I’m an unapologetic SF evangelist. To the mentally feeble haters, I prescribe 1 course of a Bay to Breakers experience, taken annually. The heart of the city lays itself bare, releasing unbridled wackiness under the shadows of timeless Victorian charm. You grab your friends and whatever is buried in your closet from 2012 halloween, stepping outdoors to open your eyes to a city defined by community, free self-expression, and the occasional naked man.
This year I was a teacher, leading along a class of 24-30 year old 1st graders. My classroom had it all: Brandon as an overzealous teacher's pet, Star as a kickball obsessed hair chewer, a classroom crush - let’s be honest, situationship - between two students, and various other oddball characters. I donned my most substitute teacher-esque dress shirt and blazer, morphing into Mr. Henry and commanding my unruly subjects through the streets of San Francisco. They say the youth has changed, and by golly has it. Behind me rang a chorus of ‘we want beer’ and ‘how about a cigarette’ and ‘do you have one of those?’ (insert gesture at a helicoptering nude man). As we wandered, our classroom stretched on ahead, a sea of undulating costumes and impropriety.
While we sang the ABCs and something about John G Jacob Jingleheimer Schmidt, the true lessons of the day bubbled up from the earth and into the minds of our aged out children. ‘People can only be free in relation to one another,’ a quote lodged in my mind from German-American philosopher Hannah Arendt. In her work, she rigorously examines the role of community, and activity in the public sphere, as prerequisites for any free peoples in pursuit of political agency. While easy to write off as a goofy aside, Bay to Breakers is an opportunity to understand what San Francisco means to its residents, in jarring relation to each other. Freedom is so viscerally expressed throughout the 7.5 mile course, exuding a sense of mutual gratitude for this city of rampant self-expression.
So to the naysayers, the Fox News prisoners, the ‘SF is a failed state’ crowd, please take your prescription to your local CVS ahead of May 2026. This city is deeply flawed, wildly original, and a treasure of seemingly dissipating American freedom.
Packed the ‘ol outback and ventured down to San Clemente this past weekend in search of warmth, good waves, and friendship. Report card: 7.3/10 warmth, 5/10 waves, 9.7/10 friendship. Brendan left some room to be desired. Cruised down the 5 going more than 5 over at 5 in the morning, a consistently introspective experience. Made it to Camp Pendleton by noon, a military base home to the world famous Trestles beach area. Admitted by Mr. Dave Molz, marine and USC friend, and accompanied by Mr. Brendan S. and Hannah M. Our winning campfire question: what’s the most physical pain you’ve ever been in? Other than fire philosophizing we spent a lot of time in the ocean. Awfully cold and windy, but a solid 3ft at 18s south swell running made up for deficiencies of weather. After two surf sessions I said farewell to the best buddies and met up with brother James at the San Mateo Campground. California towhee and song sparrows dominated our campsite, welcome respite from the trains, backhoes, and U.S. military might that so dominated the night prior. James and I hiked around, found bizarre animals, played frisbee, and undercooked some steak over an almond blaze. Had some good fireside company in Garrett, Taylor, and canine Mocha Silverman, who became subjects to my steak-infused cinnamon rolls, courtesy of my 1960s Lodge cast iron. So special to share time with these wonderful people and reminisce on freshman antics – Garrett was my roommate for 2.5 years!
Being back in San Clemente was a tad jarring. This was my locale for much of covid and long bits of college years, both because of a relationship past and a summer internship in Dana Point. Trestles in particular is a vessel of powerful nostalgia, infused with memories of sun exhaustion, military ordinance tests, perfect waves, asshole surf dads, and scents of the last remaining California mangrove. It’s a ~45 minute walk to Lowers, the crown jewel of Trestles and wave of choice for the upcoming 2028 Olympics. The long pilgrimage, wielding board and neoprene and zinc, is half of the Lowers appeal for me. Zipping by on the latest Electric Bike 2000 are hundreds of wave-hungry youths, fittingly analogous for our respective speeds in the surf. The sky and ocean were confused by their transit of season. A stiff Pacific wind not quite defeated by a formidable UV index. Pulsing south swell mixing cruelly with upwelling’s frigid promise. Spring here is an icy hot skirmish, providing comfort in the chaos of change. The seals didn’t know how to act and neither did I. It's good to not be alone.
Bugs. There's bugs crawling under my skin. Recycled poison pulsing through my bronchi. Dread seeping out my fingertips. Oh I'm shopping at Macy's, buying it all. Good riddance to the mall.
And I like my new reversible Tommy Hilfiger belt.
The big apple, the big kahuna, the city that never sleeps, el ciudad sucio. Spent the last 4 days wandering NYC, sighting and smelling and smiling. Much time yapping and filibustering with homies new and old: Lucas/Bella, Gabe/Chris, Mr. Phil, T - a guy who hazed me in college, Maya, and Madison. My first two nights were splendid - staying with Lucas / Bella and their two whimsical pups, Indie and Bluey, in Park Slope. Grateful to have known Lucas since Spring 2018, where we initially crossed paths at USC’s freshman orientation. Will never forget meeting the boisterous New Yorker saying ‘yo that’s doooope’ after every nervous 18 year old’s introductory ramble. He’d come to be one of my closest friends, with a heart of gold and a zeal for the latest Sheck Wes audiofile. Never forget his essay analyzing the hit single Mo Bamba. I digress, while staying with Lucas and Bella I got out to see the T Rex at the Natural History Museum, walked through blooming magnolias in Central Park, dined on fantastic Thai food, contemptuously consumed a racist bagel, and admired the bonzai collection at the Prospect Park botanical garden. T’was great to see Park Slope and the relatively quiet and cozy side of NYC living, much more manageable than much of Manhattan. I also enjoyed making engagement jokes, as Lucas and Bella have been dating for 10! years.
For the next two evenings I crashed with Gabe and his girlfriend Chris(tina) in their Murray Hill apartment. The Empire State Building, in its absolute grandeur, imposes itself on any open-eyed looker. Gabe, with his two monitors facing the NYC skyline, is a true ‘Have of Wall Street.’ His nickname from our two years working in investment banking together is ‘Have,’ don’t ask why… Highly enjoyed catching up, hearing about his and Chris’ lives, waltzing down to the Guggenheim, and getting bouncy at a Barry Can’t Swim show. The show ended at 12:30, enabling plenty of smug remarks from this San Franciscan who’s tired of hearing complaints of early endings. Other highlights include: ridiculously delicious food at Soothr, getting in Larry David-esque feuds with Central Park employees over tortoise management / air control, blowing up the Gugg bathroom, and a 4am kitchen politics chat.
NYC delivered upon all preconceptions: its energy, diverse experiences, respect for aesthetics, and financial viciousness. Going to try to keep a tradition of several days in the big ol stinky apple each year - always good to see friends and live live live it up. Henry out
The goal here, I’ve decided, is to get words onto paper as a time capsule for what I was doing and how I was feeling at various stages of life. Thus we begin. I am indeed in my mid 20’s, some apparently call it mid to late 20s, which is both rude and incorrect at 25. As for employment, I spend 20ish hours a week with Jaris – a Series B fintech startup - helping with investor messaging, financial modeling, and deck creation ahead of an anticipated funding round. Regarding housing, I am in a Hayes Valley apartment with Star, Emma, and Christine. Even after a romp around the world I maintain the opinion that SF is the best city in the world. I’m writing these words from Baltimore, Maryland, where Edgar Allen Poe mysteriously passed. Gracie, my wonderful and studious girlfriend, sits across from me working away on some MCAT preparation. Last, but not least, her roommate's cat, Poopi Corny, is curled up in a ball on the couch. He is worn out from climbing in an Amazon box, and then shuffling it off the edge of the table whilst still inside.
Ok, the bones of my life are on paper! As for words to describe the mental state in this stage of life, I have the following list: cautious optimism, sunlight, melancholic discombobulation, tumultuous, full, self-discovery. It’s been an odd chapter since quitting my finance job in July, travelling to 13 countries, and then returning to SF in November with no concrete plan beyond finding fulfillment. I have considered a variety of avenues, from private equity to teaching to working in finance at a weather balloon company. Jaris is a blessing, providing income and a resume filler as I take a moment to assess the world and my own aspirations. Change is everywhere, seemingly at an unprecedented pace. The technological aspect of this is especially evident in Hayes Valley, but other domains of change are just as if not more pressing: political, environmental, and personal. Somehow this is the first time in my life where I’ve truly had to choose my direction, and it’s terrifying. The school-> more school -> internship -> full time offer chain is broken, and I now have the opportunity to poke my head up. And what a strange time to do so. My approach this far has been to pursue knowledge anywhere I can: reading a ton of varied literature, meeting interesting people (some call it networking :(), and trying to carve out time to reflect on it all. So far all this has done is sew more confusion! My information sponge is soaked and it needs a squeeze. That sounds really weird. The hope is that one day the clouds clear and a path becomes obvious, though I know this is unrealistic and the vast majority of people are just taking one step after another. It’s helpful to be here in Baltimore, trying to keep up with Gracie’s study time, which forces me to sit down, look at job opportunities, make a plan, and be more intentional with my time. That’s all for now, but we shall see what happens!
And it's day 1 of writing my words in this semi-public blog. Not sure exactly what the goal is here - I suppose to document my life experiences, ruminations, and miscellaneous brain stirrings. It's a beautiful day at Mercury Cafe and things are looking up. Except we are sitting across from the indoor fake snowboarding shop (that runs something like $300 an hour), which always puts me in a bit of a funk. Shoot, positivity didn't last long - until next time.