Castles in the Sky is a weekly dose of truth, beauty, and humor to combat intellectual loneliness and existential boredom. For more essays, stories, and curated content visit the archive.
Note from Charlie: Welcome to the first full issue of Castles in the Sky!
“The more of a noob you are locally, the less of a noob you are globally.”
Paul Graham

My two favorite hobbies are reading good stories and meeting weirdos.
Reading a good story is a great way to really learn something. It short-circuits the intellectual scripts we have that tell us what is familiar or unfamiliar. I’ve been writing a lot of fiction lately because there are good ideas I want to share. Stories use beauty, humor, or suspense to launch an idea straight past our defenses. So I’m practicing writing fiction and gathering inspiration from more straightforward essays full of good ideas by people like Paul Graham.
Paul Graham is the founder of Y Combinator, a Silicon Valley accelerator responsible for having its finger on the pulse of technological innovation since 2005. He’s referred to as “the Yoda of Silicon Valley,” both because of his prescience as an investor, and because of the wise, concise essays he posts on his website. One of my favorite essays of his is “Being a Noob.” (Noob is a term borrowed from online multiplayer video games, a shortened form of “newbie” that means someone who is new to something and unfamiliar.)
In his essay, Graham makes the case that nobody wants to feel like a noob because it is embarrassing and uncomfortable. He explains this makes sense as this discomfort was a helpful signal for a long time. For most of human history, the world didn’t change that much over the course of someone’s life, so it was better to stick to what was familiar. But now, the world is changing so rapidly, that we should update our ideas about being a noob: mainly, that it is preferable to lean into this feeling, and not denigrate noobs. He also makes the great observation that, “the more of a noob you are locally, the less of a noob you are globally.” Meaning, that for every situation you put yourself into as a noob, you bring that much wisdom and resilience to a future situation.
This idea that “the more of a noob you are locally, the less of a noob you are globally,” really spoke to me. For three years, I lived in China, and I made a lot of friends from China and from other places all over the world. When you live in another country around other people from other countries, you may start to often play this game with yourself where, every time someone does something weird, you ask yourself, “cultural difference or personal idiosyncrasy?” After a while, you start to develop an idea of why people from certain parts of the world act the way they do, and how some people are just stone-cold weirdos. The longer I’ve been alive, the more I’ve found that I gravitate to the latter.
I was raised in a bookstore among book people. I spent a lot of my twenties traveling, hanging out with digital nomad types. I’ve spent the last eight years working with entrepreneurs. Since adolescence, I have spent long periods of my life doing (some standup and a lot of) improv comedy. Many of my closest friends and loved ones are in recovery. This is to say that from digital nomads, entrepreneurs, comedians, book people, and people in recovery--I love weirdos. I love people who don't really fit in. I love people who are rebuilding their life or have had to rebuild it before. I think that the mix of kindness, gallows humor, unusual interests, and outside-the-box thinking you find among many weirdos is the most fertile soil out of which to grow an interesting, fulfilling relationship. These are the people I like helping and spending time with, and among whom I’m most myself.
There are two weirdos in particular I remember quite well from China. Their names were Savant and Seamus.
Savant was a Chinese guy in his mid-twenties who I met at a Couchsurfing meetup. For the uninitiated, Couchsurfing was like Airbnb before Airbnb, but it was free and run off vibes and community vouching. It was incredible until a finance firm bought it up to find a way to make money from it and ruined it. Anyway, I thought Savant was super aloof. He went by Savant, but I never even learned what his real name was. He had the affect of a sensitive artist, taking lots of thoughtful pauses, speaking slowly and serenely with a soft voice and light hand gestures, and had exquisite taste.
Like a sensitive artist, Savant was aloof but this never came across as pretense or touchiness. On the contrary, he was exceptionally disarming. I remember the second time I met him I asked what he’d done that day and over two minutes of thoughtful pauses, he slowly said, “I walked to the Catholic church to sit and think. It was my first time, and I am not Christian. But I could feel something, like people’s feelings and hopes were in there.” The cocktail party we were at fell away and I was mesmerized—it was like I was there with him in the pew. I grew up in Catholic churches and one throwaway line from him had added a new shade of how I feel about them.
Then one day, Savant just disappeared and quit answering all our messages. I have no reason to suspect anything bad happened as this was common on Couchsurfing.
Seamus was an old Irish guy. I only hung out with him for one night. In all candor, I don’t know his real name because we never exchanged names. But we hung out for about five hours. I was standing by the bar at a nightclub in Shenzhen, and suddenly he had materialized next to me. He was cracking jokes and buying drinks, but looked very out of place. He was very short, wearing a beanie and a trenchcoat, despite the fact the bar was outside and the weather was muggy. He was also about forty years older than everyone else in the club. On his other side were two friends he came with named Ralf (from the Netherlands) and Nils (from Germany), who were both closer to their mid-twenties like me.
Seamus had me and his friends laughing all night. Multiple times he would buy a round of drinks for people nearby, or start a miniature dance party with us and some women walking by, or tell a loud, well-received joke in English or Irish-accented Chinese to a group of people waiting at the bar. I was having such a good time I shared taxis with Seamus, Ralf, and Nils to three other clubs that night, and around 4:00 am we ended up at an after-hours restaurant. As we arrived at the restaurant, Seamus went to have a smoke or something and disappeared. Ralf, Nils, and I waited a few minutes then sat at a table and decided to order food and start eating.
When the main courses started arriving, I asked Ralf and Nils how long they had known each other, and how long they had known Seamus. Cue some hilarious stories and tons of laughter as the three of us realized that actually, none of us had met before that night, or known Seamus from anywhere except the bars we had been to. All of us had a similar story of Seamus materializing under our elbow and is getting caught up in his party whirlwind. Ralf and Nils went on to become two of my best friends during my time in China. I never saw Seamus again.
Savant, Seamus, and other people like them were some of my inspirations when I wrote the character Sami, in The Masculine Urge to Visit a Psychic Giraffe in Khartoum. In this scene, the narrator and main character is explaining what happens after he first meets Sami and is entranced with him:
I followed Sami as he busked across Barcelona. A few times we narrowly escaped fines and capture from the authorities, as Sami never had a permit to play music publicly. He also never wore shoes. He always wanted to dance. He would eat off strangers’ plates. He was paranoid in ways that inspired paranoia in others. He was intoxicating to listen to but infuriating to argue with. He was highly logical but all of his premises were false, outright bullshit, things he misheard, and things he just plain made up. He would burp and fart and laugh like a horse after he ate or drank anything. He had an annoying habit of noting any negative emotions he sensed in you. He would not have fit in anywhere. But that did not matter, because he had a mischievous smile, kind eyes, and he could sing or play anything on his weather-beaten Spanish guitar.
In the story about Sami, and my anecdotes about Savant and Seamus, I am trying to convey a shade of what I think Graham meant when he said “the more of a noob you are locally, the less of a noob you are globally.” In weirdos, we often find something transcendent. They are not devoid of their origins: Savant loved speaking in Chinese parables called Chengyu, and Seamus had an incredibly thick Dublin accent, plus he ordered Guinness at each of the four bars we went to. But you realize that, although they seem ill-fitted for a given situation, they are uniquely themselves across different situations.
Meeting weirdos is powerful because it makes you consider what you think is “normal,” and what is “abnormal.” This kind of reassessment is one way to make your life happier, more interesting, and more psychologically rich. A good story can do the same thing.
Writing and Life Updates
Writing Update
Starting next week, I hope to change the cadence of the newsletter.
Monday will be for longer or standalone essays. This is where I will release book reviews, long-form essays, commentary, and any special occasion essays. The first will come out in the next two weeks. I am starting something new called The Enchanter Series, where I spotlight the work I enjoy most from some of my favorite writers.
Wednesday will be for the numbered Castles in the Sky newsletters. These will keep the same format they have now, where there is a 500-2,000 word essay, followed by updates on my writing and personal life, and a melange of links and excerpts I think you’ll enjoy.
Friday will now be for fiction.
You can count on receiving a newsletter every Wednesday, but Mondays and Fridays will be on an as-finished basis.
Personal Update
Through the magic of the internet, last year I was exposed to some funny videos made by people who were diagnosed with ADHD as adults. I was like, “haha–that’s funny, but that’s how everyone is, right? . . . right?”
I have since talked to a ton of people with ADHD, and each conversation was like a cascading series of epiphanies that lead to me looking for a professional who could tell me definitively whether or not I have ADHD. As it turns out, this is much more difficult than it sounds.
I’ve always been interested in identities–how they are cultivated, what meaning they have, and whether or not they can be changed. Many of the symptoms and behaviors associated with ADHD are things I have always assumed were my personality. So I plan to get an official diagnosis and seek treatment if necessary, if only for the certainty of knowing that I have ADHD.
Then, I plan to explore, in writing, (both the Kafkaesque ritual of navigating the US healthcare system and) the way receiving or not receiving a diagnosis of ADHD changes my concept of who I am.
Thoughts and Threads
When Being a Noob is an Asset
One of my favorite writers of all time is Joseph Conrad. Considered one of the greatest prose stylists of all time, he did not speak fluent English until his twenties. Certainly, this made him a Noob. However, as he learned to speak English fluently, this newness, the sense of novelty in his writing, gave him a “weird” sensibility that made him stand out. As noted on Wikipedia:
Rudyard Kipling felt that "with a pen in his hand he was first amongst us" but that there was nothing English in Conrad's mentality: "When I am reading him, I always have the impression that I am reading an excellent translation of a foreign author."[6] Cf. Zdzisław Najder's similar observation: "He was [...] an English writer who grew up in other linguistic and cultural environments. His work can be seen as located in the borderland of auto-translation."[7]
Weirdos to Watch Out For
As much as I love a weirdo, I hope this newsletter doesn’t come off as an unthinking endorsement of anybody who’s a little eccentric. On the contrary, as much as I believe we should embrace our weird side, we should be just as wary of weirdos as we are of everyone else.
Last week The Atlantic made this case better than I could in their story, The Internet Loves an Extremophile. These are some of my favorite passages:
On where the weirdos are suddenly coming from:
As churchgoing declines in the United States and Britain, people are turning instead to internet gurus, and some personality types are particularly suited to thriving in this attention economy. Look at the online preachers of seduction, productivity, wellness, cryptocurrency, and the rest, and you will find extremophiles everywhere, filling online spaces with a cacophony of certainty. Added to this, the algorithms governing social media reward strong views, provocative claims, and divisive rhetoric. The internet is built to enable extremophiles.
On why they are doing it:
Not every internet guru follows this pattern. Some influencers have developed a genuine interest in a single topic and decided to make it into a career. But many other corners of the internet are full of serial enthusiasts who have pinballed from one ideology to another, believing in each one deeply as they go. These flexible evangelists are perfectly suited to becoming online gurus. They believe, and they need to preach—and because of the lack of gatekeeping on social media, the most talented talkers can easily find an audience online.
On what makes them different from normal people:
Unlike most of us, with our needling doubts and fumbling hesitation, extremophiles are fervent in whatever their current belief is. And they want to tell other people about it. For this reason, extremophiles have always made particularly good op-ed columnists—and now podcasters and YouTubers.
Extremophiles are more like the sociologist Eric Hoffer’s “true believers,” the people who fuel mass movements. “The opposite of the religious fanatic is not the fanatical atheist but the gentle cynic who cares not whether there is a God or not,” Hoffer wrote in 1951.
On origins, further research, effects, and why it’s suddenly such a huge problem:
Researchers of extremism are now studying its psychological causes as keenly as they are its political ones. “Psychological distress—defined as a sense of meaninglessness that stems from anxious uncertainty—stimulates adherence to extreme ideologies,” wrote the authors of a 2019 paper on the topic. Many people become radicalized through “a quest for significance—the need to feel important and respected by supporting a meaningful cause.” The COVID pandemic was so radicalizing because one single highly conspicuous issue presented itself at exactly the same time that many people were bored, lonely, and anxious. Cults usually try to isolate their followers from their social-support networks; during the pandemic, people did that all by themselves.
Crowd Work
In standup comedy, crowd work is when the comic speaks directly with the audience. I want to hear from you! Heckles and cheers go here.
I didn’t realize you lived in China for three whole years, that’s incredible!
Your point about questioning cultural differences reminds me of my favourite quote about moving abroad:
“When overseas, you learn more about your own country than you do the place you're visiting.”
– Clint Borgen
Charlie!! I was also informed by some that I might have ADHD and when I watch ADHD videos I am like "wait isn't this...everyone's experience?? no?? hello???" Very interested to follow along your journey of exploration here