This issue is different.
Last week, a reader asked: "Can you share custom GPTs you've built?"
So I built one. Based on reader demand.
Today you're getting:
The framework: Sahil Bloom's Annual Planning system
The prompt: Copy-paste ready
The tool: A custom GPT that coaches you through the process
📚 Framework in Focus: Sahil Bloom's Annual Planning Guide has four layers + three execution models:
Big Goals → Your summit. Ambitious, year-long targets. If they don't scare you, think bigger.
Checkpoint Goals → Your campsites. Quarterly milestones that lead to the summit.
Daily Systems → Your feet. 2-3 simple actions that compound. James Clear: "You fall to the level of your systems."
Anti-Goals → Your guardrails. What you refuse to sacrifice. Charlie Munger: "Tell me where I'm going to die, so I'll never go there."
ABC System → Three levels per habit: A (perfect day), B (normal), C (minimum). Hit C and you're still compounding.
Two-Day Rule → Never skip more than one day in a row. Missing once doesn't break habits. Missing twice does.
Monthly Check-in → Three questions on the last Friday of each month: Are my goals still aligned? Are my systems creating momentum? Am I violating my anti-goals?
2️⃣ Powerful Prompt
Use this on one real goal you're considering for 2026: a career move, health target, side project, or relationship priority.
Role
You are an annual planning coach helping leaders build plans they'll actually execute.
Context
- Focus area: [Professional / Personal / Both]
- What I want to achieve: [Insert ambition]
- What I refuse to sacrifice: [Insert non-negotiables]
- Time I can commit daily: [Insert realistic time]
Task
Define 1-3 Big Goals (if they don't scare me, push bigger)
Set Checkpoint Goals (quarterly milestones)
Create Daily Systems (2-3 actions that compound)
Build ABC Levels for each system: A (perfect), B (normal), C (minimum)
Establish Anti-Goals with warning signs to watch
Design a 3-question monthly check-in
Guardrails
Flag conflicts between goals and anti-goals
C level must be achievable on my worst day
Output Format
Annual plan with goals, systems, anti-goals, and monthly review template
(Copy-paste into ChatGPT, Claude, Gemini.)
🤖 The Tool: Annual Planning Coach GPT
Don't want to fill in the blanks yourself? I built a GPT that does the heavy lifting.
What you get:
→ Guided conversation: It asks you questions one at a time instead of dumping a template on you
→ Pushback when you play small: If your goals aren't ambitious enough, it challenges you
→ Conflict detection: It flags when your Big Goals and Anti-Goals don't align
→ ABC system built in: For every Daily System, it creates realistic A, B, and C levels
→ Monthly review template: Walk away with three questions to ask yourself every month
→ Exportable plan: Get a clean summary you can save, print, or revisit
It's like having a planning coach in your pocket, without the $500/hour fee.
✨ The goal isn't more goals. It's daily systems that compound.
↗︎ Think Better. Clarity Prompts
