Planning
What does done look like — specifically?
Vision without a plan is fantasy. A plan without vision is busywork. Planning bridges the gap.
| Without Planning | With Planning |
|---|---|
| Reactive chaos | Proactive flow |
| Constant firefighting | Anticipated obstacles |
| Energy scattered | Energy focused |
| "We'll figure it out" | "Here's how" |
Define Done
Before anything else, answer these:
| Question | Why It Matters |
|---|---|
| What does the outcome look like? | Vague goals produce vague results |
| How will you measure success? | If you can't measure it, you can't know |
| What's explicitly out of scope? | Scope creep kills plans |
| Who needs to agree it's done? | Unclear ownership = unfinished work |
Write it down. If you can't describe done in one sentence, you don't understand the problem yet.
Work Backward
Start from the outcome, trace back to now:
DONE (what success looks like)
↑
MILESTONE 3 (final validation)
↑
MILESTONE 2 (core work complete)
↑
MILESTONE 1 (foundation in place)
↑
FIRST ACTION (the next physical thing you can do)
The first action is the most important output of any plan. If you don't know what to do next, the plan hasn't worked yet.
Critical Path
Not everything needs to happen in sequence. Identify what does:
| Concept | What It Means | Example |
|---|---|---|
| Sequential | B can't start until A finishes | Can't test until built |
| Parallel | A and B happen simultaneously | Design and research at once |
| Dependency | C requires both A and B | Launch requires product + marketing |
| Blocker | Nothing moves until this resolves | Waiting on approval |
The critical path is the longest chain of sequential dependencies. It determines the earliest possible completion. Everything else has slack.
Buffer Rules
Plans always take longer than expected. Use these multipliers:
| Situation | Multiply Estimate By |
|---|---|
| You've done this before | 1.2x |
| Similar to something you've done | 1.5x |
| Never done this before | 2x |
| Depends on other people | 2.5x |
| Depends on other people you haven't worked with | 3x |
Hofstadter's Law: It always takes longer than you expect, even when you take into account Hofstadter's Law.
Review Cadence
Plans that aren't reviewed don't survive contact with reality:
| Frequency | What to Check |
|---|---|
| Daily | What's the next action? Any blockers? |
| Weekly | Are milestones on track? What's changed? |
| Per milestone | Is done still defined the same way? Should we adjust scope? |
| Post-mortem | What did we miss? What took longer? What will we do differently? |
Adjust the plan, don't abandon it. The plan is a tool, not a promise.
The Shadow
Over-planning. Plans that never execute. Rigidity when conditions change. Planning as procrastination — the comfort of preparation without the risk of action.
By Archetype
| Archetype | Planning Style |
|---|---|
| Engineer | Sequences tasks, maps dependencies, builds systems |
| Realist | Validates the plan against constraints and evidence |
| Dreamer | Sets the vision that the plan works backward from |
Context
- Systems Thinking — See the whole before planning parts
- Critical Path — What must happen first
- Work Charts — Planning capability deployment
- Focus — Plans without focus are wish lists