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 visionToolmaker with tractionSystems 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