Seeing Trouble Before It Strikes: Stoic Lessons for Business Leaders

How deliberate rehearsal of setbacks builds stronger leaders and organisations.

Optimism Alone Can’t Withstand the First Blow

Business leadership often celebrates optimism — the vision to see opportunity where others see risk. But optimism without preparation is fragile. The Stoics understood this and practiced Premeditatio Malorum — the ‘premeditation of evils’ — a discipline of deliberately imagining failure. Not to wallow in fear or feed risk aversion, but to strip misfortune of its surprise. They knew the hardest blow is the one you don’t see coming. By rehearsing setbacks in advance, they were ready when life delivered them.

This is Stoicism in business leadership at its most practical: rehearse the difficult, then act with clarity.

Why Early-Stage Founders Need to Rehearse Failure

Leadership is no different and nowhere is this clearer than in the early days of a startup. When you’re chasing the first clients, every rejection feels existential. The temptation is to assume the next pitch will land, the next demo will close, the next investor will finally see the potential — many won’t. Prospects ghost, competitors undercut, funding dries up, and the team begins to doubt.

Founders who prepare for these blows are less likely to collapse under them. They’ve already pictured the failed pitch, the lost deal, the investor walking away — and decided how they will respond. That rehearsal separates the founder who panics from the one who adjusts, perseveres, and breaks through.

Treat Setbacks as Constants, Not Surprises

What the Stoics practiced as philosophy, modern leaders can apply as strategy: setbacks are not accidents, they are constants. Companies don’t stumble because bad things happen; they stumble because they didn’t expect them to. The supply chain will break. Regulations will shift. Competitors will launch something faster, louder, cheaper. Pretending otherwise is not optimism; it’s denial.

The resilient leader is the one who has already considered these possibilities and prepared countermeasures such as a cash runway, alternative go-to-market (GTM) approaches, or technical pivots. By planning contingencies in the open, leaders build a culture that expects turbulence and isn’t undone by it. 

What Stoics and Security Engineers Have in Common

In cybersecurity, this discipline has a name: threat modelling. Security teams don’t wait for an attacker to strike before thinking about what might break. They deliberately map out the system, imagine how it could be exploited, and ask hard questions about consequences.

Leaders can borrow the same mindset. Every business has its vulnerabilities — talent gaps, financial dependencies, single points of failure in process or technology. The Stoic lens of Premeditatio Malorum asks leaders to treat these not as abstract possibilities but as real threats already on the table.

Just as engineers stress-test systems, resilient leaders stress-test their strategies. They walk through worst-case scenarios before they happen, stripping away surprise and deciding in advance how to respond.

How to Imagine the Worst Without Freezing

The main danger with Premeditatio Malorum is overindulgence. A leader who spends all their time mapping disaster ends up paralysed, planning for every possible collapse and consuming energy better spent building. Stoics were clear on this point: the exercise was meant to strengthen resolve, not breed anxiety.

That means setting limits. Run the exercise until you have identified the critical risks — the ones most likely to occur, or most damaging if they did. Then stop. Preparation is useful only when it leads to action. In cybersecurity, threat models aren’t exhaustive; they stop once the main weaknesses to mitigate are clear.

It’s not a one-off exercise either. Risks evolve, and so must the response. Premeditatio Malorum — like threat modelling — works best as an iterative discipline. By revisiting it regularly, leaders can account for new vulnerabilities, shifting markets, or emerging pressures. The aim isn’t endless theorising, but a regular review cadence that keeps the organisation a step ahead of the setbacks most likely to derail it.

Practical Ways to Stress-Test Strategy — and Know When to Stop

Premeditatio Malorum works best when it is structured. Left unchecked, it can spiral into endless “what ifs.” Leaders need techniques that focus the exercise, create actionable insights, and then signal when it’s time to move from thinking to doing. Use the mnemonic MAPS — Model, Attack, Prioritise, Stop.

1. Pre-mortems (Model the failure)Before launching a project, gather the team and assume it has already failed. Ask: What went wrong? Capture every plausible cause. The value of this exercise is in surfacing blind spots — overlooked dependencies, weak assumptions, or fragile processes — before they become costly. The point isn’t to predict failure perfectly, but to uncover the areas most likely to trip the effort.

2. Red Team Thinking (Attack the plan)Assign a person or group to deliberately break the strategy. Their task is to challenge assumptions that insiders can’t see. A product launch team, for instance, may be blind to the fact that support capacity is already at breaking point. The red team raises this, leadership adjusts, and the launch moves ahead stronger. The boundary here is clear: capture insights, make adjustments, then move on. Endless critique kills progress.

3. Scenario Planning (Prioritise what matters)Not every imagined disaster deserves attention. Focus only on those that are both plausible and consequential. A professional services firm might explore three: the sudden loss of a major client, regulatory change in its key market, and a hiring freeze that stalls delivery capacity. These are the kinds of risks that can sink the business. Wild hypotheticals — meteor strikes or a competitor with limitless capital — make for interesting thought experiments, but they don’t belong on the strategy table.

4. Decision Guardrails (Stop theorising and act)Once the critical risks are identified, translate them into playbooks. If the biggest client churns, activate the diversification plan. If a funding round falls through, trigger contingency cost controls. If a supply partner fails, switch to pre-vetted alternatives. Guardrails convert theory into execution. They also signal when to stop analysing — once you know what you’ll do, further speculation adds no value.

By following MAPS — Model, Attack, Prioritise, Stop — leaders can practice Premeditatio Malorum without being consumed by it. The exercise sharpens foresight, protects against blind spots, and produces actionable responses — while also building in a natural endpoint so the organisation doesn’t stall in endless preparation.

Resilient Leaders Build Resilient Cultures

When leaders practice Premeditatio Malorum, they do more than steady themselves — they shape how their organisations respond to uncertainty. Teams watch closely. If leaders panic when things go wrong, the organisation turns reactive: priorities lurch, plans are abandoned mid-course, and energy flows to quick fixes over meaningful progress. Over time, morale dips and people hesitate, unsure which direction to follow.

If leaders remain calm because they’ve already considered the setback, the opposite happens. The team sees consistency. They know there is a plan, that setbacks are expected, and that leadership is not flailing in the dark. That steadiness builds confidence and strengthens the culture.

The result is not paranoia, but resilience. People stop being surprised that bad things happen, and instead focus on responding effectively when they do. Over time, this creates an organisation that absorbs blows, adapts, and keeps moving forward.

The Stoics never sought a life without hardship; they sought the strength to face hardship without collapse. Business leadership is no different. Setbacks will come — from competitors, from markets, from within your own walls. The test of leadership is whether you meet them unprepared and shaken, or prepared and composed — having already rehearsed the response and ready to lead with calm conviction.