] point, Jordan is gone.

[00:01:19]Welcome, Chicago Jordan. But the safe zone is moving, and Chicago Jordan needs some local guidance. For step two, learn the lingo. So, what are some slang terms in Chicago?

[00:01:30]>> So, one that comes right off the top of my mind is probably like merchet, which means like swear to god, like put it on something like >> Merchet?

[00:01:38]>> say merch.

[00:01:39]>> Merch?

[00:01:40]>> If you say merch, that's like saying swear to god.

[00:01:42]>> Never heard of that. Merchet. What a wonderful phrase. Like Hakuna Matata.

[00:01:46]Lingo learned. Step three, integration.

[00:01:52]Ow.

[00:01:53]Is that cool? If I'm going to become a Chicagoan Wait, is that what they're called?

[00:01:59]Yes, but I got to find out what Chicagoans actually do. So, what's one thing we must do in Chicago?

[00:02:05]>> I would say go to a Blackhawks game.

[00:02:07]>> Have you seen the Bean yet?

[00:02:08]>> No, I haven't.

[00:02:09]>> iconic. The Bean?

[00:02:11]>> The Bean?

[00:02:12]>> [laughter] >> So many people said go to the Chicago Bean. I don't have time for a Blackhawks game, and I looked up where the Chicago Bean is. It's a little too far. The timer has run out. My world has shrunk down a size, and now I think it's time to open the hour two envelope. And this one reads, "Earn money. You'll need it later." Winky face. Earn money? I've been a local for exactly 1 hour. Chicago Jordan doesn't have a resume. I don't even have a job. But if I'm going to survive the night, I need to earn some money, and I need it in 60 minutes.

[00:02:43]The envelope never said how much money I needed. I'll shoot for 20 bucks. I'm an entrepreneur. Go Grocer. Looking for employees today? Hey, you guys mind if I work here for like 5 minutes? Just to like mop or clean your windows or anything like that?

[00:02:58]>> Yeah, that's fine.

[00:02:59]>> Yeah?

[00:03:00]Yeah, put me to work. Sweet. Well, there you have it. Chicago Jordan is employed.

[00:03:19]Job [music] well done. I think squeaky clean floors in here. Thank you.

[00:03:25]So, I got a job at Go Grocer and made a whole $10.

[00:03:29]They really put me to work in there.

[00:03:31]That was so nice of them. Let's keep going. You guys, it's really hot out here. I really hope tonight there's a way for me to shower. Waffles!

[00:03:39]How about that? Unfortunately, I was walking in right as they were closing, so I asked if I could help them close down shop.

[00:03:46]Like, can I work here for today?

[00:03:48]>> Oh, you want to work here?

[00:03:49]>> Yeah.

[00:03:49]>> There it is. There's a table for you.

[00:03:51]>> We're hired again.

[00:03:53]>> [music] [music] >> I charge 50 bucks an hour by the way, guys. No.

[00:04:06]>> [music] >> Job well done. Great. Thanks.

[00:04:13]>> See you.

[00:04:14]>> All right, thank you, Felix. Guys, Chicago Jordan buckled up and made a whole $20 today. I just got hired by two places and it took up a basically all of my time. So, I have to open envelope three now. We're at the park. Beautiful day in Chicago, but I just spent money for lemonade at this kid's lemonade stand over there, [music] which was thirst-acquenching, by the way. But, that was $5. Chicago Jordan already burning through hard-earned money, but the zone has shrunk down. Now, I have to open envelope number three. Envelope three reads, "Make a friend." That's nice. A true local never stands alone, you know. And that's on merch. I don't know if I'm using that right. Will you be my friend? I'm going to name you Jake. This is so awkward. I feel so awkward doing this. To be honest, I don't really know where to start. The search begins for friendship. So, I went out looking for friends, which I assumed would be much easier than making money. I was so wrong. I don't want to have to ask somebody to be my friend. Should come on naturally, and nobody seems to want to stick around.

[00:05:18]Oh, is that what you do? Photographer?

[00:05:20]Very cool. Okay, they just kind of walked away from me. Guys, so this can't stand. I have not been able to make a friend yet. Maybe it's cuz I'm by the legs. I don't know. I hope I don't fail this one. I'm on my last leg. All right, that's it. I spent so much time walking around looking for friends. At this point, Jake was looking like my only friend today. Jake's a beast. After searching the city for a friend, I returned back to my perch. But now, Chicago Jordan is forced to move on. The world has shrunk down and soon I won't be able to leave a room the size of a microwave. Hour four, show me mercy.

[00:05:53]Okay, there's two things in here. Travel to 130 East Randolph Street with no phone. Brother, I don't even know where north is. However, it did come with a map. The map of length. Regular Jordan would panic in a situation like this, but Chicago Jordan also panics. Because first of all, I need to find it and absolutely lock in and summon my inner Pocahontas. Okay, I found it. It's right here.

[00:06:21]On the map. Now, I have to put my phone away in the bag of trash and scraps and clothes at the bottom. But now I got to find it without getting lost. No Google Maps, I can navigate flawlessly. Oh, no.

[00:06:34]I'm on the wrong side. But at least I know where it is now. Let's go.

[00:06:39]Hey.

[00:06:40]Yeah. [laughter] Yeah.

[00:06:42]Hey, take care. That guy right there would have solved all my hour four problems. Friendship with silence. Okay, guys, hallelujah. I think I'm here. This is it. I think I'm in the right spot.

[00:06:52]But the envelope doesn't tell me what to do here. It just says come here. Without a phone, this was not easy. Envelope number four through Chicago Jordan through the ringer. I need to figure out what to do here. So unfortunately, my world is collapsing again. Let's open envelope number five. Use money you earned. Deep dish time. I don't understand. I don't see any deep dish pizza here. Maybe I'm in the wrong place. Use money I earned. I also only have 15 bucks. Now, I don't know how much a deep dish is, but I also don't know where to find one. Uh Let me So, I walked over to the corner hoping I'd finally figure out where I was supposed to go. And at first, I saw absolutely nothing. Until I noticed something peeking through the trees. You guessed it. It was Giordano's.

[00:07:39]I could feel us thinking that together.

[00:07:41]At this point I was starving and Giordano's felt perfect [music] until I saw the prices. Okay guys, immediately this is a little too pricey I think. But then by some miracle I found a deep dish I could actually afford. All my money earned on the table. I just ordered a Sierra Mist. I might be over budget because of Sierra Mist.

[00:08:01]It's already been such a long day and these envelopes are kicking me down.

[00:08:05]After I ordered my pizza I struck up a conversation with the guy sitting next to me. His name's Armando. I told him I was here solo and he wanted to send a quick message back home.

[00:08:14]>> Hey Melania, my name's Armando. Uh I want to say hi.

[00:08:18]Welcome to Chicago.

[00:08:20]This time you can make you can make it but for sure next time you have to.

[00:08:26]>> That's so nice of you. Thank you. That's the best part about this city. No matter how chaotic the challenge got [music] the people here always made me feel right at home. He absolutely loves it here. That's super cool cuz everybody in Chicago has been so nice. You know, I'm a guest here but I'm Chicago Jordan today. Look at this pizza. It's [music] like a bowl. Armando, how do they normally eat Chicago deep dish? Do you go fork? [music] >> No.

[00:08:52]>> No fork. You got to go with the hands here.

[00:08:56]Uh I'm hyped. I'm so hungry. I haven't eaten all day. You know, I had a goal this year to run 10 miles. This might just be setting me back a little bit.

[00:09:04]But totally worth it. The clock's a ticking. I got to open the next envelope. So I deleted my pizza and it was time to pay the bill. Turns out Sierra Mist had consequences. I had to borrow a few dollars from regular Jordan. I said goodbye to Armando and headed back into Chicago. The pizza is happily in my stomach now but my world is shrinking and I need to open envelope number six. And the good part is I'm right near the pod. Okay guys, the last envelope.

[00:09:31]Buy pajamas. Time is running out. These envelopes are getting way too comfortable making decisions for me, but this is terrible. I am a right next to the pod and now I have to go look for pajamas. You know, a few hours ago I was trying to make money, but now I'm speed running bedtime.

[00:09:49]All right, let's go find it. Luckily, I found a Target right around the corner, but the only problem was I had to get there without crossing into the danger [music] zone. And when I arrived, I found the perfect pajamas and there was only one thing left to do. Head into the [music] pod hotel and face my destiny.

[00:10:04]And actually, it was kind of adorable.

[00:10:06]Like someone built a tiny neighborhood indoors. And at the end of it was my pod and it is tiny. I think I'm just going to lay down here for a minute, but this place is super cozy. Those envelopes straight up bluffed me. But I think I'm going to shower cuz I just realized something terrible. I can no longer leave. I wanted to go take a shower. Oh, no.

[00:10:28]But I guess it's a pajama party.

[00:10:33]I don't know what that was. Guys, I'm dressed like somebody's uncle in a continental breakfast at the hotel.

[00:10:38]>> [laughter] >> You know what?

[00:10:40]Chicago Jordan. But now I think it's time for a room tour. We have a mirror for light, a little pocket for things, USB charging port that's pretty dusty, an outlet with some gunk on it. I got my own little window, a vent [music] blowing cool air, random switches, the bed, all while being protected by four AA batteries. There you have it. Not much else in here cuz it's so small, but why do I keep doing this to myself?

[00:11:04]Chicago Jordan shirt deserves a nice resting place. And unfortunately, the shoes that I was walking around in all day left some blisters on my heels. It's funny how these things work, huh?

[00:11:15]Challenges that you sentence yourself to. But it's time for me to cozy on up.

[00:11:20]These envelopes really didn't hold back this time. This was much harder than New York, but good night Chicago Jordan. I'm going to press that button and it will be morning.

[00:11:35]>> Good morning, sleepy heads. I actually slept pretty good, but I have an early flight to catch today, which means I'm free. I'm allowed to go back out into the world. I really want to take a shower.

[00:11:47]So, I guess it's time to get up, lazy bones. I'm free. So, I brushed my teeth, packed my things, and officially escaped the world's [music] tiniest neighborhood. It was hard to believe that just yesterday morning, I got dropped into a city I've never been to before. But somewhere between getting lost, working my first Chicago job, and making a friend, I stopped feeling like I was visiting Chicago and started feeling like Chicago Jordan. He had confidence for absolutely no reason. You know, Chicago Jordan had a good run, but I should probably give regular Jordan his life back.

[00:12:22]Most of it, anyway. I made it to The Bean, by the way.

[00:12:26]Watch another video.

[00:12:28]Have a great day.