Afghanistan Isn't a Headline
Biking to Japan Week #28
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
Multiple people told me $40m. But there’s no credible evidence that U.S. sends Taliban tens of millions per week as direct payments. Here's what’s verified:
The $40 million/week figure comes from a political statement and likely refers to cash routed through the UN into the Taliban controlled central bank, not direct payments to the Taliban as a group.
Much larger sums ($80 million every 10–14 days) represent humanitarian cash deliveries overseen by the UN for the benefit of the Afghan people, not the Taliban.



Ian - I found your account on Monday and am in a complete parasocial relationship by Sunday. This Afghanistan chapter really stressed me out and I’m wondering if our relationship can survive you going to Russia 😂😜 in all seriousness I’ve absolutely love this disruption to my young kids - mom - 30s something -themed feed. Reminds me of the vastness of our world.
You leave me with more questions:
How did people react to seeing you film? Especially while at checkpoints.
How are you able to navigate seamlessly without knowing the language (I’m in awe).
Were you able to speak to any women in Afghanistan about their experience?
Anyways, I’m glad you made it through the border safely. Keep going! Myself, and I’m sure others, are invested in your journey. It’s inspiring. I’m grateful for a raw and colorful look into other parts of the world.