Second Level Thinking

Ideas to help you see things differently.

Every fortnight I share one idea from my own work and reading on leadership, decision-making and performance. Free, straight to your inbox.

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The Last Human Edge

The Last Human Edge

Published on: 13/08/2026

Issue 50: As AI makes execution cheap, the quality of your decisions becomes your last real edge. Annie Duke’s thinking in bets, sharpened.

None of It Matters

None of It Matters

Published on: 08/04/2026

Issue 44: Chamath Palihapitiya on holding ambition and contentment at once, curiosity as an edge, and splitting decisions into two portfolios.

Building the Future By Thinking For Yourself

Building the Future By Thinking For Yourself

Published on: 26/02/2026

Issue 42: Lessons from Peter Thiel’s Zero to One on competition, definite optimism, secrets and the power law, and why thinking for yourself matters.

Complexity is Procrastination in Disguise

Complexity is Procrastination in Disguise

Published on: 02/10/2025

Issue 36: Why the simplest path is usually the most effective, and how to build a bias to action instead of letting the world happen to you.

Growth is Vanity, Cash Flow is Sanity

Growth is Vanity, Cash Flow is Sanity

Published on: 10/09/2025

Issue 35: Navigating the tension between expansion and insolvency. How to master COGS, burn rate and runway, with simple tools to stay afloat.

How to Lower the Cost of Being Wrong

How to Lower the Cost of Being Wrong

Published on: 21/08/2025

Issue 34: Lessons from Steve Jobs’ signal-to-noise ratio. Why the best leaders protect the few tasks that matter and build systems that survive bad calls.

Why Your "Mental Accounts" Are Costing You Money

Why Your "Mental Accounts" Are Costing You Money

Published on: 29/05/2025

Issue 30: Examining the sunk cost fallacy and how we organise our lives. Plus, why strategic laziness is a required form of founder discipline.

The Naval Framework: Navigating the Path to Success

The Naval Framework: Navigating the Path to Success

Published on: 17/04/2025

Issue 28: Why the best entrepreneurs treat life like a game of leverage. Inside: the Build vs. Buy debate and why ability alone is never enough.

Is Your School Choice Based on Data or Personality?

Is Your School Choice Based on Data or Personality?

Published on: 03/04/2025

Issue 27: The co-ed vs. single-gender school debate, why we struggle to decide, and how probabilistic thinking helps manage the unknown.

Thinking in Bets: The Art of Strategic Decision Making

Thinking in Bets: The Art of Strategic Decision Making

Published on: 20/03/2025

Issue 26: Navigating uncertainty without the fear of being wrong. Why great leadership is about sound process, not lucky breaks, according to Annie Duke.

Designing a Trading System That Survives Yourself

Designing a Trading System That Survives Yourself

Published on: 06/02/2025

Issue 23: How to build a personalised trading methodology, and why discipline is all that stands between a small error and a total collapse.

How to Optimise Your Portfolio and Your Mind

How to Optimise Your Portfolio and Your Mind

Published on: 17/10/2024

Issue 17: Position sizing like a pro with the Kelly Criterion, five essential gratitude practices, and the power of radical self-discipline.

Upgrade Your Thinking: Risk Models and Mental Tools

Upgrade Your Thinking: Risk Models and Mental Tools

Published on: 03/10/2024

Issue 16: Using mental models to navigate uncertainty, Howard Marks on what risk really is, and why cynicism is a liability, not an asset.

Overcoming Paralysis: Fear Setting and Financial Conviction

Overcoming Paralysis: Fear Setting and Financial Conviction

Published on: 19/09/2024

Issue 15: Why Tim Ferriss' fear setting is a prerequisite for action, and how to apply Stanley Druckenmiller's approach to risk in your portfolio.

Have You Outgrown the Person You Used to Be?

Have You Outgrown the Person You Used to Be?

Published on: 22/08/2024

Issue 13: Why your ego is the primary enemy of progress and how to audit your beliefs, plus R-multiples, the metric that matters for your trading system.

Is the US Recession Here?

Is the US Recession Here?

Published on: 08/08/2024

Issue 12: The US recession indicators, the yen carry trade unwind and what drove the selloff, plus Roger Federer on why perfection is impossible.

Winning Tomorrow Starts with the Framework You Build Today

Winning Tomorrow Starts with the Framework You Build Today

Published on: 27/06/2024

Issue 11: Moving beyond corporate speak to create a mission, vision and values that scale, and how to spot where we are in the market cycle.

Principles, Values, and the Death of the 60/40 Portfolio

Principles, Values, and the Death of the 60/40 Portfolio

Published on: 13/06/2024

Issue 10: The crucial difference between principles and values, how to build your own, and whether the traditional 60/40 portfolio is dead.

Better Decision Making and the New Japan Trade

Better Decision Making and the New Japan Trade

Published on: 21/03/2024

Issue 4: A six-step framework for better decisions, and why global investors are piling into Japan as the Nikkei breaks 40,000.

Deep Logic: Mastering Second-Level Thinking

Deep Logic: Mastering Second-Level Thinking

Published on: 07/03/2024

Issue 3: How to out-think the consensus with second-level thinking, and the second-order impacts of Nvidia, 'the most important stock'.