Previously, on Leading Through Chaos: Chaos is hard because we can’t plan for it. Our protection? Nassim Nicholas Taleb’s “barbell strategy”: avoid ruin while finding opportunity. Use “effectuation” to find upside opportunity when planning...
strategy
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Leading Through Chaos, part 4: The Leverage Point of Change
Leading Through Chaos: The Leverage for Change What came before: In part 1, we saw that chaos is a problem because it makes prediction hard. A barbell strategy helps us make it through. In part 2 we dealt with risk of ruin, and part 3, covered upside opportunity. I’ve...
Leading Through Chaos, part 3: Seizing Opportunity!
In part 1 we covered the need for predictability. We took Nassim Nicholas Taleb’s advice in part 2 to cover our worst-case scenarios. Reader Shari Aaron asked: My business faces short-term disruption. Client budget approvals are very slow, due to so much uncertainty....
Leading Through Chaos part 2: Don’t Die! (aka Barbells and Risk of Ruin)
I have long planned to buy a new computer in 2026. My current desktop is nearing its end of life, but it still limps along. I’d rather not invest right now; cash is tight, tariffs are high, and my portfolio is down. But supply chain disruptions might mean that prices...
Leading Through Chaos, part 1: What’s the Root Problem?
When change is too fast, we stop investing for the future. Consider college: Who wants to spend four years and thousands to learn advanced skills that might be obsolete in ten years? When college is a path to success, it’s a no-brainer. When the job market changes so fast that college is a six-figure gamble? Not so much.
We can’t plan long-term during unpredictability, so we have to settle for short-term tactics. But that’s dangerous. Because short-term gains often come at the expense of long-term health.
The way to deal with chaos is to find predictability wherever you can.
Want to tank your profit margin? Just do a successful merger!
A fable of Maximus Grandeur, CEO of Gaping Maw Co[1]. Think you understand “synergies”? Think again. Most people don’t. Synergies can happen. The boost revenues and profits, but tank profit margin. In fact, math often guarantees it. Here’s an example. In the Beginning...
What is market size?
I'm a judge for Mass Challenge, as well as the Harvard Business School competition, and I've noticed that many entrepreneurs don't know what market size means. Let me call out two of the most common mistakes, which can be the difference between recognizing a real...
The Business of a Magician
All businesses share the same underlying foundation: a flow of money in and out. The money in has to cover the costs of the money out. It has to pay for the production of your product or service, and have enough left over to fund growth and expansion for the future....
What do CEOs do? A CEO Job Description
The Chief Executive Officer is one of the most coveted titles, and least understood jobs in a company. Everyone believes that CEOs can do whatever they want, are all powerful, and are magically competent. Nothing could be further from the truth. By its very nature,...
How you scale an organization
I just returned from Black Rock City, NV, better known as Burning Man. Burning Man is an annual event where 70,000 artists, engineers, performers, and makers descend on the Black Rock Desert in Nevada. In one week, they build and inhabit a city made of...