The Investment Already Made Is Not a Reason. It Just Feels Like One.

Here's a scenario that should feel uncomfortably familiar. A competitor suffers a high-profile data breach. The story runs on LinkedIn for two weeks. Executives testify before a co…

Here's a thought experiment. You have $1,000 and you spend it on a conference ticket. What did that decision cost you? The obvious answer: $1,000. But that's not the full answer. I…

Here's a scene that probably sounds familiar. An engineering director is sitting in a quarterly review, looking at a slide showing a migration that's 72% complete. He asks a simple…

A student in one of Guhan Subramanian's negotiation simulations at Harvard Business School spent most of the exercise arguing that a wage rate of $10.69 per hour was completely unr…

Here's a thinking habit that sounds almost too simple to be useful: before you figure out how to solve a problem, spend time figuring out how you'd guarantee failure. This is inver…

A competitor suffers a data breach. The story runs on LinkedIn for two weeks. Three executives testify before a parliamentary committee. A month later, your leadership team sits do…

(A note before we start: I wrote about sunk cost briefly in the June 18 issue — specifically how the model breaks down when building costs collapse. That was about when the framewo…

You walk into a salary negotiation having done your homework. You know the market rate. You have a number in mind. Then the hiring manager opens with something lower than you expec…

Here's a pattern that shows up in deal post-mortems with uncomfortable regularity: the red flags were visible in the data room. They were there in the financials, in the customer c…

Somewhere in a boardroom after the 2008 financial crisis, a risk committee added "mortgage-backed securities" to their list of things to worry about. Which would have been useful a…

Meta spent over $80 billion building a virtual world that peaked at 300,000 monthly active users — and then kept spending. Reality Labs lost $19.2 billion in 2025 alone on $955 mil…

A student in a Harvard Business School negotiation simulation spent most of the exercise arguing, with genuine conviction, that a wage rate of $10.69 per hour was completely unreas…

Most strategy sessions start with a question like "How do we make this succeed?" It sounds rigorous. It isn't. It's optimism wearing a whiteboard. The more useful question — the on…

A single data breach story in the news can temporarily tank conversion rates across an entire industry. Not because the actual risk of fraud increased. Because the mental availabil…

You're in a product review meeting. The feature has missed its adoption targets for three quarters running. The engineering team has quietly stopped believing in it. Two of your be…

Here's a strange experiment. Researchers spin a roulette wheel — rigged to land on either 10 or 65 — then ask participants to estimate the percentage of African countries in the Un…

After the 2001 anthrax attacks, Americans flooded emergency rooms with anxiety about bioterrorism. Billions in federal funding shifted toward biodefense. Meanwhile, the flu killed…

Here's a question worth sitting with: if 90% of startups fail, why does almost all startup advice come from the 10% that succeeded? The answer is obvious once you say it out loud.…

You're three months past the original deadline. The budget has been revised twice. The team is tired. And in your last status meeting, you caught yourself explaining — again — why…