Should I stay or should I go? Lessons in strategy from Kant to The Clash

Punk Rock, Principles, and the Strategic Dilemma

There’s a line from a Clash song that has haunted leaders — whether they realise it or not — for decades: “Should I stay or should I go?”

It might sound like a punk anthem for restless teenagers in leather jackets, but strip away the guitars and snarling vocals, and you’ve got the core of strategy itself. The most difficult strategic decisions are not about budgets, technologies, or quarterly forecasts. They’re about knowing whether to stay true to the principles you’ve always lived by — or whether to go with the flow of the moment and adapt to the context.

That tension is not just about personal choices. It runs through every organisation that faces a moment of truth.

The Business Dilemma

Imagine you are CEO of a fast-growing company. From the very beginning, you’ve built your brand on a guiding principle:

“We never discount our product. Price integrity is non-negotiable.”

It has worked beautifully. Customers trust you. Investors admire the consistency. Your brand feels premium because you’ve stood firm while others blinked.

But then a new competitor bursts onto the scene. They undercut your pricing by 30%. Your sales team panics: unless you respond, they say, you’ll lose customers and growth will stall.

You’re now standing in the Clash’s chorus.

• Stay? Stick to your principle, hold your ground, never discount.

• Go? Break your own rule this once, bend to the context, and fight fire with fire.

This is not just a pricing question. It’s a strategic question about how you lead.

Rule or Context?

Philosophers have wrestled with this same tension for centuries. Immanuel Kant insisted that morality — and by extension leadership — rests on rules that never bend. If honesty is your principle, then lying is always wrong, no matter the situation. That clarity is powerful. But it can also be unforgiving.

On the other side are the utilitarians, who argue that what matters is not rigid principle but outcome. What creates the best result for the most people? Sometimes that means bending the rules, if bending prevents greater harm.

Both approaches bleed into business strategy.

• Principle-based leadership is consistent, predictable, and trusted. People know what you stand for.

• Context-based leadership is flexible, adaptive, and pragmatic. People know you’ll do what’s necessary.

The real question is not which camp you belong to. It’s whether you can tell, in the moment, whether a situation demands staying true to principle or going with the context.

The Clash in the Boardroom

Let’s bring it back to the product-flaw case study.

A company discovers a flaw in its flagship product. The flaw won’t cause physical harm but could cost customers time and money. If disclosed immediately, it will damage the company’s reputation, share price, and potentially cost jobs. If concealed, the company buys time to fix the problem quietly, but customers will suffer in the meantime.

• The Kantian CEO (Stay): Disclose immediately. Never mislead customers. The rule of truth comes first.

• The Utilitarian CEO (Go): Delay disclosure until a fix is ready. Minimise overall harm, even if it means bending principle.

Both decisions come with pain. Both are defensible. Neither is easy.

But the chorus plays again: “Should I stay or should I go?”

Why This Matters Strategically

Leaders often think the hardest part of decision-making is data: gathering the facts, forecasting the numbers, running the scenarios. That’s important, but it’s not the heart of the struggle.

The heart of strategy is choosing between the rule that has guided you until now and the context that demands something different.

• Stay, and you signal strength, stability, and integrity. But you risk rigidity, missing the turn of events that makes your principle unsustainable.

• Go, and you show agility, pragmatism, and responsiveness. But you risk appearing opportunistic, eroding trust and undermining your own credibility.

Either way, the stakes are identity and trust: what your company stands for, and how others perceive it.

Lessons from Punk Rock

Here’s what The Clash remind us: the decision is never abstract. It is urgent, noisy, uncomfortable, and unavoidable. You can’t mute the chorus.

Strategic leadership is not about having a rulebook that answers every dilemma. Nor is it about bending with every breeze of context. It’s about recognising that the real test of leadership is knowing when to hold the line and when to break it.

Sometimes you “stay” because your principle is your anchor. Sometimes you “go” because survival requires adaptation. The tragedy comes not from either choice, but from pretending the choice doesn’t exist — drifting in indecision while the chorus blares on repeat.

Closing Thought

“Should I stay or should I go?” is more than a punk refrain. It’s the ultimate strategic question. Whether you’re a CEO facing a pricing dilemma, a board grappling with disclosure, or a leader charting the future of your organisation, the tension between rules and context will always return.

The Clash asked it with guitars. Leaders face it with strategy. But the decision is the same: stay, or go.