Hi friends,

Here’s what I want to share this week:

​How Philosophers Think: I’ve made studying philosophy with friends one of my top priorities. I audited a class at Columbia and hired tutors to help us. To my surprise, absorbing their method of thinking and not necessarily the ideas themselves has given me the biggest benefit. This essay is a step-by-step demonstration of how philosophers navigate the intellectual world.

The essay is now a YouTube video too.

Coolest Things I Learned This Week

Social Writing

In school, writing is a solo experience. Usually, the writing process looks something like this: we take notes while a teacher lectures until it’s time to start writing an essay. Then we complete the assignment by locking ourselves in the library, and once it’s time to publish, we share our work with one person: the teacher.

The Internet is different. It turns writing into a social experience because publishing ideas attracts like-minded people who become friends and conversation partners.

Social writing is much more enjoyable and you can reap the benefits without a big audience. Many of my best Internet friends were people I met in the early days, just after I started this newsletter. It’s like music. Ask an artist when they met their favorite fans, and they’ll tell you not about the normies they met at Madison Square Garden but the die-hards who attended their early shows at cozy bars and small theaters.

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Why Writers Don’t Publish

The purest vision of perfection is reserved for people who never take action. Ask them why they haven’t written anything in a while and they’ll tell you they’ve been “busy with work” or “thinking through an idea.” Deep down, they dream of becoming a writer. Because of that, they spend a bunch of time reading. Whenever they encounter a brilliant piece of writing, they say: “I could do that.”

And yet, they never publish anything themselves. They’re afraid to expose their ideas to criticism and tormented by the judgment of friends and family. What if I embarrass myself? What if I get something wrong?

And when it’s time to put words on paper, the quality of their first draft rarely matches the image of perfection in their mind. Since it’s easier to live in that perfect vision, no writing gets done. The excuses pile up too. “Busy at work” turns into “I’m waiting for a better writing setup,” which turns into “the kids are keeping me occupied.”

When that vision of perfection gets too cozy, writers ignore the call to create work. It’s okay to ignore it for a day. A week, even. But the consequences of ignoring it for a lifetime can be haunting. Best to start now.

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When Spending Money is a Problem

When there’s a problem in an organization, our first instinct is to spend money. People close to the problem assume it exists because of a lack of resources, so they ask for funding to solve it.

But often, the problem doesn’t stem from a lack of resources. It stems from bad thinking. And when bad thinking is the culprit and you spend money to fix the problem, you fund the further existence of the problem. People learn that they’ll get more money if the problem persists, which incentivizes them to make the problem worse — even if they say they’re trying to make it better.

The Write of Passage team talks about this all the time. Whenever somebody wants to spend money, we ask: “What root problem are we ignoring?”

Only once the problem has been examined and we’ve applied free solutions will we look into spending money. Earlier this year, we were receiving a flurry of customer service emails during launch week. Our impulse was to immediately hire a customer service representative. But once we investigated the problem, we saw the need for various projects that didn’t require a major financial investment. First, we added an FAQ page. Then we created an internal guide to answering common questions. Both accelerated our response times with much less effort. Because of them, the customer service representative was much more productive once he joined too.

From government to healthcare to corporate balance sheets, the problem is often a spending problem instead of a revenue one. The challenge is that creative solutions take time. Their pain is felt in the present, while their benefits are felt in the future. Financial solutions are the opposite. Their benefits are felt in the present, while their pain is felt in the future.

Lengthen your time horizon and resist the urge to immediately spend money.

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​Psychological Moonshots​

Rory Sutherland calls these non-financial based improvements “psychological moonshots.”

Here are some examples:

• Passengers on the train from London to Manchester might complain that the train is taking too long. The obvious solution is the most expensive: make the train faster. But what if you made it more enjoyable? You could speed up the WiFi or improve the food service, both of which are much cheaper.
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• Waiting for taxis is annoying when you don't know when it'll arrive. The obvious solution is to increase liquidity and make them drive faster. But Uber’s genius wasn’t reducing waiting time. Instead, by sharing the car’s location and giving you an ETA, the map makes the wait less frustrating.

How many of our problems come from a lack of creativity, not a lack of resources?

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​The Wisdom of Markets​

When markets work, they're like a pointillist painting.

Zoom in and the brushstrokes look chaotic and disorganized. But zoom out and you’ll find a cohesive synthesis of individual actions.

Photo of the Week

I visited Montreal for the first time this weekend.

Here are my general impressions of the city, based on walks around town and casual conversations with friends:

1. Culture: My favorite thing about Montreal is its commitment to culture. French is the dominant language, which is partially why it feels more like Europe than North America. Restaurant names must have French in them. Starbucks is called Café Starbucks and a restaurant I went to yesterday called Darling is formally known as Le Darling. This respect for tradition shows up in beautiful buildings and a respect for culture as an end in itself that’s increasingly rare in the 50 States.
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2. Groceries: Maple syrup is sold in cans. Milk is sold in bags.
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3. Vibe: Architecturally, the city feels like a combination of Paris, Detroit, Amsterdam, and New York. The French fingerprints are evident in its Haussmann architecture, the Detroit feel comes from old manufacturing plants, the Amsterdam influence shows up in the narrow and walkable streets, and the New York vibe shines through in Art Deco office buildings and tenement-style homes.
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4. Cost of Living: Montreal is much cheaper than Toronto, in part because people need to speak French in order to work here. When fewer people move here, demand for housing falls, and when the demand for housing falls, so does the cost of living.
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5. Maid’s Quarters: Like Paris, the top floor of the Haussmann style apartment buildings are painted a different color and have a sun blocker over the windows. Today, we think of the top floor as a luxury. But before the invention of the elevator, these top floors were reserved for the maids who had to walk up the stairs.
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6. Density: Wages are further driven down by urban density. Like Paris, since so many of the homes are three-unit apartments, the city is dense even though there aren’t many high-rises.
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7. Moving Day: A disproportionate number of apartment leases end on the same day: July 1st. According to a 2013 estimate, 7% of the city’s population moves on this single day. The tradition began as a humanitarian measure instituted by the French colonial government so people wouldn’t be evicted from their homes before the winter snow had melted. But can you imagine the headache for moving companies? To make matters more difficult, apartments in Montreal don’t come with kitchen appliances which makes moving even more difficult.
   
8. Staircases: Many homes have outside staircases that lead to 2nd and 3rd floor apartments. I was perplexed by them because they freeze in sub-zero temperatures, which make them dangerous. Why then would such a cold climate have outdoor staircases? Two reasons: (1) most homes are setback from the sidewalk to limit crowding and prevent ice from falling on pedestrians' heads, and (2) putting staircases outside the home reduces the square footage, which limits property taxes and the amount of space you have to heat.
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9. Construction: I’ve never seen a city with so much street construction. On the 10 minute walk from my friend’s home to the gym, there are six different construction projects happening, half of which are blocking the entire street. The charitable interpretation is that the weather makes it hard to keep the roads in good shape. But locals blame organized crime. According to one whistleblower, the Montreal mafia controls 80 percent of road contracts. Another headline reads: "We rigged contracts and paid a 2.5 percent cut to the mafia.” Also, urban roads cost 46 percent more to build in Quebec than the rest of Canada.
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10. Toronto vs. Montreal: At the beginning of the 20th century, more than 50% of Canada’s GDP originated in Montreal. According to one estimate, it was also home to more than 70% of the country’s manufacturing, which is why Montreal is such a rail hub and had one of North America’s busiest ports. But Montreal’s dominance began to decline when the St. Lawrence Seaway, a system of canals and channels that allow ships to travel from the Atlantic Ocean to the Great Lakes, opened in 1954. Since then, Canada’s economic center of gravity has shifted to Toronto. Succession is also to blame. Though the calls for Quebec to secede from Canada have died down, multinational companies like Sun Life anticipated the threat and proactively moved their headquarters to Toronto in 1978.
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11. Downtown Montreal: Based on the city’s architecture, it seems like Montreal lost a lot of momentum after the 1980s. For starters, the city hosted the 1976 Summer Olympics, which implies that it was quite prominent then. Walk through downtown and you won’t find many buildings constructed after the late 1980s. My two favorite buildings, the Royal Bank and the Aldred Building, were constructed in 1928 and 1931 respectively.

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