Negative Convexity

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Topic

Emotions & Finance

A collection of 73 issues

Toxic Leadership: Passing the Buck (Part 4 of 7)

Part 4 of my toxic leadership series explores blame-shifting and scapegoating—why leaders deflect responsibility, how it erodes trust and productivity, and why the most secure leaders own their mistakes while the insecure create a culture of fear and CYA.

Toxic Leadership: Fight-or-Flight and the Poisoning of Teams (Part 3 of 7)

Unregulated anger in leaders acts like emotional radiation, poisoning team performance over time. This post explores how bullying, dominance games, and unpredictable aggression trigger fight‑or‑flight, burn out employees, and ultimately erode a leader’s influence.

Toxic Leadership: Dishonesty and the Time Value of Truth (Part 2 of 7)

Toxic leaders lie to avoid discomfort—but the cost compounds. This piece explores three common forms of dishonesty in leadership and introduces a key idea: the time value of truth. The longer you delay it, the more trust—and power—you lose.

The Hidden Risk on Your Balance Sheet: Toxic Leadership (Part 1 of 7)

Culture is a leading indicator, financials are a lagging one. This 7-part series breaks down how toxic leadership behaviors—like bullying, dishonesty, and micromanagement—dysregulate teams and quietly erode company performance.

Planning for Your Worst Day of the Year

Bad days are inevitable—even for the most careful planner. This essay explores why mistakes happen, how to reduce their damage, and how to build the emotional and practical reserves to survive them. Planning well means preparing for your worst day of the year.

Attention as Capital

Attention is your scarcest resource. Like capital in a portfolio, it needs to be allocated deliberately. This essay explores how we waste attention, how to budget it better, and how to invest it in the goals that matter most.

Cosplaying as a Rich Person

Many chase the appearance of wealth or knowledge instead of the real thing. This essay explores why signaling matters, why it’s incomplete without substance, and challenges readers to show their real value without fear of looking fake.

Buy High, Cry Later: The Calm Investor (Part 3 of 3)

The final piece in a 3-part series on the emotions of investing. This post explores what happens when we consistently apply systems: the fear fades, execution becomes automatic, and we evolve into calm, disciplined investors. Mastery is boring—and it works.

Buy High, Cry Later: Systems Save You When Your Brain Melts Down (Part 2 of 3)

How to use systems—like diversification, budgeting, and stop-losses—to protect yourself from ego, fear, and impulsivity in investing. Part 2 of a 3-part series on the emotional challenges of investing and how to build resilience through structure.

Buy High, Cry Later: Welcome to the Emotional Hellscape of Being Wrong (Part 1 of 3)

Investing is emotionally rough because being wrong feels like failure—loud, public, and painful. This essay explores why the emotional toll of investing is so high and sets the stage for tools and mindset shifts to help you panic less next time the market crashes.