The article (paywalled) asks whether Instagram is encouraging people to take reckless trips. And they use me as a case study. I rode my bike into Iran on June 1, 2025. Two weeks later, Israel started bombing ’em.

Perfect.

I learned the article was up because my old tech bro bud from San Francisco sent me a screenshot. I asked what he thought. Kind of hoping he would convince me this wasn’t a disaster.

“I hated it lol. They just spun it in the most negative simplistic way … It just felt like there was a much more interesting and nuanced story to be told.”

And he got me thinking.

The New York Times and Instagram are in the same business. So am I. We’re all fighting over attention.

The Times gets subscriptions from it. Instagram sells ads against it. I make a lil money on Substack because of it. Different platforms, same economy.

But Instagram has become something much bigger than a media company.

It’s a church.

I spent four hours and 51 minutes on Instagram yesterday. Almost a full workday. If you had told me ten years ago that the thing shaping my life the hardest would be a recommendation system built in the Bay Area, I would’ve called you a nutter.

But it financed a bike ride across Asia. It introduced me to millions of people. It taught me how to tell stories. It changed how I see the world.

And I think it has become one of the most powerful moral authorities on Earth.

Most people think Instagram is where you put pictures and videos. But I think it’s actually church. Because churches answer the question: What deserves your attention?

For thousands of years, different groups answered that question. Parents. Churches. Neighbors. Teachers. Local papers. Communities. They taught you what was to be admired, what was shameful, what success looked like, who deserved respect, what kind of life was worth living.

I learned firsthand, almost every Sunday from birth until the age of 16.

Today, billions of people wake up, reach for a rectangle on their nightstand, and ask a recommendation system the same question:

What’s important today?

Instagram doesn’t tell you what to think. It tells you what to pay attention to. Maybe that sounds like a small difference. I don’t think it is.

You can’t admire what you don’t notice. You can’t fear what you don’t see. You can’t aim for a life you’ve never imagined.

Before values comes attention. And whoever consistently directs attention eventually shapes values. Not perfectly. But enough.

I used to think influencers had influence. I think that’s backwards. The algorithm influences the influencers first. I know because it happened to me.

I know the first three seconds count more than the last thirty. I know curiosity beats explanation. I know tension beats nuance. I know exactly when people leave a video.

Every post gets graded. Millions of tiny lessons. Do that again. Don’t do that again.

After enough reps, something weird happens. You stop making content and start seeing the world as content. A beautiful sunset becomes a drone shot. An awkward conversation becomes a story arc. A guy pulling over and trying to solicit you becomes a hook.

You start experiencing your own life through the eyes of an audience that isn’t even there.

And there’s another lesson the algorithm teaches you. Normal is invisible.

An incomprehensible amount of content gets posted every day. You have to stand out.

That doesn’t always mean taking more risk. Sometimes it means being funnier, more provocative, more vulnerable, or more embarrassing. But risk is one of the cleanest ways to create attention because danger gives a story stakes.

A bike ride across Minnesota is exercise. A bike ride across Afghanistan is a story.

Instagram never told me to ride into Iran. There was no notification saying, “Ian, tensions in the Middle East are high. This could perform.”

It’s subtler.

Every post teaches you what people care about. Every spike in views tells you what version of yourself is worth watching. Eventually, you don’t need the algorithm to tell you to make the story bigger. You already learned.

Here’s the funny thing, imo. The New York Times understands attention just as well as Instagram does.

The article about me begins with danger. Stakes. Then it creates tension and makes you wonder what happens next. That’s good storytelling. I would’ve done the same thing.

Because we all learned from the same teacher.

People talk all the time about social media making us lonely. Maybe. But I think that’s the wrong question.

For me, the more interesting question is: What disappeared that made social media so irresistible?

Tech doesn’t win just because it’s new. It wins because it replaces something old. Uber over taxis. Airbnb over hotels.

What did Instagram replace?

I don’t think it replaced cameras. Or Facebook. I think it replaced the village.

For most of human history, your community told you what was happening. Who got married. Who embarrassed themselves. Who was succeeding. Who needed help. Who everyone was talking about.

Instagram does all of that. Just globally.

The difference is that your village knew your name. It could show up at your front door if you didn’t come around for a few days.

Instagram can keep you scrolling for five hours.

I did heroin in my twenties. Instagram isn’t heroin, of course. But struggling with fent or hydrocodone or heroin teaches you to become suspicious of anything that understands your brain better than you do.

Yesterday, I spent 4 hours and 51 minutes on Instagram. Yes, I have an addictive personality. Yes, staying current is part of my job.

But it’s engineered.

Really smart people in the Bay Area wake up every morning trying to get me to spend four hours and 52 minutes.

And the nuttiest part is that Instagram got me here. Without Instagram, I’d likely still be working construction, building Walmarts out of Boise, Idaho.

No bike ride across Asia. No Substack. No New York Times.

I’m here noticing all this stuff from the inside.

The Times asked whether Instagram is encouraging dangerous travel. Maybe. Young men were doing dumb stuff for clout before social media too.

But I don’t think that’s the biggest story.

For me, the biggest story is that one of the most powerful authorities in modern life doesn’t wear robes, stand behind a pulpit, or print newspapers.

It ranks.

Every second of every day, it answers a question that used to belong to families, churches, teachers, editors, and communities:

What deserves your attention?

Most of us don’t think of that as authority.

Probably we should.

I’ve been a little quiet.

Finished Japan, flew to Panama almost immediately, and thought I might stitch up the skipped sections. Darien Gap, Sudan, east Iran. Clean up the story. Finish it properly you know.

I got to Panama City, sat there for a few days, looked into the Darien, and left.

I’ve put myself in bad spots before and felt clear about it. This one did not feel clear. First of all it’s illegal. Then there’s cartels, coyotes, everybody in Panama City telling you some version of “don’t be dumb.” Probably part of it was fear. Part of it was coming off a year of pushing and not having it in me to throw myself right back into the fire. Either way I bailed and flew back to Minnesota.

So now I’m still trying to raise the stakes but with the safer 4th option. Now it’s Antarctica.

And Antarctica is forcing me into a completely different zone.

Up to now, most of this project has been pretty scrappy. Bike, bags, patch kit, phone, passport, send it. If something breaks, fix it (kinda) and keep movin’. If conditions are rough, deal with it. If I need to sleep, find a drainpipe or a field or a budget hotel and keep going.

Antarctica does not work like that.

There are no towns. No hot meal ten miles away. No random guesthouse for when you are cooked. No margin for error. The people I’ve talked to made that pretty clear. The rough number I got for logistics was around $90k, and that is before you even get into the question of whether riding a loaded bike on Antarctic snow is a dumb idea in the first place.

So now the project looks less like “go ride somewhere” and more like “build a test facility and start finding out what breaks.”

That’s the pivot.

I bought a truck because now I need to haul material instead of just hauling myself. I’m looking for somewhere in or around Minneapolis where I can drop a container for a month and work on it without getting all my tools stolen. Fenced yard, industrial area, maybe an old warehouse. Somewhere I can actually get work done instead of being told no by six layers of zoning and noise ordinances.

The idea is to buy a shipping container and turn it into a cold chamber. Not a polished lab. More like a rough prototype that lets me test systems in public.

• Industrial size fans

• Refrigeration Unit

• Insulation

• Bike rollers

• Lighting

• Cameras

A place to sit in the dark and see what happens when your body and gear are in an environment closer to the real thing.

Basically if Antarctica is the final test, I need a place to fail early.

And it’s got me excited.

Because now there is an actual build in front of me. Steel, insulation, power, airflow, condensation, batteries, gloves, sleep systems, what freezes first, what stops working. Whether a bike setup can survive repeated cold cycles. Or whether the lube freezes and plastic bits snap off.

There’s also the dirty part, which is money.

Japan was still scrappy enough to brute force it with savings, Substack, some help from you guys, and a general willingness to live like a bum. Antarctica is different. That means sponsors. So I found a manager. He’ll take 20% but it’s money well spent if we can lock a few good partners. He’s pitching outdoor brands. Making the case that this is real, not just some guy with a nicotine problem and a silly idea.

I think that’s what this phase is now.

Not simply planning an expedition. Building the machinery around the expedition. Truck, container, acreage, fans, cash, systems, reps.

A lot less scroll-stopping than “biking across continents.”

Also probably more real.

Route Recap

Biking to Japan is done. The rest of the map is done. The skipped edges are still there:

• Darien Gap

• Sudan

• East Iran

I don’t love it. But right now the bigger picture is Antarctica.

What’s Next

Today’s job is finding a place to put the container and starting the conversion.

That means:

• Finding a yard or lot around Minneapolis where I can park it and work

• Buying the container

• Figuring out power

• Figuring out how to create usable cold and airflow

• Building a two-chamber setup where I can test gear and not accidentally kill myself

I want the space to be harsh enough to teach me something useful. If it works, I’ll use it to test gear, sleep systems, clothing, cameras, charging, rollers, food, and whether my body can tolerate repeated exposure.

If it doesn’t work, that’s useful too.

Either way, this is the project now.

Gear Update

Current new piece of gear is sexy: 1998 Dodge Dakota Sport - 3.6L V6, 5 speed manual. $1,600 bones.

I did not finish Japan and think, you know what would make this story better, a pickup. But here we are.

The bike is still the core object, but Antarctica is going to require way more infrastructure around it than anything I’ve done before. The truck is basically step one in accepting that the next thing is a build.

Reflection / What I’ve learned

One thing I’ve noticed is that a lot of people like the clean version of a project. Man has idea, man sends it, man posts cool videos.

This part is less clean.

This is the part where the idea is more about data. Theories tested in reality.

• How cold

• How much power

• How much money

• Where do you park the thing

• Who lets you do it

• What breaks

• What’s workable

Thanks

Appreciate you sticking around while the project pivots.

Biking to Japan was a simple story. Now it’s something different. More materials. More dead ends. Hit the phones. Then more testing. Less traveling. Less cultural learnings. Less obvious motion. But it feels like real work. And I’ll keep showing up as it happens.

Have a lovely week,

Ian

If you want to watch me read this post, you can do it here ⬆

Since Last Time

Stepping off the boat in Japan felt.. flat.

No triumph. Not some movie finish line. No glory. No cinematic music. No big emotional release. Just satisfaction mixed with a weird anxiety. Like alright. Now what the hell am I supposed to do.

For a year the job was simple. Ride east. Wake up. Pack the bike. Crush miles. Suck down calories. Tell a story about it. Go to sleep. Do it again the next day.

And somehow that felt so incredibly meaningful.

From the outside this probably looked like unlimited freedom. Travel creator life. Do whatever you want. No. It was constraint. Fewer choices. Daily physical effort. One clear objective. Real stakes. Feedback from actual people instead of theories.

Biking to Japan ended up being an experiment I didn’t know I was running. Can only see looking back.

Most of us are taught meaning comes from adding things. More security. More money. More comfort. More choices. If we can just build the right setup, life will click.

This trip did the opposite. I kept stripping things away and the meaning didn’t disappear. No privacy. No long term plan. No certainty things would work.

Same clothes every day. Same bike. Same routine.

Almost always uncomfortable. Hot or cold. Sweaty. Dirty. Tired. But the days felt full. Sometimes more full than the life I left behind. I thought this journey would teach me about my ceiling. How far I could push myself.

Instead it taught me about the floor. How little I actually need. How much uncertainty I can tolerate. How bad things can get before I consider quitting or cheating myself. It turns out meaning didn’t come from comfort. It came from structure.

• Clear directions. I always knew what needed to get done in a day.

• Effort. My body had to be involved. Primal. Hunter gatherer type shit. The day ended when I was tired.

• Constraint. Not 57 options. One.

• Consequences. If I didn’t ride, nothing happened. If I did, the world opened.

• Progress. That you can measure on a map.

• Witness. I shared it. You watched. The effort landed somewhere.

When those things were present, life worked.

That doesn’t mean it was easy. There was fear. Loneliness. Plenty of days that sucked ass. But mixed into that were moments of real happiness that felt earned instead of manufactured.

Favorite Moment

Meeting many of you along the way. Different meetups. Almaty, Ulaanbaatar. Beijing. Seoul. Hiroshima. Osaka. Tokyo.

Those meetups are not my natural habitat. Being the center of attention in a room is uncomfortable. But they meant more than I expected. Because they closed the loop.

Online, this story is numbers. Views. Subscribers. DMs (OF collab invites, nudes (srs))

In person, it’s just people sharing a drink and talking about their own lives. That made the whole thing feel real. We all want to know our effort is seen. Doesn’t matter if you’re riding across continents or sitting at a desk. That recognition is important.

You were a huge part of why this worked.

What I Learned / Reflection

Finishing is unsettling because the structure is gone. For a year I didn’t have to decide what to do with my life. We’re biking to Japan. The road decided. The direction decided. Now there’s choice again. And choice is harder than biking.

I learned that, at least for me, meaning doesn’t require being too comfortable. But it does require deliberately creating the conditions that made those uncomfortable days work.

So now I have to build that again without the obvious container of biking to Japan.

Progress on the Map

Ride at a Glance

Start: Lisbon, Portugal

Finish: Japan

Continents crossed: Europe & Asia

Borders crossed by land: 15+

Ferry crossings: Italy to Albania, Caspian Sea, Qingdao to Incheon, Busan to Fukuoka

Major chunks skipped: 1 (east Iran)

Typical day: Wake up, ride 60 to 80 miles, find food, fix something that broke, make content, sleep, repeat

Average speed of travel: 12 mph (20 kph). Slow enough to see everything. Fast enough to not belong anywhere.

Navigation: Phone + instinct + asking strangers

Mechanical failures: Constant but fixable.

Lodging mix: Wild camping, cowboy camping, drainpipes, abandoned buildings, hostels, budget hotels, fancy hotels, restaurants, strangers’ floors, yurts, chaikanas, and everything in between.

Temps: -20°F (-29°C) to 115°F (49°C)

Biomes: Mediterranean, Anatolian Plateau, Central Asian Steppe, Gobi Desert, North China Plain, Korean Peninsula, Japan Archipelago

Number of countries: 20

Total distance ridden: 11,189 miles (18,007 km)

Time: Just over 1 year on the road

What’s Next

I write to you from Tokyo. But there are unfinished edges that still pull at me. Darien Gap. Sudan. East Iran. Course Antarctica. Those feel like natural continuations of the 7 continent story.

But there are other questions now too.

What does this look like when I’m not riding all day. Is there a way to tell stories when nothing interesting is happening. Do I try to find corporate sponsors. Break the streak. Will brands even want that (I was heroin user. I rip cigs, drink too much. Have a record. Two felony charges.)

Where do I put down a home base. Do I organize this into a longer film. Write more. Speak. Something else entirely.

I don’t know yet.

The only thing I do know is that I’m incredibly grateful you’re here. You followed this weird idea across continents. You showed up online. Some of you showed up in real life. I appreciate it so so much.

I can’t promise perfectly scheduled posts going forward. This phase will probably be messier. But I can promise I’ll keep showing up. Keep working hard as fuck. Keep being honest about whatever comes next.

This one is done and dusted. But there is more work to be done. And that’s the part I know how to do.

Have a lovely week and THANK YOU

Ian

Since Last Time

For almost a year now the project has been abstract. Biking to Japan. Something far away to be worried about later. The last two weeks it stopped feeling abstract.

I rolled out of Beijing Wednesday Jan 21 and for the first time ever it feels like the end is coming. Every morning lately I wake up sore, pack the bike, and realize there are only a handful of rides left before this thing is over. After almost a year of pushing east, the finish line feels close enough to taste.

It’s weird now. Part excitement. Part relief. Part terror in what I’m supposed to do after.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~11,000 miles (~18,000 kilometers)

• Key gear: patch kit, tent, cigs

• Key stops so far: Portugal, Spain, France, Italy, Albania, North Macedonia, Greece, Turkey, Iran, Azerbaijan, Kazakhstan, Uzbekistan, Afghanistan, Tajikistan, Kyrgyzstan, Kazakhstan, Russia, Mongolia, China, Korea

• Key stops coming up: Japan

What I Learned / Reflection

I tried flying the American flag in Beijing. I like putting myself in situations where I’m not totally sure how things will go. Stirring the pot. Before I even put the flag up I kinda knew there’d be a problem. Sure enough police stopped me w/i five minutes.

Detained for two hours. Questioned. Photos of me, the flag, my passport, the bike.

Then escorted out of Beijing by a cop on a little motorized scooter like some cute CCP convoy. They said it was against road regulations. Totally fair. What’s interesting to me is how different countries react to you just by being American.

In places friendly to the US it’s usually curiosity, respect, jokes, smiles. Sometimes envy. In places that aren’t, it’s colder. Sometimes hostile.

From Beijing I cruised to Qingdao and took the ferry to Incheon. Buttery smooth. Then biked about 30 miles into Seoul.

And holy smokes.

The emotional whiplash. After Afghanistan, Mongolia, China tensions. Korea feels unbelievably civilized. Like the whole country agreed to be considerate. People follow rules. Nobody cuts, nobody yells. Traffic flows. It’s tidy. It doesn’t actually feel stiff though. Just a calming energy. I feel more comfortable here than anywhere I’ve ever traveled to. Like your nervous system finally gets to unclench.

I put a call out for a meetup thinking maybe one or two people might show up. Nine did. Which shocked me. Nine folks showing up on a random Monday night halfway across the world to share stories and sip Korean beer.

Favorite Moment

Collaborating with Woody. Greatest content creator in Korea IMO. Timeless wisdom with a great sense of humor — totally disarming.

Progress on the Map

Distance Ridden Since Last Time: 431 miles (693 km)

Total Distance Ridden: 10,847 miles (17,457 km)

Body Update

I had a cyst on my nose from a bug bite in Afghanistan that kept coming back.

Since I’m now in the plastic surgery capital of the world, I figured I’d get it properly checked out.

Ended up in a clinic that mostly does rhinoplasty. I didn’t tell them so much what I wanted but asked what they would do to make me more attractive. Zoomers call it looksmaxing.

They said nose is fine. Eyes are fine. But that my skin is bad. Months under the mideast sun has done damage.

Doc said he’d give me a treatment for free in exchange for a shoutout. I was like maybe what’s the treatment. “We inject your face and neck with salmon sperm hundreds of times using a hypodermic needle. It’s extremely painful. And actually illegal in USA, not FDA approved.” Say no more I’m in.

They told me it’s normally $600 and women fly here to get it done. The risk is that you’re allergic but I eat salmon all the time so. I’ll tell you in a few weeks if I’m glowing or not.

What’s Next

February 5th to 9th, Seoul to Busan by bike. I am biking to Japan so this whole mission ends when my wheels touch Japanese soil. Obviously it’s an island. There’s about a 2% chance I find a paddling swan in Busan and island hop my way across the channel. (Not happening. Also dangerous.)

Plan B is to ride 184 miles on a stationary bike in Busan. Then board the ferry to Fukuoka. Journey officially ends when the boat docks.

My flight out of Tokyo is Feb 24. Two week epilogue through Japan to meet you between Osaka and Tokyo if you’re around.

Rough dates:

• Feb 5 Leave Seoul

• Feb 9 Busan

• Feb 11 Fukuoka

• Feb 13 Hiroshima

• Feb 16 Osaka

• Feb 18 Hamamatsu

• Feb 20 Tokyo

Nutty to think this thing is almost done and dusted.

Thank you for reading,

Ian

Since Last Time

There was a lot of anticipation around the Gobi. Months of people messaging me about 20 below wind chill. Hypothermia. About knocking Mongolian gers for a place to sleep. Whether this was finally the part where I’d need a truck.

And then I biked it. And it was fine. Boring even.

Can’t manufacture drama where there isn’t any. Truth is I got lucky. Today, Jan 19, 2026, it’s -40°F in Ulaanbaatar. Raw. Three weeks ago it was balmy -10 and the wind mostly pushed me from behind. Kept me warm and cruising quick. I had the right clothes. Kept my water unfrozen. Mentally I never hit that breaking point where you start debating with yourself about hitchhiking. I kept waiting for the moment where it gets hard. And it never really came.

Almost without ceremony, Mongolia ended and China began. A couple standard questions from Chinese border patrol about where I’m headed, where I’ve come from.

“Do you have any pictures of your trip?” Of course I do.

I delete photos as I go to save space on my phone, so I opened Instagram to show him my profile. I had pinned reels, and the first thing he saw was me in Afghan clothes holding an AK. Great. This triggered lots more questions.

Even with a visa, border patrol can still reject you. So it’s best not to be interesting in any way that makes you stand out.

Otherwise a straightforward crossing. And a straightforward ride down to Beijing.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~11,000 miles (~18,000 kilometers)

• Key gear: patch kit, tent, cigs

• Key stops so far: Portugal, Spain, France, Italy, Albania, North Macedonia, Greece, Turkey, Iran, Azerbaijan, Kazakhstan, Uzbekistan, Afghanistan, Tajikistan, Kyrgyzstan, Kazakhstan, Russia, Mongolia

• Key stops coming up: Korea, Japan

Favorite Moment

Realizing I could leave my bike outside a store in a random Chinese town and not worry about it at all. It sounds small. But after months of worry, rushing in & out of stores, that felt nutty.

CCP Politics

One of the best parts of traveling is that when you learn new information it’s much stickier in your mind. You notice details you would normally ignore, and don’t forget them easily.

The first thing you notice is the cameras. They’re everywhere. Someone told me 700 million. One for every two citizens. I believe it. You feel watched constantly. At first it’s unsettling. That tingly hair on the back of your neck feeling.

Then you start to appreciate them. The streets are safe. Theft feels impossible. There’s an order to it. A feeling that someone is always paying attention to you, even if you don’t know who or why.

One night I’m eating dinner in a little village. Four well-dressed guys come in, sit down, order food. Started asking me casual questions through phone translation. Nosy. Where are you staying, where are you biking tomorrow.

That caught me off guard. I hadn’t told anyone about the bike. The only explanation was cameras. Secret police were tracking me.

They were polite. Friendly, even. Shared wine. One of them sat next to me for a few mins and I FaceTimed his son. Mostly they sat at a different table watching, observing. Encouraging me to drink.

Before I left I asked if I could take a selfie with them. Just gestured with my phone.

Immediate panic. No no no with their hands up. Absolutely not.

I told this story to a local guy the next day and it freaked him out. Said that our iPhones are probably listening to us. And that we shouldn’t talk any more about the government.

Chinese Food

One way to judge a countries food culture is how easy it is to eat well without really trying. I prefer spots that are unpretentious, off the tourist trail, and full of healthy looking locals.

Usually I pick a restaurant when I get hungry almost at random. Order something blind. Suck the calories down, enjoy the normal dining experience, and hope for the best.

China passes the test hard. Dumplings. Hot pot. Noodles. Duck. Kung pao chicken. Stuff I can’t pronounce. Less than five dollars for a full meal. And it has mostly been excellent.

Scale

Cities here feel enormous in a way the maps don’t show. The scale is strange. Spread out. Wide roads. A lot of the old fabric has been flattened and rebuilt into something post-modern, beige, global. Office-campus energy. Efficient. A little soulless.

Beijing surprised me though. No smog. Clean air. They moved the factories out years ago and it shows. Three concentric rings of beautiful traditional-style architecture.

Connectivity

The app ecosystem is the other big adjustment. Google, Instagram, WhatsApp don’t work unless you jump through hoops. People live inside WeChat. Payments. Messages. Ride hailing. Everything.

For internet I went with an eSIM from a global provider this time. More expensive but it just works. No VPN stress.

What I Learned / Reflection

There’s a tension I can’t quite resolve yet. The country feels safe. People are happy. Locals tell me that the economy is good. And at the same time there’s an iron grip underneath it all. Cameras. Apps. Surveillance. Things you can’t say.

China learned from the failure of the Soviet Union. They’re doing Communism different. And it seems to work for them.

I’m less certain these days about declaring systems right or wrong. Maybe some things work for some places.

Traveler Tip of the Week

If you’re coming to China, sort your apps before you arrive. It’s what I’ve personally struggled with the most. A lil pre-coordination goes a long way.

Amap for navigation. Dianping for Yelp style reviews. WeChat for literally everything else: ride share, messaging, payments.

Progress on the Map

Distance Ridden Since Last Time: 619 miles (996 km)

Total Distance Ridden: 10,416 miles (16,763 km)

Gear Update

Does anyone in Japan want a free bike? Surly Disc Trucker, size 58cm. It’s good for someone 5’9” to 6’4”. The bones are solid.

Give her new gears, pulleys, chain, cables, cable housings, brake pads, front tire and you’ll be ready to rip another 10,000 miles.

If you read this blog and can pick up in Tokyo mid-February, it’s yours. Send me a DM or put a comment.

What’s Next

I write to you now from Beijing. First real megacity in a long time. Damn near ecstatic to be in proper 1st world convenience. And a little emotional about being so close to the finish line.

Got a one week push to Qiandao, catch a ferry to Seoul, ride South Korea, then another ferry from Busan to Osaka.

Would any of you be interested in a US-based group ride. Or maybe another country. Afghanistan?

My bud suggested one of those party bike/pedal pub things. Coast to coast across US. Sounds nutty and fun.

Would you ride with me on any kind of tour?

Have a lovely week,

Ian

Well the visa finally came through. Two months in Ulaanbaatar. A process that was supposed to take 3 to 5 days somehow stretched into fifty five. I paid the expedited fee—164 bones. Then checked most every Monday, Wednesday, Friday. Same answer every time. No.

And then suddenly there it was. A real Chinese visa in my passport. Ten entries. Valid for ten years. Sixty days per entry. Relief hit first. Then something else I wasn’t expecting. Dread about starting again.

Waiting sounds easy until you gotta do it for 55 days. Sitting still messes with your head in ways constantly moving never does. You start overthinking everything. Content. Life direction. Money. What comes after Japan. What comes after all this.

The answer came eventually. Always does.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~11,000 miles (~18,000 kilometers)

• Key gear: patch kit, tent, cigs

• Key stops so far: Portugal, Spain, France, Italy, Albania, North Macedonia, Greece, Turkey, Iran, Azerbaijan, Kazakhstan, Uzbekistan, Afghanistan, Tajikistan, Kyrgyzstan, Kazakhstan, Russia, Mongolia

• Key stops coming up: Gobi Desert, China, Korea, Japan

Favorite Moment

Getting a DM from someone who reads this.

“Hey, I know a businessman in Mongolia. He might be able to help with the visa.”

Next thing I know I’m getting a call.

“Hello, this is Bagi.”

Bagi turns out to be the richest man in Mongolia.

He sends a driver. I get picked up. Taken to a penthouse office at Shunkhlai HQ. He makes a few calls. It doesn’t change the visa outcome, but he takes care of me anyway. Cashmere distributor tour. Mongolian vodka factory. Invited me to a Mongolian rock show with throat singing and traditional clothes.

Didn’t fix the visa problem. But it was surreal.

It reminded me that the internet isn’t just numbers and likes. It’s people quietly watching for a long time. And sometimes one of them reaches out and changes the texture of your real life for an afternoon.

Once I’m closer to China I’ll start sharing my daily routes. If you’re nearby and want to ride a few miles or share a coffee, I’d love that. This thing is better when it spills into real life.

Reflection / What I Learned

Leaving Ulaanbaatar on January 1 felt like starting over. Not physically—still got quads and a strong taint. But mentally. After two months of not riding that first morning back on the bike felt identical to leaving Portugal with my mom almost a year ago. Same doubt. Can I actually do this?

Minus 10 degrees Fahrenheit when I rolled out of UB. My drinking water froze so fast Starting with boiling from the kettle buys you a few extra hours. Hand and foot warmers help. Same riding layers that smell like cigarettes and old sweat and road dust.

The steppe isn’t hard because of distance or infrastructure. It’s the wind. When it’s at your back, you’re warm and cruising. When it blades off from the side, windchill hits minus 20 and then the doubt creeps in.

The loneliness is the harder part. Ulaanbaatar gave me a routine. Friendly faces that I saw in everyday. Breakfast in the common kitchen. Gigi lounging on the couch. New friends. Dates. Normal life.

Leaving that behind is harder than leaving empty desert. I used to think loneliness came from absence. Turns out it comes from contrast. The first few days I kept looking for excuses to bring a support vehicle. A friend. Anyone. I guess it’s not because I need like rescuing. But cause starting again alone feels harder than continuing alone. I made some phone calls, but luckily nobody was available.

I’m about 20 kilometers from the Gobi now. It’s harsh but manageable. Antarctica is summer right now, and weirdly the weather here isn’t that different. The difference is consequences. Here I have bailouts. Traffic I can flag. Shops to duck into. There I won’t. That’s the part that counts.

Traveler Tip of the Week

If you ever stop for long enough that starting again feels scary, that’s not a sign you should quit. That’s the exact moment you should move.

Progress on the Map

Distance Ridden Since Last Time: 204 miles (328 km)

Total Distance Ridden: 9,797 miles (15,766 km)

What’s Next

Now it’s simple. Bike southeast through the Gobi. Into China. Down to Beijing. Over to Korea. Bike paths all the way to Busan, ferry to Japan.

For the first time, the fear isn’t whether I can finish. It’s who I am when I do.

I am fully committed to Antartica. And it has to be done in Summer. Southern hemisphere summer is December and January. That leaves a long 2026 to figure out what is going on here when the biking finally stops. In 2025 this went from 500 subscribers on Substack to 13,000. Serious growth + serious responsibility. I don’t want to waste it.

What do I do for you in 2026?

Here’s something I’m carrying into this year. I don’t want to do this life alone forever. This road teaches you a lot. One of those things is that experiences hit harder when they’re shared. I want a partner. An ally. Someone to build with.

I’m want to find a wife, man.

And thank you. Truly.

This waiting period only worked because some of you stepped up and paid. That income covered my $14 room, hot meals, and the time to wait and finish this the right way.

And the rest of you, reading, sharing, sending messages, sticking around while nothing was happening. Thank you too. Waiting is easier when you know someone’s on the other side of the screen as has got your back.

Starting over at mile 9,593 feels weird. But it’s still forward.

Have a lovely week,

Ian

Everyone asks about the bike. The bike is maybe 5 percent of the problem. The dirty little secret is that all bikes are basically the same. And biking sucks no matter what you’re riding. It is a good way to travel. Free. Healthy. But it is work. And the degree to which you enjoy it mostly depends on the weather and the wind.

This is a mental, logistical, and emotional project disguised as a cycling trip.

Start with the wrong question

People ask me, “How do you even train for something like this?”

I have tried to answer before. But after 30,000 miles across six continents I’ve realized that it’s actually the wrong question. The better question is, “How do you keep going when quitting is rational?”

Most days, quitting makes sense. You are tired. You are sore. The weather is bad. Nothing interesting happens. No one would judge you for stopping or sticking your thumb out. That is what makes endurance trips deceptive. The failure mode is not dramatic. It is quiet and reasonable.

For me, the solution has been aligning direction with purpose. I chose the goal of biking across all seven continents because it was better than any alternative I could think of at the time. It was just scary enough to be interesting. I wanted a direction that would pull me forward on days when motivation disappeared.

I was curious about places most people do not go. Kenya. El Salvador. Bolivia. Iran. So I biked to them.

This is on the job training. You do not need to be fit to start. You become fit by starting. Ride 10 miles on day one. Ride a little farther the next.

Packing

I have written about packing before: clothes, essentials, and everything else. Less is more. Not to save space but to buy freedom.

A helpful place to start: take inventory of what you didn’t use after your next trip. Almost always it’s going to be a lot. Don’t bring that stuff next time.

I always bring too much clothes. So just don’t bring clothes except the ones you’re wearing. Buy local clothes after you arrive. It forces adaptation. It helps keep you from overpacking. It reduces decisions. It helps you blend. And it makes clothes easier to ditch when you don’t need them anymore.

The exception is footwear. I think sandals are the peak of performance footwear on and off the bike. So it’s worth bringing a good pair. Shimano SD5 if you ride clipless. Teva Hurricanes if you don’t. I’ve biked around the world in sandals. And only switched to sneakers in Kazakhstan because of slush.

It’s okay to go heavy on under packing because what you need you can buy when you get there.

Essentials:

• iPhone

• Macbook

• Good headlamp

• Passport

• Credit card

• Heaping pile of USD

Hair ties are surprisingly useful. Leatherman is predictably useful. A zip-lock of wash powder and a universal sink plug let you wash clothes anywhere. Here is my full packing list.

Choosing a country: fear as a guide

There are two ways to travel.

• R and R. A ten day vacation to recover from your normal life. Be pampered. Eat well. Reset.

• Exploration. To learn how people live. To be changed by friction.

This guide is about the second.

When choosing a country, I let fear guide me. Not reckless fear. Informational fear. Borders that make you slightly nervous are usually the right ones. The safest route is rarely the most meaningful.

That said, fear is data, not a commandment.

During my Africa trek, I had an opportunity to continue through Yemen. On paper it worked. In reality, the Houthis were firing missiles at tankers in the Red Sea in 2023, and the stretch I needed to pass through was under Houthi control. I wanted the story.

But I didn’t go.

Sometimes the correct move is restraint. Courage is not doing the most dangerous thing available. It is choosing risk deliberately. I did not feel pulled forward by Yemen. I felt dared by it. That’s a different feeling.2

Find the edge of your comfort zone. That edge will be different for you than for me. You learn more from the edge than from jumping off the cliff.

Choosing a route: weather and wind

Weather determines enjoyment more than fitness. Always check the prevailing wind direction.

The Pacific Coast Highway north to south in August and September is popular for a reason. It was some of the best riding of my life.

Interesting detours matter more than efficiency. Tertiary roads reduce traffic, but in many countries only one road is paved. Wear bright colors on highways. Access to water, food, and shelter matters more than shaving miles.

If villages appear every 60 miles or less, it is workable. You can use LLMs to help you plan.

Best navigation apps:

• OSMandMaps

• Mapy.cz

• Google Maps

Distance is not the hard part

People fixate on mileage. But long flat days are easier than short brutal ones. The real tax is not distance. It is accumulation. Wind that never stops. Heat that drains you. Knee pain that lingers. Mechanical issues that pile up. Bureaucracy. Visas. Borders.

Then there is waiting.

Weeks stuck in one city doing nothing. Momentum dies here. Your identity as a moving person evaporates. You start to question the entire project. This is where most people quit. Not in crisis, but in comfort.

It all comes down to visas. Bureaucratic attrition. You can do research on the US State Departmen website3 until the cows come home. But ultimately embassy workers have final say. And nobody rushes the CCP when it comes to national security. Waiting exposes whether your commitment is circumstantial or directional.

What to eat: fuel, nothing fussy

You eat what exists, not what is optimal. Simple carbs, fat, protein, salt. Whatever is local. Eat before hunger. Drink before thirst. Sugar is your buddy. I carry Haribo gummy bears at all times. High glycemic sugar can stop a bonk as it is happening.

In heat, I drink salted water. Sometimes followed by a few gulps of pop (Pro tip. Leave it open the night before so that it’s easier to chug.)

Good food is often cheap food. Food snobbery is overrated. Any place that is unpretentious, filled with locals, and off the tourist trail is usually just fine.

Food is my favorite lens into a place. Because it forces contact with people, towns, reality. 90% of the reason I like to travel really. Milk vodka. Yak butter. Bad coffee. Cafeteria meals. Food starts as logistics, becomes comfort, then culture.

Where to sleep

My love for sleeping on the ground after a sponge bath is inversely correlated with my income.

A good night of sleep is almost always worth $15. I’ll sometimes go up to $25 which covers you almost everywhere except North America, Europe, and Australia. Recovery saves more miles than fitness.

Camping is freedom until it is not. Guesthouses, cheap hotels, floors, couches. Warmshowers and Couchsurfing work well. The best places are not online. Gotta ask.

Stealth camping works, but the anxiety degrades sleep. Asking permission works better. It turns a problem into a conversation and usually the best stories.

Staying connected

Modern connectivity changes everything. Most countries now support eSIMs, even ones you would not expect like Afghanistan. Local plans are dramatically cheaper than global providers. So setting it up in country is worth the effort. Research the biggest telecom, pin the stores on your map, then figure out a way there after you arrive.

A good VPN is extremely useful. Many countries throttle, monitor, even block basic services. Email, substack, WhatsApp, banking, all behave differently by country. Two free VPNs I’ve used are OstrichVPN and RayVPN. I also pay a yearly subscription for Nord.

iPhone satellite texting is a quiet revolution. Not for drama, but for margin. Knowing you can reach someone if things go sideways lowers baseline stress.

Power discipline matters. Airplane mode. Low power mode. Charge whenever you can. Carry at least one 20,000 mAh battery. Add a second before considering one of those goofy portable solar panels.

I met some Bulgarians who did not carry phones. It helped them live in the moment. But realistically being reachable reduces background anxiety. Disconnection sounds romantic until something breaks.

Money: liquidity plus ATM card plus credit card

Always have multiple ways to pay. Cash is king in weird places. USD opens doors.

I carry lots of 50s and 100s. Some 20s. Crisp, newly minted bills with no tears or blemishes. You should also bring 1s because they’re a great token of friendship.

I keep most cash and cards in my fanny pack, with a backup stash hidden deep in my bike bag. I trust myself more than the staff at budget hotels.

Ninety percent of payments are cheapest using a credit card. Plus fraud protection. But pull local currency from an ATM as soon as you arrive. If the ATMs aren’t working you can exchange USD at the bank. Local plus USD liquidity buys peace of mind.

Health

I have never had travel insurance. Everyone should make their own decision. Not carrying makes sense for me given my risk tolerance. Costa Rica treated my heat exhaustion for free. I have paid out of pocket for antibiotics a few times. I got my ears cleaned in Uzbekistan for $4.

In a catastrophe, I could be on the hook for thousands. So I keep a contingency bucket for emergencies.

The most common issues are knee pain, saddle sores, and travelers diarrhea. Most can be managed with basic first aid, new padded shorts, and rest days.

Rest days are not weakness.

I learned it the hard way. One morning I had food poisoning. Diarrhea. Cramps. I told myself I could ride anyway. I got on the bike and almost immediately shit my pants. That was a clear message. I should have rested. I didn’t.

Hygiene matters more the longer you go. You cannot dominate the road by abusing your body.

Language and signaling

Body language matters more than vocabulary. Smile. Be polite. Somehow when you put your best, most trusting self out there, you get the same energy back from the people you meet. Not sure how this works, but it does.

Respect is safety. Humility travels better than confidence. Being understood matters less than being non threatening.

Wear bright clothes on highways. Neutral clothes in cities.

You also have the option to peacock. Wear something outrageous to draw attention. A green skin suit. Cowboy hat. Whatever is wild. You can engineer interesting travel this way. But attention increases risk. Context and your personality matter.

Safety without paranoia

People in the rest of the world are not angels. Some will try to take advantage of you.

Staying humble and kind works most of the time, but not always. Iranian secret police once tried to confiscate my American flag. I tried arguing respectfully. It did not work. I got aggressive. Thinking about them burning it got me fired up. Next thing I knew, we were in a full strength tug of war.

He cuffed my ear, but ultimately let me keep the flag.

Trust your gut early, not late. Leave before things feel wrong. Police, soldiers, and truckers are not the same everywhere.

Courage is not ignoring risk. It is doing your homework, assessing the real danger, and acting in spite of fear. Have an exit plan, nearest airport, borders that don’t require paperwork.

Documenting on social media

People do not connect with content. They connect with people. Your job is not to be impressive. It is to make people feel something.

Follow your fear here too. Do or say things that scare you. Ideally both. For me, that meant biking Ethiopia and Afghanistan, and letting more personality into my stories.

iPhone has now reached a point where it takes better video than most cameras. It’s less intimidating than waving a beefy DSLR (or even mirrorless) in someone’s face. And it’s always on you. I go for the small storage option and then backup to a 2TB SSD.

Camera gear and tactics matter less than honesty. Two questions I try to keep in mind as I create: 1) If I saw this content on my feed, would I share it with a bud. 2) Is this unique to me, something that people can’t get anywhere else.

Relationships on the road

One of my favorite books is Into the Wild. Mom plugged it on her “happy movies” list. The line everyone remembers is that happiness is only real when shared. Doing this all solo, I feel a bit lonely almost all the time.

Friendships on the road are intense and temporary. Sometimes I feel jealous of people with continuity. Families. Kitchens they know. Friends they see every week.

I guess feeling jealous doesn’t mean I made the wrong choice. Just that choices cost something.

Ending

I still hate waking up and getting on the bike. That never really goes away. A thousand miles in, you don’t suddenly start to love it.

But it does give you enough evidence to stop negotiating with yourself. Enough days where quitting made sense and you did not. Enough discomfort to realize it will not kill you.

A thousand miles is not a special number. But it’s enough to make you slightly more trustworthy to yourself. And that helps beyond the bike.

Progress on the Map

Distance Ridden Since Last Time: 0 miles (0 km)

Total Distance Ridden: 9,593 miles (15,438 km)

Have a lovely weekend,

Ian

I downloaded Bumble. Not cause I expect to meet my wife in the next month. But maybe. Mostly it’s because I am bored and cold and stuck in the middle of Mongolia. Browsing is fun. Everyone reaches for something when they’re cold and bored and stuck somewhere. Mine just happens to be Bumble in Mongolia.

It is not the first time I have been on Bumble, but maybe it’s the last.

The Tweet That Broke My Brain Yesterday

For me, the part that seems true is the idea of chasing a dopamine hit without earning anything.

I read it while swiping in my Ulaanbaatar hotel room. A man who biked across Afghanistan and Africa reduced to hours of thumb flicking. My brain can do Taliban checkpoints but not dating app convos.

For me, porn and masturbation killed motivation in my twenties. Cutting them out helped, but I wonder how much time I wasted without noticing. And I wonder where I’d be today if things had been different. I think lots of guys feel this way even if we never say it out loud.

What happens is you trick the mechanism that is supposed to pull you forward. It is like failing to climb the mountain but giving yourself the summit photo anyway.

Now it’s Bumble doing the same thing. And no wonder writing has felt like shoveling wet snow.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~11,000 miles (16,000 kilometers)

• Key gear: patch kit, tent, cigs

• Key stops so far: Portugal, Spain, France, Italy, Albania, North Macedonia, Greece, Turkey, Iran, Azerbaijan, Kazakhstan, Uzbekistan, Afghanistan, Tajikistan, Kyrgyzstan, Kazakhstan, Russia, Mongolia

• Key stops coming up: ???

Least Favorite Moment

I coordinated a date on Bumble and got stood up. Apparently you are supposed to maintain a slow drip of WhatsApp messages before the date so the girl knows it’s still happening. I did not know this rule.

The truth is I am awkward and dating has always made me nervous. I never know the right pace or signals. I can bike through war zones but a twenty five year old girl at a Mongolian techno show can scramble my brain.

I deleted the app the next morning.

Reflection

My problem now is not tugging or porn or a lack of interested women. If you saw my DMs you would know. Weird autism works.

My biggest problem is leaking energy in a thousand lil ways. Apps. Flirting. Tiny dopamine hits. All of it pulls attention away from the bigger goal to rip across seven continents. Build something big.

I’m not against sex. I just notice that when things come to easy, I stop going after the things that actually matter. There is power in staying hungry for your goal and only letting yourself eat when you earn it.

Traveler Tip of the Week

When I look back on the best times of my life, it’s never laying down with a beautiful woman. It is doing hard shit with the boys and feeling alive after. Probably not a universal rule, just the one I keep relearning. So my tip is to do more of that. And less swiping.

Progress on the Map

Distance Ridden Since Last Time: 0 miles (0 km)

Total Distance Ridden: 9,593 miles (15,438 km)

The Chinese consul worker finally showed me sympathy. Showing up 3 times per week and being polite helped. My Mongolia visa expires Jan 13. She said she will try to get me the Chinese visa before then. Her hands are tied since the issue is with China. But she’ll do what she can.

What’s Next

This journey only works if I stay hungry. Not thirsty. The gobi desert in January is looking real. And it is going to take more preps.

A Note About My Uncle

My uncle Jack passed last week. He lived the kind of life people pretend they will live someday. He hunted, set ski records, backpacked, skydived, scubadove, sheared sheep, judged bird dogs, wrote for a living, and traveled the world. He made a life out of saying yes to the hard and scary things. He was the first person who coached me to be a creator. He always had my back.

His obituary said he grew up knowing neither envy nor fear and pursued life with unquenchable curiosity and optimism. He was grateful for the battles he fought, for the friends he made, and for the woman he loved.

Sitting here in Mongolia, I keep thinking about him. How he chose real difficulty over cheap reward. I want to move closer to that.

Have a lovely week,

Ian

I wake up every morning in the same $14 hotel room feeling like the walls are slowly closing in. The mattress is hard. The pillowcase has fabric softener which is giving me acne. Outside the window is Ulaanbaatar smog so thick it turns the sun orange by 9 am. I lie there for a minute staring at the ceiling. Wondering if today’s the day the visa magically appears or if I’m just gonna rot here till spring.

Then I get up, put on the same three layers I’ve worn for months, and shuffle to the kettle in the kitchen. Breakfast is a pack of pre-cooked chicken and instant coffee+milk that actually tastes like heaven (Mongolia has the best milk). After that it’s hours of killing time—walking the same four blocks because it’s too cold to explore properly, dodging traffic that almost makes Kabul look organized. Ripping darts. Drinking overpriced lattes in a cafes where people are mostly too shy to talk to me.

Monday, Wednesday, Friday at 3 pm I put on my nicest (only) crewneck and hike across the city to the Chinese embassy. Same security guard, same metal detector that I no longer have to use because they know me. “Any update?” the consul employee barely looks up. “No.” Cool. See you Wednesday.

Back to the cafe. Open the laptop. Stare at premiere pro. Try to make content about waiting.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~11,000 miles (16,000 kilometers)

• Key gear: patch kit, tent, cigs

• Key stops so far: Portugal, Spain, France, Italy, Albania, North Macedonia, Greece, Turkey, Iran, Azerbaijan, Kazakhstan, Uzbekistan, Afghanistan, Tajikistan, Kyrgyzstan, Kazakhstan, Russia, Mongolia

• Key stops coming up: ???

Reflection / What I learned

People think I’m fearless. A confident world traveler running wildly from near-death experience to near-death experience. I’m not. Every big thing i’ve ever done first felt like it was gonna kill me. Biking afghanistan. Ethiopia. Iran while bombs were falling. Jumping out of planes. Moving to North Dakota with no plan and sleeping in my car until I got a $13/hr job picking parts at a truck dealership. Every single time my stomach dropped and my brain said stop.

Here’s the trick I stumbled into: when I have two options and one scares me way more, that’s the one I take. It’s never failed me yet.

Fear isn’t the stop sign we were sold. It’s a compass. The sharp stomach twist is just your body saying “this one actually matters.” Most people treat it like a wall. They turn around. And growth stops right there.

There’s survival fear (Taliban checkpoint, 4,000m pass in a blizzard) and there’s expansion fear (hitting publish on something raw, having a conversation that you’ve been avoiding.) Some real ones I’ve felt lately:

• Hitting publish on the post where I talk about doing heroin in my twenties. My finger hovered over the button for like 20 minutes.

• Talking with a girl at a techno show in Mongolia. Sounds stupid but it scares me more than the Taliban.

• Telling my dad I’m proud of him. We’ve never said that kind of thing out loud. Makes me nervous just thinking about it.

• Getting paid. I’ve never charged for anything on Substack. Do I really offer that kinda value. Imposter syndrome.

• Admitting on camera that I still get sad even after all this “dream life” traveling. Feels like I’m ruining the brand.

• Asking for help. Any kind. Feels like I’m proving I don’t have my shit together.

The pattern is always the same: the thing that could actually change who I am is the thing that scares me most. So when the IG poll said fly to Korea and keep moving (by 55%), it felt wrong.

When I’m stuck on a decision now I just ask: which option makes me feel a lil sick?

This time it is festering in uncertainty. Biking in -20 through the Gobi. That’s the one. It’s never wrong.

Traveler Tip of the Week

Do one thing every day that scares you. Eleanor Roosevelt said it, but I’m stealing it. Works on bikes. Works off bikes. Works everywhere.

Be more brave.

Progress on the Map

Distance Ridden Since Last Time: 0 miles (0 km)

Total Distance Ridden: 9,593 miles (15,438 km)

What’s Next

Keep waiting on china. Keep riding east. Keep choosing the option that makes my hands shake a lil. If the visa comes through I ride east and freeze. If it doesn’t maybe I’ll fold and take the plane. Or I might do something dumb with a Russian train.

Have a lovely weekend,

Ian

Since Last Time

Made it to Ulaanbaatar. Capital city of Mongolia. After weeks of wind and emptiness the noise feels weird. Almost fake. ~50% of Mongolians live here. Traffic lights. Proper coffee shops. Grocery stores with actual aisles. I don’t even know what to do with the options.

First night here I went to a techno show. Went alone. Needed to be around people again. There was a girl dancing next to me for like 45 minutes. She clearly wanted me to say something. But I froze up. Finally before leaving I asked for her Instagram. She typed it in and I left. We’ll count it as a win, baby.

Now I’m waiting on the Chinese visa. Submitted it on Friday. They rejected the first one. Said fix the headshot, fix the address, upload the visa stamp. Resubmitted. They say I can pick it up on Wednesday but another cyclist said it took him 13 days. So who knows.

While waiting I sat down and read through all your comments from last week’s issue.

• Grampy said that he’s proud of me: “Loving with a big L” (Can’t overstate the love that flows back, Grampy.)

• Harry said he can’t imagine the mental games I must be playing out there. (It’s true brother.)

• Lucy wrote about the reel where I was smoking in the rain. Said I was, “the brightest star in the quagmire of Insta.” (an honor that you think so highly of the insta videos Lucy.)

Others wrote about marathons, their own bike trips, waking up in a cold sweat while launching a business. It hit me how many of you are out there doing your own hard thing.

Anyways I read them all. Every single one. Thanks.

Favorite Moment

Sleeping on a couch inside a restaurant my second-to-last night before the city. I asked if I could pitch my tent outside and they said no, sleep inside. They stoked the wood stove all night with whatever was lying around. Cow dung, thick strips of plastic sheeting, even some real wood. Smelled terrible but I didn’t care. It was warm.

Reflection / What I learned

When you’re out in the middle of nowhere, the goal is just to survive the day. Food, water, shelter, miles. In the city, it gets messy again. Noise. People. Too much choices. This is my first proper rest in months. I caught myself pacing my hostel room just to feel like I was still moving.

I’ve been thinking a lot about why I keep going. I tell myself it’s about finishing what I started. But I think it’s also about not knowing how to stop.

About one year ago today I stood in my ex’s doorway with a cardboard box. We were together for 4 years. Had biked halfway across Africa side-by-side. Seeing her again reminded me why we tried to make it work for so long. She was perfect. Small, gentle, adorable. But also capable and determined.

As I carried the last of my crap to the car she cried. I did not. I didn’t feel bad. I was too busy biking across continents and posting reels that maybe 200 people would watch. She wanted home and I wanted the road. I tell myself it’s about finishing what I started. Maybe it is. But really my only dedication is to the work. I guess that’s okay for now.

Traveler Tip of the Week

If you’re traveling through cold places, never trust the Apple forecast. It’s wrong. Always assume it’ll be ten degrees colder and the wind twice as bad. Likely from the front. Bring layers.

Gear Update

Two broken spokes this week. Rear wheel, drive side again. Need to find a shop tomorrow.

Progress on the Map

Distance Ridden Since Last Time: 464 miles (748 km)

Total Distance Ridden: 9,593 miles (15,438 km)

What’s Next

Waiting game. Chinese visa approval hopefully this week. If it works, I’ll cruise south toward the border, ferry to Korea, then Japan. If it doesn’t, I’ll have to find another way east. Either way, still moving. Just a bit slower for now.

Thanks again for sticking around through all this.

Have a lovely week,

Ian

Since Last Time

We crossed halfway through Mongolia. It’s been rough. Like, really rough. Cold. Wind. Limited access to towns/resources. Same scenery for days. The kind of riding that eats away at motivation. I came so close to breaking. Thought about flagging down a truck, throwing the bike in the back, calling it good. I didn’t though. Not yet at least.

Mongolia’s a different kind of hard. Not danger-hard like Afghanistan or altitude-hard like the Pamirs. Just this long, slow psychological grind. Space so big it starts to feel like it’s swallowing you. Some days I go hours without seeing a house. Maybe 10 cars the whole day. Like pedaling through a country that forgot it needed people.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~10,000 miles (16,000 kilometers)

• Key gear: patch kit, tent, cigs

• Key stops so far: Portugal, Spain, France, Italy, Albania, North Macedonia, Greece, Turkey, Iran, Azerbaijan, Kazakhstan, Uzbekistan, Afghanistan, Tajikistan, Kyrgyzstan, Kazakhstan, Russia, Mongolia

• Key stops coming up: China

Favorite Moment

Staying with a Mongolian family in a yurt after a brutal cold day. I showed up in the dark, nobody there. The door was locked, so I waited outside with my bike, half frozen. One dog was loose, terrified and going ballistic. The other one was tied up, quiet, friendly and eager for petting. After a while I saw headlights bouncing across the plain. Mom and daughter in a Prius, dad on a motorcycle corralling cattle back home as a team. They pulled up, saw me, didn’t even ask questions. Just unlocked the yurt, waved me in, poured tea.

Salty yak milk tea. Warm. Smoky. Smelled like dung and boiled meat. But I swear it was the best cup I’ve ever had.

They powered the yurt off truck batteries hooked to solar panels. Burned dried yak patties in the stove. Break-action USSR shotgun on the wall for wolves. Everything smelled like smoke and milk and animal fat, but it was home.

That’s what I’ll remember about Mongolia. You don’t have to earn people’s kindness here. It’s just given.

Reflection / What I learned

I used to do heroin. It was the easy way out. Bandaid on a broken arm. Everything wrong in life could disappear for a little while—like laying down in a warm field of daisies and not wanting to leave. The problem was always the same: eventually you run out, the daisies vanish, and the pain comes back.

Adventure became the replacement. Literal and spiritual. It’s still escape, just a better one. When things get hard out here—like this week—I can feel that old temptation creeping back. To make it stop. To find the easy path.

So I started visualizing two futures:

One where I push through. Japan. Snow. Pride. The kind of quiet victory no one else will ever fully get but me.

And the other: where I give up. Thumb out. Ride over. Ten years from now looking back with shame, remembering that I folded when no one was watching.

That comparison shut the mental chatter up fast.

Because quitting feels good right now, but the cost comes later and twice as bad.

Traveler Tip of the Week

Music and podcast recs. Because sometimes you need the crutch of distracting yourself from the ride.

Morgan Wallen. Some of my favorites: Thought You Should Know, Just In Case, 20 Cigarettes. Years from now he’ll be remembered for making country music a global pop force again. Like drake did for rap. Best artist of the 2020’s in my opinion.

And for podcasts: Waking Up, Conversations with Tyler, The Colin and Samir Show.

Also, for cold weather, double up with a second rectangle sleeping bag instead of upgrading to a down-filled mummy bag. We’re talking $40 versus $400. Way more comfortable and you can sit cross-legged or roll over inside instead of with it. Looks dumb but works.

Gear Update

Left knee is still hurting but it’s much better. Bit less climbing lately, and it’s warm enough to camp again. I’m really happy with the Nemo Kunai 3-4 season tent. I saw it in an old Outdoor Boys video. Good enough for them, good enough for me. Sold out most places, but maybe you could find it second hand.

Double sleeping bag setup is clutch—rectangle shape synthetic fill, cheap and bulky but warm. Everything smells like dung smoke. Accepting it as part of the brand now.

Progress on the Map

I write to you now from Bayankhongor. Roughly halfway across Mongolia. No major cities between here and Ulaanbaatar. Maybe 400 miles to go.

Distance Ridden Since Last Time: 648 miles (1,043 km)

Total Distance Ridden: 9,128 miles (14,690 km)

What’s Next

Push to Ulaanbaatar. Apply for Chinese visa. If it works, cross into China then maybe ferry from Beijing to Korea to Japan. I’m not going to make it home before Christmas.

Some days I wonder what the hell I’m doing out here. Then I remember: this is the work. Choosing the hard thing. Because it’s the only way that ever actually feels worth it.

Have a lovely weekend,

Ian

Crossed the Russian border with my transit visa. Ten days to get across Siberia before the clock ran out. Tried camping once. And only once. Too cold. Mornings started below freezing and stayed there. Roads built by prisoners under Stalin. Long flat stretches of nothing, then endless climbing.

The border patrol interviews felt more like a background check. Asked about family, religion, Ukraine, even if I had gay friends. They took my phone into a backroom and logged into my WhatsApp through their computer (without asking of course.) Russia is not a place that trusts easily.

Still, I made it through. Head down, quiet, polite. No police trouble. Just snow, ice, and the sound of my derailleur clunking abnormally, then freezing in place.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~10,000 miles (16,000 kilometers)

• Key gear: patch kit, tent, cigs

• Key stops so far: Portugal, Spain, France, Italy, Albania, North Macedonia, Greece, Turkey, Iran, Azerbaijan, Kazakhstan, Uzbekistan, Afghanistan, Tajikistan, Kyrgyzstan, Kazakhstan, Russia, Mongolia

• Key stops coming up: China

Favorite Moment

I arrived to a small town with one hotel. Fully booked. Temp forecast below zero. I was thinking I’d sleep behind the building or in a bus stop. Then two local tradesmen pulled up, offered me a bed in their room if I didn’t mind them drinking beers. Absolutely not.

They told me jokes in Russian I only half understood. Talked about our families, their favorite American movies. We shared beer, cigs, and lots of silence. Sometimes that’s all you need.

Last Week’s Videos

Clips from the Chuysky Trakt. The most famous road in Russia, fifth most famous in the world according to Nat Geo. Soviet engineering and prisoner labor carved it through the mountains. There’s a weight to it. Frozen rivers, ghost towns, Lenin statues. It’s history on asphalt.

Reflection / What I learned

Russia is heavy. The landscapes are cinematic but cold, distant. Everything feels built for endurance. Even the people. They don’t open up right away, but when they do, it’s deep and honest.

I got a lot of criticism online for going here. But being on the ground strips away the noise. The Russians I met were kind. Curious. Generous with tea, directions, space. Politics are top of mind, but face-to-face it’s just humans. Most people I talked to about Ukraine said some version of the same thing: “People are the ones who suffer.”

After a while I stopped trying to decode it. Just listened. Watched the snow swallow the road. Watched smoke rise from chimneys at dawn. Thought about how this country used to control half the planet, and now it’s quieter, older, still standing.

Traveler Tip of the Week

Bring cash into Russia. Foreign cards don’t work. You can’t buy a SIM card without a Russian passport. I used hotel Wi-Fi and limped through.

Gear Update

Buying clothes as I go to stay warm. “No such thing as bad weather, just bad clothing,” us Minnesotans like to say. My derailleurs froze solid from ice buildup. No Minnesotaism for that one. Front tire is balding but should make it. Gas station coffee has been the real fuel. That and sugar waffles.

Progress on the Map

Knee pain kicked in bad. Left knee. Cold mixed with climbing miles. Letting it heal now in Mongolia before pushing east.

Distance Ridden Since Last Time: 753 miles (1,211 km)

Total Distance Ridden: 8,480 miles (13,647 km)

What’s Next

Rest a few days. Let the knee recover. Then cruise east through Mongolia toward Ulaanbaatar. If all goes right, I’ll apply for the China visa early November. If that works, the home stretch begins. Japan on the horizon.

Have a lovely weekend,

Ian

We left Almaty after 10 days of visa purgatory. Russia said YES. I’ll be crossing the border on Monday morning. Then a ten day push through Siberia, drop into Mongolia, apply for the China visa in Ulaanbaatar, then ride across China and catch a boat to Japan. If disaster strikes in Ulaanbaatar, I have no idea what I’ll do.

From Almaty I rode north, all the way to a small Kazakh town about 115 km from the Russian border. Kazakhstan is endless. You stare at a black ribbon of asphalt stretching forever, like if you rode fast enough you could loop around the planet and see yourself coming. Locals say “close” and mean two days. Scale is broken here. Ninth largest country in the world and you feel it every mile.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~10,000 miles (16,000 kilometers)

• Key gear: patch kit, tent, cigs

• Key stops so far: Lisbon, Barcelona, Rome, Istanbul, Tabriz (Iran), Baku (Azerbaijan), Samarkand (Uzbekistan), Kabul, Bishkek (Kyrgyzstan), Almaty (Kazakhstan)

• Key stops coming up: Russia → Mongolia → China

Favorite Moment

Bike snapped three spokes back to back mid-ride. All on the drive side of the rear wheel. I actually thought that the wheel might taco under the weight of my gear. Within two minutes, someone stopped. We loaded the bike into the back of his truck, and he drove me all the way to the next town. At the shop, a woman brought out socks, bread, coffee, and snacks for no reason. The mechanic refused to take money. I asked why they were being so nice to me, and she just smiled. Didn’t understand the words, but I understood the feeling. There’s a kind of generosity here that sneaks up on you. Found throughout the Central Asia but certain pockets have bucketfuls.

Reflection / What I learned

Everyone here says the same thing when I ask how Kazakhstan is misunderstood: Borat. The movie wrecked their image. In reality, this is the richest, most developed of all the ‘stans. Almaty could be a European city—green parks, tree-lined boulevards, cafes, good wine. People dress sharp. Kids ride fixies downtown.

I went on a date with a Kazakh who grew up in Moscow. Seven years there, Russian university, but still raised Kazakh. Dual identity. She said most locals look down on Russians now. War changed things. Post-Soviet hangover, plus Ukraine. She said people assume all Russians support the government, and they don’t. She feels trapped between worlds.

Kazakhstan feels that way too. Half Soviet concrete, half glass towers. Nomad heart wrapped in modern skin.

Progress on the Map

Total distance ridden: 7,727 miles (12,435 km)

Traveler Tip of the Week

I’ve been workshopping gift-giving for months. Trying to find the best “token of friendship”. Let me tell you what I got so far:

• Small US dollars. Lots of $1s. Locals love them, not just as money, but as little souvenirs.

• Cigarettes. Reds.

• And bring an American flag. Everyone wants a selfie, and the flag makes every photo ten times better.

Gear Update

New rear tire (finally). Five broken spokes fixed. Chain-side job so needed a proper shop. The main reason that I hitched yesterday (Friday) was to make it before the weekend closure.

I’ve “cheated” six times so far: 1) Riding with mom in Barcelona, she got scared in traffic so we took the train: 20 miles. 2) Ferry from Italy to Albania: 135 miles. 3) war broke out in Iran mid-June, skipped half of it: 700 miles. 4/5) Two Kyrgyz tunnels were closed to cyclists: 2 miles each. 6) Broken spokes, hitchhike yesterday: 50 miles.

Grand total skipped: 909 miles

Grand total biked: 7,727 miles

Snow hit this week. Temperatures down to 25°F, colder with wind/rain. Dizzy riding sometimes. Could be the chill, could be the diet. Feels like the body’s running on fumes. But the road’s perfect, brand-new asphalt, decent shoulder, almost no traffic.

Kazakhstan feels safe. People don’t scam you. No fake taxi prices, no nonsense. Just straight shooters.

Random Notes

• National dish is Manti. Beef and onion dumplings, kind of like Central Asian xiaolongbao. Sweet, garlicky, chewy.

• Best cigs: Chapman Reds.

• Hotels cheap. Meals cheaper. Spending roughly $800-$1000/month total.

• Helmets technically mandatory, but nobody cares. (Except two police, but they really just wanted a selfie with my flag.)

• Drivers sometimes pass too close. Every time it happens, I swear, flip them off, then laugh about it. Probably fear disguised as anger.

What’s Next

Racing through Siberia and Mongolia. Winter is slamming shut.

If China denies my visa in Ulamnbaataar, I have no backup plan.

Either way, the road keeps going.

Have a lovely week,

Ian

Made it to Almaty (Kazakhstan). It’s a big deal. Last week was just grinding visa research, planning, logistics. My Russian embassy appointment was yesterday and I got the paperwork in. Fingers crossed for Tuesday when they tell me if I can go through Siberia or not. China visa not possible from here for Americans, so Russia is the route. If I get approved, it’s a 10-day push through siberia, drop into Mongolia, apply for China visa in Ulanbaatar, then cross China. Beijing → Shanghai → boat to Japan. We are about 3 months from finish line now.

I rode with Denis for a bit which was nice, then we split up—he’s going for china direct, easier for polish citizens. So I’m back to solo on Wednesday morning if the visa comes through.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~10,000 miles (16,000 kilometers)

• Key gear: patch kit, tent, cigs

• Key stops so far: Lisbon, Barcelona, Rome, Istanbul, Tabriz (Iran), Baku (Azerbaijan), Samarkand (Uzbekistan), Kabul, Bishkek (Kyrgyzstan), Almaty (Kazakhstan)

• Key stops coming up: Kazakhstan is done-ish, next is Russia → Mongolia → China

Quick AMA Recap:

• Kel – Do I smoke at home? No, only while traveling (price-based, skipped Australia completely.)

• Julie – Been cycling like this since 2016 (Alaska–Argentina first, then Africa, Australia, now Portugal–Japan.)

• Mie Harris – Most memorable human encounter? afghan guy with 4 wives & 30 kids, he lived in a huge compound, I slept on floor, woke up with hairy leg on my face. Some money got stolen but still wild story. Winter gear update: extra midlayer, gloves, double sleeping bag, new undies.

• Jess – Wind under your wings comment. I said yeah, I know how lucky I am to do this as a man, women can’t cross Afghanistan the same way.

• Merriah – don’t stress visas, it’ll work out. Agreed.

• Maggie – Loneliest moment? Getting chased out of afghan village, sleeping in a field. Most joyful? Camping with Denis last week, fire, we found a central asian pit viper.

• Justin Carroll – pedals: cheap flat platform pedals (Wellgo), if you’re a clipless rider it’s best to go shimano SD-EH500

• MJ – Google translate? Yes, constant. Diarrhea? Probably bad water. Stretching? Pushups, situps, sometimes pullups.

• Nic – How do I pick routes? Wind + traffic first, then which road has more towns/resources. Sometimes yell at ChatGPT until it gives me oddball sightseeing & WWII bunkers.

• Jacob – Winter plan: warm clothes + buy more as needed, double sleeping bag.

• Brianne – Human interactions are harder than nature. More unpredictable.

• Romano – Burnout: take breaks, then hammer again. Main driver is because I said I would finish this. Choose this life over corporate life. Worth the pay cut.

• CRD – 26” tube in 28” tire was because I couldn’t find the right size through Afghanistan/Tajikistan. Keep a short supply chain: only ship tech if I have to.

• Chels – Favorite cigs back home: American Spirit light blues if I’m fancy, otherwise whatever is cheap.

• Renate – sunscreen/sunglasses comment — I do hands & face sunscreen, let the rest get vitamin D. Not sure about sunglasses science.

• Dnise – Yes, financial hardship, but it’s tradeoffs. Many years of ramen & tent life. Substack makes cheap hotels possible now.

Favorite Moment

Pit viper night with Denis — campfire, cowboy camping under the stars, good conversation. Felt like a little living room in the middle of nowhere.

Reflection / What I learned

Been thinking a lot about tradeoffs. Money vs. freedom. Comfort vs. meaning. Can’t have both but I’m okay with that.

I’m technically unemployed right now. And it’s weird because that used to scare me. Back in the day I did what everyone said you were supposed to do: school, job, paycheck, benefits, weekends at the bar, binging netflix. And I was miserable. I escaped by using hard drugs.

Getting sober was when I started learning to make choices for myself instead of what society expected. You start asking, what do I actually want? And this is what I wanted. Riding my bike across continents, freezing my ass off in the Pamirs, eating boiled eggs in a tent, stressing over visas. I’d take that a thousand times over a fluorescent-lit office. I even liquidated my 401k. Just cashed it out and decided I’d rather spend my best years living than save it all for some hypothetical retirement that may never come.

It’s not glamorous all the time. It’s lonely sometimes. It’s hard sometimes. But this is me living the life I actually chose. Not one that was handed to me by default. And that’s worth way more than money.

Progress on the Map

Gear Update

Winter kit upgrades: crewneck midlayer, mitten-gloves, double sleeping bag system, fresh socks/undies, waterproof shoes, new rear tire. I ditched my stove to offset winter-gear weight gains. Bread and sardines from this point forward.

What’s Next

If the embassy comes through on Tuesday, I get my Russian visa and it’s game on. Siberia in October: ten days of cold, empty road. Logging trucks, tiny villages, steaming bowls of borscht. Campfires in the snow. This next stretch feels like the final boss. Last real “unknown” before the finish line. If you’ve been following along, now’s the time to strap in, we’re about to find out what I’m made of.

Have a lovely week,

Ian

We made it out of Tajikistan and into Kyrgyzstan. Stress levels dropped big time since last week’s issue. Compared to Taliban Afghanistan life feels more relaxed, a bit more familiar, easier to settle back into rhythm. Afghanistan was a mess, hard on the head. Tajikistan wasn’t easier, just a different kind of hard. Less politics, more landscape. Thin air, remote roads, little internet, and endless vertical gain every day.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~10,000 miles (16,000 kilometers)

• Key gear: stove, patch kit, tent, cigs

• Key stops so far: Lisbon, Barcelona, Rome, Istanbul, Tabriz, Baku, Samarkand, Kabul, Osh

• Key stops coming up: Bishkek (Kyrgyzstan), Almaty (Kazakhstan)

Last Week’s Videos

Two longer vlogs from Tajikistan. About the harassment incident that ended up highlighting more positive people and landscapes. And the wood-chipper chronicles with Denis, another long distance rider.

Favorite Moment

Staying with a Tajik family who run snowplows in winter. Their property sat near the 4,655m pass. They had a baby. Fed me yak yogurt, yak butter, and fresh bread. Offered a place to sleep next to their wood stove, and hours of talking. I’ll drop a photo of the baby down below.

Reflection / What I learned

Afghanistan was a cultural and political test. Tajikistan has been a landscape test. Out here the air is thin and metallic, like you’re breathing through a coin. I’d wake up with frost on the tent most mornings. Even boiling water takes forever.

The Pamirs aren’t just scenery. They’re characters. They tower over you, lean into you, ultimately test you. After cruising across Afghanistan I thought Pamirs would be easy. In some ways they were, but the climbing was endless. Trucks aren’t so common, and they drive fast, so it’s not possible to hang on. But the quiet is peaceful. Silence broken only by wind, squeaky pedals, or rocks clattering down onto the road.

Yaks move across the valleys like they own the place. Like they belong here in a way that you don’t. Tajik people feel the same way, built tough, but quick to soften with generosity. The ritual of chai repeats everywhere in Central Asia. Always a reminder that you’re not just surviving but being carried through by the people that live here.

The Pamirs remind me a bit of Bolivia. But here the harshness is constant. No break, no flat “easy days.” Just mountains that never let you forget how small you are.

Traveler Tip of the Week

Carry cigarettes even if you don’t smoke. Cigs work as currency, gratitude, friend-making. (Example: wood chipper guy in latest video) Also the brand matters. If you offer reds you might make someone’s year.

Progress on the Map

I write to you now from the end of the Pamir hwy in Osh, Kyrgyzstan. All the climbing put us significantly behind schedule, racing the calendar. Mongolia/Russia/China in October means snow.

Total distance ridden: 6,322 miles (10,224 km)

Gear Update

I’ve been running a 26” tube in a 28” tire for months now. It works. I told ChatGPT about this and he thought I was nuts. My rain fly pulled double duty as a blanket. Cigarettes still proving their worth. Everything holding up good but we still need tires.

What’s Next

Critical two weeks ahead. The route is Osh to Bishkek (Kyrgyzstan) to Almaty (Kazakhstan). Need to try for Russian and/or Chinese visas there. Both are tough for Americans. From Ulaanbaatar onward, the route depends on whichever one I can land. Anxiety is high because there is a chance that neither visa comes through. And then Ulaanbaatar is a dead end.

Q&A Invite

If you’ve got questions, drop a comment. I’ll answer them in next week’s post.

Have a lovely week,

Ian

We hit the Pamirs. 8,000 meters of elevation over 400 km (that’s like climbing Everest. almost.) Wakan Valley was brutal. Legs are smoked. Cortisol’s finally dropping now that we’re out of Afghanistan, but I’m still tense. Shouted at a kid this week and kinda hate myself for it. Haven’t posted much, just trying to reset.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~10,000 miles (16,000 kilometers)

• Key gear: stove, patch kit, tent, cigs

• Key stops so far: Lisbon, Barcelona, Rome, Istanbul, Tabriz, Baku, Samarkand, Kabul

• Key stops coming up: Osh, Kyrgyzstan

Last Week’s Videos

Very little worth shilling this week. Took a break. Here is the final Afghanistan video.

Favorite Moment

Guy at a roadblock standing next to his Land Cruiser. Said he used to live in Lansing, Michigan. I asked what he’s doing now.

“I live in Khorog.”

Are you a businessman?

“No.”

Just deadpan. Classic Russian personality.

Makes sense. Russian still lingers everywhere here. People say “hello” in Russian instead of English or Tajik. Big blocky soviet style apartment buildings. Old Lenin statues in a few towns, cracked but untouched.

Reflection / What I learned

That one moment shouting at a kid, he was just being a kid, chasing after me like they all do. But I snapped and swore at him. Felt bad after. I think it says a lot about my headspace. A month of survival mode in Afghanistan, being the center of attention 24/7. Not harassment. But it was relentless.

And I’m weird. I get overstimulated and don’t always respond right. I chose to be here. That’s something I keep reminding myself. I don’t get to pick how people act, only how I receive it. Lately been failing at that and took a bit of a video break.

Tajikistan has been a reset in some ways. More used to tourists, more chill. I asked a guy if there’s such thing as the “Tajikistan dream.” He just said, “There is no such thing as Tajikistan dream. There is only survival.”

It is a dictatorship here. They’ve had the same president since 1992. His face is everywhere, watching. At the border, posters warned against “extremism.”

Not as openly brutal as the Taliban. But maybe more subtle. Dissent is dangerous. A long beard can get you labeled an extremist. Too much visible religion and you’re suddenly a revolutionary. The lines are blurry on purpose.

Soldiers show up too, they woke me up one morning and told me camping near the border was forbidden. They weren’t threatening, just bureaucratic. Clipboard guys, not Kalashnikov guys. Funny to think Afghanistan was only a stone’s throw away, but my stress levels were already way down.

Traveler Tip of the Week

This one’s from Afghanistan, but it works everywhere. ChatGPT voice mode as a translator. I speak English, it spits out Pashto. The local speaks Pashto, it gives me English. So smooth most afghans thought they were talking to a real person. One guy thought it was a British woman (he was visibly uncomfortable) so I changed the voice to male to avoid breaking taboos. Worked like magic.

Progress on the Map

Last week’s distance ridden: 293 miles (472 km)

Total distance ridden: 5,779 miles (9,300 km)

Gear Update

Bike’s holding up. Me not so much. My right knee has been telling me it’s not happy. And we’re about to hit 4,655 meters (15,272 feet).

What’s Next

We go higher. The Pamir Highway properly starts now. It’s one of the highest roads in the world. Then into Kyrgyzstan. Then Mongolia. Then Siberia. Racing winter. Not sure if I’m mentally ready. But we’re doing it either way.

Have a lovely week,

Ian

Since Last Time

I listened to you. Read through every comment from last week’s issue. Went with option two, medium risk, medium adventure. That was solid advice. Because it meant I could ask around about the Tajikistan border without committing fully to it. Turns out the crossing I was aiming for was closed. Saved me from wasting the last days of my visa. So I turned back, and with that, my time in Afghanistan comes to a close.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~10,000 miles (16,000 kilometers)

• Key gear: stove, patch kit, tent, cigs

• Key stops so far: Lisbon, Barcelona, Rome, Istanbul, Tabriz, Baku, Samarkand, Kabul

• Key stops coming up: The Pamir Mountains

Last Week’s Videos

Obligatory shilling. I take you on a tour of an afghanistan cave house and the exterior wall of the US embassy in Kabul. Then we punch through the guts of Kabul traffic and clear the 2,500 m pass over the Afghan Kush mountain range. Locals kick me out of Khanabad, we ride 100 miles to make up time, find out the border is closed, and finally head backwards to Kunduz.

The last Afghanistan video will be in next weeks’ issue.

Progress on the Map

Last week’s distance ridden: 305 miles (491 km)

Total distance ridden: 5,486 miles (8,828 km)

Afghanistan

The word itself feels heavy. It’s been flattened into headlines for twenty years. Terrorism. Taliban. Bombs. Occupation. Withdrawal. It’s like the place only exists as a headline. But after (4) weeks here, I can say it’s a real place. And the reality is messy, nuanced, complicated.

Most of my experiences here have been positive. Overwhelmingly so. If I had to put a number on it, maybe 99 percent. Smiles, generosity, kindness, bottomless chai and endless meals. People who had nothing offering me something. People that should have been hardened by war instead showing me hospitality.

But to only say that would be dishonest. There were negatives. Someone stole ~4,000 afghani off me. I was heckled by bikers in Kandahar. I was kicked out of Khanabad, wondering if I’d actually make it out alive. My hotel room was raided, every corner of my bike searched. Detained at a checkpoint, brought deep into a Taliban stronghold where hundreds of fighters milled around. It ended peacefully, but it could have gone the other way easy.

Two Taliban once asked if I was military. If I’d said yes, I don’t think I’d be writing this. They used the word jihad in conversation. They debated what to do with me. What saved me was the little Taliban flag I carried, lots of smiles, and maybe just the fact that they knew if they killed me there would be consequences. America sends them forty million dollars a week.1 Self-preservation goes a long way.

Still, they offered me tea. They offered me food. They shook my hand and let me through checkpoints. That’s also the reality. It doesn’t fit neatly into good or bad.

Weirdest Moment

Men bringing young boys into hotels and chaikanas. Openly. I don’t need to describe it further, you know what it means. It’s part of life here. Same with rules where women are hidden, covered, kept indoors.

And then you think: if 80-90 percent of the population believes girls shouldn’t go to school past sixth grade, or women shouldn’t be seen in public without permission, do we really want to import that worldview?

What they do in their country is their business. We tried to change it. Spent 300 million dollars a day for twenty years. They weren’t interested. But if they come to America, that’s different. That becomes our business.

Thing I’ll Miss Most

The bread. The ice cream. Cardamom, rose water, creamy but not too sweet. The smiles, the chai, the meals shared with strangers. Invitations to sit. To stay. You never have to be alone here unless you want to be.

One afternoon I talked with a Taliban elder who, according to the shopkeeper, was a landmine placing expert. We laughed together. He offered to butcher chickens for a feast on my behalf. Sitting in the middle of nowhere, chatting with someone who might be on an FBI wanted list, and he’s offering to cook you lunch. Afghanistan, man.

Thing I Won’t Miss

Every single day someone asked me to take them to America. Tuk-tuk drivers, shopkeepers, kids on bikes, men in chaikanas. Everyone wants out. Everyone wants opportunity. But it’s relentless.

A few more details that stick:

• Kandahar is most conservative city in the world. They bashed on my hotel room door at 4:30 am to drag me to morning prayer.

• Shrines and mosques, architecture unlike anything I’ve ever seen. Colors that an iPhone can’t capture.

• Kids popping wheelies in full Afghan clothes—proof that some things are universal.

• Temperatures north of 100 degrees, me sweating through long sleeves and pants every day, trying to respect the culture.

• The best bread in the world. Chewy, crispy, perfect. And the best ice cream too.

• Taliban murals on the old U.S. Embassy wall, an American flag tumbling down, verbiage about islam and unity.

Afghanistan is Contradiction

It’s chai and kebabs on the floor with strangers who treat you like family. It’s checkpoints where one wrong answer might end you. It’s the most generous people I’ve ever met, and also some of the most restrictive laws I’ve ever seen. It’s mosques that take your breath away, and traffic that nearly kills you.

It’s kids popping wheelies. It’s Taliban giving me water on the highway. It’s men telling me America killed their family, but still sitting down to talk.

It’s all of it. At once.

What’s Next

Tajikistan. The Pamirs. The long road north toward Japan.

Have a lovely week,

Ian

Since Last Time

We left Kandahar and cruised into Kabul. Stayed in more chaikanas along the way. They’re cheap, filthy, but they do the job. Usually they’d recommend me to lock the door from the inside before I went to sleep. Yesterday I finally learned that many afghans won’t stay at them, too dangerous. Another case of the less you know. In Kabul I splurged on a nice hotel. Mostly because you’ve been good to me. Substack has grown from 500 to 3,000+ in just a few weeks. A lot of you upgraded to paid and that seriously helps. Thank you.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~10,000 miles (16,000 kilometers)

• Key gear: stove, patch kit, tent, cigs

• Key stops so far: Lisbon, Barcelona, Rome, Istanbul, Tabriz, Baku, Samarkand, Kabul

• Key stops coming up: Tajikistan

Last Week’s Videos

• Afghanistan so far, 20 pics from the road (19 now, Instagram deleted one.)

• The story of being banned from Instagram Live

• Arrival to Kabul, the most chaotic city in the world for traffic

• The story of the Bamiyan Buddhas

Progress on the Map

Last week’s distance ridden: 254 miles (409 km)

Total distance ridden: 5,181 miles (8,338 km)

Favorite Moment

Sleeping in a cave at Band-e Amir national park. Freezing cold. Like some Muslim hermit. I slept better than I had in weeks. This park is unfortunately off limits to women. Heard 6 Australian women got turned away by Taliban 100 meters from the lake. Band-e Amir is the destination in Afghanistan. What a shame.

What I Learned

After (3) weeks, I’ve had the chance to speak with different afghans about their culture. I’m going to share what I’ve learned, but this topic touches a lot of taboos. Just a warning.

To start, I think I finally understand why so many people here accept Taliban rule. It’s not about brainwashing or fear. It’s that for most Afghans, especially rural ones, the Taliban’s rules align with how life has always been, pre US occupation.

A girl kicked out of school after 6th grade isn’t a bad thing for them. It’s just normal. Her job is to raise kids. A man’s job is to work the land. The family structure is everything. And a good thing. ~80% of Afghans feel this way.

Even people who don’t like the rules mostly accept them. Because this country runs on deferring to elders. Talibs follow the council. The council speaks for God. You just don’t question that chain of command.

The sex taboos here are different too. People joke about it openly. My Bamiyan guide told me about his cousin, dirt poor and illiterate, that used to have sex with cows. The guy ended up working with Americans and got evacuated to the U.S. Meanwhile, my guide—savvy, fluent in English—is still stuck here. He jokes that maybe he should have been doing the same all along.

And then there is the phenomenon of older men having "sons.” Young boys that they raise, protect, and also sleep with. It's not considered gay and it’s not seen as abuse. It’s just part of how some men fulfill their obligations to their communities. It’s about love, mentorship, family. Nobody questions it, at least not publicly. When the boy hits puberty, the relationship ends, and the man helps him start his life.

Marrying your sibling is forbidden by islam but cousin marriage is common. It's a way to control land and assets. You know you can trust both “sides” of the family which is no small thing in a country like this. Inbreeding is a real issue, but it's not viewed as a problem, just part of the tradition.

Conclusion: My view is that you don’t have to agree with any of this to try and understand it. Afghanistan isn’t just conservative but extremely structured. Everything: gender, sex, family, education, is tightly controlled. And for a lot of people here, that’s not oppression. It’s stability.

Traveler Tips of the Week

• Don’t linger in one town too long. The longer you stay the more attention you draw. And not all of it is good.

• Dress local. It’s one of the best ways to stay low profile. Seriously underrated.

• Show respect to Talibs. They have the authority to slap, arrest, or kill anyone. As a tourist, you’ll get more leeway, but you shouldn’t test it.

• Have your travel papers in order. You’ll need them often.

• Afghans are extremely generous, even when they have very little. Always refuse free food and drink at least once, sometimes two or three times depending on how strong they’re insisting.

Gear Updates

Tubes are still holding air. Tires are worn out. Cigs go for 50 cents per pack. Body is tired but spirits are high. One more push to Tajikistan—should be easier to find resources there.

What’s Next

I need your input, there are two ways to get to Tajikistan:

1. High risk, high adventure. Gravel roads, remote valleys, deep rural areas. No internet. Lots of uncertainty. Exciting and kind of terrifying.

2. Medium risk, medium adventure. Mostly paved roads, mid-size towns. Still no internet. Less chance of things going sideways.

I don’t want to take the easy way out, but I also don’t want to get in over my head. What do you think?

Have a lovely week,

Ian

Since Last Time

We left Herat, headed for Kandahar. And on day one had the first of many flats. I spent the rest of the week fighting with my tires—350 miles over 5 days to arrive in Kandahar. Early morning riding, dust, heat, traffic.

I also got banned from Instagram Live for a year for “glorifying the Taliban.” So that’s cool. I realize now that Instagram could simply decide to kill my account at any moment. And so I appreciate you for coming to Substack from Instagram/TikTok.

Anyways we’re officially back on our original route, heading east from Iran across the entirety of Afghanistan. Herat to Kabul to Tajikistan.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~10,000 miles (16,000 kilometers)

• Key gear: stove, patch kit, tent, cigs

• Key stops so far: Lisbon, Barcelona, Rome, Istanbul, Tabriz, Baku, Samarkand, Kandahar

• Key stops coming up: Kabul

Last Week’s Videos

Getting hosted by Naqibullah and Fardin

Four flats in one day

POV: fixing a flat and this guy decides that it is a good place to pray to Mecca

Arrival to Kandahar

Rest day in Kandahar

And for today, pushing off from Kandahar towards Kabul—meeting so many strangers, trying local food, and sleeping in another weird hotel:

Progress on the Map

Last week’s distance ridden: 301 miles (484 km)

Total distance ridden: 4,796 miles (7,718 km)

Favorite Moment

Early morning rides between 3:45-sunrise. They would reveal a whole different Afghanistan. Peaceful, sleepy—I would see people sleeping outside on rooftops, sidewalks, anywhere really. Whole towns curled up in the open air trying to beat the 110°F days.

What I Learned

Meta flagged my content as “pro-Taliban.” Hopefully you know me better than Meta’s AI content moderation algorithm. But I don’t think it’s smart to be critical while in Taliban controlled territory.

Here’s what I’m trying to do:

• Show what daily life is like here, without inserting my own opinions too much.

• Document the kindness I receive, without suggesting that speaks for everyone’s experience.

• Stay safe, both in person and online.

Really, I am treated like royalty. People invite me in, give me food, offer their homes. But I’m also aware that it’s optics. I’m a guest and a symbol.

And at the same time there is tension. Resentment just under the surface. Some people look at me like I’m famous, and others like I personally ordered strikes. Both can happen in the same afternoon. It’s complicated and I’m still figuring it out.

Mentally I’m doing good, just a bit overstimulated. It’s like being the only fish in a tank at a restaurant full of curious eyes. Every 15 minutes someone pulls over, wants to take a selfie, chat, offer tea. It’s nice, but it adds up. Chaikanas (tea houses where you can sleep) are my only real decompression zone right now.

Traveler Tip of the Week

Hydration tips: every time I stop I try to chug 1.5 liters of water. Sometimes it’s boiling hot. But the body requires it. Roughly 1 out of 2 bottles that I chug are salted. For my animals in the audience doing similar hard things, take the amount of salt that you think you need, then double it.

Gear Updates

14 patches on one tube. That’s a new record.

Also. Taliban checkpoint guards suspicious of three things:

1. Tripod (looks like a bipod)

2. Peak Design Out-Front phone mount (they think it’s military)

3. Bike computer (counts kilometers, not laser targeting, I swear).

Also. My phone overheats constantly. There was a clip in a recent video where I was skitching next to car full of tomatoes. They had a tire blowout, huge curveball. I didn’t get it on camera because my phone overheated and shut itself down. Everything is running hot.

What’s Next

Heading to Kabul, then onto Bamyan to see the buddhas. Staying in cheap chaikanas (~$7/night) just to get a break from the constant attention. Trying not to advertise I’m American too loudly. In Kandahar the vibe changed, more suspicious and less friendly. Still safe, but staying sharp. We’ll see what Kabul is like.

About the theft, someone stole ~4,000 afghani (~50 USD) from my bag during the night. First time that it’s happened in years. I didn’t notice until long after, but I’m not upset. Just a bummer. Happens.

Finally, take a look at this state media produced Facebook video that I didn’t know I was acting in. 500K views. People keep showing it to me when I stop. The secret is out that an American is biking across Afghanistan.

Have a lovely week,

Ian

We crossed into Afghanistan six days ago and have now ridden for two. First impressions are way different than I expected. I was kind of bracing for chaos, and it has been chaotic. But it’s also extremely welcoming. The culture here really values helping travelers. I get offered food and drinks daily. A few folks straight up refused to let me pay, and not for trivial amounts of money.

Afghanistan is dirty, hot, harsh. But the people have been good to me.

Route Recap

• Start: Lisbon, Portugal

• End: Tokyo, Japan

• Total Distance: ~10,000 miles (16,000 kilometers)

• Key gear: stove, patch kit, tent, cigs

• Key stops so far: Lisbon, Barcelona, Rome, Istanbul, Tabriz, Baku, Samarkand

• Key stops coming up: Kandahar, Kabul

Last Week’s Videos

• Getting a Visa to Afghanistan

• Entry to Afghanistan

• Riding from the Border with Iran to Herat

• A Rest Day in Herat

• And Yesterday we rode southeast out of Herat—starting at 5 am to beat the heat. Lasted 120 km before tire problems killed the day. Here is the video:

Progress on the Map

(We’re heading backwards now—riding the same road we bussed before, Herat to Kandahar.)

Last week’s distance ridden: 149 miles (240 km)

Total distance ridden: 4,495 miles (7,249 km)

Favorite Moment

Taliban checkpoint waved me through with tea and BIG smiles. One Afghani sign of grace: when a man puts his left hand over his heart while shaking hands with his right. You can see it from the Talibs in the video.

Also I showed them my Taliban flag. They liked it.

What I Learned

Afghanistan is not what the news tells you. At least, I haven’t seen it yet. The assumptions I had: danger, theft, hostility, haven't really lined up with reality. People are proud of their country. They want tourism. They want connection. And they’re excited to see a foreigner riding through.

There is also a kind of quiet grief. On the busses I talked to a railway engineer and then a professor. The railway engineer, wants to study in Germany or Japan, study their railways, and then build a modern rail network across afghanistan. He said war is what stopped them from developing one already. The professor I talked to told me straight up that he’s not a fan of the current government. Most of the educated people I’ve talked to, they’ve got family in Australia or Europe or USA. And they’d like to go join their family abroad.

It’s hard not to feel that. The tension between pride in country and their desire to leave it. It’s the reason that I try never to complain. My movement here is by choice but for so many people, all around the world, it’s about escape.

Despite all that there is unbelievable friendliness. There’s a deep cultural pride in helping strangers. And that’s what I keep running into.

So yeah, this week’s learning is that the boots on the ground view doesn’t match what you get in the headlines. The reality is messier, more nuanced, more human that what you expect. You don’t get it from the headlines but you get it at a Taliban checkpoint. Or chatting up a stranger on a bus.

Traveler Tip of the Week

You can’t buy a 700c tube in Afghanistan. Patch what you’ve got. Pray it holds. Two is one. One is none.

Gear Update

Flat tire -> fixed it -> pinch flat while reinflating -> more glue -> out of glue -> hitched a ride on a moped back 10k to next town -> moped broke down -> we called another moped -> temporary fix -> fix failed -> bus back to Herat -> tried to buy new tube -> no dice -> now trying to repatch the repatched repatch and hope it sticks.

Short version: the supply chain in Afghanistan doesn’t support international bike gear. Bring extras or suffer.

What’s Next

I’m going to try and limp to Kandahar on the tube that I got. I’ll continue riding at dawn to avoid the heat. It’s 100+ degrees daily, there is no shade, and dust everywhere. Not exactly ideal cycling weather but this is the hand I’ve got, and honestly, I dig it.

Have a lovely week,

Ian