How to Optimize Your Life (Rigorously)
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Dear Prompt Experimenters,
I’m going to share the deepest prompt I’ve ever written.
What if we could inventory everything that is going on in your life? The people, the projects, the skills you have (and the ones you lack), the visions and goals, and everything else.
And then…what if we could rigorously model all of that? With real numbers, to get real answers. What is the specific roadmap you need to achieve your dreams?
Not fluff. Everything calculated with actuarial precision.
Wouldn’t that be something?
HERE’S HOW IT WORKS
This process is made for the builders, strivers, and seekers who don’t just want more productivity, but more purpose per unit of time.
First, AI will interview you, DEEPLY. It will take about an hour. Why so long? This is not about surface-level understanding. It’s about digging into all the dynamics of your world. About understanding what you want.
Then, we optimize, with the quantitative rigor of a hedge fund manager. Money matters, but it’s not everything. And that will be our approach. We’ll take your financial goals into consideration, all the monetization pathways of your talents and projects. But we’ll go way beyond that, focused on optimizing what makes your life meaningful, not just the dollars.
What will you get when you are finished with the process? Here is the table of contents of the report it generated for me:
📘 Guide to Your Optimized Life Strategy
This document is designed to function like a venture capital portfolio memo for your life, career, and creative pursuits. It reflects deep synthesis of your personal utility function, your current assets (from skills to projects to health), and your unique aspirations across finance, impact, and genius-level growth.
Below is a walkthrough of each section, what it contains, and how to use it.
1. Portfolio Summary Map
What It Is:
Your entire life distilled into a venture-style portfolio. Each major "asset"—like your corporate role, Substack, skills, health—is analyzed like a startup: its value, risk, potential, and alignment with your goals.How to Use It:
Quickly scan to understand where your life’s leverage points are. Use it as a high-level dashboard for weekly/monthly reflection on what's compounding and what’s stagnant.2. Valuation & Optionality Dashboards
What It Is:
A detailed breakdown of how each asset might grow in value—financially, personally, or socially. Includes expected value calculations, risks, time horizons, and effort multipliers.How to Use It:
Treat this like your “investment thesis” sheet. Pick 1–2 asset clusters where the upside is high and risk is acceptable. Track their growth quarterly. Revisit effort multipliers to recalibrate.3. Value Lever Matrix (Ranked)
What It Is:
Your top opportunities for explosive, compounding gains—ranked. Each lever has a high-effort-to-optionality ratio, meaning it gives you more bang for your time and energy.How to Use It:
Focus your weekly 20 discretionary hours here. Keep this matrix visible in your workspace. Reassess if you’re allocating time to your top-ranked levers—or stuck in low-return activity.4. Recommended Playbooks
What It Is:
Bespoke implementation guides for your most high-impact ideas: from corporate initiatives to Substack monetization to launching your “AI + Philosophy” platform.How to Use It:
Use each playbook as a tactical action plan. Commit to 1 playbook per quarter. Follow the checkpoints and metrics. Use them in Notion or a personal OKR system to stay on track.5. Time/Focus Reallocation Plan
What It Is:
A rebalancing of your calendar and cognitive effort. Cuts waste, protects your fitness & genius time, and channels surplus into compounding zones.How to Use It:
Update your weekly calendar. Timebox admin tasks. Gamify your top levers (especially Substack, narrative cohorts, quant R&D). Reassess monthly using energy tracking.6. Final Observations: Blind Spots, Risks & Unused Edges
What It Is:
A synthesis of strategic blind spots, biases, and underutilized assets—designed to help you avoid self-sabotage and uncover dormant power.How to Use It:
Reread this section quarterly. Identify 1 dormant edge to activate (e.g., “operator-agent hire”) and 1 cognitive bias to correct (e.g., novelty-chasing over compounding). Journal on these.🔍 BONUS INTELLECTUAL TOOLS
• Stochastic Value Maps — Future scenario modeling for uncertain projects
→ Sketch decision trees for narrative IP, GPT products, or internal roles• Regret Minimization Framework — Protects against long-term misallocation
→ Use when choosing between safe jobs vs. launching “AI + Philosophy”• Edge Amplification — Identifies where you’re rare and valuable
→ Recraft LinkedIn & internal brand to position you as an “AI systems philosopher”• Compound Interest Engine — Focuses on what grows exponentially
→ Apply to Substack, skill stack cross-training, and internal brand value• Market Analogs — Maps your life to venture/hedge fund models
→ Treat your strategy like a barbell fund: cash-rich core + high-convexity bets🛠 How to Work With This Over Time
Quarterly Review: Reassess Portfolio Map & Lever Matrix. Rebalance based on real-world feedback.
Monthly Sprint Planning: Choose one playbook or lever to emphasize. Gamify progress.
Weekly Check-ins: Track effort allocation vs. Utility ROI. Are you chasing novelty or compounding value?
Annual Strategy Reset: Update your goals, risk profile, and utility weights. Reassess optionality tree.
Want a venture-grade roadmap for your life, fully personalized to your goals, skills, and vision? Start here. Paid subscribers, read on!
PART ONE: DIAGNOSTIC INTERVIEW
Use this prompt for a comprehensive (50-question) interview to build a comprehensive fact base on your goals, projects, and capabilities. This will be the baseline for your optimization. I recommend model 4o or 4.5