A decade forecast from first principles. Synthesizing career trajectory, values alignment, behavior change systems, and modular tooling. This is a living map—subject to adaptation.
Core Trajectory
From 2025 to 2035, I transition from:
- Engineer with vision → Toolmaker with traction → Systems architect with impact
- Building solo tools → Operating a product studio → Designing humane infrastructure for focus, health, and fulfillment
Key Life Themes
- Alignment over achievement — less hustle, more congruence
- Modular systems over hacks — rituals and agents, not dopamine tricks
- Flow-first design — tools that help me and others enter deep focus
- Obsidian + VS Code as basecamp — all life systems orbit here
Forecast by Year
2025 — Refinement & Foundation
Context:
- On paid leave, recalibrating post-layoff
- Launching: Oru, Sprout, Interview Analyzer
- Deep introspection: diet, identity, values
Milestones:
- Ship MVP of Sprout + Oru
- Begin regular digital gardening (Quartz / darlington.dev)
- Relocate to Portugal or return to SE Asia
- Land remote role at a mission-aligned startup
Systems Activated:
- Observer agent MVP
- Modular Obsidian templates (weekly review, rituals)
- iOS Shortcuts + Supabase backend for Oru logging
2026 — Traction & Duality
Theme: Day job vs mission
Milestones:
- Sprout + Oru gain early traction from indie devs
- First paid users or toolkit sales
- Start cohort-based experiments (e.g. “30-Day Flow Sprint”)
- Publish content on system design, automation, and behavior
Growth Edge:
- Clarify product/mission identity
- Tighter community curation
- Solidify rituals that scale
2027 — Integration Year
Theme: All-in on alignment
Milestones:
- Exit job to go indie OR create a dual-mode lifestyle (90% async)
- Launch Sprout Pro (VS Code extension, visual overlays)
- Publish first full framework: Digital Ritualist Handbook
- Hire 1st collaborator (frontend, designer, or GPT engineer)
2028 — Recognition
Theme: The world starts watching
Milestones:
- Speak at a developer or productivity-focused event
- Frameworks become memes (Sprout plant, Observer agent, etc.)
- 10k+ users
- Partner with other builders or wellness startups
Meta:
The project evolves from tools → philosophy.
2029 — Product Studio Era
Milestones:
- Launch “Darlington Systems” or “Modular Being”
- Cohort-based offerings + async curriculum + consulting
- Begin investing back into OSS: agent tools, rituals API
- Establish clear GTM channel (e.g. content + community)
Focus:
- Less execution, more mentoring
- Delegation and design systems
- Remote culture around deep work
2030–2032 — Life OS Stack
Milestones:
- AI-augmented Obsidian + GPT system running 100%
- Full release of Modular Life Agents (Observer, Pathfinder, Ritualist, Connector)
- Book in progress: Tending the Digital Garden
- Launch public vault + open toolkit library
Behavioral Infrastructure:
- GPT + Shortcuts automation for habits
- Deep tracking of flow, energy, values alignment
- Cross-device rituals
2033–2035 — Legacy Mode
Milestones:
- Publish first book + expand community
- Launch digital fellowship: Systems Design for Personal Transformation
- Mentor next-gen indie toolmakers
- Personal mission transitions into collective design
Long-term Vision:
A modular, privacy-first stack of tools and rituals to help anyone live better—with clear metaphors, open protocols, and humane defaults.
Constants (Agents Running)
- Observer Agent → Weekly reflection, energy tracking, value alignment
- Pathfinder Agent → Mission tracking, long-term goal progress
- Ritualist Agent → Daily routines, stretch/hydration/popups, habit nudges
- Connector Agent → Maintains social graph, connection loops, serendipity triggers
Living Framework
This document is a live object—revisit each quarter via the Observer Agent during your Weekly Review. Re-align forecast with current data.
- Add this to your Weekly Review System
- Create MOC:
10-Year Plan
linking out to major sub-systems - Visualize this as a roadmap using Mermaid or Notion-style board
timeline title 10-Year Life Trajectory 2025 : Foundation – Launch Sprout, Oru, relocate, reset systems 2026 : Traction – First users, digital garden, system rituals 2027 : Indie Shift – Leave job, Sprout Pro, publish handbook 2028 : Recognition – Talks, 10K users, virality 2029 : Studio – Launch Darlington Systems, async cohorts 2030 : Modular OS – GPT + Obsidian stack, LifeOS toolkit 2033 : Legacy – Publish book, launch fellowship, mentor builders