Why Great Business Leaders Use "Fear-Setting" to Make Decisions in Uncertain Times

Lessons from Jeff Bezos, Tim Ferriss and Ray Dalio

I've had some of my most confronting professional and personal conversations recently.

• What if AI redundancies escalate and reshape the market we operate in? What if they don't and we've over-corrected? 

• What if the situation between the US and Iran deteriorates even further? What if it doesn't? 

• A single post on X is moving stock markets. 

• A $110 billion investment in OpenAI lands.

Volatility is now the standard operating environment.

Where are the real threats right now, and where, underneath all of it, are the opportunities we might be too distracted or too anxious to see?

I've been doing a deliberately confronting exercise: fear-setting. Asking the questions I don't want to ask. For my own business and with clients.

Here's why.

The two extremes and the minority sitting between them

The conversations playing out around me are at two very different poles.

On one side: "AI won't disrupt my business," "AI won't disrupt my role" or even "AI is banned." Whether that's denial, avoidance, or genuine belief, I'm genuinely not sure. Maybe all three.

On the other: Borderline doomsday planning.

In March, Jack Dorsey cut 4,000 people, nearly half of Block's entire workforce, not because the business is struggling. Gross profit grew 24% year-on-year. He did it because, in his words, "intelligence tools have changed what it means to build and run a company." He predicted most companies will make the same call within a year.

The same week, Amazon committed $50 billion to OpenAI as part of a $110 billion round, the largest private funding raise in history. Amazon, Nvidia, and SoftBank are collectively betting that this isn't slowing down.

And meanwhile, escalating tension in the Middle East is adding a layer of geopolitical uncertainty that most revenue forecasts aren't pricing in at all.

Very few of us are sitting in the middle, running the scenario planning that challenges our thinking, exposes our biases and forces a plan.

The leaders I'm betting on aren't necessarily the ones who predicted it correctly (none of us have a crystal ball sadly). They'll be the ones who kept asking the hard questions.

So what do we actually do with this?

Jeff Bezos had a useful framework for navigating uncertainty at scale. He didn't try to predict every outcome of the e-commerce boom. He couldn't. So instead he asked: what's not going to change?

For Amazon: customers will always want speed, and customers will always want excellent service. He built strategy around the dependables, not the unknowns.

Ray Dalio runs a version of the same discipline at Bridgewater, one of the world's largest hedge funds. He calls it stress-testing reality: documenting his assumptions, pressure-testing them against the worst-case scenario, & building positions that survive being wrong.

In his own words, "He who lives by the crystal ball will eat shattered glass." Dalio doesn't try to predict. He prepares for multiple outcomes and builds the thinking muscle to navigate whichever one arrives.

That's the question we've been sitting with. Not "what will AI look like in five years?" but "what won't change, regardless?" And: "if we're wrong, what breaks first?"

The framework high performers are running

Tim Ferriss calls it "fear-setting." It's rooted in Stoic philosophy, specifically the practice of premeditatio malorum: the deliberate premeditation of what could go wrong. Ferriss credits it with his biggest business wins and biggest disasters averted. He runs it once a quarter, sometimes once a month.

The process: Define the worst-case scenarios in detail. Ask what could prevent them. Ask how you'd repair the damage if they happened anyway.

What most people find, when they actually go through it, is that the worst case is rarely as catastrophic or irreversible as the vague anxiety in their head.

Bezos used a version of the same thinking when deciding whether to leave Wall Street to start Amazon. He called it his "Regret Minimisation Framework." Project yourself to age 80. Which decision would you regret more: trying and failing, or never trying at all? The answer, he said, made the decision easy.

Dalio formalises it further. At Bridgewater, every major decision is stress-tested against failure before it's made. Not as pessimism, as precision. The goal isn't to predict the outcome. It's to know exactly what you'd do if things went wrong, so the decision is made from clarity, not fear.

They're forcing functions for clear thinking under uncertainty.

We been working with our clients and ourselves on all of these questions. It's resulted in new risks identified and new opportunities.

Our bias as humans is to anchor on whichever scenario feels most familiar. It's cognitive dissonance: holding contradictory beliefs because examining them honestly is uncomfortable. It's a very human response, but in revenue leadership, comfort with uncertainty is one of the highest-value skills we have.

One useful reality check before we catastrophise: Oxford Economics research found many layoffs labelled "AI-driven" were actually the result of pandemic-era overhiring. AI became the PR message, not the cause. We need to read these signals carefully.

Action:

Run a fear-setting session with your leadership team this quarter.

Questions on the table: What's the worst case, how do we prevent it, how do we recover? What are we sitting on that we're not moving on? What decision would we regret most if we don't make it now?

You don't need the answers. You need the conversation.

The question underneath all of this

None of us know exactly how this plays out. But there's a real cost to waiting until the picture is clearer. Because the picture isn't going to get clearer before the ground shifts. That's the nature of this moment.

Complacency isn't staying still. In a market moving this fast, it's falling behind.

Can we afford the risk of not even asking the hard questions?

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