Building in Public: Markdown based TaskOS updates -> Orchestrator layer

TLDR:

My task system handled daily tasks fine, but high-level tracks like personal brand and sleep kept dropping when energy was low because the system had no concept of a strategic layer. I built an orchestrator on top - an application of week # 4 contest, and tonight inspired by week # 5 contest i added a coach to enforce the planning.

https://github.com/rocleemusic/TaskSystem/tree/orchestrator

original post --> https://www.skool.com/cliefnotes/a-completely-markdown-based-task-management-system?p=604aaf74

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In a previous post I shared a markdown based task management system. To contiue the thread of building in public I wanted to share updates that I've made to it in the last month. The taskOS was working great at first, when life was slower it was easy to knock out my todo list 2-3 things at a time. But with growing work responsibilities and life commitments and career planning (and AI learning), I kept dropping the same things when energy got low: where my personal brand was going, whether I was handling the local community organizing I was hoping to do, or whether sleep was actually improving. None of it had a place in the system.

TaskOS knows what I'm doing today. It doesn't know that June is the go-window before the AI class starts, or that sleep is the engine for everything else, or that if I don't batch LinkedIn posts before July 7 they won't get written. When I was running on empty, I'd open the board, handle whatever was easiest to do, and close it. The strategic layer never showed up.

So I built an orchestrator on top, this came from thinking about the file system as an OS, and when the week 4 contest showed up this really helped to drive home that thinking.

My first version was a single `tracks.md` with 10 sections, one per area I'm trying to move: Work, Personal Brand, AI Learning, Sleep, and six others including life and meal planning, each with a goal, horizon, energy cost, current status, and next action. It worked until it didn't. On low-energy days only low-energy tasks got surfaced, so I'd read the first two and close it. The detail was always there whether or not I had room for it. To improve upon V1 I added a daily report on the open tracks and then also have it surface the #1 task needed to progress the highest priority task. But after adding the sleep track I'm finding it needed enforcement.

So inspired by week 5 contest, I wired a coach into the orchestrator along with a refactor of the system.

I refactored to two tiers. `tracks.md` is now a dashboard, one row per track, scannable in 60 seconds, and the detail moved to per-track files in a `tracks/` folder. The orchestrator manages everything. I also added Sleep as a first-class track with a 4-phase intervention plan (phases 1 and 2 active now), and `coach.md` to hold the coaching rules: ask before analyzing, one action per track per session, name the block directly when the same pattern repeats. Session start now begins with a check-in before anything else.

The full spec, build sequence, file templates, and V1→V2 history are on GitHub in the TaskSystem repo under the `orchestrator` branch. (Link below)

Another worth mentioning feature is a daily `work-log.md`, three bullets written at the end of the day or on sync (i have my repo in GitHub so I can use it across multiple computers). As part of my work I maintain a company linkedin page and a personal linkedin page for visibility in my industry, and I also need to log interesting stories for use in creating conference talks for credibility, so now that's wired in to my day to day as a ritual so that in 3-4 months from now I can just have Claude read my work-log and surface patterns or work case studies to start posts or talks about.

In the repo link is the original task system anybody can pull and look at and use, and if you go to the orchestrator branch you can pull the updates and wire that in if you want. I plan to keep on updating this and will put new features on new branches so the history and stages of the system can be used to learn from.

https://github.com/rocleemusic/TaskSystem/tree/orchestrator

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