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: I had a long month and missed a few issues, so this is a long issue. But for everything I left in here, I cut four or five things—so I hope you enjoy.
“It is good to have an end to journey toward, but it is the journey that matters in the end."
Ursula K. Le Guin

My daughter was just promoted to her first toddler classroom. They decide whether or not she is ready based on how well she can walk.
It is impressive to see her now, toddling around. I can remember a little over a year ago she was basically a very demanding houseplant. Now she has a personality. She mimics me. She asks for things. She likes and dislikes things. And yet, she still has so far to go. She can go about twenty steps at a brisk pace before losing her balance, but that is enough for her to get moved up to a new class.
Transitions in adult life are much less clear. Sometimes I wish there were someone watching me saying, “you’re ready now for the next thing–let’s go.” Especially as someone doing something creative, it’s hard to know when you’ve leveled up.
I feel bashful saying, “I’ve leveled up,” but I do feel like I am in a new place. I feel more attuned than ever to the intersection of what I want to write, what I am good at writing, and what people like to read. I am also more comfortable with the ambiguity that comes with leaning into doing something creative.
And so I am trying new things. For the last year, while I’ve been writing, I have also been working with other writers. Many of the writers I work with have said they would like to continue working together in a more structured environment. After talking it over with a lot of them, I am taking inspiration from my daughter, and crossing that threshold to offer a writers’ workshop called Limitless Writers.
I have been building the course under the advice of Alexandra Allen, who has worked with some of the internet’s most successful course creators. She says:
Charlie will transform you into a prolific writer by going beyond the mechanics of how to write. He'll help you discover a love of reading and make you a better self-editor. He was one of the top mentors for Write of Passage and will make you feel supported as a student.
I already filled most of the course from a private waiting list, but I’ve opened up a few more spots for subscribers to this newsletter. The class meets online for two weeks and starts on Thursday, March 23rd. I plan on growing this workshop and offering it again in the summer, but it will never again be this small or this inexpensive. For more information and to buy a seat, click here or the logo below.
Writing Updates
New Essay: A Pilgrimage for Book People
This is my favorite essay I’ve ever written. It is part travelogue and part chronicle of the family business, but most of all a love letter to books. It took nine months of drafting and editing, and I think it is the closest to my ideal “style” and message I have gotten so far. Please check it out and tell me what you think.
New Essay: Get into Character
This is an essay about what it means to “be a character” and why I think that’s a good thing. It’s about one of the biggest characters I know, my Mom, and how I became a character after learning from her.
New Essay: Who Cries for the Robot?
This is an essay about my close working relationship with an artificial intelligence: chatGPT. I make a few guesses on how I think that this whole AI thing will pan out.
Flash Fiction Featured in Fictitious
One of my friends from the Soaring Twenties Social Club solicited short fiction about childhood. I wrote a funny story about when I was twelve years old and embarrassed myself in front of a bus full of teenage girls. I recommend clicking through to check it and the rest of the stories out.
Life Updates
I ran my first 5K.
I ran a 5K with a friend despite getting a flat tire on the way the race. The story really took off on Twitter and I met a lot of really interesting people and got a lot of unexpected compliments as a result. Click below to read the tweet thread.


I started and stopped an ADHD Medication.
I’ve shared before about my belief that I have ADHD and my journey to see a professional about it. I have an essay on the way that tells the story of my most recent stage in this journey: starting and abruptly stopping an ADHD medication. If you have experience taking ADHD medication, please shoot me an email if you’re comfortable reading something and answering a few questions.
I visited New Mexico.
Last week, I visited New Mexico (from where my Mom the character originates). I had a great time seeing family, eating sopaipillas and green chiles, and enjoying the very different vibe and culture of New Mexico. New Mexico and Louisiana are two of my favorite states to visit because they each have a distinct feeling that you can’t really capture anywhere else in the US.
Even though I wasn’t able to sign up for this session, I plan on taking my friend
's new course: Photography for Creatives. Based on just one free workshop he did, I was already inspired to take better photos–and here are my three favorite photos from Albuquerque and Santa Fe.
Crowd Work
Secret Geniuses
I am really enjoying reading Little, Big by John Crowley. I was so impressed that I decided to look him up online. What I discovered is that Crowley’s fans love him—like place him alongside Dostoevsky, Pynchon, and Tolkien.

In a future edition of Castles in the Sky, I want to explore some more of these secret geniuses—those creatives who are relatively unknown but whose fans put them alongside the greatest of all time. Do you know of any?
As always, I welcome comments and feedback. Thanks and see you next time!
Somehow when I hit the "life updates" section I was expecting to see an announcement about you starting your podcast. : ) Now that's an update I'll cheer for when the time arrives.
Congrats on the course, Charlie!!