Castles in the Sky's Seven Most Underrated Essays
A look back to celebrate my son being ~7 days old
My son, our second child, was born eight days ago—huge, healthy, and sleepy. Having a newborn again reminds me of when I launched this blog, right after my daughter was born three years ago. Thinking back on that time, I went looking for an old essay I wrote about fatherhood.
In the process, I found pieces that “flopped” back then or feel tonally different from what I write now—but that I still love rereading. Now that my audience is bigger, I wanted to share these essays again and see what resonates.
Below are seven essays. For each, I’ve included a brief overview, an excerpt, and a reflection on how I see it now. Let me know which ones stand out to you—or, if you’ve been here a while, what’s your favorite deep-cut essay that should have made the list?
What Becoming a Father Taught Me About Self-Care
This is the essay that I was looking for when I started reviewing my back catalog. Someone messaged after reading it and told me, "I never like it when people write about their dreams. It never comes out right and isn't usually relatable or compelling. But this was excellent."
Sometimes my eight month old daughter falls asleep slumped against my chest, sitting on my left arm like a barstool, with her face against my shoulder, her arms fallen to her side because they’re not long enough to meet around my neck.
To convey the responsibility I feel toward her in that moment is impossible. Metaphors would strain credulity. My commitment is total. My love is unconditional. My every breath is slowed to keep her asleep yet I am more alert than I have ever been to keep her safe.
At the end of that essay, I discussed three things I was doing to take better care of myself. Two years later. I'm happy to share I've kept all of those commitments.
11:59 in Dearborn
When I started writing, I was primarily interested in writing fiction. This was the first short story I published on Substack. There's a lot I'd change now, but it holds up surprisingly well.
They shouted "two!" and then ten thousand breaths caught in ten thousand throats. The silence smothered the throng of revelers in Times Square. One by one, they began to exhale. "One?" a little girl asked her mother. The number 2 was frozen on a four story screen behind the ball. The giant ball was suspended in air. People at home checked the connection on their TV's. People in Times Square began to check their phones and watches--all stopped at 11:59:59. Once they opened their phones, they realized all the apps that updated in real time were frozen. A few had video calls still going. Small faces asked, "What's going on there?" Nobody had an answer.
This and another story I wrote were inspired by a Twitter bot that spat out short magical realism prompts. When Elon Musk bought Twitter, he changed the rules for bots, and the account stopped tweeting. I moved on and mostly forgot about it. I also found that writing both fiction and nonfiction was tricky—the audience overlap was minimal. But if you enjoy this, let me know. I might dust off and publish some older stories I never released.
Simplicity, Expertise, and Bullshit: Being Taught vs. Being Convinced
Without inviting too many current events into the happy place of this blog, I've had occasion recently to think a lot about mass messaging, communication, and truth. A lot of smart people believe that you don't really understand something unless you can explain it simply. I think this is fair in many contexts, but one problem is that this idea has mutated from its original meaning.
Many people pervert the original intent so that it now means, "if something isn't simple, it's wrong." Which you can imagine often decays into, "if I don't understand it, it's wrong." Aside from the obvious drawbacks of this worldview, one not-so-obvious negative is that this makes you easy pickings for bullshitters.
There is a popular piece of folk wisdom that I think is misguided. It’s best exemplified by the following Albert Einstein quote people like to share:
“If you can't explain it simply, you don't understand it well enough.”
I don’t really agree, and after doing some research, I’m not sure Einstein did either. He never said this. It’s not a misquote–it’s just completely made up.
I write less "commentary" like this these days, although I think I'l bring it back.
Note: this was also a landmark essay for me because it was the first time someone I hadn't met previously wrote a "response essay" to one of my essays. The response was excellent and raised some great points. Read it here.
Making, Not Finding, Your Way: Review of The Pathless Path by Paul Millerd
Not only did I enjoy this book, and enjoy writing this review, but it plays a pivotal role in my journey as a writer. Before I took Write of Passage, I joined a community called The Soaring Twenties Social Club, which is a Discord for writers and artists. Early on, I wrote this review and asked for feedback. Someone tagged Paul Millerd, the author of the book I was reviewing--who I did not realize was also in the Discord! He was immensely flattering and supportive of my review, and I cannot imagine I would have thrown myself into writing the way I did had my first foray into putting something out there not been such a positive experience.
Through summary, review, context, and memoir, I want to make the case that the book, The Pathless Path by Paul Millerd, is immensely important because of both its content and its context. On its own, the book has a wide range of interesting and useful ideas to offer concerning careers, the nature of work, leisure, society, and how we measure our lives. Beyond that, the book serves as the most recent interest development in a centuries long debate about how to decide what to do with your life.
Paul has since written a second book that I hope to finish and review soon, and he is one of the people who has most inspired and encouraged me to write my own book.
Good Lessons from Bad Men: Paradoxical Lessons in Masculinity from Crime Cinema
In this essay, I wrote about the distinction between being a good man and a good person, and how this is most obvious in the way we assess the worthiness of men in crime cinema.
I love gangster movies–not just for the violence, intrigue, and bravado–but because these ruthless, vindictive criminals have taught me how to be a better man and a better person.
One idea I had after writing this essay is to do a podcast where I get a rotating cast of men together, share this essay with them. Then we watch gangster movies and TV shows on our own and discuss them using this framework later. If you're a guy (or not) and that sounds like something you'd be interested in, let me know.
Thought Bananas 9 | "a huge spectrum of multi-sensory, thematic modes of expression"
As I am considering changing the name of Castles in the Sky soon, I want to share a bit of Castles in the Sky lore with you. The original name of this blog was Thought Bananas. I named it that based on a conversation I had with someone about my hesitation in writing online. I said I was putting my future output on too high of a pedestal so I needed an unpretentious name. But in looking for something unpretentious I overshot and picked the dumbest name I could think of.
However, back then I was a little better at writing every week. I would share a quote alongside vignettes and ideas I thought of during the week as bite-sized essays. This is a format I am considering bringing back for the future, so it's fun to go back and look at one of the issues where I think I did it well.
An Experiment in Newsletter Formatting
This was one of my favorite things I ever wrote, but it also shows a little bit why I didn't keep up well with weekly newsletters. At the beginning, I share that readers are going to start getting TWO pieces of writing every week, and that the second will be a newsletter that is segmented into three distinct parts, where I share ideas and links according to each thematic section.
I don't write much about two of the three of these thematic streams anymore. But the irony of this is that my tentative thoughts about renaming the blog are mostly around creating a more expansive brand into which I can bring back these ideas.
Which is your favorite? What’s missing?
I am setting some creative goals for the year and would love to hear from you about what resonates. Which of these is your favorite? Which other essays have you liked? Which of the series I started and abandoned should I bring back? Let me know in a comment or via email.
Big congrats, Charlie!!