in yearcompass/year20162025-codex-summary.org , another iteration of you and i have summarized the last 10 years of year compasses. Try to avoid consuming other files in this directory, as you'll blow up your context window. My goal right now is to set up leantime with some "life project management" to establish a system for planning my future during my sabbatical. Basically, todo management isn't really a problem for me, but what is is managing larger projects over a long period of time, so i figured i'd do for my life what I do for work: use a project management tool. Leantime has some interesting ways to help do project management, for example you can set "Goals" to track TODOs and Milestones at, and all this is lumped under Projects. So far I've set up a project for my coop 508, generally learning (math, philosophy, politics, literature in teneral), writing, Organizing people / activism, creativity (art, photography, music), mandarin, the wedding, writing, and engineering. Now i'm thinking, hm, what are my goals for these things? There's some TODOs using my old system of tracking against year, month, week, and day goals in 2026.org, so for example I'd put some of the AI tools I want to try as TODOs under engineering, or "set up peer tube" as maybe under 'creativity' since it serves my goal of getting my youtube channel going (or maybe i'll convert "writing" project to "content creation" and lump video creation and writing under it), "europe trip 2025" would go there, "make post about jankathon" would go under 508 since it's a 508 related blogpost… but yeah basically i just have been collecting various ambitions in TODOs without any real clear goal or plan, just vibes. I started adding 'ambitions' to my daily review where i've been capturing ones like organizing people more, or, learning watercolor etc, so that would also be vague ambitions i have, but I want to get more clear about what exactly i'm trying to do so i can form more clear plans. That's what i need your help with. Please take a look at my journal 2026 file as well as my last 10 year year compass summary, and let's get to discussing and figuring it out.

Note that the codex summary year compass has a "next 10 years" section that should be ignored, it's just an LLM's generated idea of my next 10 years, I don't necessarily agree with it.

For the 2026.org year journal, probably just grab the first 200 or so lines to grab all the top level TODOs, then grab the ~250 lines after each month header (january through june) to grab all the month reviews, and then grab everything after the "july" header since it'll have my month, week, and day TODOs set up for this month.

You can see what i've been blogging about recently at blog.calebjay.com

1. interviews.508.dev is a decent candidate since it's deployed and just has a few concrete TODOs left to do, like setting up the TOS / contract, integrating with our ERP, and onboarding some more interviewers. It's not the greatest in terms of closing out the goal since it's still selling our labor - every interview requires a person's billed time. I mean, it would generate revenue for me and any other contributor based on the markup structure I established, so… well maybe it is good then lol actually. I have a couple other projects that would be more pure "revenue" on ship, though, like the tamagachi/streetpass hardware product i want to make, or the cozy castsle game i started working on with a friend, both of which would be established under the corporate structure of 508 and could onboard more engineers eventually.
2. I hesitate for school, i just don't do well in school. I mean, i did great in the bootcamp, so it's possible, but i'm also aware that school would basically become my #1 focus and priority over all else by the nature of it. Maybe that's what I need, but I hesitate since I feel like I could accomplish similar on my own, and in a way that's more aligned with my personal goals around politics and whatnot. It's been captured because it's been a recurring question - i'm on sabbatical, school is a strong contender for a good use of time right now. I do weekly lessons with a tutor already, i do daily hand writing practice using an anki deck, and i've started reading graded readers as well. I gave up on my vocabulary cards a long time ago because it was so tedious, after a while it'd be like a hundred cards a day to clear out my backlog of several thousand words, but it may be necessary to pick it up again to learn new words. Anyway, for school, I'd say dread above all else. I dread the loss of daily freedom I have to just pick a cafe and go to it with friends, or move my schedule around to accomodate events and activites.
3. Quarterly makes sense. The LLM written thing is actually pulled from somewhere in my previous year compasses verbatim i believe, pretty sure i wrote that myself at one point I'm aware that's still what i'm doing now with this system setup in leantime, but, oh well, i've been developing systems for myself year on year for the last decade, and they have always been an improvement. The latest project for the last 2 years has been to find a way to capture longer term, larger projects, rather than just simple TODOs, and lay them out temporally, hence the 2026.org structure (adapted from my previous trilium setup) where I have yearly, monthly, weekly, and daily TODOs. When i'm really activated i can create future weeks, and move month todos to the week i want to try to do it. Then i have a custom org view that will show me a calendar with those todos. But that doesn't really group them under the idea of a given goal, e.g. i want to try these LLM tools as part of being a better engineer that's staying on top of the latest AI tooling and potentially creating an AI consultancy arm through 508. So, it's ok with me that i'm yet again building a system in leantime, that might change again in the future. The through line of my life has been self review, self improvement, learning how to work with my ADHD to maximize my "productivity" or "potential", but also to feel actualized and good and happy. I was even thinking of dedicating this year to learning as much as I can about motivation and organization, but I figure the best way to do that is to do that through organizing these other ambitions. Point is, whatever we accomplish today will be a blog post at the end of the year lol.
4. Wedding might get chucked in leantime as a project just for practicality reasons; i need to track tasks for it somehow. Another LLM suggested categorizing wedding under a "Weding / Home / Family" so it can exist after october for goals i have for home and family, which, fair, there will be some in terms of getting my parents back to taiwan, or creating a home space for myself that lets me host friends more often, or improvements with my relationshp with my soon wife.

1. The Tuesday test. It's an ordinary Tuesday in 2036, in the version of life where this all went well.

Walk me through the day — where you wake up, who's around, what you do before lunch, what people in your community come to you for. Not the highlight reel; the default day. Identity lives in the default day, not in the mission statement.

1. Founder, builder, or member? In the commune/food-forest future — are you the one who runs it, the one

who built the systems it runs on and then stepped back, or a member who also runs 508? Be honest about which role you'd actually enjoy in year three, not year one.

1. Theory of change ranking. Prefiguration, mutual aid, movement building — force-rank them. Not

intellectually ("they're all important" is true and useless) but by where you'd rather spend a thousand hours.

1. Which future is shared? Has Tammy read this list? Which items would she put on hers?

Your hypothesis about me may be right. I think what I love most to do is enable, enrich, maximize the potential of, and ease the burden of, other people. So for example, to many friends of mine, I say, why pay for netflix, use my jellyfin instead! Or, I founded the co-op because I was infuriated by the existence of regional labor costs - the same engineer gets paid 40,000/year in Taiwan for a job that pays 240,000/year in SF, meanwhile the boss still pulls tens of millions. Disgusting greed, and because i'm an american i can just grab those 200k/year contracts and subcontract them nearly at cost to a taiwan engineer, who at the same time is a co-owner of the business. I make basically no money from this unless i close a contract myself, in which case I get up to 10% of the contract rate (another 5% goes to the co-op itself for either redistribution or just costs) - an opportunity available to anyone.

I guess basically I do want to just enable people to detach from capitalism. If I was mega rich, I would buy a building, fill it with artists, and pay for daily food deliveries, and say "do whatever you want," just for the sheer joy of enabling some humans to purely follow their craft. I HATE capitalism.

That said, the restaurant failed because of capitalism: I made a business-motivated decision to close when running the numbers didn't show a path to profitability in any reasonable timeline, and I couldn't sustain it and my own life while juggling contracts to keep the money moving. If I had a net worth of 10 million, I would have no issue keeping the restaurant open, staffing it, and letting it run at a loss for several years until it hit profitability (it likely would have within 5 years), and I would have also been fine pulling shifts myself - just not all of them like I was doing before. After all, some of the greatest joy I have is running Food Camp at Burning Man Taiwan, where I spend an entire burn building a camp, cooking food, and serving it to people, on my feet 14 hours running a kitchen. I LOVE it. It's capitalism that keeps me from fully actualizing this love of mine.

So, to answer your excellent questions

1. How fantastical can I get? The highest version of this dream is a normal day on a fully paralleled (detached from capitalism) commune, with all the rote chores that would come with it - cleaning things up, meal prep, hell, milking cows if need be. I'm a techno-utopianist so of course I'm hoping it'd be like Walkaway by Cory Doctorow where I can build and maintain a lot of automation and "ticket" management for needs around the commune, but even if it's just ensuring the farm is doing well enough to feed our community and cleaning toilets, I would be happy if it means we've created a sustainable external-to-capitalism world. But maybe that's the default day in 2046, not 2036? Perhaps the default day in 2036 is checking in on various 508 projects, resolving some question from some members about how to handle some issue with a client, and then perhaps checking in on whatever other projects I'm spinning. I'm not sure how detailed to get into this… I guess this is what i'm trying to figure out. I know for sure I want to be around people - my favorite is when I stay in a hostel with a shared kitchen, wake up and start making food for people. They wake up to pancakes, I love it. I want shared spaces. I want to host a movie night and make some snacks and people can come enjoy that.
2. My dream isn't to lead people but to actualize within everyone their own ability to lead themselves and others. I am perhaps a naive anarchist. I constantly want to doubt that there's something special about me and other activist "leaders" beyond our privilege that causes us to run movements or be the key organizers - surely EVERYONE is capable of this, but just hasn't been given the right tools, or confidence, or had the space of privilege to discover this power in themselves? I don't want to be a leader, I want to be a competent, confident individual in a community of competent, confident individuals. Though to answer your question in short, I suppose the building of the system is what I enjoy the most, though I am often thrust into leadership roles because I have confidence and good public speaking, or just have the stupidity to think a thing is possible, so the role is thrust upon me.
3. By prefiguration do you mean, building systems that enable people? The order would be 1. Prefiguration 2. Movement building 3. Mutual aid. Though mutual aid is the simplest to do: I could simply go right now buy 20 bento boxes and hand them out at taipei main station to some of the presumably homeless there.
4. Tammy's a liberal and normie but she's onboard with my dream of living in a commune / having people around. We've worked out specific constraints like the fact that she needs her own individual private space (especially bathroom) that she can retreat to when she gets socially overwhelemed, also so she can guarantee a cleansliness standard for herself (bad experience with roommates in the past I guess). Regardless, her ambitions are much more heteronormative: grow her career, put money in savings. She already has practically enough to retire in Taiwan, but has a lot of cultural financial pressure from her Chinese parents that she's working through. Regardless, I'm confident it's not a big issue nor something that will divide us. We've talked about it a lot, and she enjoyed "Walkaway" and gets where I'm coming from.

5. The fork, made concrete: when the 508 SaaS/product revenue arrives, what is it for — your personal runway, or the seed of a members' commons fund (pooled runway for the building, the land, the loss-making-for-five-years experiments)? You don't have to pick today, but the answer determines whether you're building toward patron or architect.

   1. The 508 experiment: will you actually run the member interviews? And what's your honest pre-registered

   prediction of what's missing — confidence, skill, network, or permission?

   1. Rung one: is "hostable home" a 2027-ish decision (next lease/purchase), and have you and Tammy ever

   sketched what it needs beyond her private bathroom — a guest room? a 12-person dinner table? a projector wall?

   Regarding 508 contracts, actually a few members do get that revenue. One in particular makes a lot of that money that way, since he pulled in a lot of contracts from his Stripe network. The key seems to be network - I didn't develop my SF network that well and maybe left there too early, who knows, but the one I closed came in from a youtube interview I was on, so I counted it for myself :P Since it's like, my personal brand. There's a couple "Small fry" members that randomly pull revenue, less than 10%, for taking the role of "client manager" (so handling invoices and some misc project management tasks). Again though it seems to come to privilege: our highest earner is a guy with a lot of crypto money, a rich dad, and a highly developed SF tech network. He's a nice guy and is onboard with the vision, but I guess, you mentioned patronage, it feels like a separate path I could have taken. I'm constantly looking at this fork: Do I just move back to SF for a couple years, hang at a startup, and try to bust out with multi millions? Or do I do as you say, take the bootstrap/co-op angle. The fork in my life in so many ways: my tech bro friends asking how I can both love the new world of LLMs while maintaining a leftists' criticism and skepticism of them as "plagiarism machines" that are torching the energy grid. I straddle so much. But you're making me realize, I should probably move away from the patronage path and more into the other path. It probably sticks around as a sort of idle "wouldn't it be nice" speculation. And also a frustrating criticism of the ultrawealthy I occassionally come in contact with: how can you have this much money, and not _?

   1. I wouldn't mind just a bit more runway for myself to take all financial pressure off me. Ensuring my future would be nice, I guess despite all my ideology, I'm trying to maintain a semblence of "rational capitalism" with a 401k. Maybe I'm a coward, but I suppose I'm leaving the possibility of me waking up at 80 and thinking "well that was all very stupid" and then looking at a bank account with 10k in it. On the other hand I have a deep suspicion that the world economy will survive in a meaningful way there… POINT is, I'm trying to balance my ideology against SOME level of rational hedging. But, outside of that, the vast majority of the money I want to leave available to the co-op to do group things with. And in fact that's what's been happening with most of the money - I've forgone taking any money from it, even cuts I could have, for the last 4 years, to keep the thing going.
   2. You mean the mock interviews? The product is, multiple members are listed, and the user would choose who they want to schedule an interview with based on the members' background, resume, skillset. So ideally everyone's pulling interviews. Myself, I'm not even that interested in running any, outside of validating the platform and maybe making some money. I'm not sure what you mean by what's missing - right now, a TOS and integration with our ERP are geniunely necessary for the financial flow and to cover us legally, and then onboarding people, and then probably just a standard marketing push. I'm fairly confident in the premise of it.
6. The home thing is a regular discussion. We have "golden handcuffs" to this apartment: landlord ignores us and hasn't raised the rent in 5 years. It's too small for what I want to do but conveniently located, and is a 10 minute walk to work for Tammy, in a brand new building, in a good location. Though, yes, we've discussed how our next apartment will need to meet each of our needs, her for private space, me for hosting. It's a terrible market right now, apartments are insanely expensive in Taipei, and to get the size we want, we basically would have to get an older building, which is a non starter for her, and for me I'm slightly worried about earthquake safety. All the new builds are total bullshit investment properties, "three bedrooms" but two are basically closets that shrank the living room by existing, and 3x what we're paying. My parents did have an incredible place in Danshui but it was a fluke, and also 3x what we were paying. So we have structural obstacles I guess, a triangle to figure out: What balance of cost, size, and location, do we strike? Beyond that we haven't figured out super specific details.