Strategic Cycles
Is this the right game — or are you optimising within the wrong one?
The quarterly cadence operates the Value System. Daily and weekly reviews ask "how am I doing?" Quarterly reviews ask "should I be doing this at all?" This is where you step outside the loop (REFLECT in the VVFL) to question the loop itself.
Quarterly Review
Half a day, four times a year. The most important review most people never do.
| Step | Question | Time |
|---|---|---|
| 1 | What did I ship? | List artifacts, outcomes, completed projects — not activity |
| 2 | What surprised me? | Unexpected wins reveal hidden strengths. Unexpected failures reveal blind spots. |
| 3 | What changed in the environment? | Markets, technology, relationships, opportunities — what's different now vs 90 days ago? |
| 4 | Are my priorities still right? | Test each priority against current evidence. Kill anything that lost its reason. |
| 5 | Who am I becoming? | Identity question. The quarterly review is where you notice drift — toward or away from who you want to be. |
| 6 | What are next quarter's 3 bets? | Not goals — bets. Specific, measurable, with stated confidence. |
Annual Review
The deepest cadence. YearCompass protocol: two halves — reflect on the past year, then plan the next.
Looking Back
| Prompt | What It Reveals |
|---|---|
| Biggest thing you completed | What you're capable of when you commit |
| Most important thing you did for others | Where your impact actually landed |
| Biggest surprise | What your prediction model missed |
| Biggest risk you took | Your relationship with uncertainty |
| Wisest decision you made | Your judgment at its best — pattern to repeat |
| Biggest lesson learned | What the year taught that no year before did |
Looking Forward
| Prompt | What It Anchors |
|---|---|
| What am I ready to let go of? | Sunk costs, dead projects, identity attachments |
| What am I willing to say no to? | Boundaries that protect what matters |
| What am I willing to dare? | Growth edge for the year |
| Who do I want to spend more time with? | Good company is the method and the measure |
External Calendars
Events that shape strategic context:
| Calendar | Frequency | Why It Matters |
|---|---|---|
| Federal Reserve | 8x/year | Rate decisions move markets, affect runway |
| Industry conferences | Quarterly | Network, signal, positioning |
| Tax deadlines | Quarterly/Annual | Financial planning constraints |
| School terms | 4x/year | Family rhythm shapes work rhythm |
| Digital security review | Quarterly | Passwords, 2FA, access audit |
Fear Setting
Tim Ferriss protocol — quarterly or when facing a difficult decision:
| Column | What You Write |
|---|---|
| Define | 10-20 worst things that could happen if you act |
| Prevent | What you could do to prevent each scenario |
| Repair | How you'd repair the damage if the worst happened |
| Benefits | What you'd gain from even partial success |
| Cost of inaction | What 6 months / 1 year / 3 years of status quo costs |
The exercise works because worst-case scenarios are rarely as bad as the fear of them. And the cost of inaction, once written down, is usually worse than the cost of trying.
The Shadow
Strategic reviews that produce vision without commitment. Grand quarterly plans that dissolve on the first busy Monday. The quarterly review must end with bets — specific, measurable predictions you're willing to be wrong about. Without bets, strategy is just daydreaming.
Context
- Monthly Cycles — The data that feeds quarterly strategy
- Predictions — Bets as the measure of conviction
- Positioning — Are you known for what you want to be known for?
- Purpose — The anchor quarterly reviews check against
- Decision Journal — Historical record of bets and outcomes