Castles in the Sky 33 - May 2023
Big, Big News!
Welcome to Castles in the Sky #33!
I apologize that you haven’t heard from me in a minute—for the last week and a half, everyone in my family has been trading a stomach bug, so writing had to take a backseat. But I am excited about three big changes to Castles in the Sky!
Big Change #1: The newsletter is now monthly.
So far, the newsletters (published as Castles in the Sky #) have served as a hodgepodge of self-promotion, riffs on ideas, personal updates, and curated content. After writing Small Oven Syndrome, I asked myself if the newsletters were still serving their purpose, and realized they were not for two reasons:
Originally the newsletter was a great forcing function to get me to put out regular writing and to spark new ideas. But after writing for more than a year, my problems have been reversed and I have too many ideas. The weekly(ish) commitment to putting out newsletters is sidelining other projects.
Having direct communication and personal updates in the newsletter is great, but paradoxically, weekly updates seem to overwhelm people and make it harder to keep up. Bigger, less frequent updates seem to work better.
Moving forward, I’ll no longer write weekly newsletters. Instead, at the beginning of each month, I’ll write one big newsletter (like the one you’re reading now) that encapsulates the previous month. Here is the content you can expect in the monthly newsletters:
Welcome - Quick hello and any urgent news that doesn’t fit elsewhere.
Writing Updates - News and updates about Castles in the Sky as well as a summary of everything I wrote in the last month.
Life Updates - Dispatches from my personal and professional life.
My Favorite Things - A rundown of my top reads, listens, and watches of the past month.
Crowd Work - A highlight reel of my favorite comments and shout-outs from the last month.
Big Change #2: There will be more varied output on a more varied timeline.
You may remember times I asked for feedback on what you liked as a reader, or when I did different experiments in niching down. I’ve exchanged emails and had conversations with some of you, and the most consistent feedback I get is, “I am never sure what to expect from Castles in the Sky, but I always love where it takes me.”
At first, this was immensely frustrating. But after hearing the chorus of chords being struck in tens of thousands of readers by Do the weirdest thing that feels right, I came to my senses! Why do I need a niche? I consider Castles in the Sky an exploration. What a blessing it is to have readers who see it the same way and want to go on this journey with me—readers who tune in every week even though I cannot tell you what Castles in the Sky is about.
Now that the newsletter is on a monthly cadence, I am not simply going to swap out and start publishing a “weekly post.” I will use the additional time to write the weirdest thing that feels right. Sometimes that will be a rapid-fire series of five posts in a week. Sometimes I will work all month on a single story. The only guarantee I make is that there will be more, it will be better, and it will be weirder.
Big Change #3: I am asking for your support—Castles in the Sky is opening paid subscriptions.
I started writing because this is my life’s work. It’s not just a fun creative pursuit on the side. I do love to tell stories and write about ideas, but I also write about my loved ones as well as my own fears, dreams, triumphs, and tragedies. There are stakes to this. I gladly do it without pay–I would probably even pay to do it.
When I started writing, I knew I needed to be confident even without a concrete objective, to be daring even without a destination. And to those of you who have been with me, I want to honor your support of this vision by doubling down. I am going to be bigger and bolder, more idiosyncratic and more prolific than ever before. I am asking for your support to validate this work by becoming a paid subscriber.
Paid subscriptions will let me increase both the quality and volume of what I'm doing. Even though I am turning on paid subscriptions, I am not going to paywall anything I write. All posts will still be open. I also will not niche down prematurely based on who's paying and who's not. There are three options for going paid:
You can pay $8 for a monthly subscription.
You can pay $80 for an annual subscription.
You can pay $250 to become a founding member, which gets you an annual subscription but is a way of showing max support.
I am grateful to each and every person who has ever read, liked, or shared a post from Castles in the Sky. (And I’m especially thankful to the shockingly large number of you who have already made “pledges,” saying you would sign up when paid subscriptions were activated.) For the rest of you, I hope you keep reading and consider becoming a paid subscriber to support the continued adventure here at Castles in the Sky.
The only guarantee I make is that there will be more, it will be better, and it will be weirder. Join me on this journey by becoming a paid subscriber.
Writing Updates
There were a lot more ideas than stories in May.
In Small Oven Syndrome, I proposed a new name for an old problem: “the way of thinking where people are just doing what they’ve always done simply because they haven’t asked why they’re doing it.” I explained the origin of the name, some of the problems of Small Oven Syndrome, some places you might see it, and where a simple trick for resisting it.
In Good Lessons from Bad Men, I reconciled my intense love of organized crime film and TV with my deep drive to be a better person and a better man. I explain that being a good person is a moral matter but being a good man is an ethical matter, and we can see this difference most clearly in gangster flicks. Then I list five of my favorites and highlight how they show this difference.
Castles in the Sky 32 was my last weekly newsletter. In it, I wrote two mini-essays. The first was on my weight loss “journey,” and the difference between our character and our environment. The second was on the three impulses of civilization: to build, to revere, and to care for. I then shared some interesting things I’d read that week.
In Do the weirdest thing that feels right, I try to reckon with the unexpected attention I received when my essay A Pilgrimage for Book People was featured in Substack Reads. I explain that when faced with a bunch of equally appealing choices, I pick the “weirdest.” I reason that weirdness is a mental stand-in for what other people think, so if you want to do something weird, it means you want to do it despite other people’s expectations.
For this issue, there are not too many additional updates as they were all in the Welcome section, but in case you skimmed past it:
The weekly newsletters are now monthly.
Between monthly newsletters, I will be writing whatever feels right on whatever cadence seems right.
Castles in the Sky is opening up paid subscriptions for those who want to support my work.
Life Updates
May was a jam-packed month. In my work as a business professor supporting students and local entrepreneurs, I was super excited to help coordinate Houston’s largest pitch day. We had over sixty entrepreneurs pitch to mixed panels of judges in an effort to raise their profile and learn how to grow their businesses.
I also took Write of Passage for the third time. Write of Passage (WOP for short) is where all of my best “online” friends come from, and taking it for the first time in Spring 2022 is what inspired me to launch Thought Bananas, which evolved into Castles in the Sky. They worked tirelessly to upgrade the curriculum and student experience. Even for an already impressive program that I consider the gold standard for online CBC’s (cohort-based courses), the quality improvements were dramatic.
This Fall, I have the honor to serve as the best man in one of my good friends’ wedding in the UK. At the end of May, I also got to serve as concierge and house dad for his bachelor party. I love weddings and bachelor parties because they are (usually) fun, always interesting, and each one is unique. When my wife and I were planning our bachelor/bachelorette parties and wedding, I said, “let’s just do exactly what we want, because all the stuff around the wedding is usually a reflection of the people involved.”
I then did an experiment where I asked her to describe married friends in a few adjectives, then describe their weddings in a few adjectives. Try this yourself–odds are, you’ll use the same adjectives. If you’re “buttoned up, traditional, and tasteful,” that’s probably how your wedding will be. If you’re “fun but kind of a mess with good taste in music,” that’s probably how your bachelorette party will be, etc.
To that end, my friend is a laid-back guy with just a few eccentric opinions who owns a bar comedy club—so he likes to party—but is mostly pretty chill. So his bachelor party was fun, funny, and full of interesting people since everyone there was a working or aspiring standup comic. It was also mostly chill, with a lot of beach grilling and fishing, a little wild at night, with a dash of some weird stuff—like when he wanted to do a taste test of a bunch of artisanal butters and eggs.
Most of the best things happening in my life have to do with my eighteen-month old daughter, but it’s the kind of things people rarely care about like, “she almost said a word” or, “she does a funny fist-pump now.” If you know, you know. In lieu of listing every single amazing thing she did last month, here is a picture of her sitting on the couch with our dog, Bingo.
My Favorite Things
Favorite Things I Watched
Last month saw the series finale of two very popular TV shows, Succession and Ted Lasso. Succession was an HBO drama loosely based on billionaire family media empires like the Redstones and Murdochs. Ted Lasso was an Apple TV comedy based loosely on a silly commercial about an American football coach becoming a UK soccer coach. I haven’t seen anyone else draw the conclusion, but they are mirror image opposites of one another.
Ted Lasso is super hokey. Every single person in it is a great communicator with an impressive amount of emotional intelligence and an encyclopedic knowledge of pop culture. Some people complained about the ending because they ran through all the storylines and gave everyone storybook endings.
On the other end, Succession was super dark. Nobody got what they wanted out of the end, and many people think that some of the characters were sacrificed (particularly Shiv) in order to fit the dark theme of the show. If you haven’t watched either, I highly recommend both–at the same time actually. When you get tired of the persistent happy endings and lack of realism in Ted Lasso, watch an episode of Sucession. When you get tired of the dark, gritty cringe of Succession, watch an episode of Ted Lasso.
I also rewatched Lawrence of Arabia, one of the best movies of all time. One thing that was funny watching it was realizing for the first time how obviously gay it is. At first I was like, “is this supposed to be have two gay leads? Am I just reading the present into this?” But then I read a few interviews by the director David Lean where he said it was intentional. All around, the movie is fantastic. Spielberg called it the movies that “started him on his journey.”
For shorter form, I really loved this YouTube video where prolific jazz drummer Dennis Chambers hears TOOL for the first time and tries to recreate the drums for Schism by only listening to the song’s other tracks. I didn’t know anything about Dennis Chambers before this, and I am merely a surface-level fan of TOOL, but I love watching artists at the top of their game appreciate art by others, analyzing it with all the weight of their skills and critical expertise. If you’re interested, here is the final reveal where Chambers hears the drum line.
Finally, I really loved this video of international pop star Bad Bunny walking into the ring for his professional wrestling match in his home of Puerto Rico. When the crowd suddenly gets loud as someone enters the arena, it’s called a “pop.” This is one of the loudest pops I’ve ever heard. Plus, it’s clear how much Bad Bunny loves professional wrestling and is investing into doing this right, really selling the whole gimmick. Beyond it just being a fun watch, it is similar to the Chambers video above because it is one artist at the height of their game bringing their skills and perspective to a new arena (literally).
Favorite Things I Read
I have been reading a lot more but only finished one book last month, All the Wrong Moves by Sasha Chapin. I have a review coming out soon, but I also wrote some thoughts in the last issue of Castles in the Sky.
When it comes to newspapers and blogs, this piece from the Free Press really piqued my interest: At high school debates, debate is no longer allowed. It’s about the politicization of the high school debate scene, specifically a concern that it’s growing too woke. It paints a very interesting picture, so eager to learn more, I started searching for people closer to the issue discussing it.
I found this discussion on Reddit, where the main theme of the comments seemed to be that not only was the story wrong, but it was rather the opposite of what was happening on the high school debate circuit. The discussion of the Free Press article was one of the most popular discussions that month on the r/debate forum on Reddit. However, I found this other fascinating post among the most popular discussions that month.
The discussion is written in debate jargon, but here is a summary courtesy of ChatGPT:
The original poster, a participant in formal debate competitions, is expressing frustration at the misuse of complex arguments critiquing capitalism, often by wealthy schools. They argue these arguments are often employed insincerely as a strategy to win, rather than to genuinely challenge the system, which they feel both devalues serious critique of capitalism and makes the debate environment less accessible for less privileged participants.
To summarize so far: I read an interesting story about high school debate seeming very woke. Then I found a bunch of debaters saying that’s not true–the debate scene is not woke enough. But then found a bunch of those same people discussing whether it was hypocritical for students from rich schools to Kritiks–a complex debate technique where you challenge the axiomatic ideology of an opposing debater–to levy harsh criticisms of capitalism. Unfortunately, I don’t have a neat wrap-up for this, but wanted to share these because I thought it was an interesting, nuanced microcosm of a huge issue, and it’s been very thought provoking for me.
From social media, I really enjoyed this Twitter thread about a young woman who used her own money and a grant from the local government to host a pop-up art gallery. It combines a lot of my favorite things: weirdos, independent artists, small business, local communities, and smart governance.
This final tweet really resonated with me. I’d been noticing patterns in the “online” writing I’d been enjoying, and while this is not entirely fair, I feel like this is a pretty accurate take as far as “broad brushes go:
Favorite Things I Listened To
Bonobo put out a fantastic album last year called Fragments that I had in heavy rotation all month. I have loved Bonobo for over ten years now, and my wife and I will be going to see them (him?) perform with Odesza in New Orleans in September for my birthday. You can stream Fragments anywhere, or check out this great Tiny Desk Concert where they debuted three of the songs on the album, as well as this great DJ set by Bonobo.
Beyond that album, I’ve been really enjoying the Acid Jazz playlist on Spotify. The whole thing is excellent, but if you want a sample (or don’t have Spotify), some of my favorites are I Juswanna Chill by Large Professor, The Light by Common, Water No Get Enemy by Fela Kuti, and Pizza Pie by Let Your Hair Down.
I love hip-hop because it really accentuates one of my favorite things about art, which is that once you hit on something really good, you can explore and celebrate what makes that art great by remixing and restyling it millions of different ways. For example, the Acid Jazz playlist has a song by Leon Haywood called I Want’a Do Something Freaky To You, which is great in its own right, but also forms the backbone of the beat for one of the best rap songs from the 90’s, Nuthin’ But a G Thang by Dr. Drea featuring Snoop Dogg. (The playlist also has one song I love called Slow Down by Brand Nubian, which samples another song I love, What I Am by Edie Brickell & New Bohemians.)
But my favorite song on the playlist is They Reminisce Over You (T.R.O.Y.) by Mecca and The Soul Brother–and not just because it was the song that played over the selection screen on NBA Street Volume 2, the game that dominated the nights, weekends, and holidays of my entire early adolescence–but because the song itself is high art. And even in the comment section, there’s a great exchange where someone makes the same, “they don’t make it like they used to” type comment:
But then fellow YouTube commenter Grambo Gringus brings the heat and riffs on the point I make above, that remixing and restyling art is a generative way to appreciate things.
Crowd Work
I have two long-form recaps of feedback on Do the weirdest thing that feels right and A Pilgrimage for Book People coming out.
For now, I want to highlight some great feedback I got on Small Oven Syndrome. Bruce Bain, Chris Wong, and Camilo Moreno-Salamanca gave me some interesting things to think about, each of them introducing me to a new term or idea for the same general idea I was getting at:
And F.B. Fanat gave me a lot to think about onGood Lessons from Bad Men:
....stooooked for the new format...
Others may have this question but will there be paid posts in addition to monthly?