San Francisco's warmest months are September and October—the fog pulls back, the sidewalks fill, and the city's social metabolism picks up. October 2025 opened with that particular combination of golden-hour light and storefronts fully committed to Halloween and Día de Muertos themes, a friend visiting from Phoenix for the Castro Street Fair, and a Thursday/Friday off from work that turned into a return trip to Puerto Vallarta before the month had found its rhythm.
🎪 Castro Street Fair
The first weekend of October, a friend visited from Phoenix and we attended the Castro Street Fair — an annual festival in San Francisco's Castro District started by Harvey Milk in 1974, celebrating the city's LGBTQ+ community and the Castro neighborhood.
🌱 Indoor Gardening
My indoor AeroGardens are continuing to thrive, with jalapeños and cherry tomatoes ripening, the cucumber vine growing up and out of the tall indoor garden, and rosemary and greens doing well in the kitchen. There's an issue with the lower part of the cucumber plant — the leaves are turning brown and dying — but so far I haven't been able to pinpoint the cause. If you search online for "cucumber leaves turning brown," there are way too many possible reasons to narrow it down.
🌴 Puerto Vallarta
The org got a Thursday and Friday off for shipping new AI tools, and by October 9 I was back in Puerto Vallarta for the third time this year—October 9–12. At 3.5 hours from SFO and $300 round-trip when booked ahead, it has become my default pressure valve: faster than driving to Los Angeles, about the same time as Tahoe or Mendocino, and considerably warmer.
💼 Work
At work, I'm now contributing to multiple orgs and projects. I'm helping build a new type of perpetual Multi-Armed Bandit (MAB) into the company's experimentation platform, where I'm developing the UI controls and reporting dashboards for those experiments. I'm also working on product and business switchers within the new AI tools and agentic-driven interface that recently began rolling out to customers.
The experimentation platform work feels more traditional, while the agentic work is very new — both to me and, I imagine, to many software engineers around the world who are exploring these novel tools and figuring out how to integrate them into existing products.
Across the web and applications, AI agents are starting to take on tasks on behalf of users, and interfaces are evolving from knobs and controls into more chat-like experiences. It's a big paradigm shift. Will customers embrace it, or reject it in favor of more traditional interfaces? I'm still undecided, though I find myself personally using and embracing more AI tools both at home and at work.
🎃 Halloween in the Castro
The month wrapped up with Halloween, which landed on a Friday for the first time in over a decade. After work, I headed to the Castro for the Castro Night Market, which ran from 5–10 p.m. on Halloween day — a street festival with stages, live music, vendors selling merchandise from booths on 18th Street (closed to traffic for the event), and city-permitted outdoor bars allowing public drinking for the evening. The neighborhood — and probably the whole city — was buzzing with that unmistakable San Francisco energy, full of people showing off their costumes and having a good time.