The Resilience Portfolio: 4 Stoic-Inspired Strategies to Thrive in a Chaotic World

As an engineer and an entrepreneur, I am trained to view the world as a system. A highly integrated and organised configuration of different inputs, outputs and their interdependences. For decades, we have optimized these systems for efficiency, speed, and growth. Yet, as we explore the landscape of our modern world, it is pretty clear that the system is running hot… We are bombarded by a relentless firehose of information, whipsawed by political and economic volatility, and haunted by a pervasive sense of career instability. The result? We all see the result, a collective state of low-grade anxiety, punctuated by moments of outrage and despair.

Our modern toolkit for dealing with this chaos is clearly failing us.

We are told to practice “positive thinking,” yet toxic positivity leaves us unprepared for genuine adversity.

We are encouraged to indulge in a culture of therapy that often pathologizes normal human struggle, leading to weakness instead of toughness.

We seek distraction in entertainment and outrage on social media, only to find our focus fractured and our spirits diminished.

We are trying to run a 21st-century world on a mental operating system that is outdated and full of bugs. It think it is about time for an upgrade. And for this, I propose we turn to the ancient world. In this article I will explore just one philosophy, Stoicism.

Stoicism was the philosophy of Roman emperors and slaves alike. It is a robust, battle-tested “operating system” for the human mind. And no, it is not about grim-faced endurance or suppressing emotion. It is about cultivating an inner citadel of calm, purpose, and resilience, no matter the external chaos.

Do not worry, I won’t approach this as an academic. I will approach this as an engineer. I will build a diversified set of practical, actionable mental models that we can deploy to thrive in our chaotic world.

So, forget abstract theory. Here are four powerful, lesser-known Stoic strategies to add to your portfolio today.

Strategy 1: The Reserve Clause - Engineering for Reality

When undertaking a project, the project manager will never assume that there will be a perfectly smooth path to the end of the project. A project manager should allow for contingencies or unknowns that may occur during the course of a project. They should also incorporate risks into his or her planning process. The success of their approach to the project is separate from the success of the final outcome of the project due to the influence of an innumerable number of external factors that can affect the outcome of the project. The Stoics referred to this idea as hupexairesis (the reserve clause).

Many have heard of premeditatio malorum, the premeditation of evils, where one imagines all the things that can go wrong. While useful, it can also devolve into simple anxiety if not paired with the reserve clause. The reserve clause reframes every intended action with a crucial caveat: “fate permitting.”

This is the highest form of realism and not pessimism. It is an engineering approach to life. So here is an example:

The Action: “I will excel in this presentation.”

The Action with the Reserve Clause: “I will prepare and deliver the best presentation I am capable of, unless something outside of my control prevents it.”

Can you see the shift? The first statement ties your success to an outcome you do not fully control (the audience’s reaction, a technical glitch, a fire alarm). The second ties your success to what you do control: your effort, your preparation, your focus. The outcome becomes secondary. Your internal excellence is primary.

How this would apply in our modern world?

Career Uncertainty: When applying for a promotion, your goal is not “to get the promotion.” Your goal is “to present the best possible case for myself, fate permitting.” This liberates you from the anxiety of the decision-makers’ biases or other candidates’ strengths, allowing you to focus entirely on delivering your best performance.

Volatile Markets: As an investor, your goal is not “to make a 20% return this year.” It is “to adhere to my well-researched investment strategy and principles, fate permitting.” This prevents panic-selling during downturns and irrational exuberance during bubbles.

The reserve clause is your contingency plan for reality. It allows you to act with full commitment and ambition, while simultaneously insulating your inner peace from the world’s inevitable disruptions. Makes sense, isn’t it?

Strategy 2: Turning the Obstacle Upside Down - The Art of Re-Tasking

Marcus Aurelius wrote,

“The impediment to action advances action. What stands in the way becomes the way.”

For many readers, this quote represents the virtue of persistence in the face of difficulties. However, the greater and stronger meaning is to see obstacles in your life not as things that need to be overcome, but as new and different types of projects to work on and to learn from.

In terms of artificial intelligence development, when a model produces an irrational or hallucinatory output, the output should not be thought of simply as a failure. Rather, the output is an important piece of data. The impediment (the incorrect output) is showing you a flaw in either your model’s training data or your model’s architecture. Therefore, the focus changes from “producing a correct answer” to “identify the flaw and modifying your training data and/or model architecture to create a better, more suitable system.” The impediment has been changed to an alternative task.

Let’s see a modern application of this strategy:

Political Polarization: You find yourself in a tense conversation with someone of an opposing political view. Your initial goal was to convince them of your position. The obstacle is their stubborn refusal to agree. Instead of battering against it, re-task the obstacle. Your new goal is no longer to “win” the argument. It is to practice the virtues of patience, active listening, and intellectual humility. Can you accurately articulate their position back to them, even if you disagree? The obstacle to persuasion has become the path to wisdom.

Information Overload: The endless, anxiety-inducing newsfeed is an obstacle to your peace of mind. Instead of simply trying to ignore it, re-task it. The challenge is no longer to “keep up.” The new challenge is to practice the virtue of discernment. Can you sift through the noise to find the signal? Can you identify one or two truly important articles and ignore the rest? The obstacle of information overload becomes a training ground for focus.

When you are blocked, do not just push harder. Ask yourself: What virtue is this obstacle giving me the opportunity to practice? Patience? Courage? Forgiveness? Discernment? The obstacle is not in your way; it is showing you a new way.

Strategy 3: The View from Above - Debugging Your Perspective

When building software, if your program is stuck in a loop (or never-ending process), developers do not continue to run the same code over and over until it works; instead, they will take a step back and look at everything in the context of the whole application: the architecture of the entire system, all the subsystems and how the overall application interacts with them. This approach is what I refer to as adopting “debugger’s perspective.” The way Stoics would approach this same method is by calling it “the view from above.”

The Stoic philosopher and Roman emperor Marcus Aurelius practiced the view from above. He would visualize the entire world from a cosmic perspective and see everything happening in his lifetime, including millions of people running around and fighting with each other, and each person’s tiny victory, all in the context of the vastness of time and space. This does not mean to act as if you are nothing or that life has no meaning; instead, it requires you to see your immediate problem down to their proper size.

The way that the modern world is now structured causes us to see our world in a very small way. We are inundated with information every day via social media, and as a result, many people perceive reality through a very limited lens of a specific set of experiences or posts, and a negative or critical comment on a post can feel like receiving the same response from the entire world at once. A failure to meet a deadline may seem like the end of the world.

How would we apply this today?

Professional Setbacks: You lost a major client or a project failed. The immediate feeling is one of crushing defeat. Now, apply the view from above. Zoom out. See your entire career, a long road of wins and losses. Zoom out further. See the entire industry, with thousands of companies and millions of people, all experiencing their own daily struggles and successes. Zoom out again. See the planet, spinning in the silent vastness of space. Now, look back at that lost client. It is still painful, but its scale has been recalibrated. It is a single data point and not the end of your story.

Social Media Outrage: You see a post that fills you with anger. Before you fire off a reactive comment, take the view from above. Imagine the person who wrote it, living a life as complex as your own. Imagine the algorithm that served it to you, designed to provoke this exact reaction. Imagine the billions of other interactions happening at this very moment. From this vantage point, is a vitriolic comment the most effective use of your limited time and energy on this planet?

The view from above is a tool for right-sizing them. It is the ultimate context-switcher, allowing you to debug your own emotional loops and regain a sense of proportion.

Strategy 4: The Inner Citadel - Your Personal Sandbox Environment

In software development, a “sandbox” is an isolated testing environment where you can run code without affecting the wider system. It is a safe place to experiment, to fail, and to learn. The Stoics argued that our most important project is to build a similar environment within our own minds, an “inner citadel.”

This citadel is a fortress built upon a single, unshakeable foundation: the clear distinction between what is in our control and what is not. The Stoic philosopher Epictetus stated it with simplicity:

“In our control are our judgments, our intentions, our desires, and our aversions. Not in our control are our bodies, our reputations, our wealth, and the actions of others.”

Your inner citadel is the space where you have absolute sovereignty over your own judgments. The world can throw anything at you, a market crash, a political revolution, a personal betrayal. These events happen outside the citadel walls. They cannot breach the fortress unless you allow them to, by forming a panicked, despairing, or hateful judgment about them.

Let’s apply this strategy today:

Building Your Citadel: This is an active, daily process. It involves constantly interrogating your own impressions. When you feel a surge of anger or anxiety, pause. Ask: “Is this feeling caused by the event itself, or by my judgment about the event?” The event is external. Your judgment is internal. You are the gatekeeper.

Testing in the Sandbox: Before a difficult conversation, run it in your sandbox. Rehearse your intended points, but more importantly, rehearse your reactions. What if they insult you? The insult is external. Your choice to feel offended is internal. In your citadel, you can choose to judge the insult as nothing more than meaningless noise from an agitated person. What if they reject your proposal? The rejection is external. Your judgment about what it means for your self-worth is internal.

Your inner citadel is your ultimate source of strength. It is the one place where you are truly free. The world will remain chaotic. Markets will be volatile, politics will be divisive, and people will be unpredictable. But with a well-stocked Resilience Portfolio, you can move through this world with purpose, clarity, and an unshakable sense of inner peace.

You can be the engineer of your own soul.