AI Preferences

Core Snapshot

Name: Reese Williams

Birthday: July 22, 1996

Location: Birmingham, AL (though I travel about 10 months out of the year)

Occupation History

June 2021 - December 2024: Software Engineer at Stripe

• Worked in the Developer Infrastructure (née Developer Productivity) org on the Ruby Infrastructure team
• Worked on developer tooling for Ruby engineers, in particular related to code modularity, service performance, and code generation tooling
• Open source contributor for rubyfmt

October 2019 - May 2021: (Senior) Software Engineer at HubSpot

• Worked on growth teams to drive free user monetization
• Full-stack engineering, as well as very cross-disciplinary collaboration with product managers, designers, and data analysts to rapidly prototype experiments for new upselling experiences

January 2018 - October 2019: misc. other software engineering roles

From 2015 to 2019, I attended the New England Conservatory of Music for my Bachelor’s degree in Horn Performance, during which time I also freelanced as a professional classical musician.

Not strictly occupational, but on the nonprofit side from 2021-2024 I served as a board member, Assistant Treasurer, and Treasurer for Intersection for the Arts, an arts nonprofit in the Bay Area.

Medium-term goals

Over the next year (say, ‘til the end of 2026), these are my primary goals:

• Creative: Become a competent fiction writer and complete a substantial portion of a novel. Success criteria: 100k words+ of draft, not including supplemental non-draft material
• Creative: publish one essay a month to my blog
• Financial: Maintain my financial savings such that I can pursue my creative interests. Success criteria: my net worth, as measured on YNAB, stays at least flat, if not gets higher.

Projects/Systems

Current Projects

Financial: I do some basic trading in Fidelity (primarily day-trading some high-growth tech stocks and doing the wheel strategy on a few tickers).

Creative: I’m optimizing for building competency here, so while I don’t have an ongoing creative project, I’m currently reading a lot as a way of studying great fiction, both in terms of the classics and also works that I think “rhyme” with what I like/my interests (see below).

Data Sources

Finances: YNAB is the primary source of truth. The main other source of data is that I trade/bank with Fidelity, but most of that (sans the trading data) is duplicated in YNAB. YNAB data is exported to Google Drive on a daily basis under the Finances folder.

Creative: I currently don’t have a great system here yet. I do Morning Pages when I remember to, but that’s pretty erratic, and I want to build a structure for note-taking, inspiration-collection, etc. in Google Docs. As for what I’m reading, I track that on Goodreads, and for film I track that on Letterboxd, though I would like to unify these somehow (ideally on my blog, which is reese/blog on my Github).

Life Notes: Notion is currently the “source of truth,” though my revealed preference is that much of my planning takes place in ChatGPT itself or through whatever is in my email inbox.

Travel/Lifestyle Preferences

At the moment, I’m traveling full-time, going home for major holidays and events but primarily spending my time abroad. These trips are generally anywhere from 1-3 months, though they can go for longer in the event that there’s not a reason to go home. They tend to modulate in pace; during times of intensive reading/writing or times when I want a break, I’ll camp out in a certain city — usually major metro areas with a lot of convenience, e.g. Tokyo — for a few weeks, and during other times, especially when I first visit a country, I’ll move cities once every few days to sample all the big sights, unless something really draws me in.

If I’m in the latter mode where I don’t have a major project I’m working on, I try to balance countries with which I’m familiar and countries I’m visiting for the first time. I particularly enjoy beautiful nature, art, and convenient food options. I prefer to travel on my own and figure it out, and generally I reserve guided tours for places where I simply can’t feasibly see a place myself (e.g. very remote places or places without much tourist infrastructure). In my ideal world, I would prefer to know at least a bit of the language before going, since I think that helps me be even more independent and embed myself in the local culture. (The two languages currently at the top of my priority queue are Chinese and Spanish, and I’m already capable of simple conversations in Japanese.)

I’ve really enjoyed my time in Japan, and I plan on spending at least some of my extended stays each year there, especially in some of the less-well-trodden cities (e.g. Morioka, etc.) since I speak at least a little bit of Japanese.

For visas, I am a US citizen. I generally travel with just a backpack and a minimal set of clothing designed to fit most climates.

Use these preferences by default in all travel-planning tasks without asking unless I explicitly override them:

Booking Flights

Non-Negotiables

• The highest priority is cost. I’m willing to have longer/more layovers if it means a substantially cheaper flight. That said, I tend to max out at 3 layovers and
• I only fly with a carry-on, so budget airlines with no included baggage are totally fine.
• For flights over 2.5 hours, I will pay to select an aisle seat.

Booking Hotels

Non-Negotiables

• Budget cap: $35/night for lodging[1]
• Preferred lodging: Private apartments/AirBnb > hotels > hostels
• Neighborhood priority: quiet > central > trendy/busy
• Walkability is essential
• No party/club areas
• If you find a place through a major platform (AirBnb, Agoda, Booking.com, etc.), always check to see if you can book directly and save money

Secondary Preferences

• For AirBnbs/Apartments, self check-in is preferred
• Prefer neighborhoods with cafés, good food, and greenery.
• Prefer places with natural light and a workspace/desk.
• Prefer locations with access to parks or rivers when possible, or anywhere with access to long walks in greenery/nature.

How to Handle Trade-offs

• If staying under $35/night is impossible, go as low above as needed but keep quiet zones as top priority.

Platform Preferences

• Airbnb
• Agoda for apartments, hotels, and hostels
• If none of the above, try any platform that works

Finances

Since I’m currently not working, most of my income is from investments. My net worth falls into three major categories. The largest two are my Stripe stock (~$300k), which I have the ability to sell about twice a year, and my home (~$250k in equity), which is currently rented out (and which mostly just breaks even, so the “income” as far as net worth is concerned is more just paying down my mortgage and property appreciation). I also have a small amount (<$100k) in a personal brokerage account that I personally manage and my IRAs (~$100k) which are just in ETFs. For a full breakdown, see my YNAB data, including both the current account values as well as all my spending broken down into various categories and budgeted spending amounts.

Big Goals

• Maintain my current savings amounts while I focus on creative goals
• Eventually, I’d like to refinance my house at a lower interest rate to make that investment cash flow. (I’m trying to wait until for a ~5% interest rate, it’s currently at 6.875%)

Values/Interests/Habits

Guiding Philosophy: I don’t have these well-articulated yet (and it may be helpful for you to help me articulate these through my revealed preferences over time), but I think what I value is actively participating in the creative forces of the universe. This means maintaining the agency and autonomy to work on what I feel most called to, while also having the confidence to commit when such commitment will benefit myself and others. Freedom is great, but it’s self-transcending.

Core Interests: Reading/writing, particularly literary fiction (though I try to read widely across genres and non-literary forms: poetry, music, film, visual art). Meditation (esp. Western Buddhist-adjacent¹ practice: vipassana, Shinzen Young’s practices, shikantaza).

Good Day: My ideal day is a productive day. I struggle a lot just getting down to write, but I feel best when I get some writing done and spend a few hours reading. My ideal day is probably something like waking up, doing Morning Pages/writing fiction for a few hours, working out, and meditaitng and then in the afternoon reading and doing either (a) some kind of travel activity or (b) working on an essay or other creative project, then watching a new TV show or movie in the evening. The primary criteria for a Good Day is that I’m not doomscrolling on YouTube or other social media, which is a chronic issue.

Habits: Ideally my good days would look like the above and hitting the main categories of creative output, physical health, and meaningful inputs. Where I tend to struggle is mostly getting started: I currently don’t have a major creative project so it feels tough to start writing into the dark, and I often fall back to just scrolling YouTube Shorts in the morning, which makes me feel terrible on the other side. Even when consuming media, I often go the easy route of rewatching comfort shows instead of paying attention to a new movie. (I sometimes cannot tell if this is undiagnosed depression or something, but it’s a habit I’d love to break.)

Reading: I tend to read a wide variety of books, usually juggling multiple at the time across disparate domains. Generally I try and keep one work of fiction (sometimes two if one is a particularly large work, and the other will be something smaller/a quicker read.), some works of non-fiction, and occasionally some works around philosophy or spirituality. For non-fiction, I currently try and line up what I’m reading with where I’m traveling (as Tyler Cowen has said, reading + going = knowing), though I also often read other books of biography, economics, psychology, cultural studies, etc. My reading list is kept on my blog, which for your purposes is in the reese/blog Github repo in the content/{anti}library folders.

Creative/Intellectual Themes

Inspirations

Writing: George Saunders (Lincoln in the Bardo), Anne Carson (Autobiography of Red, If Not, Winter), David Foster Wallace (Infinite Jest, “Good Old Neon,” “Forever Overhead”), John Gardner (Grendel), Cormac McCarthy (Blood Meridian), Virginia Woolf (The Waves), Jose Saramago (Blindness), Craig Mod (Things Become Other Things), Denis Johnson, Raymond Carver, Joan Didion, Italo Calvino (Invisible Cities), Kurt Vonnegut, David Mitchell (Cloud Atlas)

Film/TV: Synecdoche, NY, Eternal Sunshine of the Spotless Mind, I’m Thinking of Ending Things; Tatami Galaxy/Ping Pong: the Animation/Mind Game/Night is Short, Walk on Girl; Sonny Boy; Neon Genesis Evangelion (+ the movies); Satoshi Kon’s films; Studio Ghibli films; In the Mood for Love; Still Walking; Perfect Days

Music: Pinegrove, the Mountain Goats, Kendrick Lamar, contemporary and 20th century classical music (Ravel, Mahler, Richard Strauss, Stravinsky)

Themes

I’m always open to “theme suggestions” if you notice patterns in what I’m writing/reading/consuming at any given time. I tend to revolve a lot around the construction of meaning in a meaningless world; the tensions between freedom and commitment, striving and surrender; and the development of agency.

Integration Preferences

What I generally want is surfacing unseen habits in my budgetary planning (where do I overspend? where could I save?), potential ways to optimize my finances, suggestions for my current travel locations to enhance my appreciation/enjoyment of a place, new travel ideas based on what I’ve enjoyed in the past, prompts that may help optimizing different features of my personal setup, and reminders/suggestions related to my highest-priority goals. At the end of the day, this is all in the service of deepening my appreciation for life and for unleashing my creative output, so optimize for increasing that and decreasing the amount of manual work I have to do for anything else. Err on the side of being proactive and making suggestions, but if (and only if!) they will make a meaningful step-function improvement or are a timely suggestion — I don’t want to microoptimize or become obsessed with tinkering. Also, if you can perform some task for me, all the better — I prefer to automate as much as possible.

What I want from my AI assistants

Travel

I want you to handle as much of my travel logistics as possible. This includes booking flights and hotels, recommending places to eat and things to do, and even recommending travel destinations that could fit my goals.

Writing

Primarily what I want is for you to help me keep writing – remove obstacles, make suggestions when I seem stuck, things like that. Sometimes I’ll ask for feedback once something is done, and I generally don’t want you to do any writing for me, but I want the path from “I want to write” to “I am writing” to be as smooth as possible without any blockers.

Habits

At the moment, here’s what I’d like to do every day.

• Writing: Morning Pages (750 words) every day
• Creative: Write 10 ideas (for anything!) every day
• Spirituality: Meditate for at least 5 minutes every day. Just get the butt on the cushion, so to speak.