Leantime Migration Plan

Table of Contents

Objective

In my TODO management and life planning, I've advanced to enough to tackle: longer term projects over months and years, which is what i've never even really been able to do at all. The thinking is, the best thing i've ever accomplished was a bootcamp where i was working 12 hours a day, 6 days a week, for 3 months, and then started a whole career from it. How? Someone set a curriculum for me. Every day was easy, I knew exactly what to do each day and in service of what: turning my life around and becoming an engineer. I don't necessarily need to get to that level of productivity again, but the general idea of waking up excited to do more work on a project i'm quite clear on is what i'm trying to achieve. Right now the most I can do is think "the long now foundation project deadline is tomorrow" which will feed a procrastinatory burst of creative work. I want to see if more planning can harness and create that energy more consistently and controlled.

Below is a draft of a couple passes with LLMs. We input 10 years of journals, my current year's granular task list, ambitions, and notes, and then output primarily the "Projects" of my life (top level headlines after "structure notes" such as "508 / indie business."). This was already an accomplishment, determining the areas of life I want to focus on for the next couple years, if not 10.

The next step was to try to fit these into the paradigm of Leantime, but we might have stumbled along the way there. YOu can see some notes on that under "structure notes."

Tool exploration task

Determine whether Leantime, OpenProject, or another planning tool is the best fit for long-horizon life/project planning. The tool should make months-to-years work visible over time, connect concrete projects and milestones back to larger objectives, and support review rhythms that create motivation rather than just store tasks. Day-to-day task execution can stay in the existing TODO system, but the planning tool should ideally help generate those granular tasks from larger goals and dated batches of work.

Working criteria

The right tool should support:

  • A temporal overview of months-to-years work, ideally across all life areas.
  • Explicit hierarchy from long-term objective -> project/initiative -> milestone or dated batch -> concrete task.
  • Review loops that make progress, stuckness, and next focus visible.
  • Low-friction generation of day-to-day tasks for the existing TODO system, rather than replacing that system.
  • Enough flexibility for non-work domains: wedding, health, activism, family, creative practice, reading, homelab, and 508.
  • Acceptable hosting/data ownership, ideally self-hosted or exportable.

Candidate read, 2026-07-09

  • Leantime

    Current read: still a strong fit for the personal motivation side.

    Why it fits:

    • Its product model explicitly says it turns big ideas into goals and milestones, and links todos to goals.
    • It has a strategy layer: vision/strategy, focus areas, strategic goals, and project goals that can report back upward.
    • Milestones are task groups with dates, shown on a timeline/Gantt chart.
    • It has ADHD/neurodivergent-friendly positioning, personal dashboard, time boxing, task sentiment/priority, retrospectives, and AI task breakdown.

    Concerns:

    • The hierarchy may be less general than we want. The current structure appears oriented around Project -> Goals/Milestones/Todos, plus a strategy layer, but not arbitrary deep hierarchy.
    • Some AI features are not available in the open-source version.
    • It may encourage planning inside projects rather than a single cross-life portfolio view, unless Program Plan/strategy views are enough.

    Source: https://leantime.io/features/

  • OpenProject

    Current read: best fit for rigorous planning structure and cross-project temporal overview, probably heavier than Leantime.

    Why it fits:

    • Work packages support relations and parent-child hierarchies.
    • Gantt charts show work packages on timelines, with drag/drop dates, dependencies, predecessors/followers, and multi-project timeline views.
    • OpenProject's OKR guidance maps Strategic Initiatives -> Objectives -> Key Results -> Tasks, preserving traceability between daily action and strategy.
    • Portfolio management can group programs/projects into a strategic hierarchy with aggregated status/progress.
    • Meetings and project home dashboards could support weekly/monthly review.

    Concerns:

    • This may feel like enterprise project management grafted onto a life system.
    • The UI and setup are probably heavier, with more ceremony.
    • "Goal motivation" would be constructed with OKR/project conventions rather than being native/personal.

    Sources:

  • Plane

    Current read: plausible modern middle ground, especially if its paid/pro features are acceptable.

    Why it fits:

    • Initiatives group strategic work across projects, with start/end dates, status, progress, and list/board/timeline layouts.
    • Epics, milestones, cycles, modules, releases, dependencies, and pages cover a lot of planning structure.
    • Milestones align work toward target dates and track completion from linked work items.
    • Timeline dependencies make sequencing visible.

    Concerns:

    • Several relevant features are marked Pro in the docs, including milestones and timeline dependencies.
    • Plane is still more product/software-project shaped than life-planning shaped.
    • It may be excellent for 508/engineering and merely okay for health/family/art.

    Sources:

  • Linear

    Current read: not the first trial unless the scope narrows to engineering/product work.

    Why it fits:

    • Initiatives group projects around objectives and support long timelines, progress review, status, priority, labels, target dates, health, and updates.

    Concerns:

    • It is optimized for software teams, not whole-life planning.
    • It does not look like the best place for wedding/health/community/creative planning unless everything is forced into product-shaped projects.
    • Initiative views are Enterprise-only.

    Source: https://linear.app/docs/initiatives

Provisional conclusion

The strongest near-term comparison is not "Leantime vs every task app"; it is:

  1. Leantime, if we want a motivational planning tool that already speaks the language of personal focus, strategy, goals, milestones, and ADHD-friendly work.
  2. OpenProject, if we want the most structurally honest model for a life portfolio: multi-project timelines, arbitrary parent-child work packages, dependencies, OKR hierarchy, and portfolio rollups.
  3. Plane, if we want a modern, lighter project/product planning tool, but only if Pro/self-hosting constraints are acceptable.

My current bet: run a hands-on trial with the same slice of data in Leantime and OpenProject. Use "Learning -> AI tooling survey" and "Wedding/Health" or another non-work domain as test cases. If OpenProject handles both without feeling oppressive, it may be the better long-term planning spine. If it feels too corporate or brittle, Leantime is probably the better motivational layer and we should adapt our structure to its concepts.

Hands-on trial script

For each candidate, import/model the same sample:

  • One strategic objective: "Build a life planning system that creates bootcamp clarity for multi-month work."
  • One domain: Learning.
  • One goal: "Ship with new languages/tool."
  • One dated batch: "AI tooling survey."
  • 5-8 todos from the current list.
  • One non-work domain with emotional stakes, such as wedding/health/community, to test whether the tool only works for software-ish projects.

Evaluate:

  • Can I see the next 3 months and the next year at the same time?
  • Can I tell why a task matters without opening five layers?
  • Can I do a weekly review in under 20 minutes?
  • Can I generate/export concrete next actions back into org/TODO flow?
  • Does the tool make me want to return, or does it feel like managerial debt?

Structure notes:

Leantime structure: Leantime's organizational thing seems to be Projects can have Goals + Milestones + Todos.

Goals are laid out on a board and can have start/end dates and numerical tracking (number, percent etc) that is manually filled out and updated. Goals also can have a single milestone linked. The tooltip says `Milestones in Leantime take a group of tasks, a date, and act a stepping stones on the path to a goal. Linking a milestone allows you to track your progress and see how you are doing.`. I guess the flow is, a goal may have multiple relevant milestones, but only the active one is linked? An alternative strategy may be to leverage a milestone's "Depends on" field which, when set, creates visual links in the GANTT chart between milestones. Or, using another tool entirely, such as openproject or something else that allows the sort of hierarchy we're looking for. Alternatively, we could break apart goals and milestones significantly, which works if we assign each Leantime construct one job: a Goal is a number we'll judge the quarter by (updated by hand during weekly review), a Milestone is a dated batch of finishable work (its Gantt bar is the schedule), and a Task is a single action. Not everything needs all three — cadences are goals without milestones, exploration tracks are milestones/tasks without goals, and the wedding is milestones all the way down.

Milestones also have start/end dates and are displayed on what looks like a GANTT chart. This seems easiest for scheduling e.g. q3 whatever and so on. Milestones contain TODOs, and a milestones' % completedness is based on how many TODOs are open/completed within it. conveninetly, in the gantt view, you can toggle to see the TODOs under each milestone, set according to the TODO's date if that exists.

508 / Indie Business

Business/co-op: contracts, finance, member tools, business-facing tech.

Goal: Keep 508 financial/admin operations current

Milestone: Q3 admin cleanup

  • [ ] update 508 addresses (Wise pending business registration confirmation)
  • [ ] pay USA taxes [#A]
  • [ ] apply for coop marque [#B]
  • [ ] fix michael hetzner payment through 508 [#B]
  • [ ] add michael's creds to google workspace for free [#A]
  • [ ] If DMARC is not p=reject, change policy from quarantine to reject [#A] (security)

Goal: Revenue through interviews.508.dev

Milestone: contract / TOS resolved

  • [ ] set up contracting agreements for interviews.508.dev (or just TOS?) [#A]

Milestone: ERP integration

Milestone: interviewers onboarded

  • [ ] ask sean if he wants to be on interview app [#B]

Milestone: First billed interview (attached to goal)

Milestone: EA project defined + scoped

Goal: Engage more on social media

Goal: Regular blog posts

Milestone: blog backlog finished

  • [ ] publish nebiyu's blog post [#B]
  • [ ] fix goatcounter on 508 blog [#B]
  • [ ] make post about jankathon [#B]

Milestone: Make a game with jesse

  • [ ] get framework more fleshed out

Backlog (no clear goal yet)

  • [ ] go through codeberg PRs [#B]
  • [ ] some sort of business with bugs or plants between riley and me
  • [ ] taiwan motorcycle tour business
  • [ ] find header image for motour site
  • [ ] add "bad boss" article from journal to resume [#C]
  • [ ] flesh out goals from last meeting

Learning

Study + personal technical exploration (merged with Engineering). Math, philosophy, politics, literature, AI/dev tools, self-hosting, homelab, political philosophy, practical techniques for parallel forms of living from capitalism

Milestone: Golang basics

  • [ ] learn golang [#C]

Milestone: AI tooling survey

  • [ ] investigate cursor 5 [#A]
  • [ ] investigate AI flows [#A]
  • [ ] look into conductor - ai harness [#B]
  • [ ] look into hermes - agent [#B]
  • [ ] ollama + unsloth [#B]
  • [ ] try running local model [#B]
  • [ ] obliterated nemotron open model [#C]
  • [ ] look into beads - jira for AI [#B]
  • [ ] look into reducto - pdf parsing [#C]
  • [ ] integrate AI into emacs more

Milestone: Theory Track

  • [ ] list unanswered questions in my ideology [#C]

Milestone: Current book queue

  • [ ] finish the count of monte cristo [#B]
  • [ ] finish peasant resistance (ambition, recurring)
  • [ ] update reading list [#C]
  • [ ] find more books to read (ambition)

Milestone: Read pale fire (by end of july)

Milestone: Read the brothers karamazov (by end of december)

Milestone: Indie hacker Survey

  • [ ] look into starter stories [#C]
  • [ ] look up marc lou indie hacker youtuber [#C]
  • [ ] look up levels io [#C]
  • [ ] look into the yc blog [#C]
  • [ ] look into "capacities" [#C]

Goal: Engage more in FOSS

  • [ ] fix lazy library transmission bug [#C]

Backlog (curiosity items, no goal yet)

  • [ ] look into the podcast "gamedev local" [#C]
  • [ ] learn about chromosomes [#C]
  • [ ] OCR my written journals (ambition)
  • [ ] look into rva 23 risc v extension [#C]
  • [ ] watch more Code Bullet / physical 100
  • [ ] practice knots
  • [ ] look into "gbl"
  • [ ] investigate "unmasking autism" [#B]
  • [ ] mouse brain in robot? [#C]

Organizing / Activism

Real-world organizing and community action - political and non-political (coworking sessions, meetups, civic projects).

Goal: Host 3 picnics by end of year

Goal: Host 3 beach days by end of summer

Goal: Host 2 more coworking events

Goal: Host an anarchist movie night in the park

Milestone: First event

  • [ ] acquire projector, screen
  • [ ] find some anarchists interested in helping

Backlog

  • [ ] do more with the Cone Club and pedestrian activism (content plays, videos, organizing)
  • [ ] hikeathon [#C]
  • [ ] food not bombs in taiwan
  • [ ] "cohiking" hiking coworking trips [#C]
  • [ ] longer term coworking thing e.g. few days airbnb in the mountains
  • [ ] volunteer firefighter
  • [ ] translate some of these g0v projects (ambition)
  • [ ] https://tech.dsausa.org/join-us/
  • [ ] plan a firestation tour

Content Creation

Writing + video, aimed at an audience (blog, YouTube/PeerTube).

Goal: Publish backlog of blog posts

Milestone: Clear the queue

  • [ ] start huandao blog post [#C]
  • [ ] finish europe trip blog post

Goal: Get video pipeline running

Milestone: PeerTube live

  • [ ] set up peer tube [#B]

Milestone: First scripted video

  • [ ] just start writing video scripts [#C]
  • [ ] make videos (ambition)

Goal: Clear backlog of photo edits

Milestone: Europe Trip 2026

Milestone: Beehive fireworks

Milestone: Europe trip 2025

Backlog

  • [ ] upload recent audio recordings [#C]

Creativity

Pure energy/joy practice: photography, music, drumming, baking, games, retro hobbies, drawing, homelab, OSM stuff. No audience obligation.

Goal: Music practice

Milestone: Drum lessons running

  • [ ] get drum lessons set up [#B]

Milestone: Homelab/self-hosting backlog

  • [ ] deploy personal wikipedia [#C]
  • [ ] deploy reitti timeline tracker [#B]
  • [ ] deploy wealthfolio [#C]
  • [ ] install znc irc bouncer [#B]
  • [ ] make NAS available over ssh tunnel [#B]
  • [ ] auto deploy personal site [#C]
  • [ ] install expo music downloader [#B]
  • [ ] fix emails on event server [#C]
  • [ ] install dashy

Backlog

  • [ ] bake more (ambition, recurring)
  • [ ] update m8 firmware [#C]
  • [ ] make music (ambition)
  • [ ] take photos and backup journal [#C]
  • [ ] find japanese artist europe photos [#C]
  • [ ] make downstairs game streaming work (ambition, in progress)
  • [ ] replace headphone cables and get balanced ones while at it [#C]
  • [ ] get a new motorcycle jacket [#C]
  • [ ] go to more plays [#C]
  • [ ] get other 3ds set up
  • [ ] download strange journey for DS
  • [ ] get 128gb sd card for 3ds
  • [ ] add korean movies to jellyfin [#C]
  • [ ] go to little new york jam session (day/location tbd) [#C]
  • [ ] upload to panoramax [#C]
  • [ ] upload to karta [#C]

Mandarin

Goal: Conversational fluency

Milestone: have political conversation with someone

Goal: 3 political blog posts written in Mandarin

Milestone: political vocabulary pipeline established

  • [ ] retire old vocab deck
  • [ ] create political deck
  • [ ] pick article to mine for words
  • [ ] send to mandarin teacher

Milestone: first post finished

Goal: Mandarin journal entries (20)

Goal: Mandarin political events attended (3)

Wedding / Home / Family / Friends

Goal: Logistics finalized

Milestone: Vendor/legal lock-in

  • [ ] visit wedding cake people [#A]
  • [ ] resolve cheese plate [#A] (in progress, messaged lady 2026-05-27)
  • [ ] get lawyer sorted for wedding [#A]
  • [ ] add stuff to wedding calendar spreadsheet [#B]
  • [ ] add stuff to wedding spreadsheet activities [#C]

Milestone: Pre wedding photoshoot

  • [ ] Get led lights for cyberpunk outfit
  • [ ] sew in LED lights
  • [ ] get boots for cyberpunk outfit
  • [ ] get shoes for normal outfit

Milestone: Write vows

Milestone: Cake decided

Milestone: The wedding itself (date: oct 17)

  • [ ] lactate pills at wedding?

Goal: Be more present / initiate more

Milestone: hmm

  • [ ] be more supportive when tammy needs help (ambition, recurring)
  • [ ] plan a lego date [#C]

Backlog

  • [ ] parents back in taiwan
  • [ ] hostable home
  • [ ] hang with jay more,
  • [ ] go to events (ambition)

Health

Body + behavior/mind. Only goals not already cemented as daily habits.

Goal: Cut to wedding-photoshoot weight to 89kg

Milestone: 89kg by photoshoot (~2 weeks out, currently 91kg, started 100kg in Jan)

  • [ ] (habit tasks: lift 3x/week, cardio 2x/week - already running per existing habit tracker)

Goal: Eliminate dopamine candy (90% adherence by end of August)

Goal: Lift routine re-established by end of August (90% dates hit)

Goal: Cardio routine re-established by end of August (90% dates hit)

Goal: No bed phone (90% adherence by end of august)

Goal: Look great for wedding (oct 17th)

Backlog

  • [ ] look into statin and its reduction of cholesterol [#C]
  • [ ] just like pay someone to tell me what to do to lose weight (maybe, if above don't work)
  • [ ] go out and do more sporty stuff (ambition)
  • [ ] get back into fencing

Relationship / Family

Backlog

  • [ ] update friend library app with new stuff i have to lend out
  • [ ] find bogdan's patch [#C]

Uncategorized / needs a decision

These are one-off personal admin/chores that don't obviously serve a growth goal in any of the 9 projects. Forcing them into a project just to have a home risks diluting what each project's Goals actually mean. They'll be moved back into the routine TODO system involving org mode and pen/paper.

  • [ ] cancel nvidia phone thing (or switch to chunghwa?) [#A]
  • [ ] texas property claim [#A]
  • [ ] investigate "sending moey to parents" tax thing in taiwan [#C]
  • [ ] look into NZ passport [#C]
  • [ ] look into alaska credit card [#C]
  • [ ] find electric imp 401k [#C]
  • [ ] whiteboard in ingredients cupboard [#C]
  • [ ] replace earplugs [#C]
  • [ ] change bun to bum [#C]
  • [ ] look into "Mostly savory" food IG / "super mei" travel blog
  • [ ] try https://www.postcrossing.com/ [#C]
  • [ ] add instructions for taipei speeding to rent motorcycle article [#C]

Created: 2026-07-16 Thu 17:54