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THE SHIRT WAS SLEEVELESS, decorated with a hundred cobalt blue sharks swimming on a sea of black. Habib said it was his favorite. It must’ve been, since he was packing as light as possible for a bike trip across Japan; anything that made the cut and ended up in his saddlebags had to have been there for a reason.

He and another friend named Ashkon arrived in Okayama City after their connection in Tokyo on a humid July evening in 2018. It was the first time I’d seen my two friends in about eight months. We embraced each other, somehow stuffed their bikes into the back of my tiny Mitsubishi, and raced into a seedy ramen restaurant that I decided would make for the best first meal in Japan.

Over noodles steeped in miso and shoyu broth we chatted about the preparations we’d made for our trip. “I’ve been doing 2-3 hill climbs per week and longer 40-60 km rides on the weekends,” I told them.

Ashkon and Habib exchanged shifty glances.

“What about you guys?” I asked.

“We did a 50-k ride once,” Ashkon said.

“And? What about the hill climbs? You know Japan is basically just one mountain after another, right?”

“I biked a couple times a week. It’ll be fine,” Ashkon said.

“Habib?” I said.

“I’ll be fine too,” he said with a broad smile. “Don’t worry about it.”

Relaxing back into my seat, I picked up a gyoza and happily popped it into my mouth. I trusted that my two friends knew what they were in for – an Achilles’ heel of mine.

The shirt was sleeveless, decorated with a hundred cobalt blue sharks swimming on a sea of black. Habib said it was his favorite.

I didn’t need to be worried about Ashkon. He’d been a good long distance runner in the past, so getting in cycling shape wouldn’t take him long. I knew less about Habib, but what I did know was that Ashkon had his doubts, saying that Habib had the kind of luck that ended with his name being misspelled on his high school diploma.

In my mind, though, that wasn’t important. They were thrilled to be in Japan and I was just happy to see them. It didn’t matter how many times I’d urged them to train harder for Japan’s mountains and heat; how much I stressed that they should be prepping the bones in their asses for a daily pounding that would make a dominatrix blush. It didn’t matter that they seemed to think this would be no harder than a stroll around the ol’ cul-de-sac. It didn’t matter. That’s what I told myself that night. Over and over.

My first true hint of what was in store came two days after Ashkon and Habib arrived and one day before we were set to leave for our trip. It was a hot day, like every day that summer. The temperature was pushing 40 degrees Celsius, and if you were in the American south people would probably say that it was as humid as the devil’s asshole. Or something like it. Thankfully, I spent that day in an air-conditioned room running the final exam for a college English class I’d been teaching, so I wasn’t choking down much of that asshole-air. My friends were supposed to have been doing the same back at my apartment. Resting up. Packing. Getting their bikes ready.

When I was finished with the exams I raced home to do the same, and when I got there I was greeted by Habib, beat-red and slouched against the wall of my living room. He wore his favorite shark-print shirt, but didn’t seem to be in a great mood.

Next to him, Ashkon explained between fits of laughter how our friend had gotten lost for more than an hour on his way back to the apartment in the middle of the noonday sun. He’d also managed to crash his bike into an old lady on a moped. After all of that, poor Habib looked like he’d been deep fried and beaten with a pillowcase full of soap bars. Just in time for a bike ride across most of Okayama prefecture the next morning.

We did our best to move onward from there, eating a hearty, home-cooked meal and gathering around the TV to play Tetris – Ashkon, myself, and my girlfriend, Saki, that is. Habib didn’t seem to have the energy for stacking digital blocks, so he mostly sat in a corner and tried not to pass out.

They were thrilled to be in Japan and I was just happy to see them. It didn’t matter how many times I’d urged them to train harder for Japan’s mountains and heat

At one point, he piped up and asked, “What does tomorrow’s route look like?”

“Well,” I started, trying to think of the gentlest way to explain it to a man that didn’t even want to look at a bicycle, let alone ride one. Somehow, I decided that the best way to finish that sentence was, “Our day starts with a three to four hundred meter climb up a mountain.”

“That’s… vertical distance,” I added to his puzzled look. “After that it’s pretty smooth sailing as we move south across Okayama prefecture. I’m shooting for eighty or ninety kilometers by the end of the day.”

Habib had been listening intently at the start, but when I mentioned biking up a mountain his head lolled back against the wall. He took in the rest of my explanation while gazing up at the ceiling with a thousand-yard stare. Maybe he was trying to reach God to ask for a miracle that wipes out all mountains across Japan. Or he might’ve just been asking for a disaster that made any departure at all impossible. I don’t know. And I wasn’t thinking too hard about it at that point, either. I was still just happy to see my friends.

I was also pretty distracted. The next morning I would start a great adventure, one that I’d been playing out in my head for years.

The morning of our departure was cloudless, as was typical for the summer that broke records for heat. Habib wasn’t happy about that. In fact, he looked downright glum, so I decided to pivot.

I’d wanted to start our course with the mountain behind my apartment because it would’ve been a symbolic beginning to a long journey for me. It was the road I’d trained on every week for the last year, after all. But the look in Habib’s eyes told me it wasn’t a good idea, so we settled on the flattest path possible.

Saki took a rare morning off from work that day, insisting that it would be rude not to see us safely out the front door. She made a hearty breakfast of eggs, sausage and toast, and after a group picture, the bright-eyed Canadian boys were waving good-bye.

20 minutes later that adventure came to a halt.

I’d been enjoying the ride along the two-lane road for a while when I decided I should check on my friends. Pulling over, I looked back. Ashkon could be seen just past a patch of bamboo trees in the distance, thirty seconds off my pace. Habib, however, was nowhere in sight, even by the time Ashkon caught up.

“Any idea where Habib is?” I asked.

“I haven’t been looking back,” he told me.

I should’ve been worried, but the fact was that I was more confused than anything; Habib looked as fit as Ashkon or I. He had classic boulder shoulders and a low body fat percentage. He had a tight booty and thigh muscles that looked like hempen rope. On top of all of that, I’d set a pace that a malnourished child could probably match.

Finally, the solution to the mystery came rounding a corner hunched over the handlebars like a brooding gorilla, knees pointing out at odd angles and legs spinning furiously on what had to have been the bike’s easiest climbing gear. Around his forehead he’d tied his favorite shirt to keep the sweat from pouring into his eyes.

Seeing form like that should tell you volumes, but I didn’t really consider it at the time. I was full of patience, kindness, and enthusiasm for this trip. I was also just glad to see my friend in one piece rather than being carried away in an ambulance from another elderly-related moped accident.

When he caught up, we practiced shifting gears in the parking lot of a convenience store. I felt like a proud papa putting his son on two wheels for the first time as the two of us went back and forth in that parking lot. I explained the importance of Rotations Per Minute and that he was doing the equivalent of pushing a Ferrari to 100 km/hour in first gear. When it seemed like the lesson was sinking in, we gave it another try.

I slowed the pace from there. Our convoy sputtered along with the gently flowing Takahashi River tempting us to jump in and escape the heat on the right and lush mountain slopes broken up by occasional rice fields completing the picture on the left. By lunch we were at the first checkpoint, a town called Soja.

We recharged with udon noodles, and for dessert Ashkon stopped at a supermarket, buying a pack of grape sorbet ice balls. He’d hardly made it to his bike in the parking lot by the time they melted into a bag of purple soup. It was 40 degrees Celsius at that point, and we weren’t spending much time in the shade.

So we pushed on past Okayama City and into the countryside beyond, and by the end of the day we’d somehow cobbled together 80 km. To say that Habib didn’t look great at the end of that road would be an understatement. He looked like patient zero in a viral outbreak. And while I wanted to chalk that up to normal fatigue, the truth was that we all knew it was something worse. Still, I had this pointless, stupid, defective feeling that he would improve from there. That he would achieve tour shape.

For that improvement to take place, I first needed to find somewhere for us to pitch our tents. So with the sun going down we bought bento dinners and went in search of something we could call a campground. For me, this was the most anxiety-inducing part of the day. Of almost any day on tour.

Before I started planning the Japan trip I read the stories of others who’d blazed the trail before me. The bulk of them speak of pitching tents seemingly anywhere, but no matter how much I read, no matter how many times I successfully do it myself, each new location haunts me with thoughts of being woken up in the middle of the night by police officers accusing me of squatting. Probably because that’s exactly what it is.

Add the pressure of caring for two new arrivals to the country – one of whom may have been hallucinating – and it makes for nervous times, whether they’re warranted or not.

Google maps showed me a likely spot not too far down the road from where we bought our dinners, so I pulled the trigger. Ashkon and Habib followed me off the main road and into a wide open public park. Inside was a gravel field surrounded by a paved path.

“Should we look at a hostel somewhere?” Ashkon asked. “I’d rather do that now than in the middle of the night if someone boots us out.”

“Don’t know how much luck we’ll have out here. We’re kind of in the sticks,” I reminded him.

That night, there was a single elderly man out for exercise under the darkening sky, so I nervously approached him as he walked along the path. He completely ignored me as I called out from the nearby benches.

“Crusty old man,” I muttered.

So I went the slightly passive-aggressive route and pretended to start setting up my tent the next time he came around. I tried another greeting and was, once again, ignored.

“I’m a little worried about this guy,” I told Ashkon. “He’s totally ignoring me. The asshole probably just doesn’t want to talk to foreigners.”

“Are you sure you don’t want to go somewhere else?” Ashkon said.

“Let me give it one more try,” I said.

This time I stood in his way on the path and waved at him until he had no choice but to interact. When he did, I realized what the problem was.

Pulling out a pair of headphones from his ears, the old man greeted me happily. “Konbanwa.”

With a huge sigh of relief, I asked him what he thought about us camping in the park for the night.

Before I started planning the Japan trip I read the stories of others who’d blazed the trail before me. The bulk of them speak of pitching tents seemingly anywhere

“Probably fine,” he shrugged. “But what about your friend? Will he be alright?”

He pointed to Habib who was laying down on a bench with his favorite shirt and my cooling towel draped over his face.

“I think he might have a bit of heat exhaustion,” I said.

The man looked puzzled, as though I’d just pointed to an unconscious person face-down in a lake and said they might be drowning ‘a little bit’.

“A lot of people have had to go to the hospital for heat stroke this year,” he said. “Take care of yourselves.”

The man left the park and we started eating our dinners. I munched away at some mackerel and rice, Ashkon ate fried chicken, and Habib did his best to take sips of water from his camelback. A few minutes later we could see a pair of figures approaching from the distance with flashlights. My stomach dropped.

“I knew it,” I said. “I knew the guy was a racist old shit.”

“What?” Ashkon said.

“The dude obviously called the cops on us.”

“Really? They would do that?”

The truth was, I didn’t know. I was just expecting the worst. But as the two silhouettes came into view I recognized one of them as the man from before. This time he’d brought his wife.

I thought I was going to have to strap Habib to the back of my bike, ditch my grilled fish, and make a run for it, so to say I was relieved would be an understatement. Instead of having a gang of neighborhood watch members with torches and pitchforks run us out of town, a pair of friendly strangers presented us with cups of jelly and slices of fresh fruit. But the best thing of all? The man’s wife not only gave express permission to camp in the park, but she also gave advice on which patch of ground would make the best spot to sleep on.

After chatting a little about where we were from and a lot about the pile of steaming human flesh hardly able to sit up on the bench to greet them, the pair went home to fetch more goodies for us. This time we got ice cream and ice packs for first-aid.

The whole thing felt surreal. If it hadn’t been for Habib’s condition I would’ve said it was too good to be true. The locals had not only opened their arms wide, they were also nursing us back to health. Suddenly I was brimming with optimism. If Habib couldn’t get better with that kind of help, there was no saving him.

We took the advice of the old lady, pitching our tents on the other side of the field on the only patch of grass in the park. There was some conversation about what we would do with Habib if he didn’t improve, but at that point we were mostly just hoping a good sleep would set him straight. After a quick shower at a nearby water fountain, we crept into our tents for the night.

The next morning we were woken at about 6:30 by the sounds of people exercising in the park. After hearing a soothing voice broadcast over loudspeakers I knew right away what was going on: God damn Radio Taiso.

With school out for summer, many kids in Japanese neighborhoods sign up to join daily stretches in the mornings. Or rather, saying they’re forced to sign up is probably closer to the mark. It’s called Radio Taiso because there’s a recording that they follow along with.

Ashkon, Habib, and I stumbled out of our tents as they were finishing up. The adult leading the stretches sent the kids off to run laps around the track and they all greeted us with an “Ohayo gozaimasu” as they flew past. Far too cheerful for that time of day, but cute.

I turned to Habib, who didn’t look much better despite snoring through most of the night. “How are you feeling?”

“Not great,” he said. “Still a bit nauseous and low on energy.”

“We need to think about putting you on a train,” I said. “It doesn’t sound like the situation is improving.”

“Let’s just go,” he said. “I’ll be fine.”

As we were rolling up our tents an elementary school-aged girl walked over with a bag of tomatoes. She pointed to a woman standing next to a car at the entrance and told us that they were from her mother. We spoke in simple English for about a minute before she skipped off, happy about the interaction. I didn’t have the heart to tell her that I hate tomatoes.

Not long after, the same old lady from the night before came into view for the third and final time, carrying yet another, better bag. This time there was a bottle of cold tea, a few pickled plums, rice balls still warm from the rice cooker, and cheese. She said good luck and goodbye, leaving us to enjoy the fresh food before we hit the road.

I was fully charged after all of the good will, and while the ride that morning was slightly more difficult than the one from the day before I decided to take Habib at his word that he would be fine. Of course, that was as much of a mistake as taking his word that he knew how to ride a bike in the first place.

45 minutes in I realized that I’d left both friends far behind. Well, maybe that’s not completely true. I knew I was leaving them behind, but didn’t want to stop.

The spot I eventually pulled over at was 20 kilometers from our camp, a rocky patch among the trees. Ashkon took two or three minutes to catch up, and Habib was once again nowhere to be seen.

So we waited. And waited. And finally, after more than ten minutes, we saw him crawling up the modest hill, hardly going faster than walking pace, shark-print shirt tied around his head and flapping in the wind.

When he caught up to us he stepped off the pedals of his bike, straddling the frame and leaning over his handlebars.

With school out for summer, many kids in Japanese neighborhoods sign up to join daily stretches in the mornings. Or rather, saying they’re forced to sign up is probably closer to the mark.

I gave him a minute to catch his breath before hesitantly asking, “How are you doing Habib?”

He looked up and made a throat slashing gesture that I took to mean that he’d murdered a local and was now on the run from the authorities. What he was probably actually trying to say was that his voice was gone. Moments later, he made a much clearer gesture, explaining that he’d reversed his morning rice balls and cheese on the side of the road a while back.

“We might have to take you to a doctor,” I said.

Habib shot up at that. His voice miraculously started working again, though it was hoarse and sounded a little like a gravely injured Jack Bauer during the climax to a season of ‘24’. With a smolder to his eyes he said, “No doctors.”

Maybe he really is on the run, I thought. “Okay, okay, but I can’t let you keep going. We’ll put you on a train for Kyoto. Hopefully our hotel is vacant tonight and you can just slide in for an extra day.”

He nodded, finally admitting defeat, and went back to leaning over his handlebars. To this day I don’t know why Habib was so against medical attention. I can only guess at what he was fleeing from.

“Do you think you can make it 15 km?” I asked. “That’s the nearest bullet train station.”

“Got no choice,” said Habib, dramatic as ever.

So we got back on our bikes and made for Aioi station, Hyogo prefecture. I had Habib ride between Ashkon and I this time so that we could keep an eye on him, and while the going was snail-paced we caught a break when the road came to a crest.

Wanting to enjoy the downhill, I overtook Habib and flew alongside Ashkon. It wasn’t the steepest of hills, but it was glorious. The two of us rode, not a care in the world, enjoying the simple pleasure of wind rushing through our hair and over our sweat-soaked skin. It was about two kilometers of heavenly reprieve, and at the bottom was a convenience store that we chose to stop at.

Lugging a bike with saddle bags for eight hours a day isn’t for everyone, particularly not during the peak of the hottest Japanese summer on record. It takes preparation and it can be challenging.

We smiled and even broke into a little fit of giddy laughter at the trip’s first stretch of exciting road. There may have even been a pat on the back or two as we parked our bikes. It was then that we saw Habib pulling in, and something was different about him. I couldn’t quite put my finger on it.

“Where’s your shirt?” Ashkon said, referring to Habib’s favorite cobalt blue on black tank top that had been tied around his head.

“It flew off as I was riding downhill,” he murmured.

There was a moment of silence as we let that sink in.

“Do you want me to ride back and get it? It’s no trouble,” I said, putting my arm on my friend’s shoulder.

“No,” he said, shaking his head. “It’s gone. It’s gone.”

If I said that I laughed, would it make me a terrible person? It seemed like the only thing left to do. First the road had taken my friend’s health. Then it took his spirit. Now it was taking his prized shark-patterned shirt.

Looking back, I wish I would’ve insisted on fetching it, but the truth is that it probably wouldn’t have made a difference. No amount of intervention by friends or strangers in parks could change the terrible run of luck Habib was on. His shirt would’ve found its way back on the road in no time. Probably would’ve torn itself to shreds to avoid more of Habib’s misfortune.

So we got him safely to Aioi station, packed his ride up in a bike bag, and walked him to the gates where an attendant assured us he would help Habib find his way to the proper platform.

At the end of the next day we would reunite in Kyoto and hear all about how he’d spent his time in the hotel room hugging either a pillow or a toilet bowl. He made the decision to end his trip there, going on to Tokyo by train rather than bike after spending a few last days with us. Unfortunately, the bad luck wasn’t done with him. It followed in the form of food poisoning, and by the time he was boarding the flight home he’d lost more than 15 pounds on an already lean frame.

There are a couple of lessons to be learned from my first of what would be many days on that tour. Number one is that bike touring means leaning on people. Whether it’s loved ones taking the morning of our first day off to give us an amazing farewell meal, compassionate strangers feeding us and doing their best to keep us cool, or even those paid to do the job like everyone who helped Habib from Aioi station to his hotel in Kyoto. They all tried to improve our journey, and they helped make the story.

The second lesson is that sometimes none of that matters. Lugging a bike with saddle bags for eight hours a day isn’t for everyone, particularly not during the peak of the hottest Japanese summer on record. It takes preparation and it can be challenging. No amount of money spent can do the work for you. Not even if it goes toward a $1,500 touring bike, as in Habib’s case. Not to mention more on saddle bags, bike shorts, and other little necessities. Then there were the flights and hotels…

No. There’s no getting around it. You have to prepare yourself and be ready to do the work.