Why Luck Isn’t Enough: The Machiavellian Guide to Security Leadership

In a world where chaos and unpredictability seem to reign, many leaders, especially in security sectors, wonder why some individuals or organisations flourish while others fall by the wayside. A poignant lens through which to view this dilemma comes from an unexpected source: Niccolò Machiavelli’s The Prince. In particular, Chapter 25 of this famous work, which discusses the role of fortune (or luck) in human affairs, provides timeless wisdom for today’s security professionals. In this blog, we’ll examine why understanding context is crucial, how adaptability determines success, and why relying solely on luck is a recipe for failure—especially in times of rapid change.

The Role of Fortune and Context: A Brief Dive into Machiavelli

Machiavelli opens Chapter 25 by acknowledging that many people believe that luck and divine forces shape the world. For those who believe in this fatalistic view, no amount of preparation or skill can alter the course of events. However, Machiavelli refutes this deterministic mindset by arguing that while luck may control half of what we do, the other half is up to us. This balance between fortune and personal agency provides a crucial lesson for leaders across industries, especially in security.

He likens fortune to a raging river that occasionally floods the plain, causing destruction wherever it goes. But just as humans build levees and dykes to manage rivers, Machiavelli believes we can also prepare for fortune’s unpredictable shifts. In other words, context matters, and those who anticipate change and adapt are more likely to thrive.

Security Management and Context: The Importance of Being Prepared

Let’s take this river analogy and apply it to modern security management. Physical security professionals, police, fire brigade and defence leadership work in environments where unpredictability is the norm. Threats evolve, geopolitical landscapes shift, and new technologies continually change the face of security risks. Leaders who fail to adapt to these changes—who merely trust that what has worked in the past will continue to work—risk being swept away by the flood of new challenges.

For example, the traditional security systems and protocols that may have worked a decade ago are no longer enough in the face of modern cyber threats, terrorism, or pandemics. Security directors and managers must be vigilant and constantly assess the broader context in which they operate. Are their strategies adaptable to changes in geopolitical climates? Do their protocols account for physical and digital threats (see NIS2)? Are they too reliant on past successes or ready to adjust their approaches when circumstances demand it?

Machiavelli’s lesson is clear: Context is king. Failure to assess and adapt to the larger environment is not just unfortunate—it’s a direct path to failure.

Adaptability: The Key to Survival in Security

According to Machiavelli, the most successful leaders can adapt their strategies to changing times. He recounts the story of Pope Julius II, a man who acted impulsively and took significant risks. His style suited the times, and he enjoyed considerable success. However, Machiavelli notes that if the times required caution and careful planning, Julius’s approach would have led to disaster.

This story resonates deeply with today’s security landscape. Security leaders must constantly ask themselves: “Am I adapting to the times?” In an era where both physical and digital threats converge, sticking to rigid strategies or relying on past successes can be fatal. The pace of technological advancement alone demands a flexible mindset. Traditional systems, such as physical barriers and access control, must now integrate seamlessly with advanced cybersecurity measures to create a unified defence strategy.

IBM’s 2017 report highlights the accelerating pace of change, noting how industry convergence and evolving threats demand quicker and more agile responses. Long-term strategy cycles, which may have worked in the past, are often too slow to respond to emerging risks. For security managers and directors, this means adopting an agile approach that continuously reevaluates risks, threats, and opportunities. The leaders who can adjust on the fly—who are willing to rethink their strategies and approaches as circumstances evolve—are the ones who will succeed.

The Human Factor: Understanding Yourself

A crucial part of adaptability is self-awareness. Machiavelli argues that people have natural biases—some are cautious, others are impulsive—and these inclinations shape how they approach challenges. While different approaches can succeed in different contexts, the inability to adjust to new circumstances can lead to failure.

For security, police and defence professionals, self-awareness is vital. Leaders must recognise their tendencies—whether they lean toward caution or bold action—and ask themselves whether these traits suit the current environment. It’s essential to cultivate the ability to step outside one’s comfort zone when necessary. The cautious leader must learn when to take risks, just as the impulsive leader must learn when to slow down and plan carefully.

A lack of self-awareness can be a significant blind spot in leadership. For instance, a director who always favours meticulous planning may struggle in situations that demand rapid decision-making, just as an impulsive leader may falter in circumstances requiring patience and diplomacy. Machiavelli’s advice is clear: if you want to control your fortune, you must learn when to act against your natural tendencies. Understanding yourself and your context is the key to shaping your destiny rather than being shaped by it.

The Modern Flood: Security in the Digital Age

Machiavelli’s metaphor of fortune as a raging river finds its modern counterpart in the digital age. As rivers swell unexpectedly and wreak havoc, digital threats can rise without warning, disrupting even the most well-prepared organisations. Cybersecurity risks have grown exponentially, and many security leaders are grappling with how to defend physical assets and digital data from an increasingly sophisticated array of adversaries.

As IBM’s report notes, despite numerous high-profile cyberattacks, many executives are still underestimating the scale of the threat. This echoes Machiavelli’s warning about those who fail to prepare for the flood. Today’s security leaders must ensure that they not only focus on current threats but also anticipate future risks. An effective security strategy must be both proactive and adaptable, building “dykes” to contain not only present dangers but also the unpredictable nature of tomorrow’s challenges.

Fortune Favors the Adaptable

Ultimately, Machiavelli’s teachings remind us that fortune isn’t something we are helpless against. While luck plays a role in shaping our successes and failures, our adaptability and preparedness determine whether we thrive or falter in changing circumstances.

For security professionals, this means a relentless focus on understanding context and staying flexible in the face of evolving threats. Whether the challenge is a natural disaster, a physical security breach, or a cyberattack, those who have built robust systems—who have anticipated the flood and prepared their defences—will emerge on top.

So, why are you unlucky? Machiavelli would say it’s because you’re clinging to an outdated strategy or failing to adapt to the times. But the good news is, you have the power to change that. Adaptability is the key, and by staying vigilant, self-aware, and prepared for the unpredictable, you can control your fortune instead of being controlled by it.

As Machiavelli wrote, “Fortune is female, and if you want to master her, you must act.”. The security leaders, male or female, who heed this advice will find themselves not at the mercy of luck but as masters of their destinies.

Sources: The Prince. (2024, 1 september). https://www.gutenberg.org/cache/epub/1232/pg1232-images.html; Business trends change faster than executives can prepare. (z.d.). IBM. https://www.ibm.com/thought-leadership/institute-business-value/en-us/blog/business-trends-change-faster.

(c) Yannick De Smet. AI-assisted newsletter. The content of this newsletter is solely the idea, work, and expression of the author, and any views or meanings expressed do not represent the opinions or interpretations of any other party.