The map is clear but the road is bumpy.
Castles in the Sky | October 27 - November 2, 2024
Castles in the Sky is a column about doing the weirdest thing that feels right. It’s part letter, part scrapbook, part workshop, part museum. Each issue shares up to seven stories, ideas, or links that resonated with me from the previous week.
This issue covers October 27 to November 2nd, 2024 and has reflections on training for a half marathon, revisiting a decade of goal setting, celebrating fifteen years of sobriety, reflecting on a great speaker, and thinking about ADHD’s relationship to shame.
Training for a half marathon has changed my idea of what's possible.
Last Sunday I ran a 10K (which for my fellow Americans is just over 6 miles) at a breezy pace of 11:38 per mile. This may not seem like much, but the only other organized race in my life was in March 2023, when I ran a 5K with a friend at 13:40 per mile, which was very painful at the time. Before that, I'd only run longer than a mile once in my life, as part of a final exam for a college course where I had to run a 5K.
Last year, while I was preparing for surgery, I knew I wanted to get fit afterward. But just finishing a 10K felt like kind of a pipe dream. Now, I run them regularly (once a week--sometimes twice) in service of training for a half marathon in January. The longest distance I've run so far is 8 miles. All this training has shifted something inside of me. Casually bursting through an obstacle I thought was impossible to overcome is changing my sense of who I am, what's possible, and what I must accept about myself.
Having the North Star goal of the the Half Marathon has been so generative for progress in running and general fitness, but also clarified my scheduling, made me new friends, and broadened my horizons in ways I never could have anticipated. I spent so much time before preparing for the right moment, or saying, “when this happens, then I’ll do that.” Now that I can just go run as much as I want, I realize that the whole time I was only really waiting until I felt like it–which is kind of empowering and terrifying at the same time? Like, what else could I do if I just decided to put on the right shoes and go do it?
(Postscript: I understand the world through books. One friend recommended What I Talk About When I Talk About Running by Haruki Murakami, which was exciting because I love Murakami. Another friend recommended Born to Run by Charles McDougall. If you've read either, drop a comment below with your thoughts.)
Reading my old goal-setting emails reminded me of the advice that gave me the idea for this column format.
My writing and creative work together are a mirror of my life. Up until now, they have been about exploration and expression. But seeing what having the Half Marathon as a North Star has done for the rest of my life has made me wonder what a similarly focused goal might do for my creative work.
When I was much younger, I had outrageously big goals—goals that were indistinguishable from dreams. As I matured, I was influenced by the likes of Tim Ferriss and James Clear, and my goals became smaller, more numerous, and less ambitious. They were mostly about optimizing my lifestyle and being productive.
As time went on, my goals became smaller and even more numerous, until goal-setting morphed into something pathological. Any time I was fearful or anxious, I would take out a piece of paper and set some goals to prove to myself I could work my way out of it. Setting goals became a displacement activity I did as a self-soothing mechanism rather than a way to guide my focus and organize my actions. I have a few years’ worth of Moleskine notebooks from about 2017-2021 that are roughly two-thirds full of lists of goals which are basically just to-do lists.
I have a pretty high fidelity record of this because for about ten years, three friends and I have tried to email each other our goals every month. We call that email the GCI: Goals Check-In. We set goals for the month, share progress on last month's goals, and "check in" about what's happening in our lives.
I don't have my earliest GCI's because I got the dumb idea to purge my Gmail in early graduate school. But between when I ran my 10K and got the urge to collect my GCI’s in October 2024, and the earliest GCI I could find in June 2016, exactly 100 months had passed. Something about this seemed like a sign—like I was onto something. Of those 100 months, I’d written something with the GCI in the subject line in over 80 of them, and written a full Goals Check-In 63 times (which was more than I’d thought).
Reading through them was equal parts cathartic, hilarious, and frustrating. They reminded me of some great advice I once received about what it means to be driven. I had this strange idea that driven people had a preternatural confidence in themselves and they always thought their goals were the absolute best things they could be doing with their lives. But I got advice that changed the way I see driven people so now I try to share that advice as often as I can:
The number of people who truly know what they want in life or have unwavering self-belief is vanishingly small. Most successful people choose a "good enough" goal for three to seven years, publicly commit to it, and structure their actions around this narrative. Privately (and with a small circle of people they trust), they allow for doubts and exploration, while maintaining a clear, socially legible story on the surface.
It also reminded me how my wife paid me a compliment secondhand. One of her friends at work told her, "Charlie's a beast—one day he was like, 'I need to lose seventy pounds for surgery' and BAM he does it." Hearing that blew my mind. I'm thirty-seven and was overweight from ages six to thirty-six. I struggled for so long, but finally, it just clicked because I asked for help and made it a priority. Even while it was happening though, there was so much self-doubt and I spent a lot of time thinking about what I'd do next if my plan didn't work out. Reading through my GCI's was similar. Looking backwards, the narrative was clear, but month-by-month, it was scattered, uncertain, kinda funny, messy, and pretty painful.
Between reading the GCI's and my wife's friend's compliment, I had a crazy realization--I'm one of those people who picked "good enough" goals, I have just never seen myself that way. I am unsure what I plan to do with this awareness. But I feel like it means I might take everything I’ve learned and circle back to setting outrageously big goals.
One of those things I’ve learned is that the day-to-day is not easy. Last week my Dad asked me how I was doing and I said, "The map is clear but the road is bumpy." Part of the formula for achieving outrageously ambitious goals will be creating space between the narrative arc of those goals and the space required for exploration or the occasional dark night of the soul.
In my creative life, that's what this weekly column (experiment) is for: leaving that open space. My intuition is that, rather than force the big goals, if I carve out space to explore, the big ambitious stuff will come naturally. For a long time, I had been trying to figure out “what I was doing,” but progress was happening on its own—in spite of my worrying. So this weekly column, which I will call castles in the sky (the same as the blog at large), is going to be a dedicated place to explore
November marks fifteen years of sobriety.
I quit drinking in November 2009, which means that at the end of this month I’ll have been in recovery for fifteen years. This is one of the most important events of my life, so important that it’s almost hard to write about because it’s so fundamental to how I see the world and move through it.
Last year, on the fourteenth anniversary of quitting drinking, I drafted an essay about what sobriety and recovery mean to me, but it became too expansive so I shelved it. I decided to revisit that essay to update and publish it but to help me sharpen its focus, I wanted to open up to your questions, comments, or stories about sobriety and recovery. Please leave anything you want to share as a comment below or feel free to send me an email.
If you’re curious about what it can look like when someone talks about their sobriety, or being in recovery, this is one of my favorite talks on the subject. It’s from Craig Ferguson, former late-night TV host, who gave this monologue years ago when Britney Spears shaved her head. A lot of people thought he was going to punch down on her but he went in a decidedly different direction. (Note: I am shocked this guy hasn’t done more stuff. I think he is among the most effortlessly witty, charming, and humane people to ever host a TV show.)
I heard a speaker share something that will stick with me for a long time.
One of my courses had a great guest speaker last week. He is the son of a South Asian immigrant whose father moved here with nothing and started a series of very successful businesses. The speaker was raised with many material blessings but his parents still discouraged him from becoming an entrepreneur going so far as to say he couldn't hack it, that he wasn’t cut out for it.
When he wanted to get into the family business, his father gave him only the very worst appointments and made him work twice as hard and earn his and the company’s trust in the business while completing his studies. For the speaker to prove he could succeed in business, he started his own business alongside his family's business while still in school. Then finally, still in early adulthood, finished with school and with his own successful, independent businesses under his belt, he took over the family businesses when his father passed.
He was mild-mannered but toward the end of the class, he had everyone on the edge of their seat. I teach people from under-resourced communities how to start businesses, so there is always the question of how much they will identify with people who admit their privilege, but the speaker was forthcoming about what he was given and what he had to work for, and everyone seemed to get so much out of it.
By the time it got to the Q&A portion, everyone was enraptured. At one point, one of the attendees asked a question referencing one of the speaker’s anecdotes where he kept getting rejected. And they asked him how he had the resolve to keep going, and how he knew it was time. He said something like, you need to figure out what you want to go after, and then you will have doubts, but you need to just do it.
Then the class was elevated to the level of a sermon and he said something like, “forgive me for sounding religious, but,” and he pointed his finger into the air and put his hand over his heart, and said, "What God's written for me, I'm going to get regardless!” I don’t know if it was just because of what I’ve been thinking about goals a lot, but man that pierced right into my soul. I’m not even particularly religious, but it’s been echoing around my brain all week. “What God’s written for me, I’m going to get regardless!”
Something I read about ADHD reminded me of an appointment I had two weeks ago.
I started reading the book Driven to Distraction by Edward M. Hallowell and this quote stood out to me:
"For most of human history, problems with learning, emotion, or behavior have been viewed through the lens of morality, often colored by theology."
A couple weeks ago I got a full battery of psychological tests for ADHD (finally). I should find out whether I have it or not, soon, although I'll be pretty shocked if I don't after that test. But during the day of tests, I was really surprised to learn that the interview was really reminiscent of like, elementary school, or Catholic confession. I was basically just telling this psychologist all the bad things I'd done over and over.
"Yes, I do forget things.
Yes, I do daydream often.
Yes, I do get distracted during conversations with other people.
No, I didn't turn in all my homework in elementary school.
Yes, I did talk to much during classes in school."
And so on for nearly eight hours.
I understand that a lot of these things might not be my fault exactly. But still, over the course of the day, I couldn't help but start to feel the accumulation of an almost physical sense of shame over answering all these questions. I'd be curious if anyone else had a similar experience.
Thank you for reading!
I will continue to release full-length standalone essays and short stories alongside this weekly column, but let me know what you think of this new (version of an old) format.
I’ve read both books! Born to Run was years ago but I remember loving it and also, that when I was reading it I became crazy motivated in my running. Went from struggling through 3-6 miles to wanting to run 10 miles for fun!
Recently I read what I talk about when I talk about writing. I enjoyed it. Lots of metaphors on running, writing, and life. He writes in a very clear and simple way that is refreshing.
Congrats on 15 years sober, now you know you can do that half marathon you know you can do 15 years more.